sync/internal_api/sync_encryption_handler_impl_unittest.cc

   1 // Copyright 2012 The Chromium Authors. All rights reserved.
   2 // Use of this source code is governed by a BSD-style license that can be
   3 // found in the LICENSE file.
   4
   5 #include "sync/internal_api/sync_encryption_handler_impl.h"
   6
   7 #include <string>
   8
   9 #include "base/base64.h"
  10 #include "base/json/json_string_value_serializer.h"
  11 #include "base/memory/scoped_ptr.h"
  12 #include "base/run_loop.h"
  13 #include "base/tracked_objects.h"
  14 #include "sync/internal_api/public/base/model_type_test_util.h"
  15 #include "sync/internal_api/public/read_node.h"
  16 #include "sync/internal_api/public/read_transaction.h"
  17 #include "sync/internal_api/public/test/test_user_share.h"
  18 #include "sync/internal_api/public/write_node.h"
  19 #include "sync/internal_api/public/write_transaction.h"
  20 #include "sync/protocol/nigori_specifics.pb.h"
  21 #include "sync/protocol/sync.pb.h"
  22 #include "sync/syncable/entry.h"
  23 #include "sync/syncable/mutable_entry.h"
  24 #include "sync/syncable/syncable_write_transaction.h"
  25 #include "sync/test/engine/test_id_factory.h"
  26 #include "sync/test/fake_encryptor.h"
  27 #include "sync/util/cryptographer.h"
  28 #include "testing/gmock/include/gmock/gmock.h"
  29 #include "testing/gtest/include/gtest/gtest.h"
  30
  31 namespace syncer {
  32
  33 namespace {
  34
  35 using ::testing::_;
  36 using ::testing::AnyNumber;
  37 using ::testing::AtLeast;
  38 using ::testing::Mock;
  39 using ::testing::SaveArg;
  40 using ::testing::StrictMock;
  41
  42 // The raw keystore key the server sends.
  43 static const char kRawKeystoreKey[] = "keystore_key";
  44 // Base64 encoded version of |kRawKeystoreKey|.
  45 static const char kKeystoreKey[] = "a2V5c3RvcmVfa2V5";
  46
  47 class SyncEncryptionHandlerObserverMock
  48     : public SyncEncryptionHandler::Observer {
  49  public:
  50   MOCK_METHOD2(OnPassphraseRequired,
  51                void(PassphraseRequiredReason,
  52                     const sync_pb::EncryptedData&));  // NOLINT
  53   MOCK_METHOD0(OnPassphraseAccepted, void());  // NOLINT
  54   MOCK_METHOD2(OnBootstrapTokenUpdated,
  55                void(const std::string&, BootstrapTokenType type));  // NOLINT
  56   MOCK_METHOD2(OnEncryptedTypesChanged,
  57                void(ModelTypeSet, bool));  // NOLINT
  58   MOCK_METHOD0(OnEncryptionComplete, void());  // NOLINT
  59   MOCK_METHOD1(OnCryptographerStateChanged, void(Cryptographer*));  // NOLINT
  60   MOCK_METHOD2(OnPassphraseTypeChanged, void(PassphraseType,
  61                                              base::Time));  // NOLINT
  62   MOCK_METHOD1(OnLocalSetPassphraseEncryption,
  63                void(const SyncEncryptionHandler::NigoriState&));  // NOLINT
  64 };
  65
  66 google::protobuf::RepeatedPtrField<google::protobuf::string>
  67 BuildEncryptionKeyProto(std::string encryption_key) {
  68   google::protobuf::RepeatedPtrField<google::protobuf::string> keys;
  69   keys.Add()->assign(encryption_key);
  70   return keys;
  71 }
  72
  73 }  // namespace
  74
  75 class SyncEncryptionHandlerImplTest : public ::testing::Test {
  76  public:
  77   SyncEncryptionHandlerImplTest() {}
  78   virtual ~SyncEncryptionHandlerImplTest() {}
  79
  80   virtual void SetUp() {
  81     test_user_share_.SetUp();
  82     SetUpEncryption();
  83     CreateRootForType(NIGORI);
  84   }
  85
  86   virtual void TearDown() {
  87     PumpLoop();
  88     test_user_share_.TearDown();
  89   }
  90
  91  protected:
  92   void SetUpEncryption() {
  93     SetUpEncryptionWithKeyForBootstrapping(std::string());
  94   }
  95
  96   void SetUpEncryptionWithKeyForBootstrapping(
  97       const std::string& key_for_bootstrapping) {
  98     encryption_handler_.reset(new SyncEncryptionHandlerImpl(
  99         user_share(), &encryptor_, key_for_bootstrapping,
 100         std::string() /* keystore key for bootstrapping */,
 101         PASSPHRASE_TRANSITION_DO_NOT_CLEAR_DATA));
 102     encryption_handler_->AddObserver(&observer_);
 103   }
 104
 105   void CreateRootForType(ModelType model_type) {
 106     syncer::syncable::Directory* directory = user_share()->directory.get();
 107
 108     std::string tag_name = ModelTypeToRootTag(model_type);
 109
 110     syncable::WriteTransaction wtrans(FROM_HERE, syncable::UNITTEST, directory);
 111     syncable::MutableEntry node(&wtrans,
 112                                 syncable::CREATE,
 113                                 model_type,
 114                                 wtrans.root_id(),
 115                                 tag_name);
 116     node.PutUniqueServerTag(tag_name);
 117     node.PutIsDir(true);
 118     node.PutServerIsDir(false);
 119     node.PutIsUnsynced(false);
 120     node.PutIsUnappliedUpdate(false);
 121     node.PutServerVersion(20);
 122     node.PutBaseVersion(20);
 123     node.PutIsDel(false);
 124     node.PutId(ids_.MakeServer(tag_name));
 125     sync_pb::EntitySpecifics specifics;
 126     syncer::AddDefaultFieldValue(model_type, &specifics);
 127     node.PutSpecifics(specifics);
 128   }
 129
 130   void PumpLoop() {
 131     base::RunLoop().RunUntilIdle();
 132   }
 133
 134   // Getters for tests.
 135   UserShare* user_share() { return test_user_share_.user_share(); }
 136   SyncEncryptionHandlerImpl* encryption_handler() {
 137       return encryption_handler_.get();
 138   }
 139   SyncEncryptionHandlerObserverMock* observer() { return &observer_; }
 140   Cryptographer* GetCryptographer() {
 141     return encryption_handler_->GetCryptographerUnsafe();
 142   }
 143
 144   void VerifyMigratedNigori(PassphraseType passphrase_type,
 145                             const std::string& passphrase) {
 146     VerifyMigratedNigoriWithTimestamp(0, passphrase_type, passphrase);
 147   }
 148
 149   void VerifyMigratedNigoriWithTimestamp(
 150       int64 migration_time,
 151       PassphraseType passphrase_type,
 152       const std::string& passphrase) {
 153     ReadTransaction trans(FROM_HERE, user_share());
 154     ReadNode nigori_node(&trans);
 155     ASSERT_EQ(nigori_node.InitTypeRoot(NIGORI), BaseNode::INIT_OK);
 156     const sync_pb::NigoriSpecifics& nigori = nigori_node.GetNigoriSpecifics();
 157     if (migration_time > 0)
 158       EXPECT_EQ(migration_time, nigori.keystore_migration_time());
 159     else
 160       EXPECT_TRUE(nigori.has_keystore_migration_time());
 161     EXPECT_TRUE(nigori.keybag_is_frozen());
 162     if (passphrase_type == CUSTOM_PASSPHRASE ||
 163         passphrase_type == FROZEN_IMPLICIT_PASSPHRASE) {
 164       EXPECT_TRUE(nigori.encrypt_everything());
 165       EXPECT_TRUE(nigori.keystore_decryptor_token().blob().empty());
 166       if (passphrase_type == CUSTOM_PASSPHRASE) {
 167         EXPECT_EQ(sync_pb::NigoriSpecifics::CUSTOM_PASSPHRASE,
 168                   nigori.passphrase_type());
 169         if (!encryption_handler()->custom_passphrase_time().is_null()) {
 170           EXPECT_EQ(nigori.custom_passphrase_time(),
 171                     TimeToProtoTime(
 172                         encryption_handler()->custom_passphrase_time()));
 173         }
 174       } else {
 175         EXPECT_EQ(sync_pb::NigoriSpecifics::FROZEN_IMPLICIT_PASSPHRASE,
 176                   nigori.passphrase_type());
 177       }
 178     } else {
 179       EXPECT_FALSE(nigori.encrypt_everything());
 180       EXPECT_FALSE(nigori.keystore_decryptor_token().blob().empty());
 181       EXPECT_EQ(sync_pb::NigoriSpecifics::KEYSTORE_PASSPHRASE,
 182                 nigori.passphrase_type());
 183       Cryptographer keystore_cryptographer(&encryptor_);
 184       KeyParams params = {"localhost", "dummy", kKeystoreKey};
 185       keystore_cryptographer.AddKey(params);
 186       EXPECT_TRUE(keystore_cryptographer.CanDecryptUsingDefaultKey(
 187           nigori.keystore_decryptor_token()));
 188     }
 189
 190     Cryptographer temp_cryptographer(&encryptor_);
 191     KeyParams params = {"localhost", "dummy", passphrase};
 192     temp_cryptographer.AddKey(params);
 193     EXPECT_TRUE(temp_cryptographer.CanDecryptUsingDefaultKey(
 194         nigori.encryption_keybag()));
 195   }
 196
 197   sync_pb::NigoriSpecifics BuildMigratedNigori(
 198       PassphraseType passphrase_type,
 199       int64 migration_time,
 200       const std::string& default_passphrase,
 201       const std::string& keystore_key) {
 202     DCHECK_NE(passphrase_type, IMPLICIT_PASSPHRASE);
 203     Cryptographer other_cryptographer(GetCryptographer()->encryptor());
 204
 205     std::string default_key = default_passphrase;
 206     if (default_key.empty()) {
 207       default_key = keystore_key;
 208     } else {
 209       KeyParams keystore_params = {"localhost", "dummy", keystore_key};
 210       other_cryptographer.AddKey(keystore_params);
 211     }
 212     KeyParams params = {"localhost", "dummy", default_key};
 213     other_cryptographer.AddKey(params);
 214     EXPECT_TRUE(other_cryptographer.is_ready());
 215
 216     sync_pb::NigoriSpecifics nigori;
 217     other_cryptographer.GetKeys(nigori.mutable_encryption_keybag());
 218     nigori.set_keybag_is_frozen(true);
 219     nigori.set_keystore_migration_time(migration_time);
 220
 221     if (passphrase_type == KEYSTORE_PASSPHRASE) {
 222       sync_pb::EncryptedData keystore_decryptor_token;
 223       EXPECT_TRUE(encryption_handler()->GetKeystoreDecryptor(
 224           other_cryptographer,
 225           keystore_key,
 226           &keystore_decryptor_token));
 227       nigori.mutable_keystore_decryptor_token()->CopyFrom(
 228           keystore_decryptor_token);
 229       nigori.set_passphrase_type(sync_pb::NigoriSpecifics::KEYSTORE_PASSPHRASE);
 230     } else {
 231       nigori.set_encrypt_everything(true);
 232       nigori.set_passphrase_type(
 233           passphrase_type == CUSTOM_PASSPHRASE ?
 234               sync_pb::NigoriSpecifics::CUSTOM_PASSPHRASE :
 235               sync_pb::NigoriSpecifics::FROZEN_IMPLICIT_PASSPHRASE);
 236     }
 237     return nigori;
 238   }
 239
 240   // Build a migrated nigori node with the specified default passphrase
 241   // and keystore key and initialize the encryption handler with it.
 242   void InitKeystoreMigratedNigori(int64 migration_time,
 243                                   const std::string& default_passphrase,
 244                                   const std::string& keystore_key) {
 245     {
 246       WriteTransaction trans(FROM_HERE, user_share());
 247       WriteNode nigori_node(&trans);
 248       ASSERT_EQ(nigori_node.InitTypeRoot(NIGORI), BaseNode::INIT_OK);
 249       sync_pb::NigoriSpecifics nigori = BuildMigratedNigori(
 250           KEYSTORE_PASSPHRASE,
 251           migration_time,
 252           default_passphrase,
 253           keystore_key);
 254       nigori_node.SetNigoriSpecifics(nigori);
 255     }
 256
 257     EXPECT_CALL(*observer(),
 258                 OnPassphraseTypeChanged(KEYSTORE_PASSPHRASE, _));
 259     EXPECT_CALL(*observer(),
 260                 OnBootstrapTokenUpdated(_, PASSPHRASE_BOOTSTRAP_TOKEN));
 261     EXPECT_CALL(*observer(),
 262                 OnCryptographerStateChanged(_)).Times(AtLeast(1));
 263     EXPECT_CALL(*observer(),
 264                 OnEncryptedTypesChanged(_, false));
 265     EXPECT_CALL(*observer(),
 266                 OnEncryptionComplete()).Times(AtLeast(1));
 267     encryption_handler()->Init();
 268     EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
 269     EXPECT_EQ(encryption_handler()->GetPassphraseType(), KEYSTORE_PASSPHRASE);
 270     EXPECT_FALSE(encryption_handler()->EncryptEverythingEnabled());
 271     Mock::VerifyAndClearExpectations(observer());
 272   }
 273
 274   // Build a migrated nigori node with the specified default passphrase
 275   // as a custom passphrase.
 276   void InitCustomPassMigratedNigori(int64 migration_time,
 277                                     const std::string& default_passphrase) {
 278     {
 279       WriteTransaction trans(FROM_HERE, user_share());
 280       WriteNode nigori_node(&trans);
 281       ASSERT_EQ(nigori_node.InitTypeRoot(NIGORI), BaseNode::INIT_OK);
 282       sync_pb::NigoriSpecifics nigori = BuildMigratedNigori(
 283           CUSTOM_PASSPHRASE,
 284           migration_time,
 285           default_passphrase,
 286           kKeystoreKey);
 287       nigori_node.SetNigoriSpecifics(nigori);
 288     }
 289
 290     EXPECT_CALL(*observer(),
 291                 OnPassphraseTypeChanged(CUSTOM_PASSPHRASE, _));
 292     EXPECT_CALL(*observer(),
 293                 OnCryptographerStateChanged(_)).Times(AtLeast(1));
 294     EXPECT_CALL(*observer(),
 295                 OnEncryptedTypesChanged(_, true)).Times(AtLeast(1));
 296     EXPECT_CALL(*observer(),
 297                 OnEncryptionComplete()).Times(AtLeast(1));
 298     encryption_handler()->Init();
 299     EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
 300     EXPECT_EQ(encryption_handler()->GetPassphraseType(), CUSTOM_PASSPHRASE);
 301     EXPECT_TRUE(encryption_handler()->EncryptEverythingEnabled());
 302     Mock::VerifyAndClearExpectations(observer());
 303   }
 304
 305   // Build an unmigrated nigori node with the specified passphrase and type and
 306   // initialize the encryption handler with it.
 307   void InitUnmigratedNigori(const std::string& default_passphrase,
 308                             PassphraseType passphrase_type) {
 309     DCHECK_NE(passphrase_type, FROZEN_IMPLICIT_PASSPHRASE);
 310     Cryptographer other_cryptographer(GetCryptographer()->encryptor());
 311     KeyParams default_key = {"localhost", "dummy", default_passphrase};
 312     other_cryptographer.AddKey(default_key);
 313     EXPECT_TRUE(other_cryptographer.is_ready());
 314
 315     {
 316       WriteTransaction trans(FROM_HERE, user_share());
 317       WriteNode nigori_node(&trans);
 318       ASSERT_EQ(nigori_node.InitTypeRoot(NIGORI), BaseNode::INIT_OK);
 319       sync_pb::NigoriSpecifics nigori;
 320       other_cryptographer.GetKeys(nigori.mutable_encryption_keybag());
 321       nigori.set_keybag_is_frozen(passphrase_type == CUSTOM_PASSPHRASE);
 322       nigori_node.SetNigoriSpecifics(nigori);
 323     }
 324
 325     if (passphrase_type != IMPLICIT_PASSPHRASE) {
 326       EXPECT_CALL(*observer(),
 327                   OnPassphraseTypeChanged(passphrase_type, _));
 328     }
 329     EXPECT_CALL(*observer(),
 330                 OnCryptographerStateChanged(_)).Times(AtLeast(1));
 331     EXPECT_CALL(*observer(),
 332                 OnEncryptedTypesChanged(_, false));
 333     encryption_handler()->Init();
 334     EXPECT_FALSE(encryption_handler()->MigratedToKeystore());
 335     EXPECT_EQ(encryption_handler()->GetPassphraseType(), passphrase_type);
 336     EXPECT_FALSE(encryption_handler()->EncryptEverythingEnabled());
 337     Mock::VerifyAndClearExpectations(observer());
 338   }
 339
 340   // Verify we can restore the SyncEncryptionHandler state using a saved
 341   // |bootstrap_token| and |nigori_state|.
 342   //
 343   // |migration_time| is the time migration occurred.
 344   //
 345   // |passphrase| is the custom passphrase.
 346   void VerifyRestoreAfterCustomPassphrase(
 347       int64 migration_time,
 348       const std::string& passphrase,
 349       const std::string& bootstrap_token,
 350       const SyncEncryptionHandler::NigoriState& nigori_state,
 351       PassphraseType passphrase_type) {
 352     TearDown();
 353     test_user_share_.SetUp();
 354     SetUpEncryptionWithKeyForBootstrapping(bootstrap_token);
 355     EXPECT_CALL(*observer(), OnCryptographerStateChanged(_)).Times(AnyNumber());
 356     EXPECT_CALL(*observer(), OnEncryptedTypesChanged(_, true))
 357         .Times(AnyNumber());
 358     EXPECT_CALL(*observer(), OnPassphraseTypeChanged(passphrase_type, _));
 359     EXPECT_CALL(*observer(), OnEncryptionComplete());
 360     encryption_handler()->RestoreNigori(nigori_state);
 361     encryption_handler()->Init();
 362     Mock::VerifyAndClearExpectations(observer());
 363     VerifyMigratedNigoriWithTimestamp(migration_time, passphrase_type,
 364                                       passphrase);
 365   }
 366
 367  protected:
 368   TestUserShare test_user_share_;
 369   FakeEncryptor encryptor_;
 370   scoped_ptr<SyncEncryptionHandlerImpl> encryption_handler_;
 371   StrictMock<SyncEncryptionHandlerObserverMock> observer_;
 372   TestIdFactory ids_;
 373   base::MessageLoop message_loop_;
 374 };
 375
 376 // Verify that the encrypted types are being written to and read from the
 377 // nigori node properly.
 378 TEST_F(SyncEncryptionHandlerImplTest, NigoriEncryptionTypes) {
 379   sync_pb::NigoriSpecifics nigori;
 380
 381   StrictMock<SyncEncryptionHandlerObserverMock> observer2;
 382   SyncEncryptionHandlerImpl handler2(user_share(), &encryptor_, std::string(),
 383                                      std::string() /* bootstrap tokens */,
 384                                      PASSPHRASE_TRANSITION_DO_NOT_CLEAR_DATA);
 385   handler2.AddObserver(&observer2);
 386
 387   // Just set the sensitive types (shouldn't trigger any notifications).
 388   ModelTypeSet encrypted_types(SyncEncryptionHandler::SensitiveTypes());
 389   {
 390     WriteTransaction trans(FROM_HERE, user_share());
 391     encryption_handler()->MergeEncryptedTypes(
 392         encrypted_types,
 393         trans.GetWrappedTrans());
 394     encryption_handler()->UpdateNigoriFromEncryptedTypes(
 395         &nigori,
 396         trans.GetWrappedTrans());
 397     handler2.UpdateEncryptedTypesFromNigori(nigori, trans.GetWrappedTrans());
 398   }
 399   EXPECT_TRUE(encrypted_types.Equals(
 400       encryption_handler()->GetEncryptedTypesUnsafe()));
 401   EXPECT_TRUE(encrypted_types.Equals(
 402       handler2.GetEncryptedTypesUnsafe()));
 403
 404   Mock::VerifyAndClearExpectations(observer());
 405   Mock::VerifyAndClearExpectations(&observer2);
 406
 407   ModelTypeSet encrypted_user_types = EncryptableUserTypes();
 408
 409   EXPECT_CALL(*observer(),
 410               OnEncryptedTypesChanged(
 411                   HasModelTypes(encrypted_user_types), false));
 412   EXPECT_CALL(observer2,
 413               OnEncryptedTypesChanged(
 414                   HasModelTypes(encrypted_user_types), false));
 415
 416   // Set all encrypted types
 417   encrypted_types = EncryptableUserTypes();
 418   {
 419     WriteTransaction trans(FROM_HERE, user_share());
 420     encryption_handler()->MergeEncryptedTypes(
 421         encrypted_types,
 422         trans.GetWrappedTrans());
 423     encryption_handler()->UpdateNigoriFromEncryptedTypes(
 424         &nigori,
 425         trans.GetWrappedTrans());
 426     handler2.UpdateEncryptedTypesFromNigori(nigori, trans.GetWrappedTrans());
 427   }
 428   EXPECT_TRUE(encrypted_types.Equals(
 429       encryption_handler()->GetEncryptedTypesUnsafe()));
 430   EXPECT_TRUE(encrypted_types.Equals(handler2.GetEncryptedTypesUnsafe()));
 431
 432   // Receiving an empty nigori should not reset any encrypted types or trigger
 433   // an observer notification.
 434   Mock::VerifyAndClearExpectations(observer());
 435   Mock::VerifyAndClearExpectations(&observer2);
 436   nigori = sync_pb::NigoriSpecifics();
 437   {
 438     WriteTransaction trans(FROM_HERE, user_share());
 439     handler2.UpdateEncryptedTypesFromNigori(nigori, trans.GetWrappedTrans());
 440   }
 441   EXPECT_TRUE(encrypted_types.Equals(
 442       encryption_handler()->GetEncryptedTypesUnsafe()));
 443 }
 444
 445 // Verify the encryption handler processes the encrypt everything field
 446 // properly.
 447 TEST_F(SyncEncryptionHandlerImplTest, EncryptEverythingExplicit) {
 448   sync_pb::NigoriSpecifics nigori;
 449   nigori.set_encrypt_everything(true);
 450
 451   EXPECT_CALL(*observer(),
 452               OnEncryptedTypesChanged(
 453                   HasModelTypes(EncryptableUserTypes()), true));
 454
 455   EXPECT_FALSE(encryption_handler()->EncryptEverythingEnabled());
 456   ModelTypeSet encrypted_types =
 457       encryption_handler()->GetEncryptedTypesUnsafe();
 458   EXPECT_TRUE(encrypted_types.Equals(
 459       ModelTypeSet(PASSWORDS, WIFI_CREDENTIALS)));
 460
 461   {
 462     WriteTransaction trans(FROM_HERE, user_share());
 463     encryption_handler()->UpdateEncryptedTypesFromNigori(
 464         nigori,
 465         trans.GetWrappedTrans());
 466   }
 467
 468   EXPECT_TRUE(encryption_handler()->EncryptEverythingEnabled());
 469   encrypted_types = encryption_handler()->GetEncryptedTypesUnsafe();
 470   EXPECT_TRUE(encrypted_types.HasAll(EncryptableUserTypes()));
 471
 472   // Receiving the nigori node again shouldn't trigger another notification.
 473   Mock::VerifyAndClearExpectations(observer());
 474   {
 475     WriteTransaction trans(FROM_HERE, user_share());
 476     encryption_handler()->UpdateEncryptedTypesFromNigori(
 477         nigori,
 478         trans.GetWrappedTrans());
 479   }
 480 }
 481
 482 // Verify the encryption handler can detect an implicit encrypt everything state
 483 // (from clients that failed to write the encrypt everything field).
 484 TEST_F(SyncEncryptionHandlerImplTest, EncryptEverythingImplicit) {
 485   sync_pb::NigoriSpecifics nigori;
 486   nigori.set_encrypt_bookmarks(true);  // Non-passwords = encrypt everything
 487
 488   EXPECT_CALL(*observer(),
 489               OnEncryptedTypesChanged(
 490                   HasModelTypes(EncryptableUserTypes()), true));
 491
 492   EXPECT_FALSE(encryption_handler()->EncryptEverythingEnabled());
 493   ModelTypeSet encrypted_types =
 494       encryption_handler()->GetEncryptedTypesUnsafe();
 495   EXPECT_TRUE(encrypted_types.Equals(
 496       ModelTypeSet(PASSWORDS, WIFI_CREDENTIALS)));
 497
 498   {
 499     WriteTransaction trans(FROM_HERE, user_share());
 500     encryption_handler()->UpdateEncryptedTypesFromNigori(
 501         nigori,
 502         trans.GetWrappedTrans());
 503   }
 504
 505   EXPECT_TRUE(encryption_handler()->EncryptEverythingEnabled());
 506   encrypted_types = encryption_handler()->GetEncryptedTypesUnsafe();
 507   EXPECT_TRUE(encrypted_types.HasAll(EncryptableUserTypes()));
 508
 509   // Receiving a nigori node with encrypt everything explicitly set shouldn't
 510   // trigger another notification.
 511   Mock::VerifyAndClearExpectations(observer());
 512   nigori.set_encrypt_everything(true);
 513   {
 514     WriteTransaction trans(FROM_HERE, user_share());
 515     encryption_handler()->UpdateEncryptedTypesFromNigori(
 516         nigori,
 517         trans.GetWrappedTrans());
 518   }
 519 }
 520
 521 // Verify the encryption handler can deal with new versions treating new types
 522 // as Sensitive, and that it does not consider this an implicit encrypt
 523 // everything case.
 524 TEST_F(SyncEncryptionHandlerImplTest, UnknownSensitiveTypes) {
 525   sync_pb::NigoriSpecifics nigori;
 526   nigori.set_encrypt_everything(false);
 527   nigori.set_encrypt_bookmarks(true);
 528
 529   ModelTypeSet expected_encrypted_types =
 530       SyncEncryptionHandler::SensitiveTypes();
 531   expected_encrypted_types.Put(BOOKMARKS);
 532
 533   EXPECT_CALL(*observer(),
 534               OnEncryptedTypesChanged(
 535                   HasModelTypes(expected_encrypted_types), false));
 536
 537   EXPECT_FALSE(encryption_handler()->EncryptEverythingEnabled());
 538   ModelTypeSet encrypted_types =
 539       encryption_handler()->GetEncryptedTypesUnsafe();
 540   EXPECT_TRUE(encrypted_types.Equals(
 541       ModelTypeSet(PASSWORDS, WIFI_CREDENTIALS)));
 542
 543   {
 544     WriteTransaction trans(FROM_HERE, user_share());
 545     encryption_handler()->UpdateEncryptedTypesFromNigori(
 546         nigori,
 547         trans.GetWrappedTrans());
 548   }
 549
 550   EXPECT_FALSE(encryption_handler()->EncryptEverythingEnabled());
 551   encrypted_types = encryption_handler()->GetEncryptedTypesUnsafe();
 552   EXPECT_TRUE(encrypted_types.Equals(
 553       ModelTypeSet(BOOKMARKS, PASSWORDS, WIFI_CREDENTIALS)));
 554 }
 555
 556 // Receive an old nigori with old encryption keys and encrypted types. We should
 557 // not revert our default key or encrypted types, and should post a task to
 558 // overwrite the existing nigori with the correct data.
 559 TEST_F(SyncEncryptionHandlerImplTest, ReceiveOldNigori) {
 560   KeyParams old_key = {"localhost", "dummy", "old"};
 561   KeyParams current_key = {"localhost", "dummy", "cur"};
 562
 563   // Data for testing encryption/decryption.
 564   Cryptographer other_cryptographer(GetCryptographer()->encryptor());
 565   other_cryptographer.AddKey(old_key);
 566   sync_pb::EntitySpecifics other_encrypted_specifics;
 567   other_encrypted_specifics.mutable_bookmark()->set_title("title");
 568   other_cryptographer.Encrypt(
 569       other_encrypted_specifics,
 570       other_encrypted_specifics.mutable_encrypted());
 571   sync_pb::EntitySpecifics our_encrypted_specifics;
 572   our_encrypted_specifics.mutable_bookmark()->set_title("title2");
 573   ModelTypeSet encrypted_types = EncryptableUserTypes();
 574
 575   // Set up the current encryption state (containing both keys and encrypt
 576   // everything).
 577   sync_pb::NigoriSpecifics current_nigori_specifics;
 578   GetCryptographer()->AddKey(old_key);
 579   GetCryptographer()->AddKey(current_key);
 580   GetCryptographer()->Encrypt(
 581       our_encrypted_specifics,
 582       our_encrypted_specifics.mutable_encrypted());
 583   GetCryptographer()->GetKeys(
 584       current_nigori_specifics.mutable_encryption_keybag());
 585   current_nigori_specifics.set_encrypt_everything(true);
 586
 587   EXPECT_CALL(*observer(), OnCryptographerStateChanged(_)).Times(AnyNumber());
 588   EXPECT_CALL(*observer(), OnEncryptedTypesChanged(
 589       HasModelTypes(EncryptableUserTypes()), true));
 590   {
 591     // Update the encryption handler.
 592     WriteTransaction trans(FROM_HERE, user_share());
 593     encryption_handler()->ApplyNigoriUpdate(
 594         current_nigori_specifics,
 595         trans.GetWrappedTrans());
 596   }
 597   Mock::VerifyAndClearExpectations(observer());
 598
 599   // Now set up the old nigori specifics and apply it on top.
 600   // Has an old set of keys, and no encrypted types.
 601   sync_pb::NigoriSpecifics old_nigori;
 602   other_cryptographer.GetKeys(old_nigori.mutable_encryption_keybag());
 603
 604   EXPECT_CALL(*observer(), OnCryptographerStateChanged(_)).Times(AnyNumber());
 605   {
 606     // Update the encryption handler.
 607     WriteTransaction trans(FROM_HERE, user_share());
 608     encryption_handler()->ApplyNigoriUpdate(
 609         old_nigori,
 610         trans.GetWrappedTrans());
 611   }
 612   EXPECT_TRUE(GetCryptographer()->is_ready());
 613   EXPECT_FALSE(GetCryptographer()->has_pending_keys());
 614
 615   // Encryption handler should have posted a task to overwrite the old
 616   // specifics.
 617   PumpLoop();
 618
 619   {
 620     // The cryptographer should be able to decrypt both sets of keys and still
 621     // be encrypting with the newest, and the encrypted types should be the
 622     // most recent.
 623     // In addition, the nigori node should match the current encryption state.
 624     ReadTransaction trans(FROM_HERE, user_share());
 625     ReadNode nigori_node(&trans);
 626     ASSERT_EQ(nigori_node.InitTypeRoot(NIGORI), BaseNode::INIT_OK);
 627     const sync_pb::NigoriSpecifics& nigori = nigori_node.GetNigoriSpecifics();
 628     EXPECT_TRUE(GetCryptographer()->CanDecryptUsingDefaultKey(
 629         our_encrypted_specifics.encrypted()));
 630     EXPECT_TRUE(GetCryptographer()->CanDecrypt(
 631         other_encrypted_specifics.encrypted()));
 632     EXPECT_TRUE(GetCryptographer()->CanDecrypt(nigori.encryption_keybag()));
 633     EXPECT_TRUE(nigori.encrypt_everything());
 634     EXPECT_TRUE(
 635         GetCryptographer()->CanDecryptUsingDefaultKey(
 636             nigori.encryption_keybag()));
 637   }
 638   EXPECT_TRUE(encryption_handler()->EncryptEverythingEnabled());
 639 }
 640
 641 // Ensure setting the keystore key works, updates the bootstrap token, and
 642 // triggers a non-backwards compatible migration. Then verify that the
 643 // bootstrap token can be correctly parsed by the encryption handler at startup
 644 // time.
 645 TEST_F(SyncEncryptionHandlerImplTest, SetKeystoreMigratesAndUpdatesBootstrap) {
 646   // Passing no keys should do nothing.
 647   EXPECT_CALL(*observer(), OnBootstrapTokenUpdated(_, _)).Times(0);
 648   {
 649     WriteTransaction trans(FROM_HERE, user_share());
 650     EXPECT_FALSE(GetCryptographer()->is_initialized());
 651     EXPECT_TRUE(encryption_handler()->NeedKeystoreKey(trans.GetWrappedTrans()));
 652     EXPECT_FALSE(encryption_handler()->SetKeystoreKeys(
 653         BuildEncryptionKeyProto(std::string()), trans.GetWrappedTrans()));
 654     EXPECT_TRUE(encryption_handler()->NeedKeystoreKey(trans.GetWrappedTrans()));
 655   }
 656   Mock::VerifyAndClearExpectations(observer());
 657
 658   // Build a set of keystore keys.
 659   const char kRawOldKeystoreKey[] = "old_keystore_key";
 660   std::string old_keystore_key;
 661   base::Base64Encode(kRawOldKeystoreKey, &old_keystore_key);
 662   google::protobuf::RepeatedPtrField<google::protobuf::string> keys;
 663   keys.Add()->assign(kRawOldKeystoreKey);
 664   keys.Add()->assign(kRawKeystoreKey);
 665
 666   // Pass them to the encryption handler, triggering a migration and bootstrap
 667   // token update.
 668   std::string encoded_key;
 669   std::string keystore_bootstrap;
 670   EXPECT_CALL(*observer(), OnEncryptionComplete());
 671   EXPECT_CALL(*observer(), OnCryptographerStateChanged(_));
 672   EXPECT_CALL(*observer(), OnPassphraseAccepted());
 673   EXPECT_CALL(*observer(), OnPassphraseTypeChanged(KEYSTORE_PASSPHRASE, _));
 674   EXPECT_CALL(*observer(),
 675               OnBootstrapTokenUpdated(_,
 676                                       KEYSTORE_BOOTSTRAP_TOKEN)).
 677       WillOnce(SaveArg<0>(&keystore_bootstrap));
 678   {
 679     WriteTransaction trans(FROM_HERE, user_share());
 680     EXPECT_TRUE(
 681         encryption_handler()->SetKeystoreKeys(
 682             keys,
 683             trans.GetWrappedTrans()));
 684     EXPECT_FALSE(
 685         encryption_handler()->NeedKeystoreKey(trans.GetWrappedTrans()));
 686     EXPECT_FALSE(GetCryptographer()->is_initialized());
 687   }
 688   PumpLoop();
 689   EXPECT_TRUE(GetCryptographer()->is_initialized());
 690   VerifyMigratedNigori(KEYSTORE_PASSPHRASE, kKeystoreKey);
 691
 692   // Ensure the bootstrap is encoded properly (a base64 encoded encrypted blob
 693   // of list values containing the keystore keys).
 694   std::string decoded_bootstrap;
 695   ASSERT_TRUE(base::Base64Decode(keystore_bootstrap, &decoded_bootstrap));
 696   std::string decrypted_bootstrap;
 697   ASSERT_TRUE(
 698       GetCryptographer()->encryptor()->DecryptString(decoded_bootstrap,
 699                                                      &decrypted_bootstrap));
 700   JSONStringValueDeserializer json(decrypted_bootstrap);
 701   scoped_ptr<base::Value> deserialized_keystore_keys(
 702       json.Deserialize(NULL, NULL));
 703   ASSERT_TRUE(deserialized_keystore_keys.get());
 704   base::ListValue* keystore_list = NULL;
 705   deserialized_keystore_keys->GetAsList(&keystore_list);
 706   ASSERT_TRUE(keystore_list);
 707   ASSERT_EQ(2U, keystore_list->GetSize());
 708   std::string test_string;
 709   keystore_list->GetString(0, &test_string);
 710   ASSERT_EQ(old_keystore_key, test_string);
 711   keystore_list->GetString(1, &test_string);
 712   ASSERT_EQ(kKeystoreKey, test_string);
 713
 714
 715   // Now make sure a new encryption handler can correctly parse the bootstrap
 716   // token.
 717   SyncEncryptionHandlerImpl handler2(user_share(), &encryptor_,
 718                                      std::string(),  // Cryptographer bootstrap.
 719                                      keystore_bootstrap,
 720                                      PASSPHRASE_TRANSITION_DO_NOT_CLEAR_DATA);
 721
 722   {
 723     WriteTransaction trans(FROM_HERE, user_share());
 724     EXPECT_FALSE(handler2.NeedKeystoreKey(trans.GetWrappedTrans()));
 725   }
 726 }
 727
 728 // Ensure GetKeystoreDecryptor only updates the keystore decryptor token if it
 729 // wasn't already set properly. Otherwise, the decryptor should remain the
 730 // same.
 731 TEST_F(SyncEncryptionHandlerImplTest, GetKeystoreDecryptor) {
 732   const char kCurKey[] = "cur";
 733   sync_pb::EncryptedData encrypted;
 734   Cryptographer other_cryptographer(GetCryptographer()->encryptor());
 735   KeyParams cur_key = {"localhost", "dummy", kCurKey};
 736   other_cryptographer.AddKey(cur_key);
 737   EXPECT_TRUE(other_cryptographer.is_ready());
 738   EXPECT_TRUE(encryption_handler()->GetKeystoreDecryptor(
 739       other_cryptographer,
 740       kKeystoreKey,
 741       &encrypted));
 742   std::string serialized = encrypted.SerializeAsString();
 743   EXPECT_TRUE(encryption_handler()->GetKeystoreDecryptor(
 744       other_cryptographer,
 745       kKeystoreKey,
 746       &encrypted));
 747   EXPECT_EQ(serialized, encrypted.SerializeAsString());
 748 }
 749
 750 // Test that we don't attempt to migrate while an implicit passphrase is pending
 751 // and that once we do decrypt pending keys we migrate the nigori. Once
 752 // migrated, we should be in keystore passphrase state.
 753 TEST_F(SyncEncryptionHandlerImplTest, MigrateOnDecryptImplicitPass) {
 754   const char kOtherKey[] = "other";
 755   {
 756     EXPECT_CALL(*observer(),
 757                 OnBootstrapTokenUpdated(_, KEYSTORE_BOOTSTRAP_TOKEN));
 758     ReadTransaction trans(FROM_HERE, user_share());
 759     encryption_handler()->SetKeystoreKeys(BuildEncryptionKeyProto(
 760                                               kRawKeystoreKey),
 761                                           trans.GetWrappedTrans());
 762     Mock::VerifyAndClearExpectations(observer());
 763   }
 764   EXPECT_FALSE(encryption_handler()->MigratedToKeystore());
 765
 766   {
 767     WriteTransaction trans(FROM_HERE, user_share());
 768     WriteNode nigori_node(&trans);
 769     ASSERT_EQ(nigori_node.InitTypeRoot(NIGORI), BaseNode::INIT_OK);
 770     Cryptographer other_cryptographer(GetCryptographer()->encryptor());
 771     KeyParams other_key = {"localhost", "dummy", kOtherKey};
 772     other_cryptographer.AddKey(other_key);
 773
 774     sync_pb::NigoriSpecifics nigori;
 775     other_cryptographer.GetKeys(nigori.mutable_encryption_keybag());
 776     nigori.set_keybag_is_frozen(false);
 777     nigori.set_encrypt_everything(false);
 778     EXPECT_CALL(*observer(),
 779                 OnCryptographerStateChanged(_)).Times(AnyNumber());
 780     EXPECT_CALL(*observer(),
 781                 OnPassphraseRequired(_, _));
 782     encryption_handler()->ApplyNigoriUpdate(nigori, trans.GetWrappedTrans());
 783     nigori_node.SetNigoriSpecifics(nigori);
 784   }
 785   // Run any tasks posted via AppplyNigoriUpdate.
 786   PumpLoop();
 787   EXPECT_FALSE(encryption_handler()->MigratedToKeystore());
 788   Mock::VerifyAndClearExpectations(observer());
 789
 790   EXPECT_CALL(*observer(),
 791               OnCryptographerStateChanged(_)).Times(AnyNumber());
 792   EXPECT_CALL(*observer(),
 793               OnPassphraseAccepted());
 794   EXPECT_CALL(*observer(),
 795               OnPassphraseTypeChanged(KEYSTORE_PASSPHRASE, _));
 796   EXPECT_CALL(*observer(),
 797               OnBootstrapTokenUpdated(_, PASSPHRASE_BOOTSTRAP_TOKEN));
 798   EXPECT_CALL(*observer(),
 799               OnEncryptionComplete());
 800   EXPECT_FALSE(encryption_handler()->MigratedToKeystore());
 801   encryption_handler()->SetDecryptionPassphrase(kOtherKey);
 802   EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
 803   EXPECT_EQ(KEYSTORE_PASSPHRASE, encryption_handler()->GetPassphraseType());
 804   VerifyMigratedNigori(KEYSTORE_PASSPHRASE, kOtherKey);
 805 }
 806
 807 // Test that we don't attempt to migrate while a custom passphrase is pending,
 808 // and that once we do decrypt pending keys we migrate the nigori. Once
 809 // migrated, we should be in custom passphrase state with encrypt everything.
 810 TEST_F(SyncEncryptionHandlerImplTest, MigrateOnDecryptCustomPass) {
 811   const char kOtherKey[] = "other";
 812   {
 813     EXPECT_CALL(*observer(),
 814                 OnBootstrapTokenUpdated(_, KEYSTORE_BOOTSTRAP_TOKEN));
 815     ReadTransaction trans(FROM_HERE, user_share());
 816     encryption_handler()->SetKeystoreKeys(BuildEncryptionKeyProto(
 817                                               kRawKeystoreKey),
 818                                           trans.GetWrappedTrans());
 819     Mock::VerifyAndClearExpectations(observer());
 820   }
 821   EXPECT_FALSE(encryption_handler()->MigratedToKeystore());
 822
 823   {
 824     WriteTransaction trans(FROM_HERE, user_share());
 825     WriteNode nigori_node(&trans);
 826     ASSERT_EQ(nigori_node.InitTypeRoot(NIGORI), BaseNode::INIT_OK);
 827     Cryptographer other_cryptographer(GetCryptographer()->encryptor());
 828     KeyParams other_key = {"localhost", "dummy", kOtherKey};
 829     other_cryptographer.AddKey(other_key);
 830
 831     sync_pb::NigoriSpecifics nigori;
 832     other_cryptographer.GetKeys(nigori.mutable_encryption_keybag());
 833     nigori.set_keybag_is_frozen(true);
 834     nigori.set_encrypt_everything(false);
 835     EXPECT_CALL(*observer(),
 836                 OnCryptographerStateChanged(_)).Times(AnyNumber());
 837     EXPECT_CALL(*observer(),
 838                 OnPassphraseRequired(_, _));
 839     EXPECT_CALL(*observer(),
 840                 OnPassphraseTypeChanged(CUSTOM_PASSPHRASE, _));
 841     encryption_handler()->ApplyNigoriUpdate(nigori, trans.GetWrappedTrans());
 842     nigori_node.SetNigoriSpecifics(nigori);
 843   }
 844   // Run any tasks posted via AppplyNigoriUpdate.
 845   PumpLoop();
 846   EXPECT_FALSE(encryption_handler()->MigratedToKeystore());
 847   Mock::VerifyAndClearExpectations(observer());
 848
 849   EXPECT_CALL(*observer(),
 850               OnCryptographerStateChanged(_)).Times(AnyNumber());
 851   EXPECT_CALL(*observer(),
 852               OnPassphraseAccepted());
 853   std::string captured_bootstrap_token;
 854   EXPECT_CALL(*observer(),
 855               OnBootstrapTokenUpdated(_, PASSPHRASE_BOOTSTRAP_TOKEN))
 856       .WillOnce(testing::SaveArg<0>(&captured_bootstrap_token));
 857   EXPECT_CALL(*observer(),
 858               OnEncryptedTypesChanged(_, true));
 859   SyncEncryptionHandler::NigoriState captured_nigori_state;
 860   EXPECT_CALL(*observer(), OnLocalSetPassphraseEncryption(_))
 861       .WillOnce(testing::SaveArg<0>(&captured_nigori_state));
 862   EXPECT_CALL(*observer(),
 863               OnEncryptionComplete()).Times(2);
 864   EXPECT_FALSE(encryption_handler()->MigratedToKeystore());
 865   encryption_handler()->SetDecryptionPassphrase(kOtherKey);
 866   EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
 867   const base::Time migration_time = encryption_handler()->migration_time();
 868   EXPECT_EQ(CUSTOM_PASSPHRASE, encryption_handler()->GetPassphraseType());
 869   VerifyMigratedNigori(CUSTOM_PASSPHRASE, kOtherKey);
 870
 871   VerifyRestoreAfterCustomPassphrase(TimeToProtoTime(migration_time), kOtherKey,
 872                                      captured_bootstrap_token,
 873                                      captured_nigori_state, CUSTOM_PASSPHRASE);
 874 }
 875
 876 // Test that we trigger a migration when we set the keystore key, had an
 877 // implicit passphrase, and did not have encrypt everything. We should switch
 878 // to KEYSTORE_PASSPHRASE.
 879 TEST_F(SyncEncryptionHandlerImplTest, MigrateOnKeystoreKeyAvailableImplicit) {
 880   const char kCurKey[] = "cur";
 881   KeyParams current_key = {"localhost", "dummy", kCurKey};
 882   GetCryptographer()->AddKey(current_key);
 883   EXPECT_CALL(*observer(),
 884               OnCryptographerStateChanged(_)).Times(AnyNumber());
 885   EXPECT_CALL(*observer(),
 886               OnEncryptedTypesChanged(_, false));
 887   EXPECT_CALL(*observer(),
 888               OnEncryptionComplete());
 889   encryption_handler()->Init();
 890   Mock::VerifyAndClearExpectations(observer());
 891
 892   {
 893     ReadTransaction trans(FROM_HERE, user_share());
 894     // Once we provide a keystore key, we should perform the migration.
 895     EXPECT_CALL(*observer(),
 896                 OnCryptographerStateChanged(_)).Times(AnyNumber());
 897     EXPECT_CALL(*observer(),
 898                 OnBootstrapTokenUpdated(_, KEYSTORE_BOOTSTRAP_TOKEN));
 899     encryption_handler()->SetKeystoreKeys(BuildEncryptionKeyProto(
 900                                               kRawKeystoreKey),
 901                                           trans.GetWrappedTrans());
 902   }
 903   EXPECT_CALL(*observer(),
 904               OnPassphraseTypeChanged(KEYSTORE_PASSPHRASE, _));
 905   // The actual migration gets posted, so run all pending tasks.
 906   PumpLoop();
 907   EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
 908   EXPECT_EQ(KEYSTORE_PASSPHRASE,
 909             encryption_handler()->GetPassphraseType());
 910   EXPECT_FALSE(encryption_handler()->EncryptEverythingEnabled());
 911   VerifyMigratedNigori(KEYSTORE_PASSPHRASE, kCurKey);
 912 }
 913
 914 // Test that we trigger a migration when we set the keystore key, had an
 915 // implicit passphrase, and encrypt everything enabled. We should switch to
 916 // FROZEN_IMPLICIT_PASSPHRASE.
 917 TEST_F(SyncEncryptionHandlerImplTest,
 918        MigrateOnKeystoreKeyAvailableFrozenImplicit) {
 919   const char kCurKey[] = "cur";
 920   KeyParams current_key = {"localhost", "dummy", kCurKey};
 921   GetCryptographer()->AddKey(current_key);
 922   EXPECT_CALL(*observer(),
 923               OnCryptographerStateChanged(_)).Times(AnyNumber());
 924   EXPECT_CALL(*observer(),
 925               OnEncryptedTypesChanged(_, false));
 926   EXPECT_CALL(*observer(),
 927               OnEncryptionComplete());
 928   encryption_handler()->Init();
 929   Mock::VerifyAndClearExpectations(observer());
 930   EXPECT_CALL(*observer(),
 931               OnEncryptedTypesChanged(_, true));
 932   SyncEncryptionHandler::NigoriState captured_nigori_state;
 933   EXPECT_CALL(*observer(), OnLocalSetPassphraseEncryption(_))
 934       .WillOnce(testing::SaveArg<0>(&captured_nigori_state));
 935   EXPECT_CALL(*observer(),
 936               OnEncryptionComplete());
 937   encryption_handler()->EnableEncryptEverything();
 938
 939   {
 940     ReadTransaction trans(FROM_HERE, user_share());
 941     // Once we provide a keystore key, we should perform the migration.
 942     EXPECT_CALL(*observer(),
 943                 OnCryptographerStateChanged(_)).Times(AnyNumber());
 944     EXPECT_CALL(*observer(),
 945                 OnBootstrapTokenUpdated(_, KEYSTORE_BOOTSTRAP_TOKEN));
 946     encryption_handler()->SetKeystoreKeys(BuildEncryptionKeyProto(
 947                                               kRawKeystoreKey),
 948                                           trans.GetWrappedTrans());
 949   }
 950   EXPECT_CALL(*observer(),
 951               OnPassphraseTypeChanged(FROZEN_IMPLICIT_PASSPHRASE, _));
 952
 953   // The actual migration gets posted, so run all pending tasks.
 954   PumpLoop();
 955   Mock::VerifyAndClearExpectations(observer());
 956
 957   EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
 958   const base::Time migration_time = encryption_handler()->migration_time();
 959   EXPECT_EQ(FROZEN_IMPLICIT_PASSPHRASE,
 960             encryption_handler()->GetPassphraseType());
 961   EXPECT_TRUE(encryption_handler()->EncryptEverythingEnabled());
 962   VerifyMigratedNigori(FROZEN_IMPLICIT_PASSPHRASE, kCurKey);
 963
 964   // We need the passphrase bootstrap token, but OnBootstrapTokenUpdated(_,
 965   // PASSPHRASE_BOOTSTRAP_TOKEN) has not been invoked (because it was invoked
 966   // during a previous instance) so get it from the Cryptographer.
 967   std::string passphrase_bootstrap_token;
 968   GetCryptographer()->GetBootstrapToken(&passphrase_bootstrap_token);
 969   VerifyRestoreAfterCustomPassphrase(
 970       TimeToProtoTime(migration_time), kCurKey, passphrase_bootstrap_token,
 971       captured_nigori_state, FROZEN_IMPLICIT_PASSPHRASE);
 972 }
 973
 974 // Test that we trigger a migration when we set the keystore key, had a
 975 // custom passphrase, and encrypt everything enabled. The passphrase state
 976 // should remain as CUSTOM_PASSPHRASE, and encrypt everything stay the same.
 977 TEST_F(SyncEncryptionHandlerImplTest,
 978        MigrateOnKeystoreKeyAvailableCustomWithEncryption) {
 979   const char kCurKey[] = "cur";
 980   EXPECT_CALL(*observer(),
 981               OnCryptographerStateChanged(_)).Times(AnyNumber());
 982   EXPECT_CALL(*observer(),
 983               OnPassphraseRequired(_, _));
 984   EXPECT_CALL(*observer(),
 985               OnPassphraseAccepted());
 986   EXPECT_CALL(*observer(),
 987               OnEncryptedTypesChanged(_, false));
 988   EXPECT_CALL(*observer(),
 989               OnEncryptionComplete());
 990   EXPECT_CALL(*observer(),
 991               OnPassphraseTypeChanged(CUSTOM_PASSPHRASE, _));
 992   std::string captured_bootstrap_token;
 993   EXPECT_CALL(*observer(),
 994               OnBootstrapTokenUpdated(_, PASSPHRASE_BOOTSTRAP_TOKEN))
 995       .WillOnce(testing::SaveArg<0>(&captured_bootstrap_token));
 996   encryption_handler()->Init();
 997   encryption_handler()->SetEncryptionPassphrase(kCurKey, true);
 998   EXPECT_FALSE(encryption_handler()->custom_passphrase_time().is_null());
 999   Mock::VerifyAndClearExpectations(observer());
1000
1001   EXPECT_CALL(*observer(),
1002               OnEncryptedTypesChanged(_, true));
1003   EXPECT_CALL(*observer(),
1004               OnEncryptionComplete());
1005   encryption_handler()->EnableEncryptEverything();
1006   Mock::VerifyAndClearExpectations(observer());
1007
1008   SyncEncryptionHandler::NigoriState captured_nigori_state;
1009   {
1010     ReadTransaction trans(FROM_HERE, user_share());
1011     // Once we provide a keystore key, we should perform the migration.
1012     EXPECT_CALL(*observer(),
1013                 OnCryptographerStateChanged(_)).Times(AnyNumber());
1014     EXPECT_CALL(*observer(),
1015                 OnBootstrapTokenUpdated(_, KEYSTORE_BOOTSTRAP_TOKEN));
1016     EXPECT_CALL(*observer(), OnLocalSetPassphraseEncryption(_))
1017         .WillOnce(testing::SaveArg<0>(&captured_nigori_state));
1018     encryption_handler()->SetKeystoreKeys(BuildEncryptionKeyProto(
1019                                               kRawKeystoreKey),
1020                                           trans.GetWrappedTrans());
1021   }
1022
1023   // The actual migration gets posted, so run all pending tasks.
1024   PumpLoop();
1025   Mock::VerifyAndClearExpectations(observer());
1026
1027   EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
1028   const base::Time migration_time = encryption_handler()->migration_time();
1029   EXPECT_EQ(CUSTOM_PASSPHRASE,
1030             encryption_handler()->GetPassphraseType());
1031   EXPECT_TRUE(encryption_handler()->EncryptEverythingEnabled());
1032   VerifyMigratedNigori(CUSTOM_PASSPHRASE, kCurKey);
1033
1034   VerifyRestoreAfterCustomPassphrase(TimeToProtoTime(migration_time), kCurKey,
1035                                      captured_bootstrap_token,
1036                                      captured_nigori_state, CUSTOM_PASSPHRASE);
1037 }
1038
1039 // Test that we trigger a migration when we set the keystore key, had a
1040 // custom passphrase, and did not have encrypt everything. The passphrase state
1041 // should remain as CUSTOM_PASSPHRASE, and encrypt everything should be enabled.
1042 TEST_F(SyncEncryptionHandlerImplTest,
1043        MigrateOnKeystoreKeyAvailableCustomNoEncryption) {
1044   const char kCurKey[] = "cur";
1045   EXPECT_CALL(*observer(),
1046               OnCryptographerStateChanged(_)).Times(AnyNumber());
1047   EXPECT_CALL(*observer(),
1048               OnPassphraseRequired(_, _));
1049   EXPECT_CALL(*observer(),
1050               OnPassphraseAccepted());
1051   EXPECT_CALL(*observer(),
1052               OnEncryptedTypesChanged(_, false));
1053   EXPECT_CALL(*observer(),
1054               OnEncryptionComplete());
1055   EXPECT_CALL(*observer(),
1056               OnPassphraseTypeChanged(CUSTOM_PASSPHRASE, _));
1057   std::string captured_bootstrap_token;
1058   EXPECT_CALL(*observer(),
1059               OnBootstrapTokenUpdated(_, PASSPHRASE_BOOTSTRAP_TOKEN))
1060       .WillOnce(testing::SaveArg<0>(&captured_bootstrap_token));
1061   encryption_handler()->Init();
1062   encryption_handler()->SetEncryptionPassphrase(kCurKey, true);
1063   EXPECT_FALSE(encryption_handler()->custom_passphrase_time().is_null());
1064   Mock::VerifyAndClearExpectations(observer());
1065
1066   {
1067     ReadTransaction trans(FROM_HERE, user_share());
1068     // Once we provide a keystore key, we should perform the migration.
1069     EXPECT_CALL(*observer(),
1070                 OnCryptographerStateChanged(_)).Times(AnyNumber());
1071     EXPECT_CALL(*observer(),
1072                 OnBootstrapTokenUpdated(_, KEYSTORE_BOOTSTRAP_TOKEN));
1073     encryption_handler()->SetKeystoreKeys(BuildEncryptionKeyProto(
1074                                               kRawKeystoreKey),
1075                                           trans.GetWrappedTrans());
1076   }
1077   EXPECT_CALL(*observer(),
1078               OnEncryptedTypesChanged(_, true));
1079   SyncEncryptionHandler::NigoriState captured_nigori_state;
1080   EXPECT_CALL(*observer(), OnLocalSetPassphraseEncryption(_))
1081       .WillOnce(testing::SaveArg<0>(&captured_nigori_state));
1082   EXPECT_CALL(*observer(),
1083               OnEncryptionComplete());
1084   // The actual migration gets posted, so run all pending tasks.
1085   PumpLoop();
1086   EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
1087   const base::Time migration_time = encryption_handler()->migration_time();
1088   EXPECT_EQ(CUSTOM_PASSPHRASE,
1089             encryption_handler()->GetPassphraseType());
1090   EXPECT_TRUE(encryption_handler()->EncryptEverythingEnabled());
1091   VerifyMigratedNigori(CUSTOM_PASSPHRASE, kCurKey);
1092
1093   VerifyRestoreAfterCustomPassphrase(TimeToProtoTime(migration_time), kCurKey,
1094                                      captured_bootstrap_token,
1095                                      captured_nigori_state, CUSTOM_PASSPHRASE);
1096 }
1097
1098 // Test that we can handle receiving a migrated nigori node in the
1099 // KEYSTORE_PASS state, and use the keystore decryptor token to decrypt the
1100 // keybag.
1101 TEST_F(SyncEncryptionHandlerImplTest, ReceiveMigratedNigoriKeystorePass) {
1102   const char kCurKey[] = "cur";
1103   sync_pb::EncryptedData keystore_decryptor_token;
1104   Cryptographer other_cryptographer(GetCryptographer()->encryptor());
1105   KeyParams cur_key = {"localhost", "dummy", kCurKey};
1106   other_cryptographer.AddKey(cur_key);
1107   EXPECT_TRUE(other_cryptographer.is_ready());
1108   EXPECT_TRUE(encryption_handler()->GetKeystoreDecryptor(
1109       other_cryptographer,
1110       kKeystoreKey,
1111       &keystore_decryptor_token));
1112   EXPECT_FALSE(encryption_handler()->MigratedToKeystore());
1113   EXPECT_FALSE(GetCryptographer()->is_ready());
1114   EXPECT_NE(encryption_handler()->GetPassphraseType(), KEYSTORE_PASSPHRASE);
1115
1116   // Now build a nigori node with the generated keystore decryptor token and
1117   // initialize the encryption handler with it. The cryptographer should be
1118   // initialized properly to decrypt both kCurKey and kKeystoreKey.
1119   {
1120     WriteTransaction trans(FROM_HERE, user_share());
1121     WriteNode nigori_node(&trans);
1122     ASSERT_EQ(nigori_node.InitTypeRoot(NIGORI), BaseNode::INIT_OK);
1123     sync_pb::NigoriSpecifics nigori;
1124     nigori.mutable_keystore_decryptor_token()->CopyFrom(
1125         keystore_decryptor_token);
1126     other_cryptographer.GetKeys(nigori.mutable_encryption_keybag());
1127     nigori.set_keybag_is_frozen(true);
1128     nigori.set_keystore_migration_time(1);
1129     nigori.set_passphrase_type(sync_pb::NigoriSpecifics::KEYSTORE_PASSPHRASE);
1130
1131     EXPECT_CALL(*observer(), OnPassphraseAccepted());
1132     EXPECT_CALL(*observer(),
1133                 OnBootstrapTokenUpdated(_, PASSPHRASE_BOOTSTRAP_TOKEN));
1134     EXPECT_CALL(*observer(),
1135                 OnBootstrapTokenUpdated(_, KEYSTORE_BOOTSTRAP_TOKEN));
1136     EXPECT_CALL(*observer(),
1137                 OnPassphraseTypeChanged(KEYSTORE_PASSPHRASE, _));
1138     EXPECT_CALL(*observer(),
1139                 OnCryptographerStateChanged(_)).Times(AnyNumber());
1140     encryption_handler()->SetKeystoreKeys(BuildEncryptionKeyProto(
1141                                               kRawKeystoreKey),
1142                                           trans.GetWrappedTrans());
1143     encryption_handler()->ApplyNigoriUpdate(nigori, trans.GetWrappedTrans());
1144     nigori_node.SetNigoriSpecifics(nigori);
1145   }
1146   // Run any tasks posted via AppplyNigoriUpdate.
1147   PumpLoop();
1148   Mock::VerifyAndClearExpectations(observer());
1149
1150   EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
1151   EXPECT_TRUE(GetCryptographer()->is_ready());
1152   EXPECT_EQ(encryption_handler()->GetPassphraseType(), KEYSTORE_PASSPHRASE);
1153   EXPECT_FALSE(encryption_handler()->EncryptEverythingEnabled());
1154   VerifyMigratedNigoriWithTimestamp(1, KEYSTORE_PASSPHRASE, kCurKey);
1155
1156   // Check that the cryptographer still encrypts with the current key.
1157   sync_pb::EncryptedData current_encrypted;
1158   other_cryptographer.EncryptString("string", &current_encrypted);
1159   EXPECT_TRUE(GetCryptographer()->CanDecryptUsingDefaultKey(current_encrypted));
1160
1161   // Check that the cryptographer can decrypt keystore key based encryption.
1162   Cryptographer keystore_cryptographer(GetCryptographer()->encryptor());
1163   KeyParams keystore_key =  {"localhost", "dummy", kKeystoreKey};
1164   keystore_cryptographer.AddKey(keystore_key);
1165   sync_pb::EncryptedData keystore_encrypted;
1166   keystore_cryptographer.EncryptString("string", &keystore_encrypted);
1167   EXPECT_TRUE(GetCryptographer()->CanDecrypt(keystore_encrypted));
1168 }
1169
1170 // Test that we handle receiving migrated nigori's with
1171 // FROZEN_IMPLICIT_PASSPHRASE state. We should be in a pending key state until
1172 // we supply the pending frozen implicit passphrase key.
1173 TEST_F(SyncEncryptionHandlerImplTest, ReceiveMigratedNigoriFrozenImplicitPass) {
1174   const char kCurKey[] = "cur";
1175   sync_pb::EncryptedData encrypted;
1176   Cryptographer other_cryptographer(GetCryptographer()->encryptor());
1177   KeyParams cur_key = {"localhost", "dummy", kCurKey};
1178   other_cryptographer.AddKey(cur_key);
1179   EXPECT_FALSE(encryption_handler()->MigratedToKeystore());
1180
1181   {
1182     EXPECT_CALL(*observer(),
1183                 OnBootstrapTokenUpdated(_, KEYSTORE_BOOTSTRAP_TOKEN));
1184     ReadTransaction trans(FROM_HERE, user_share());
1185     encryption_handler()->SetKeystoreKeys(BuildEncryptionKeyProto(
1186                                               kRawKeystoreKey),
1187                                           trans.GetWrappedTrans());
1188   }
1189   EXPECT_FALSE(encryption_handler()->MigratedToKeystore());
1190
1191   {
1192     EXPECT_CALL(*observer(),
1193                 OnPassphraseTypeChanged(FROZEN_IMPLICIT_PASSPHRASE, _));
1194     EXPECT_CALL(*observer(),
1195                 OnPassphraseRequired(_, _));
1196     EXPECT_CALL(*observer(),
1197                 OnCryptographerStateChanged(_)).Times(AnyNumber());
1198     EXPECT_CALL(*observer(),
1199                 OnEncryptedTypesChanged(_, true));
1200     WriteTransaction trans(FROM_HERE, user_share());
1201     WriteNode nigori_node(&trans);
1202     ASSERT_EQ(nigori_node.InitTypeRoot(NIGORI), BaseNode::INIT_OK);
1203     sync_pb::NigoriSpecifics nigori;
1204     nigori.set_keybag_is_frozen(true);
1205     nigori.set_passphrase_type(
1206         sync_pb::NigoriSpecifics::FROZEN_IMPLICIT_PASSPHRASE);
1207     nigori.set_keystore_migration_time(1);
1208     nigori.set_encrypt_everything(true);
1209     other_cryptographer.GetKeys(nigori.mutable_encryption_keybag());
1210     encryption_handler()->ApplyNigoriUpdate(nigori, trans.GetWrappedTrans());
1211     nigori_node.SetNigoriSpecifics(nigori);
1212   }
1213   // Run any tasks posted via AppplyNigoriUpdate.
1214   PumpLoop();
1215   Mock::VerifyAndClearExpectations(observer());
1216
1217   EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
1218   EXPECT_EQ(FROZEN_IMPLICIT_PASSPHRASE,
1219             encryption_handler()->GetPassphraseType());
1220   EXPECT_TRUE(GetCryptographer()->has_pending_keys());
1221   EXPECT_TRUE(encryption_handler()->EncryptEverythingEnabled());
1222
1223   EXPECT_CALL(*observer(),
1224               OnBootstrapTokenUpdated(_, PASSPHRASE_BOOTSTRAP_TOKEN));
1225   EXPECT_CALL(*observer(),
1226               OnCryptographerStateChanged(_)).Times(AnyNumber());
1227   EXPECT_CALL(*observer(),
1228               OnEncryptionComplete());
1229   EXPECT_CALL(*observer(),
1230               OnPassphraseAccepted());
1231   encryption_handler()->SetDecryptionPassphrase(kCurKey);
1232   EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
1233   EXPECT_TRUE(GetCryptographer()->is_ready());
1234   VerifyMigratedNigoriWithTimestamp(1, FROZEN_IMPLICIT_PASSPHRASE, kCurKey);
1235
1236   // Check that the cryptographer still encrypts with the current key.
1237   sync_pb::EncryptedData current_encrypted;
1238   other_cryptographer.EncryptString("string", &current_encrypted);
1239   EXPECT_TRUE(GetCryptographer()->CanDecryptUsingDefaultKey(current_encrypted));
1240
1241   // Check that the cryptographer can decrypt keystore key based encryption.
1242   Cryptographer keystore_cryptographer(GetCryptographer()->encryptor());
1243   KeyParams keystore_key =  {"localhost", "dummy", kKeystoreKey};
1244   keystore_cryptographer.AddKey(keystore_key);
1245   sync_pb::EncryptedData keystore_encrypted;
1246   keystore_cryptographer.EncryptString("string", &keystore_encrypted);
1247   EXPECT_TRUE(GetCryptographer()->CanDecrypt(keystore_encrypted));
1248 }
1249
1250 // Test that we handle receiving migrated nigori's with
1251 // CUSTOM_PASSPHRASE state. We should be in a pending key state until we
1252 // provide the custom passphrase key.
1253 TEST_F(SyncEncryptionHandlerImplTest, ReceiveMigratedNigoriCustomPass) {
1254   const char kCurKey[] = "cur";
1255   sync_pb::EncryptedData encrypted;
1256   Cryptographer other_cryptographer(GetCryptographer()->encryptor());
1257   KeyParams cur_key = {"localhost", "dummy", kCurKey};
1258   other_cryptographer.AddKey(cur_key);
1259   EXPECT_FALSE(encryption_handler()->MigratedToKeystore());
1260
1261   {
1262     EXPECT_CALL(*observer(),
1263                 OnBootstrapTokenUpdated(_, KEYSTORE_BOOTSTRAP_TOKEN));
1264     ReadTransaction trans(FROM_HERE, user_share());
1265     encryption_handler()->SetKeystoreKeys(BuildEncryptionKeyProto(
1266                                               kRawKeystoreKey),
1267                                           trans.GetWrappedTrans());
1268   }
1269   EXPECT_FALSE(encryption_handler()->MigratedToKeystore());
1270
1271   {
1272     EXPECT_CALL(*observer(),
1273                 OnPassphraseTypeChanged(CUSTOM_PASSPHRASE, _));
1274     EXPECT_CALL(*observer(),
1275                 OnPassphraseRequired(_, _));
1276     EXPECT_CALL(*observer(),
1277                 OnCryptographerStateChanged(_)).Times(AnyNumber());
1278     EXPECT_CALL(*observer(),
1279                 OnEncryptedTypesChanged(_, true));
1280     WriteTransaction trans(FROM_HERE, user_share());
1281     WriteNode nigori_node(&trans);
1282     ASSERT_EQ(nigori_node.InitTypeRoot(NIGORI), BaseNode::INIT_OK);
1283     sync_pb::NigoriSpecifics nigori;
1284     nigori.set_keybag_is_frozen(true);
1285     nigori.set_passphrase_type(sync_pb::NigoriSpecifics::CUSTOM_PASSPHRASE);
1286     nigori.set_keystore_migration_time(1);
1287     nigori.set_encrypt_everything(true);
1288     other_cryptographer.GetKeys(nigori.mutable_encryption_keybag());
1289     encryption_handler()->ApplyNigoriUpdate(nigori, trans.GetWrappedTrans());
1290     nigori_node.SetNigoriSpecifics(nigori);
1291   }
1292   // Run any tasks posted via AppplyNigoriUpdate.
1293   PumpLoop();
1294   Mock::VerifyAndClearExpectations(observer());
1295
1296   EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
1297   EXPECT_EQ(CUSTOM_PASSPHRASE, encryption_handler()->GetPassphraseType());
1298   EXPECT_TRUE(GetCryptographer()->has_pending_keys());
1299   EXPECT_TRUE(encryption_handler()->EncryptEverythingEnabled());
1300
1301   EXPECT_CALL(*observer(),
1302               OnBootstrapTokenUpdated(_, PASSPHRASE_BOOTSTRAP_TOKEN));
1303   EXPECT_CALL(*observer(),
1304               OnCryptographerStateChanged(_)).Times(AnyNumber());
1305   EXPECT_CALL(*observer(),
1306               OnEncryptionComplete());
1307   EXPECT_CALL(*observer(),
1308               OnPassphraseAccepted());
1309   encryption_handler()->SetDecryptionPassphrase(kCurKey);
1310   EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
1311   EXPECT_TRUE(GetCryptographer()->is_ready());
1312   VerifyMigratedNigoriWithTimestamp(1, CUSTOM_PASSPHRASE, kCurKey);
1313
1314   // Check that the cryptographer still encrypts with the current key.
1315   sync_pb::EncryptedData current_encrypted;
1316   other_cryptographer.EncryptString("string", &current_encrypted);
1317   EXPECT_TRUE(GetCryptographer()->CanDecryptUsingDefaultKey(current_encrypted));
1318
1319   // Check that the cryptographer can decrypt keystore key based encryption.
1320   Cryptographer keystore_cryptographer(GetCryptographer()->encryptor());
1321   KeyParams keystore_key =  {"localhost", "dummy", kKeystoreKey};
1322   keystore_cryptographer.AddKey(keystore_key);
1323   sync_pb::EncryptedData keystore_encrypted;
1324   keystore_cryptographer.EncryptString("string", &keystore_encrypted);
1325   EXPECT_TRUE(GetCryptographer()->CanDecrypt(keystore_encrypted));
1326 }
1327
1328 // Test that if we have a migrated nigori with a custom passphrase, then receive
1329 // and old implicit passphrase nigori, we properly overwrite it with the current
1330 // state.
1331 TEST_F(SyncEncryptionHandlerImplTest, ReceiveUnmigratedNigoriAfterMigration) {
1332   const char kOldKey[] = "old";
1333   const char kCurKey[] = "cur";
1334   sync_pb::EncryptedData encrypted;
1335   KeyParams old_key = {"localhost", "dummy", kOldKey};
1336   KeyParams cur_key = {"localhost", "dummy", kCurKey};
1337   GetCryptographer()->AddKey(old_key);
1338   GetCryptographer()->AddKey(cur_key);
1339
1340   // Build a migrated nigori with full encryption.
1341   const int64 migration_time = 1;
1342   {
1343     WriteTransaction trans(FROM_HERE, user_share());
1344     WriteNode nigori_node(&trans);
1345     ASSERT_EQ(nigori_node.InitTypeRoot(NIGORI), BaseNode::INIT_OK);
1346     sync_pb::NigoriSpecifics nigori;
1347     GetCryptographer()->GetKeys(nigori.mutable_encryption_keybag());
1348     nigori.set_keybag_is_frozen(true);
1349     nigori.set_keystore_migration_time(1);
1350     nigori.set_passphrase_type(sync_pb::NigoriSpecifics::CUSTOM_PASSPHRASE);
1351     nigori.set_encrypt_everything(true);
1352     nigori_node.SetNigoriSpecifics(nigori);
1353   }
1354
1355   EXPECT_CALL(*observer(),
1356               OnPassphraseTypeChanged(CUSTOM_PASSPHRASE, _));
1357   EXPECT_CALL(*observer(),
1358               OnCryptographerStateChanged(_)).Times(AnyNumber());
1359   EXPECT_CALL(*observer(),
1360               OnEncryptedTypesChanged(_, true)).Times(2);
1361   EXPECT_CALL(*observer(),
1362               OnEncryptionComplete());
1363   encryption_handler()->Init();
1364   EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
1365   EXPECT_TRUE(GetCryptographer()->is_ready());
1366   EXPECT_EQ(encryption_handler()->GetPassphraseType(), CUSTOM_PASSPHRASE);
1367   EXPECT_TRUE(encryption_handler()->EncryptEverythingEnabled());
1368   VerifyMigratedNigoriWithTimestamp(migration_time, CUSTOM_PASSPHRASE, kCurKey);
1369
1370   {
1371     EXPECT_CALL(*observer(),
1372                 OnBootstrapTokenUpdated(_, KEYSTORE_BOOTSTRAP_TOKEN));
1373     ReadTransaction trans(FROM_HERE, user_share());
1374     encryption_handler()->SetKeystoreKeys(BuildEncryptionKeyProto(
1375                                               kRawKeystoreKey),
1376                                           trans.GetWrappedTrans());
1377   }
1378   Mock::VerifyAndClearExpectations(observer());
1379
1380   // Now build an old unmigrated nigori node with old encrypted types. We should
1381   // properly overwrite it with the migrated + encrypt everything state.
1382   EXPECT_CALL(*observer(),
1383               OnCryptographerStateChanged(_)).Times(AnyNumber());
1384   SyncEncryptionHandler::NigoriState captured_nigori_state;
1385   EXPECT_CALL(*observer(), OnLocalSetPassphraseEncryption(_))
1386       .WillOnce(testing::SaveArg<0>(&captured_nigori_state));
1387   EXPECT_CALL(*observer(), OnEncryptionComplete());
1388   {
1389     Cryptographer other_cryptographer(GetCryptographer()->encryptor());
1390     other_cryptographer.AddKey(old_key);
1391     WriteTransaction trans(FROM_HERE, user_share());
1392     WriteNode nigori_node(&trans);
1393     ASSERT_EQ(nigori_node.InitTypeRoot(NIGORI), BaseNode::INIT_OK);
1394     sync_pb::NigoriSpecifics nigori;
1395     other_cryptographer.GetKeys(nigori.mutable_encryption_keybag());
1396     nigori.set_keybag_is_frozen(false);
1397     nigori.set_encrypt_everything(false);
1398     encryption_handler()->ApplyNigoriUpdate(nigori, trans.GetWrappedTrans());
1399     nigori_node.SetNigoriSpecifics(nigori);
1400   }
1401   PumpLoop();
1402
1403   // Verify we're still migrated and have proper encryption state.
1404   EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
1405   EXPECT_TRUE(GetCryptographer()->is_ready());
1406   EXPECT_EQ(encryption_handler()->GetPassphraseType(), CUSTOM_PASSPHRASE);
1407   EXPECT_TRUE(encryption_handler()->EncryptEverythingEnabled());
1408   VerifyMigratedNigoriWithTimestamp(1, CUSTOM_PASSPHRASE, kCurKey);
1409
1410   // We need the passphrase bootstrap token, but OnBootstrapTokenUpdated(_,
1411   // PASSPHRASE_BOOTSTRAP_TOKEN) has not been invoked (because it was invoked
1412   // during a previous instance) so get it from the Cryptographer.
1413   std::string passphrase_bootstrap_token;
1414   GetCryptographer()->GetBootstrapToken(&passphrase_bootstrap_token);
1415   VerifyRestoreAfterCustomPassphrase(migration_time, kCurKey,
1416                                      passphrase_bootstrap_token,
1417                                      captured_nigori_state, CUSTOM_PASSPHRASE);
1418 }
1419
1420 // Test that if we have a migrated nigori with a custom passphrase, then receive
1421 // a migrated nigori with a keystore passphrase, we properly overwrite it with
1422 // the current state.
1423 TEST_F(SyncEncryptionHandlerImplTest, ReceiveOldMigratedNigori) {
1424   const char kOldKey[] = "old";
1425   const char kCurKey[] = "cur";
1426   sync_pb::EncryptedData encrypted;
1427   KeyParams old_key = {"localhost", "dummy", kOldKey};
1428   KeyParams cur_key = {"localhost", "dummy", kCurKey};
1429   GetCryptographer()->AddKey(old_key);
1430   GetCryptographer()->AddKey(cur_key);
1431
1432   // Build a migrated nigori with full encryption.
1433   {
1434     WriteTransaction trans(FROM_HERE, user_share());
1435     WriteNode nigori_node(&trans);
1436     ASSERT_EQ(nigori_node.InitTypeRoot(NIGORI), BaseNode::INIT_OK);
1437     sync_pb::NigoriSpecifics nigori;
1438     GetCryptographer()->GetKeys(nigori.mutable_encryption_keybag());
1439     nigori.set_keybag_is_frozen(true);
1440     nigori.set_keystore_migration_time(1);
1441     nigori.set_passphrase_type(sync_pb::NigoriSpecifics::CUSTOM_PASSPHRASE);
1442     nigori.set_encrypt_everything(true);
1443     nigori_node.SetNigoriSpecifics(nigori);
1444   }
1445
1446   EXPECT_CALL(*observer(),
1447               OnPassphraseTypeChanged(CUSTOM_PASSPHRASE, _));
1448   EXPECT_CALL(*observer(),
1449               OnCryptographerStateChanged(_)).Times(AnyNumber());
1450   EXPECT_CALL(*observer(),
1451               OnEncryptedTypesChanged(_, true)).Times(2);
1452   EXPECT_CALL(*observer(),
1453               OnEncryptionComplete());
1454   encryption_handler()->Init();
1455   EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
1456   EXPECT_TRUE(GetCryptographer()->is_ready());
1457   EXPECT_EQ(encryption_handler()->GetPassphraseType(), CUSTOM_PASSPHRASE);
1458   EXPECT_TRUE(encryption_handler()->EncryptEverythingEnabled());
1459   VerifyMigratedNigoriWithTimestamp(1, CUSTOM_PASSPHRASE, kCurKey);
1460
1461   {
1462     EXPECT_CALL(*observer(),
1463                 OnBootstrapTokenUpdated(_, KEYSTORE_BOOTSTRAP_TOKEN));
1464     ReadTransaction trans(FROM_HERE, user_share());
1465     encryption_handler()->SetKeystoreKeys(BuildEncryptionKeyProto(
1466                                               kRawKeystoreKey),
1467                                           trans.GetWrappedTrans());
1468   }
1469   Mock::VerifyAndClearExpectations(observer());
1470
1471   // Now build an old keystore nigori node with old encrypted types. We should
1472   // properly overwrite it with the migrated + encrypt everything state.
1473   EXPECT_CALL(*observer(),
1474               OnCryptographerStateChanged(_)).Times(AnyNumber());
1475   SyncEncryptionHandler::NigoriState captured_nigori_state;
1476   EXPECT_CALL(*observer(), OnLocalSetPassphraseEncryption(_))
1477       .WillOnce(testing::SaveArg<0>(&captured_nigori_state));
1478   EXPECT_CALL(*observer(), OnEncryptionComplete());
1479   const int64 migration_time = 1;
1480   {
1481     WriteTransaction trans(FROM_HERE, user_share());
1482     WriteNode nigori_node(&trans);
1483     ASSERT_EQ(nigori_node.InitTypeRoot(NIGORI), BaseNode::INIT_OK);
1484     sync_pb::NigoriSpecifics nigori;
1485     Cryptographer other_cryptographer(GetCryptographer()->encryptor());
1486     other_cryptographer.AddKey(old_key);
1487     encryption_handler()->GetKeystoreDecryptor(
1488         other_cryptographer,
1489         kKeystoreKey,
1490         nigori.mutable_keystore_decryptor_token());
1491     other_cryptographer.GetKeys(nigori.mutable_encryption_keybag());
1492     nigori.set_keybag_is_frozen(true);
1493     nigori.set_encrypt_everything(false);
1494     nigori.set_passphrase_type(sync_pb::NigoriSpecifics::KEYSTORE_PASSPHRASE);
1495     nigori.set_keystore_migration_time(migration_time);
1496     encryption_handler()->ApplyNigoriUpdate(nigori, trans.GetWrappedTrans());
1497     nigori_node.SetNigoriSpecifics(nigori);
1498   }
1499   PumpLoop();
1500
1501   // Verify we're still migrated and have proper encryption state.
1502   EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
1503   EXPECT_TRUE(GetCryptographer()->is_ready());
1504   EXPECT_EQ(encryption_handler()->GetPassphraseType(), CUSTOM_PASSPHRASE);
1505   EXPECT_TRUE(encryption_handler()->EncryptEverythingEnabled());
1506   VerifyMigratedNigoriWithTimestamp(migration_time, CUSTOM_PASSPHRASE, kCurKey);
1507
1508   // We need the passphrase bootstrap token, but OnBootstrapTokenUpdated(_,
1509   // PASSPHRASE_BOOTSTRAP_TOKEN) has not been invoked (because it was invoked
1510   // during a previous instance) so get it from the Cryptographer.
1511   std::string passphrase_bootstrap_token;
1512   GetCryptographer()->GetBootstrapToken(&passphrase_bootstrap_token);
1513   VerifyRestoreAfterCustomPassphrase(migration_time, kCurKey,
1514                                      passphrase_bootstrap_token,
1515                                      captured_nigori_state, CUSTOM_PASSPHRASE);
1516 }
1517
1518 // Test that if we receive the keystore key after receiving a migrated nigori
1519 // node, we properly use the keystore decryptor token to decrypt the keybag.
1520 TEST_F(SyncEncryptionHandlerImplTest, SetKeystoreAfterReceivingMigratedNigori) {
1521   const char kCurKey[] = "cur";
1522   sync_pb::EncryptedData keystore_decryptor_token;
1523   Cryptographer other_cryptographer(GetCryptographer()->encryptor());
1524   KeyParams cur_key = {"localhost", "dummy", kCurKey};
1525   other_cryptographer.AddKey(cur_key);
1526   EXPECT_TRUE(other_cryptographer.is_ready());
1527   EXPECT_TRUE(encryption_handler()->GetKeystoreDecryptor(
1528       other_cryptographer,
1529       kKeystoreKey,
1530       &keystore_decryptor_token));
1531   EXPECT_FALSE(encryption_handler()->MigratedToKeystore());
1532   EXPECT_FALSE(GetCryptographer()->is_ready());
1533   EXPECT_NE(encryption_handler()->GetPassphraseType(), KEYSTORE_PASSPHRASE);
1534
1535   // Now build a nigori node with the generated keystore decryptor token and
1536   // initialize the encryption handler with it. The cryptographer should be
1537   // initialized properly to decrypt both kCurKey and kKeystoreKey.
1538   {
1539     WriteTransaction trans(FROM_HERE, user_share());
1540     WriteNode nigori_node(&trans);
1541     ASSERT_EQ(nigori_node.InitTypeRoot(NIGORI), BaseNode::INIT_OK);
1542     sync_pb::NigoriSpecifics nigori;
1543     nigori.mutable_keystore_decryptor_token()->CopyFrom(
1544         keystore_decryptor_token);
1545     other_cryptographer.GetKeys(nigori.mutable_encryption_keybag());
1546     nigori.set_keybag_is_frozen(true);
1547     nigori.set_keystore_migration_time(1);
1548     nigori.set_passphrase_type(sync_pb::NigoriSpecifics::KEYSTORE_PASSPHRASE);
1549
1550     EXPECT_CALL(*observer(),
1551                 OnPassphraseTypeChanged(KEYSTORE_PASSPHRASE, _));
1552     EXPECT_CALL(*observer(),
1553                 OnCryptographerStateChanged(_)).Times(AnyNumber());
1554     EXPECT_CALL(*observer(),
1555                 OnPassphraseRequired(_, _));
1556     encryption_handler()->ApplyNigoriUpdate(nigori, trans.GetWrappedTrans());
1557     nigori_node.SetNigoriSpecifics(nigori);
1558   }
1559   // Run any tasks posted via AppplyNigoriUpdate.
1560   PumpLoop();
1561   EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
1562   EXPECT_TRUE(GetCryptographer()->has_pending_keys());
1563   EXPECT_EQ(encryption_handler()->GetPassphraseType(), KEYSTORE_PASSPHRASE);
1564   EXPECT_FALSE(encryption_handler()->EncryptEverythingEnabled());
1565   Mock::VerifyAndClearExpectations(observer());
1566
1567   EXPECT_CALL(*observer(), OnPassphraseAccepted());
1568   EXPECT_CALL(*observer(),
1569               OnCryptographerStateChanged(_)).Times(AnyNumber());
1570   EXPECT_CALL(*observer(),
1571               OnBootstrapTokenUpdated(_, PASSPHRASE_BOOTSTRAP_TOKEN));
1572   {
1573     EXPECT_CALL(*observer(),
1574                 OnBootstrapTokenUpdated(_, KEYSTORE_BOOTSTRAP_TOKEN));
1575     ReadTransaction trans(FROM_HERE, user_share());
1576     encryption_handler()->SetKeystoreKeys(BuildEncryptionKeyProto(
1577                                               kRawKeystoreKey),
1578                                           trans.GetWrappedTrans());
1579   }
1580   PumpLoop();
1581   EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
1582   EXPECT_TRUE(GetCryptographer()->is_ready());
1583   EXPECT_EQ(encryption_handler()->GetPassphraseType(), KEYSTORE_PASSPHRASE);
1584   EXPECT_FALSE(encryption_handler()->EncryptEverythingEnabled());
1585   VerifyMigratedNigoriWithTimestamp(1, KEYSTORE_PASSPHRASE, kCurKey);
1586
1587   // Check that the cryptographer still encrypts with the current key.
1588   sync_pb::EncryptedData current_encrypted;
1589   other_cryptographer.EncryptString("string", &current_encrypted);
1590   EXPECT_TRUE(GetCryptographer()->CanDecryptUsingDefaultKey(current_encrypted));
1591
1592   // Check that the cryptographer can decrypt keystore key based encryption.
1593   Cryptographer keystore_cryptographer(GetCryptographer()->encryptor());
1594   KeyParams keystore_key =  {"localhost", "dummy", kKeystoreKey};
1595   keystore_cryptographer.AddKey(keystore_key);
1596   sync_pb::EncryptedData keystore_encrypted;
1597   keystore_cryptographer.EncryptString("string", &keystore_encrypted);
1598   EXPECT_TRUE(GetCryptographer()->CanDecrypt(keystore_encrypted));
1599 }
1600
1601 // Test that after receiving a migrated nigori and decrypting it using the
1602 // keystore key, we can then switch to a custom passphrase. The nigori should
1603 // remain migrated and encrypt everything should be enabled.
1604 TEST_F(SyncEncryptionHandlerImplTest, SetCustomPassAfterMigration) {
1605   const char kOldKey[] = "old";
1606   sync_pb::EncryptedData keystore_decryptor_token;
1607   Cryptographer other_cryptographer(GetCryptographer()->encryptor());
1608   KeyParams cur_key = {"localhost", "dummy", kOldKey};
1609   other_cryptographer.AddKey(cur_key);
1610   EXPECT_TRUE(other_cryptographer.is_ready());
1611   EXPECT_TRUE(encryption_handler()->GetKeystoreDecryptor(
1612       other_cryptographer,
1613       kKeystoreKey,
1614       &keystore_decryptor_token));
1615
1616   // Build a nigori node with the generated keystore decryptor token and
1617   // initialize the encryption handler with it. The cryptographer should be
1618   // initialized properly to decrypt both kOldKey and kKeystoreKey.
1619   const int64 migration_time = 1;
1620   {
1621     WriteTransaction trans(FROM_HERE, user_share());
1622     WriteNode nigori_node(&trans);
1623     ASSERT_EQ(nigori_node.InitTypeRoot(NIGORI), BaseNode::INIT_OK);
1624     sync_pb::NigoriSpecifics nigori;
1625     nigori.mutable_keystore_decryptor_token()->CopyFrom(
1626         keystore_decryptor_token);
1627     other_cryptographer.GetKeys(nigori.mutable_encryption_keybag());
1628     nigori.set_keybag_is_frozen(true);
1629     nigori.set_keystore_migration_time(migration_time);
1630     nigori.set_passphrase_type(sync_pb::NigoriSpecifics::KEYSTORE_PASSPHRASE);
1631     nigori_node.SetNigoriSpecifics(nigori);
1632     EXPECT_CALL(*observer(),
1633                 OnBootstrapTokenUpdated(_, KEYSTORE_BOOTSTRAP_TOKEN));
1634     encryption_handler()->SetKeystoreKeys(BuildEncryptionKeyProto(
1635                                               kRawKeystoreKey),
1636                                           trans.GetWrappedTrans());
1637   }
1638
1639   EXPECT_CALL(*observer(), OnPassphraseAccepted());
1640   EXPECT_CALL(*observer(),
1641               OnPassphraseTypeChanged(KEYSTORE_PASSPHRASE, _));
1642   EXPECT_CALL(*observer(),
1643               OnCryptographerStateChanged(_)).Times(AnyNumber());
1644   EXPECT_CALL(*observer(),
1645               OnEncryptedTypesChanged(_, false));
1646   EXPECT_CALL(*observer(),
1647               OnBootstrapTokenUpdated(_, PASSPHRASE_BOOTSTRAP_TOKEN));
1648   EXPECT_CALL(*observer(),
1649               OnEncryptionComplete());
1650   encryption_handler()->Init();
1651   EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
1652   EXPECT_TRUE(GetCryptographer()->is_ready());
1653   EXPECT_EQ(encryption_handler()->GetPassphraseType(), KEYSTORE_PASSPHRASE);
1654   EXPECT_FALSE(encryption_handler()->EncryptEverythingEnabled());
1655   Mock::VerifyAndClearExpectations(observer());
1656
1657   const char kNewKey[] = "new_key";
1658   EXPECT_CALL(*observer(),
1659               OnCryptographerStateChanged(_)).Times(AnyNumber());
1660   EXPECT_CALL(*observer(),
1661               OnPassphraseTypeChanged(CUSTOM_PASSPHRASE, _));
1662   SyncEncryptionHandler::NigoriState captured_nigori_state;
1663   EXPECT_CALL(*observer(), OnLocalSetPassphraseEncryption(_))
1664       .WillOnce(testing::SaveArg<0>(&captured_nigori_state));
1665   std::string captured_bootstrap_token;
1666   EXPECT_CALL(*observer(),
1667               OnBootstrapTokenUpdated(_, PASSPHRASE_BOOTSTRAP_TOKEN))
1668       .WillOnce(testing::SaveArg<0>(&captured_bootstrap_token));
1669   EXPECT_CALL(*observer(),
1670               OnPassphraseAccepted());
1671   EXPECT_CALL(*observer(),
1672               OnEncryptedTypesChanged(_, true));
1673   EXPECT_CALL(*observer(),
1674               OnEncryptionComplete()).Times(2);
1675   encryption_handler()->SetEncryptionPassphrase(kNewKey, true);
1676   Mock::VerifyAndClearExpectations(observer());
1677
1678   EXPECT_FALSE(captured_bootstrap_token.empty());
1679   EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
1680   EXPECT_TRUE(GetCryptographer()->is_ready());
1681   EXPECT_EQ(encryption_handler()->GetPassphraseType(), CUSTOM_PASSPHRASE);
1682   EXPECT_TRUE(encryption_handler()->EncryptEverythingEnabled());
1683   EXPECT_FALSE(encryption_handler()->custom_passphrase_time().is_null());
1684   VerifyMigratedNigoriWithTimestamp(migration_time, CUSTOM_PASSPHRASE, kNewKey);
1685
1686   // Check that the cryptographer can decrypt the old key.
1687   sync_pb::EncryptedData old_encrypted;
1688   other_cryptographer.EncryptString("string", &old_encrypted);
1689   EXPECT_TRUE(GetCryptographer()->CanDecrypt(old_encrypted));
1690
1691   // Check that the cryptographer can decrypt keystore key based encryption.
1692   Cryptographer keystore_cryptographer(GetCryptographer()->encryptor());
1693   KeyParams keystore_key =  {"localhost", "dummy", kKeystoreKey};
1694   keystore_cryptographer.AddKey(keystore_key);
1695   sync_pb::EncryptedData keystore_encrypted;
1696   keystore_cryptographer.EncryptString("string", &keystore_encrypted);
1697   EXPECT_TRUE(GetCryptographer()->CanDecrypt(keystore_encrypted));
1698
1699   // Check the the cryptographer is encrypting with the new key.
1700   KeyParams new_key = {"localhost", "dummy", kNewKey};
1701   Cryptographer new_cryptographer(GetCryptographer()->encryptor());
1702   new_cryptographer.AddKey(new_key);
1703   sync_pb::EncryptedData new_encrypted;
1704   new_cryptographer.EncryptString("string", &new_encrypted);
1705   EXPECT_TRUE(GetCryptographer()->CanDecryptUsingDefaultKey(new_encrypted));
1706
1707   // Now verify that we can restore the current state using the captured
1708   // bootstrap token and nigori state.
1709   VerifyRestoreAfterCustomPassphrase(migration_time, kNewKey,
1710                                      captured_bootstrap_token,
1711                                      captured_nigori_state, CUSTOM_PASSPHRASE);
1712 }
1713
1714 // Test that if a client without a keystore key (e.g. one without keystore
1715 // encryption enabled) receives a migrated nigori and then attempts to set a
1716 // custom passphrase, it also enables encrypt everything. The nigori node
1717 // should remain migrated.
1718 TEST_F(SyncEncryptionHandlerImplTest,
1719        SetCustomPassAfterMigrationNoKeystoreKey) {
1720   const char kOldKey[] = "old";
1721   sync_pb::EncryptedData keystore_decryptor_token;
1722   Cryptographer other_cryptographer(GetCryptographer()->encryptor());
1723   KeyParams cur_key = {"localhost", "dummy", kOldKey};
1724   other_cryptographer.AddKey(cur_key);
1725   KeyParams keystore_key = {"localhost", "dummy", kKeystoreKey};
1726   other_cryptographer.AddNonDefaultKey(keystore_key);
1727   EXPECT_TRUE(other_cryptographer.is_ready());
1728   EXPECT_TRUE(encryption_handler()->GetKeystoreDecryptor(
1729       other_cryptographer,
1730       kKeystoreKey,
1731       &keystore_decryptor_token));
1732
1733   // Build a nigori node with the generated keystore decryptor token and
1734   // initialize the encryption handler with it. The cryptographer will have
1735   // pending keys until we provide the decryption passphrase.
1736   const int64 migration_time = 1;
1737   {
1738     WriteTransaction trans(FROM_HERE, user_share());
1739     WriteNode nigori_node(&trans);
1740     ASSERT_EQ(nigori_node.InitTypeRoot(NIGORI), BaseNode::INIT_OK);
1741     sync_pb::NigoriSpecifics nigori;
1742     nigori.mutable_keystore_decryptor_token()->CopyFrom(
1743         keystore_decryptor_token);
1744     other_cryptographer.GetKeys(nigori.mutable_encryption_keybag());
1745     nigori.set_keybag_is_frozen(true);
1746     nigori.set_keystore_migration_time(migration_time);
1747     nigori.set_passphrase_type(sync_pb::NigoriSpecifics::KEYSTORE_PASSPHRASE);
1748     nigori_node.SetNigoriSpecifics(nigori);
1749   }
1750
1751   EXPECT_CALL(*observer(),
1752               OnPassphraseRequired(_, _));
1753   EXPECT_CALL(*observer(),
1754               OnPassphraseTypeChanged(KEYSTORE_PASSPHRASE, _));
1755   EXPECT_CALL(*observer(),
1756               OnCryptographerStateChanged(_)).Times(AnyNumber());
1757   EXPECT_CALL(*observer(),
1758               OnEncryptedTypesChanged(_, false));
1759   encryption_handler()->Init();
1760   EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
1761   EXPECT_TRUE(GetCryptographer()->has_pending_keys());
1762   EXPECT_EQ(encryption_handler()->GetPassphraseType(), KEYSTORE_PASSPHRASE);
1763   EXPECT_FALSE(encryption_handler()->EncryptEverythingEnabled());
1764   Mock::VerifyAndClearExpectations(observer());
1765
1766   EXPECT_CALL(*observer(),
1767               OnPassphraseAccepted());
1768   EXPECT_CALL(*observer(),
1769               OnCryptographerStateChanged(_)).Times(AnyNumber());
1770   EXPECT_CALL(*observer(),
1771               OnBootstrapTokenUpdated(_, PASSPHRASE_BOOTSTRAP_TOKEN));
1772   EXPECT_CALL(*observer(),
1773               OnEncryptionComplete());
1774   encryption_handler()->SetDecryptionPassphrase(kOldKey);
1775   EXPECT_TRUE(GetCryptographer()->is_ready());
1776   EXPECT_FALSE(encryption_handler()->EncryptEverythingEnabled());
1777   Mock::VerifyAndClearExpectations(observer());
1778
1779   const char kNewKey[] = "new_key";
1780   EXPECT_CALL(*observer(),
1781               OnCryptographerStateChanged(_)).Times(AnyNumber());
1782   EXPECT_CALL(*observer(),
1783               OnPassphraseTypeChanged(CUSTOM_PASSPHRASE, _));
1784   SyncEncryptionHandler::NigoriState captured_nigori_state;
1785   EXPECT_CALL(*observer(), OnLocalSetPassphraseEncryption(_))
1786       .WillOnce(testing::SaveArg<0>(&captured_nigori_state));
1787   std::string captured_bootstrap_token;
1788   EXPECT_CALL(*observer(),
1789               OnBootstrapTokenUpdated(_, PASSPHRASE_BOOTSTRAP_TOKEN))
1790       .WillOnce(testing::SaveArg<0>(&captured_bootstrap_token));
1791   EXPECT_CALL(*observer(),
1792               OnPassphraseAccepted());
1793   EXPECT_CALL(*observer(),
1794               OnEncryptedTypesChanged(_, true));
1795   EXPECT_CALL(*observer(),
1796               OnEncryptionComplete()).Times(2);
1797   encryption_handler()->SetEncryptionPassphrase(kNewKey, true);
1798   EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
1799   EXPECT_TRUE(GetCryptographer()->is_ready());
1800   EXPECT_EQ(encryption_handler()->GetPassphraseType(), CUSTOM_PASSPHRASE);
1801   EXPECT_TRUE(encryption_handler()->EncryptEverythingEnabled());
1802   EXPECT_FALSE(encryption_handler()->custom_passphrase_time().is_null());
1803   VerifyMigratedNigoriWithTimestamp(migration_time, CUSTOM_PASSPHRASE, kNewKey);
1804
1805   // Check that the cryptographer can decrypt the old key.
1806   sync_pb::EncryptedData old_encrypted;
1807   other_cryptographer.EncryptString("string", &old_encrypted);
1808   EXPECT_TRUE(GetCryptographer()->CanDecrypt(old_encrypted));
1809
1810   // Check that the cryptographer can still decrypt keystore key based
1811   // encryption (should have been extracted from the encryption keybag).
1812   Cryptographer keystore_cryptographer(GetCryptographer()->encryptor());
1813   keystore_cryptographer.AddKey(keystore_key);
1814   sync_pb::EncryptedData keystore_encrypted;
1815   keystore_cryptographer.EncryptString("string", &keystore_encrypted);
1816   EXPECT_TRUE(GetCryptographer()->CanDecrypt(keystore_encrypted));
1817
1818   // Check the the cryptographer is encrypting with the new key.
1819   KeyParams new_key = {"localhost", "dummy", kNewKey};
1820   Cryptographer new_cryptographer(GetCryptographer()->encryptor());
1821   new_cryptographer.AddKey(new_key);
1822   sync_pb::EncryptedData new_encrypted;
1823   new_cryptographer.EncryptString("string", &new_encrypted);
1824   EXPECT_TRUE(GetCryptographer()->CanDecryptUsingDefaultKey(new_encrypted));
1825
1826   // Now verify that we can restore the current state using the captured
1827   // bootstrap token and nigori state.
1828   VerifyRestoreAfterCustomPassphrase(migration_time, kNewKey,
1829                                      captured_bootstrap_token,
1830                                      captured_nigori_state, CUSTOM_PASSPHRASE);
1831 }
1832
1833 // Test that if a client without a keystore key (e.g. one without keystore
1834 // encryption enabled) receives a migrated nigori and then attempts to set a
1835 // new implicit passphrase, we do not modify the nigori node (the implicit
1836 // passphrase is dropped).
1837 TEST_F(SyncEncryptionHandlerImplTest,
1838        SetImplicitPassAfterMigrationNoKeystoreKey) {
1839   const char kOldKey[] = "old";
1840   sync_pb::EncryptedData keystore_decryptor_token;
1841   Cryptographer other_cryptographer(GetCryptographer()->encryptor());
1842   KeyParams cur_key = {"localhost", "dummy", kOldKey};
1843   other_cryptographer.AddKey(cur_key);
1844   KeyParams keystore_key = {"localhost", "dummy", kKeystoreKey};
1845   other_cryptographer.AddNonDefaultKey(keystore_key);
1846   EXPECT_TRUE(other_cryptographer.is_ready());
1847   EXPECT_TRUE(encryption_handler()->GetKeystoreDecryptor(
1848       other_cryptographer,
1849       kKeystoreKey,
1850       &keystore_decryptor_token));
1851
1852   // Build a nigori node with the generated keystore decryptor token and
1853   // initialize the encryption handler with it. The cryptographer will have
1854   // pending keys until we provide the decryption passphrase.
1855   {
1856     WriteTransaction trans(FROM_HERE, user_share());
1857     WriteNode nigori_node(&trans);
1858     ASSERT_EQ(nigori_node.InitTypeRoot(NIGORI), BaseNode::INIT_OK);
1859     sync_pb::NigoriSpecifics nigori;
1860     nigori.mutable_keystore_decryptor_token()->CopyFrom(
1861         keystore_decryptor_token);
1862     other_cryptographer.GetKeys(nigori.mutable_encryption_keybag());
1863     nigori.set_keybag_is_frozen(true);
1864     nigori.set_keystore_migration_time(1);
1865     nigori.set_passphrase_type(sync_pb::NigoriSpecifics::KEYSTORE_PASSPHRASE);
1866     nigori_node.SetNigoriSpecifics(nigori);
1867   }
1868
1869   EXPECT_CALL(*observer(),
1870               OnPassphraseRequired(_, _));
1871   EXPECT_CALL(*observer(),
1872               OnPassphraseTypeChanged(KEYSTORE_PASSPHRASE, _));
1873   EXPECT_CALL(*observer(),
1874               OnCryptographerStateChanged(_)).Times(AnyNumber());
1875   EXPECT_CALL(*observer(),
1876               OnEncryptedTypesChanged(_, false));
1877   encryption_handler()->Init();
1878   EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
1879   EXPECT_TRUE(GetCryptographer()->has_pending_keys());
1880   EXPECT_EQ(encryption_handler()->GetPassphraseType(), KEYSTORE_PASSPHRASE);
1881   EXPECT_FALSE(encryption_handler()->EncryptEverythingEnabled());
1882   Mock::VerifyAndClearExpectations(observer());
1883
1884   EXPECT_CALL(*observer(),
1885               OnPassphraseAccepted());
1886   EXPECT_CALL(*observer(),
1887               OnCryptographerStateChanged(_)).Times(AnyNumber());
1888   EXPECT_CALL(*observer(),
1889               OnBootstrapTokenUpdated(_, PASSPHRASE_BOOTSTRAP_TOKEN));
1890   EXPECT_CALL(*observer(),
1891               OnEncryptionComplete());
1892   encryption_handler()->SetDecryptionPassphrase(kOldKey);
1893   EXPECT_TRUE(GetCryptographer()->is_ready());
1894   EXPECT_FALSE(encryption_handler()->EncryptEverythingEnabled());
1895   Mock::VerifyAndClearExpectations(observer());
1896
1897   // Should get dropped on the floor silently.
1898   const char kNewKey[] = "new_key";
1899   encryption_handler()->SetEncryptionPassphrase(kNewKey, false);
1900   EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
1901   EXPECT_TRUE(GetCryptographer()->is_ready());
1902   EXPECT_EQ(encryption_handler()->GetPassphraseType(), KEYSTORE_PASSPHRASE);
1903   EXPECT_FALSE(encryption_handler()->EncryptEverythingEnabled());
1904   VerifyMigratedNigoriWithTimestamp(1, KEYSTORE_PASSPHRASE, kOldKey);
1905
1906   // Check that the cryptographer can decrypt the old key.
1907   sync_pb::EncryptedData old_encrypted;
1908   other_cryptographer.EncryptString("string", &old_encrypted);
1909   EXPECT_TRUE(GetCryptographer()->CanDecryptUsingDefaultKey(old_encrypted));
1910
1911   // Check that the cryptographer can still decrypt keystore key based
1912   // encryption (due to extracting the keystore key from the encryption keybag).
1913   Cryptographer keystore_cryptographer(GetCryptographer()->encryptor());
1914   keystore_cryptographer.AddKey(keystore_key);
1915   sync_pb::EncryptedData keystore_encrypted;
1916   keystore_cryptographer.EncryptString("string", &keystore_encrypted);
1917   EXPECT_TRUE(GetCryptographer()->CanDecrypt(keystore_encrypted));
1918
1919   // Check the the cryptographer does not have the new key.
1920   KeyParams new_key = {"localhost", "dummy", kNewKey};
1921   Cryptographer new_cryptographer(GetCryptographer()->encryptor());
1922   new_cryptographer.AddKey(new_key);
1923   sync_pb::EncryptedData new_encrypted;
1924   new_cryptographer.EncryptString("string", &new_encrypted);
1925   EXPECT_FALSE(GetCryptographer()->CanDecryptUsingDefaultKey(new_encrypted));
1926 }
1927
1928 // Test that if a client without a keystore key (e.g. one without keystore
1929 // encryption enabled) receives a migrated nigori in keystore passphrase state
1930 // and then attempts to enable encrypt everything, we switch to a custom
1931 // passphrase. The nigori should remain migrated.
1932 TEST_F(SyncEncryptionHandlerImplTest,
1933        MigrateOnEncryptEverythingKeystorePassphrase) {
1934   const char kCurKey[] = "cur";
1935   sync_pb::EncryptedData keystore_decryptor_token;
1936   Cryptographer other_cryptographer(GetCryptographer()->encryptor());
1937   KeyParams cur_key = {"localhost", "dummy", kCurKey};
1938   other_cryptographer.AddKey(cur_key);
1939   KeyParams keystore_key = {"localhost", "dummy", kKeystoreKey};
1940   other_cryptographer.AddNonDefaultKey(keystore_key);
1941   EXPECT_TRUE(other_cryptographer.is_ready());
1942   EXPECT_TRUE(encryption_handler()->GetKeystoreDecryptor(
1943       other_cryptographer,
1944       kKeystoreKey,
1945       &keystore_decryptor_token));
1946
1947   // Build a nigori node with the generated keystore decryptor token and
1948   // initialize the encryption handler with it. The cryptographer will have
1949   // pending keys until we provide the decryption passphrase.
1950   const int64 migration_time = 1;
1951   {
1952     WriteTransaction trans(FROM_HERE, user_share());
1953     WriteNode nigori_node(&trans);
1954     ASSERT_EQ(nigori_node.InitTypeRoot(NIGORI), BaseNode::INIT_OK);
1955     sync_pb::NigoriSpecifics nigori;
1956     nigori.mutable_keystore_decryptor_token()->CopyFrom(
1957         keystore_decryptor_token);
1958     other_cryptographer.GetKeys(nigori.mutable_encryption_keybag());
1959     nigori.set_keybag_is_frozen(true);
1960     nigori.set_keystore_migration_time(migration_time);
1961     nigori.set_passphrase_type(sync_pb::NigoriSpecifics::KEYSTORE_PASSPHRASE);
1962     nigori_node.SetNigoriSpecifics(nigori);
1963   }
1964   EXPECT_CALL(*observer(),
1965               OnPassphraseRequired(_, _));
1966   EXPECT_CALL(*observer(),
1967               OnPassphraseTypeChanged(KEYSTORE_PASSPHRASE, _));
1968   EXPECT_CALL(*observer(),
1969               OnCryptographerStateChanged(_)).Times(AnyNumber());
1970   EXPECT_CALL(*observer(),
1971               OnEncryptedTypesChanged(_, false));
1972   encryption_handler()->Init();
1973   EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
1974   EXPECT_TRUE(GetCryptographer()->has_pending_keys());
1975   EXPECT_EQ(encryption_handler()->GetPassphraseType(), KEYSTORE_PASSPHRASE);
1976   EXPECT_FALSE(encryption_handler()->EncryptEverythingEnabled());
1977   Mock::VerifyAndClearExpectations(observer());
1978
1979   EXPECT_CALL(*observer(),
1980               OnPassphraseAccepted());
1981   EXPECT_CALL(*observer(),
1982               OnCryptographerStateChanged(_)).Times(AnyNumber());
1983   std::string captured_bootstrap_token;
1984   EXPECT_CALL(*observer(),
1985               OnBootstrapTokenUpdated(_, PASSPHRASE_BOOTSTRAP_TOKEN))
1986       .WillOnce(testing::SaveArg<0>(&captured_bootstrap_token));
1987   EXPECT_CALL(*observer(),
1988               OnEncryptionComplete());
1989   encryption_handler()->SetDecryptionPassphrase(kCurKey);
1990   Mock::VerifyAndClearExpectations(observer());
1991
1992   EXPECT_CALL(*observer(),
1993               OnPassphraseTypeChanged(FROZEN_IMPLICIT_PASSPHRASE, _));
1994   EXPECT_CALL(*observer(),
1995               OnEncryptionComplete());
1996   EXPECT_CALL(*observer(),
1997               OnEncryptedTypesChanged(_, true));
1998   SyncEncryptionHandler::NigoriState captured_nigori_state;
1999   EXPECT_CALL(*observer(), OnLocalSetPassphraseEncryption(_))
2000       .WillOnce(testing::SaveArg<0>(&captured_nigori_state));
2001   EXPECT_CALL(*observer(),
2002                 OnCryptographerStateChanged(_)).Times(AnyNumber());
2003   encryption_handler()->EnableEncryptEverything();
2004   Mock::VerifyAndClearExpectations(observer());
2005
2006   EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
2007   EXPECT_TRUE(GetCryptographer()->is_ready());
2008   EXPECT_EQ(FROZEN_IMPLICIT_PASSPHRASE,
2009             encryption_handler()->GetPassphraseType());
2010   EXPECT_TRUE(encryption_handler()->EncryptEverythingEnabled());
2011   VerifyMigratedNigoriWithTimestamp(1, FROZEN_IMPLICIT_PASSPHRASE, kCurKey);
2012
2013   // Check that the cryptographer is encrypting using the frozen current key.
2014   sync_pb::EncryptedData current_encrypted;
2015   other_cryptographer.EncryptString("string", &current_encrypted);
2016   EXPECT_TRUE(GetCryptographer()->CanDecryptUsingDefaultKey(current_encrypted));
2017
2018   // Check that the cryptographer can still decrypt keystore key based
2019   // encryption (due to extracting the keystore key from the encryption keybag).
2020   Cryptographer keystore_cryptographer(GetCryptographer()->encryptor());
2021   keystore_cryptographer.AddKey(keystore_key);
2022   sync_pb::EncryptedData keystore_encrypted;
2023   keystore_cryptographer.EncryptString("string", &keystore_encrypted);
2024   EXPECT_TRUE(GetCryptographer()->CanDecrypt(keystore_encrypted));
2025
2026   VerifyRestoreAfterCustomPassphrase(
2027       migration_time, kCurKey, captured_bootstrap_token, captured_nigori_state,
2028       FROZEN_IMPLICIT_PASSPHRASE);
2029 }
2030
2031 // If we receive a nigori migrated and with a KEYSTORE_PASSPHRASE type, but
2032 // using an old default key (i.e. old GAIA password), we should overwrite the
2033 // nigori, updating the keybag and keystore decryptor.
2034 TEST_F(SyncEncryptionHandlerImplTest,
2035        ReceiveMigratedNigoriWithOldPassphrase) {
2036   const char kOldKey[] = "old";
2037   const char kCurKey[] = "cur";
2038   sync_pb::EncryptedData encrypted;
2039   KeyParams old_key = {"localhost", "dummy", kOldKey};
2040   KeyParams cur_key = {"localhost", "dummy", kCurKey};
2041   GetCryptographer()->AddKey(old_key);
2042   GetCryptographer()->AddKey(cur_key);
2043
2044   Cryptographer other_cryptographer(GetCryptographer()->encryptor());
2045   other_cryptographer.AddKey(old_key);
2046   EXPECT_TRUE(other_cryptographer.is_ready());
2047
2048   EXPECT_CALL(*observer(),
2049               OnCryptographerStateChanged(_)).Times(AnyNumber());
2050   EXPECT_CALL(*observer(),
2051               OnEncryptedTypesChanged(_, false));
2052   EXPECT_CALL(*observer(),
2053               OnEncryptionComplete());
2054   encryption_handler()->Init();
2055   EXPECT_TRUE(GetCryptographer()->is_ready());
2056   EXPECT_FALSE(encryption_handler()->EncryptEverythingEnabled());
2057
2058   {
2059     EXPECT_CALL(*observer(),
2060                 OnBootstrapTokenUpdated(_, KEYSTORE_BOOTSTRAP_TOKEN));
2061     ReadTransaction trans(FROM_HERE, user_share());
2062     encryption_handler()->SetKeystoreKeys(BuildEncryptionKeyProto(
2063                                               kRawKeystoreKey),
2064                                           trans.GetWrappedTrans());
2065   }
2066   EXPECT_CALL(*observer(),
2067               OnPassphraseTypeChanged(KEYSTORE_PASSPHRASE, _));
2068   PumpLoop();
2069   Mock::VerifyAndClearExpectations(observer());
2070   EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
2071   EXPECT_EQ(encryption_handler()->GetPassphraseType(), KEYSTORE_PASSPHRASE);
2072   VerifyMigratedNigori(KEYSTORE_PASSPHRASE, kCurKey);
2073
2074   // Now build an old keystore passphrase nigori node.
2075   EXPECT_CALL(*observer(),
2076               OnCryptographerStateChanged(_)).Times(AnyNumber());
2077   EXPECT_CALL(*observer(), OnEncryptionComplete());
2078   {
2079     WriteTransaction trans(FROM_HERE, user_share());
2080     WriteNode nigori_node(&trans);
2081     ASSERT_EQ(nigori_node.InitTypeRoot(NIGORI), BaseNode::INIT_OK);
2082     sync_pb::NigoriSpecifics nigori;
2083     Cryptographer other_cryptographer(GetCryptographer()->encryptor());
2084     other_cryptographer.AddKey(old_key);
2085     encryption_handler()->GetKeystoreDecryptor(
2086         other_cryptographer,
2087         kKeystoreKey,
2088         nigori.mutable_keystore_decryptor_token());
2089     other_cryptographer.GetKeys(nigori.mutable_encryption_keybag());
2090     nigori.set_keybag_is_frozen(true);
2091     nigori.set_encrypt_everything(false);
2092     nigori.set_passphrase_type(sync_pb::NigoriSpecifics::KEYSTORE_PASSPHRASE);
2093     nigori.set_keystore_migration_time(1);
2094     encryption_handler()->ApplyNigoriUpdate(nigori, trans.GetWrappedTrans());
2095     nigori_node.SetNigoriSpecifics(nigori);
2096   }
2097   PumpLoop();
2098
2099   // Verify we're still migrated and have proper encryption state.
2100   EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
2101   EXPECT_TRUE(GetCryptographer()->is_ready());
2102   EXPECT_EQ(encryption_handler()->GetPassphraseType(), KEYSTORE_PASSPHRASE);
2103   EXPECT_FALSE(encryption_handler()->EncryptEverythingEnabled());
2104   VerifyMigratedNigori(KEYSTORE_PASSPHRASE, kCurKey);
2105 }
2106
2107 // Trigger a key rotation upon receiving new keys if we already had a keystore
2108 // migrated nigori with the gaia key as the default (still in backwards
2109 // compatible mode).
2110 TEST_F(SyncEncryptionHandlerImplTest, RotateKeysGaiaDefault) {
2111   // Destroy the existing nigori node so we init without a nigori node.
2112   TearDown();
2113   test_user_share_.SetUp();
2114   SetUpEncryption();
2115
2116   const char kOldGaiaKey[] = "old_gaia_key";
2117   const char kRawOldKeystoreKey[] = "old_keystore_key";
2118   std::string old_keystore_key;
2119   base::Base64Encode(kRawOldKeystoreKey, &old_keystore_key);
2120   {
2121     ReadTransaction trans(FROM_HERE, user_share());
2122     EXPECT_CALL(*observer(),
2123                 OnBootstrapTokenUpdated(_, KEYSTORE_BOOTSTRAP_TOKEN));
2124       encryption_handler()->SetKeystoreKeys(BuildEncryptionKeyProto(
2125                                                 kRawOldKeystoreKey),
2126                                             trans.GetWrappedTrans());
2127   }
2128   PumpLoop();
2129   Mock::VerifyAndClearExpectations(observer());
2130
2131   // Then init the nigori node with a backwards compatible set of keys.
2132   CreateRootForType(NIGORI);
2133   EXPECT_CALL(*observer(), OnPassphraseAccepted());
2134   InitKeystoreMigratedNigori(1, kOldGaiaKey, old_keystore_key);
2135
2136   // Now set some new keystore keys.
2137   EXPECT_CALL(*observer(), OnCryptographerStateChanged(_)).Times(AnyNumber());
2138   EXPECT_CALL(*observer(), OnEncryptionComplete());
2139   {
2140     google::protobuf::RepeatedPtrField<google::protobuf::string> keys;
2141     keys.Add()->assign(kRawOldKeystoreKey);
2142     keys.Add()->assign(kRawKeystoreKey);
2143     EXPECT_CALL(*observer(),
2144                 OnBootstrapTokenUpdated(_, KEYSTORE_BOOTSTRAP_TOKEN));
2145     ReadTransaction trans(FROM_HERE, user_share());
2146     encryption_handler()->SetKeystoreKeys(keys,
2147                                           trans.GetWrappedTrans());
2148   }
2149   // Pump for any posted tasks.
2150   PumpLoop();
2151   Mock::VerifyAndClearExpectations(observer());
2152
2153   // Verify we're still migrated and have proper encryption state. We should
2154   // have rotated the keybag so that it's now encrypted with the newest keystore
2155   // key (instead of the old gaia key).
2156   EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
2157   EXPECT_TRUE(GetCryptographer()->is_ready());
2158   EXPECT_EQ(encryption_handler()->GetPassphraseType(), KEYSTORE_PASSPHRASE);
2159   EXPECT_FALSE(encryption_handler()->EncryptEverythingEnabled());
2160   VerifyMigratedNigori(KEYSTORE_PASSPHRASE, kKeystoreKey);
2161 }
2162
2163 // Trigger a key rotation upon receiving new keys if we already had a keystore
2164 // migrated nigori with the keystore key as the default.
2165 TEST_F(SyncEncryptionHandlerImplTest, RotateKeysKeystoreDefault) {
2166   // Destroy the existing nigori node so we init without a nigori node.
2167   TearDown();
2168   test_user_share_.SetUp();
2169   SetUpEncryption();
2170
2171   const char kRawOldKeystoreKey[] = "old_keystore_key";
2172   std::string old_keystore_key;
2173   base::Base64Encode(kRawOldKeystoreKey, &old_keystore_key);
2174   {
2175     ReadTransaction trans(FROM_HERE, user_share());
2176     EXPECT_CALL(*observer(),
2177                 OnBootstrapTokenUpdated(_, KEYSTORE_BOOTSTRAP_TOKEN));
2178       encryption_handler()->SetKeystoreKeys(BuildEncryptionKeyProto(
2179                                                 kRawOldKeystoreKey),
2180                                             trans.GetWrappedTrans());
2181   }
2182   PumpLoop();
2183   Mock::VerifyAndClearExpectations(observer());
2184
2185   // Then init the nigori node with a non-backwards compatible set of keys.
2186   CreateRootForType(NIGORI);
2187   EXPECT_CALL(*observer(), OnPassphraseAccepted());
2188   InitKeystoreMigratedNigori(1, old_keystore_key, old_keystore_key);
2189
2190   // Now set some new keystore keys.
2191   EXPECT_CALL(*observer(), OnCryptographerStateChanged(_)).Times(AnyNumber());
2192   EXPECT_CALL(*observer(), OnEncryptionComplete());
2193   {
2194     google::protobuf::RepeatedPtrField<google::protobuf::string> keys;
2195     keys.Add()->assign(kRawOldKeystoreKey);
2196     keys.Add()->assign(kRawKeystoreKey);
2197     EXPECT_CALL(*observer(),
2198                 OnBootstrapTokenUpdated(_, KEYSTORE_BOOTSTRAP_TOKEN));
2199     ReadTransaction trans(FROM_HERE, user_share());
2200     encryption_handler()->SetKeystoreKeys(keys,
2201                                           trans.GetWrappedTrans());
2202   }
2203   // Pump for any posted tasks.
2204   PumpLoop();
2205   Mock::VerifyAndClearExpectations(observer());
2206
2207   // Verify we're still migrated and have proper encryption state. We should
2208   // have rotated the keybag so that it's now encrypted with the newest keystore
2209   // key (instead of the old gaia key).
2210   EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
2211   EXPECT_TRUE(GetCryptographer()->is_ready());
2212   EXPECT_EQ(encryption_handler()->GetPassphraseType(), KEYSTORE_PASSPHRASE);
2213   EXPECT_FALSE(encryption_handler()->EncryptEverythingEnabled());
2214   VerifyMigratedNigori(KEYSTORE_PASSPHRASE, kKeystoreKey);
2215 }
2216
2217 // Trigger a key rotation upon when a pending gaia passphrase is resolved.
2218 TEST_F(SyncEncryptionHandlerImplTest, RotateKeysAfterPendingGaiaResolved) {
2219   const char kOldGaiaKey[] = "old_gaia_key";
2220   const char kRawOldKeystoreKey[] = "old_keystore_key";
2221
2222   EXPECT_CALL(*observer(), OnPassphraseRequired(_, _));
2223   InitUnmigratedNigori(kOldGaiaKey, IMPLICIT_PASSPHRASE);
2224
2225   {
2226     // Pass multiple keystore keys, signaling a rotation has happened.
2227     google::protobuf::RepeatedPtrField<google::protobuf::string> keys;
2228     keys.Add()->assign(kRawOldKeystoreKey);
2229     keys.Add()->assign(kRawKeystoreKey);
2230     ReadTransaction trans(FROM_HERE, user_share());
2231     EXPECT_CALL(*observer(),
2232                 OnBootstrapTokenUpdated(_, KEYSTORE_BOOTSTRAP_TOKEN));
2233     encryption_handler()->SetKeystoreKeys(keys,
2234                                           trans.GetWrappedTrans());
2235   }
2236   PumpLoop();
2237   Mock::VerifyAndClearExpectations(observer());
2238
2239   // Resolve the pending keys. This should trigger the key rotation.
2240   EXPECT_CALL(*observer(),
2241               OnCryptographerStateChanged(_)).Times(AnyNumber());
2242   EXPECT_CALL(*observer(),
2243               OnPassphraseAccepted());
2244   EXPECT_CALL(*observer(),
2245               OnPassphraseTypeChanged(KEYSTORE_PASSPHRASE, _));
2246   EXPECT_CALL(*observer(),
2247               OnBootstrapTokenUpdated(_, PASSPHRASE_BOOTSTRAP_TOKEN));
2248   EXPECT_CALL(*observer(),
2249               OnEncryptionComplete()).Times(AtLeast(1));
2250   EXPECT_FALSE(encryption_handler()->MigratedToKeystore());
2251   encryption_handler()->SetDecryptionPassphrase(kOldGaiaKey);
2252   EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
2253   EXPECT_EQ(KEYSTORE_PASSPHRASE, encryption_handler()->GetPassphraseType());
2254   VerifyMigratedNigori(KEYSTORE_PASSPHRASE, kKeystoreKey);
2255 }
2256
2257 // When signing in for the first time, make sure we can rotate keys if we
2258 // already have a keystore migrated nigori.
2259 TEST_F(SyncEncryptionHandlerImplTest, RotateKeysGaiaDefaultOnInit) {
2260   // Destroy the existing nigori node so we init without a nigori node.
2261   TearDown();
2262   test_user_share_.SetUp();
2263   SetUpEncryption();
2264
2265   const char kOldGaiaKey[] = "old_gaia_key";
2266   const char kRawOldKeystoreKey[] = "old_keystore_key";
2267   std::string old_keystore_key;
2268   base::Base64Encode(kRawOldKeystoreKey, &old_keystore_key);
2269
2270   // Set two keys, signaling that a rotation has been performed. No nigori
2271   // node is present yet, so we can't rotate.
2272   {
2273     google::protobuf::RepeatedPtrField<google::protobuf::string> keys;
2274     keys.Add()->assign(kRawOldKeystoreKey);
2275     keys.Add()->assign(kRawKeystoreKey);
2276     EXPECT_CALL(*observer(),
2277                 OnBootstrapTokenUpdated(_, KEYSTORE_BOOTSTRAP_TOKEN));
2278     ReadTransaction trans(FROM_HERE, user_share());
2279     encryption_handler()->SetKeystoreKeys(keys,
2280                                           trans.GetWrappedTrans());
2281   }
2282
2283   // Then init the nigori node with an old set of keys.
2284   CreateRootForType(NIGORI);
2285   EXPECT_CALL(*observer(), OnPassphraseAccepted());
2286   InitKeystoreMigratedNigori(1, kOldGaiaKey, old_keystore_key);
2287   PumpLoop();
2288   Mock::VerifyAndClearExpectations(observer());
2289
2290   // Verify we're still migrated and have proper encryption state. We should
2291   // have rotated the keybag so that it's now encrypted with the newest keystore
2292   // key (instead of the old gaia key).
2293   EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
2294   EXPECT_TRUE(GetCryptographer()->is_ready());
2295   EXPECT_EQ(encryption_handler()->GetPassphraseType(), KEYSTORE_PASSPHRASE);
2296   EXPECT_FALSE(encryption_handler()->EncryptEverythingEnabled());
2297   VerifyMigratedNigori(KEYSTORE_PASSPHRASE, kKeystoreKey);
2298 }
2299
2300 // Trigger a key rotation when a migrated nigori (with an old keystore key) is
2301 // applied.
2302 TEST_F(SyncEncryptionHandlerImplTest, RotateKeysWhenMigratedNigoriArrives) {
2303   const char kOldGaiaKey[] = "old_gaia_key";
2304   const char kRawOldKeystoreKey[] = "old_keystore_key";
2305   std::string old_keystore_key;
2306   base::Base64Encode(kRawOldKeystoreKey, &old_keystore_key);
2307
2308   EXPECT_CALL(*observer(), OnPassphraseRequired(_, _));
2309   InitUnmigratedNigori(kOldGaiaKey, IMPLICIT_PASSPHRASE);
2310
2311   {
2312     // Pass multiple keystore keys, signaling a rotation has happened.
2313     google::protobuf::RepeatedPtrField<google::protobuf::string> keys;
2314     keys.Add()->assign(kRawOldKeystoreKey);
2315     keys.Add()->assign(kRawKeystoreKey);
2316     ReadTransaction trans(FROM_HERE, user_share());
2317     EXPECT_CALL(*observer(),
2318                 OnBootstrapTokenUpdated(_, KEYSTORE_BOOTSTRAP_TOKEN));
2319     encryption_handler()->SetKeystoreKeys(keys,
2320                                           trans.GetWrappedTrans());
2321   }
2322   PumpLoop();
2323   Mock::VerifyAndClearExpectations(observer());
2324
2325   // Now simulate downloading a nigori node that was migrated before the
2326   // keys were rotated, and hence still encrypt with the old gaia key.
2327   EXPECT_CALL(*observer(),
2328               OnCryptographerStateChanged(_)).Times(AnyNumber());
2329   EXPECT_CALL(*observer(),
2330               OnPassphraseAccepted());
2331   EXPECT_CALL(*observer(),
2332               OnPassphraseTypeChanged(KEYSTORE_PASSPHRASE, _));
2333   EXPECT_CALL(*observer(),
2334               OnBootstrapTokenUpdated(_, PASSPHRASE_BOOTSTRAP_TOKEN));
2335   EXPECT_CALL(*observer(),
2336               OnEncryptionComplete()).Times(AtLeast(1));
2337   {
2338     sync_pb::NigoriSpecifics nigori = BuildMigratedNigori(
2339         KEYSTORE_PASSPHRASE,
2340         1,
2341         kOldGaiaKey,
2342         old_keystore_key);
2343     // Update the encryption handler.
2344     WriteTransaction trans(FROM_HERE, user_share());
2345     encryption_handler()->ApplyNigoriUpdate(
2346         nigori,
2347         trans.GetWrappedTrans());
2348   }
2349   EXPECT_FALSE(encryption_handler()->MigratedToKeystore());
2350   PumpLoop();
2351
2352   EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
2353   EXPECT_EQ(KEYSTORE_PASSPHRASE, encryption_handler()->GetPassphraseType());
2354   VerifyMigratedNigori(KEYSTORE_PASSPHRASE, kKeystoreKey);
2355 }
2356
2357 // Verify that performing a migration while having more than one keystore key
2358 // preserves a custom passphrase.
2359 TEST_F(SyncEncryptionHandlerImplTest, RotateKeysUnmigratedCustomPassphrase) {
2360   const char kCustomPass[] = "custom_passphrase";
2361   const char kRawOldKeystoreKey[] = "old_keystore_key";
2362
2363   EXPECT_CALL(*observer(), OnPassphraseRequired(_, _));
2364   InitUnmigratedNigori(kCustomPass, CUSTOM_PASSPHRASE);
2365
2366   {
2367     // Pass multiple keystore keys, signaling a rotation has happened.
2368     google::protobuf::RepeatedPtrField<google::protobuf::string> keys;
2369     keys.Add()->assign(kRawOldKeystoreKey);
2370     keys.Add()->assign(kRawKeystoreKey);
2371     ReadTransaction trans(FROM_HERE, user_share());
2372     EXPECT_CALL(*observer(),
2373                 OnBootstrapTokenUpdated(_, KEYSTORE_BOOTSTRAP_TOKEN));
2374     encryption_handler()->SetKeystoreKeys(keys,
2375                                           trans.GetWrappedTrans());
2376   }
2377   PumpLoop();
2378   Mock::VerifyAndClearExpectations(observer());
2379
2380   // Pass the decryption passphrase. This will also trigger the migration,
2381   // but should not overwrite the default key.
2382   EXPECT_CALL(*observer(),
2383               OnCryptographerStateChanged(_)).Times(AnyNumber());
2384   EXPECT_CALL(*observer(),
2385               OnPassphraseAccepted());
2386   EXPECT_CALL(*observer(),
2387               OnEncryptedTypesChanged(_, true));
2388   SyncEncryptionHandler::NigoriState captured_nigori_state;
2389   EXPECT_CALL(*observer(), OnLocalSetPassphraseEncryption(_))
2390       .WillOnce(testing::SaveArg<0>(&captured_nigori_state));
2391   EXPECT_CALL(*observer(),
2392               OnEncryptionComplete()).Times(AnyNumber());
2393   std::string captured_bootstrap_token;
2394   EXPECT_CALL(*observer(),
2395               OnBootstrapTokenUpdated(_, PASSPHRASE_BOOTSTRAP_TOKEN))
2396       .WillOnce(testing::SaveArg<0>(&captured_bootstrap_token));
2397   encryption_handler()->SetDecryptionPassphrase(kCustomPass);
2398   Mock::VerifyAndClearExpectations(observer());
2399
2400   VerifyMigratedNigori(CUSTOM_PASSPHRASE, kCustomPass);
2401
2402   const base::Time migration_time = encryption_handler()->migration_time();
2403   VerifyRestoreAfterCustomPassphrase(TimeToProtoTime(migration_time),
2404                                      kCustomPass, captured_bootstrap_token,
2405                                      captured_nigori_state, CUSTOM_PASSPHRASE);
2406 }
2407
2408 // Verify that a key rotation done after we've migrated a custom passphrase
2409 // nigori node preserves the custom passphrase.
2410 TEST_F(SyncEncryptionHandlerImplTest, RotateKeysMigratedCustomPassphrase) {
2411   const char kCustomPass[] = "custom_passphrase";
2412   const char kRawOldKeystoreKey[] = "old_keystore_key";
2413
2414   KeyParams custom_key = {"localhost", "dummy", kCustomPass};
2415   GetCryptographer()->AddKey(custom_key);
2416
2417   const int64 migration_time = 1;
2418   InitCustomPassMigratedNigori(migration_time, kCustomPass);
2419   VerifyMigratedNigoriWithTimestamp(migration_time, CUSTOM_PASSPHRASE,
2420                                     kCustomPass);
2421
2422   SyncEncryptionHandler::NigoriState captured_nigori_state;
2423   {
2424     // Pass multiple keystore keys, signaling a rotation has happened.
2425     google::protobuf::RepeatedPtrField<google::protobuf::string> keys;
2426     keys.Add()->assign(kRawOldKeystoreKey);
2427     keys.Add()->assign(kRawKeystoreKey);
2428     ReadTransaction trans(FROM_HERE, user_share());
2429     EXPECT_CALL(*observer(),
2430                 OnBootstrapTokenUpdated(_, KEYSTORE_BOOTSTRAP_TOKEN));
2431     EXPECT_CALL(*observer(),
2432                 OnCryptographerStateChanged(_)).Times(AnyNumber());
2433     EXPECT_CALL(*observer(), OnLocalSetPassphraseEncryption(_))
2434         .WillOnce(testing::SaveArg<0>(&captured_nigori_state));
2435     encryption_handler()->SetKeystoreKeys(keys,
2436                                           trans.GetWrappedTrans());
2437   }
2438   PumpLoop();
2439   Mock::VerifyAndClearExpectations(observer());
2440
2441   VerifyMigratedNigoriWithTimestamp(migration_time, CUSTOM_PASSPHRASE,
2442                                     kCustomPass);
2443
2444   // We need the passphrase bootstrap token, but OnBootstrapTokenUpdated(_,
2445   // PASSPHRASE_BOOTSTRAP_TOKEN) has not been invoked (because it was invoked
2446   // during a previous instance) so get it from the Cryptographer.
2447   std::string passphrase_bootstrap_token;
2448   GetCryptographer()->GetBootstrapToken(&passphrase_bootstrap_token);
2449   VerifyRestoreAfterCustomPassphrase(migration_time, kCustomPass,
2450                                      passphrase_bootstrap_token,
2451                                      captured_nigori_state, CUSTOM_PASSPHRASE);
2452 }
2453
2454 }  // namespace syncer