[Sync] Implement keystore migration support.

sync/internal_api/sync_encryption_handler_impl_unittest.cc

 // Copyright (c) 2012 The Chromium Authors. All rights reserved.
 // Use of this source code is governed by a BSD-style license that can be
 // found in the LICENSE file.
 
 #include "sync/internal_api/sync_encryption_handler_impl.h"
 
 #include <string>
 
 #include "base/memory/scoped_ptr.h"
 #include "base/message_loop.h"
 #include "base/tracked_objects.h"
 #include "sync/internal_api/public/base/model_type_test_util.h"
 #include "sync/internal_api/public/read_node.h"
 #include "sync/internal_api/public/read_transaction.h"
+#include "sync/internal_api/public/write_node.h"
 #include "sync/internal_api/public/write_transaction.h"
 #include "sync/internal_api/public/test/test_user_share.h"
 #include "sync/protocol/nigori_specifics.pb.h"
 #include "sync/protocol/sync.pb.h"
 #include "sync/syncable/entry.h"
 #include "sync/syncable/mutable_entry.h"
 #include "sync/syncable/write_transaction.h"
 #include "sync/test/engine/test_id_factory.h"
 #include "sync/test/fake_encryptor.h"
 #include "sync/util/cryptographer.h"
 #include "testing/gmock/include/gmock/gmock.h"
 #include "testing/gtest/include/gtest/gtest.h"
 
 namespace syncer {
 
 namespace {
 
 using ::testing::_;
 using ::testing::Mock;
 using ::testing::StrictMock;
 
+static const char kKeystoreKey[] = "keystore_key";
+
 class SyncEncryptionHandlerObserverMock
     : public SyncEncryptionHandler::Observer {
  public:
   MOCK_METHOD2(OnPassphraseRequired,
                void(PassphraseRequiredReason,
                     const sync_pb::EncryptedData&));  // NOLINT
   MOCK_METHOD0(OnPassphraseAccepted, void());  // NOLINT
   MOCK_METHOD2(OnBootstrapTokenUpdated,
                void(const std::string&, BootstrapTokenType type));  // NOLINT
   MOCK_METHOD2(OnEncryptedTypesChanged,
@@ skipping 10 matching lines @@
   SyncEncryptionHandlerImplTest() {}
   virtual ~SyncEncryptionHandlerImplTest() {}
 
   virtual void SetUp() {
     test_user_share_.SetUp();
     SetUpEncryption();
     CreateRootForType(NIGORI);
   }
 
   virtual void TearDown() {
+    PumpLoop();
     test_user_share_.TearDown();
   }
 
  protected:
   void SetUpEncryption() {
     encryption_handler_.reset(
         new SyncEncryptionHandlerImpl(user_share(),
                                       &encryptor_,
                                       "", ""  /* bootstrap tokens */));
     encryption_handler_->AddObserver(&observer_);
@@ skipping 30 matching lines @@
   // Getters for tests.
   UserShare* user_share() { return test_user_share_.user_share(); }
   SyncEncryptionHandlerImpl* encryption_handler() {
       return encryption_handler_.get();
   }
   SyncEncryptionHandlerObserverMock* observer() { return &observer_; }
   Cryptographer* GetCryptographer() {
     return encryption_handler_->GetCryptographerUnsafe();
   }
 
+  void VerifyMigratedNigori(PassphraseState passphrase_state,
+                            const std::string& passphrase) {
+    VerifyMigratedNigoriWithTimestamp(0, passphrase_state, passphrase);
+  }
+
+  void VerifyMigratedNigoriWithTimestamp(
+      int64 migration_time,
+      PassphraseState passphrase_state,
+      const std::string& passphrase) {
+    ReadTransaction trans(FROM_HERE, user_share());
+    ReadNode nigori_node(&trans);
+    ASSERT_EQ(nigori_node.InitByTagLookup(kNigoriTag), BaseNode::INIT_OK);
+    const sync_pb::NigoriSpecifics& nigori = nigori_node.GetNigoriSpecifics();
+    if (migration_time > 0)
+      EXPECT_EQ(migration_time, nigori.keystore_migration_time());
+    else
+      EXPECT_TRUE(nigori.has_keystore_migration_time());
+    EXPECT_TRUE(nigori.frozen_keybag());
+    if (passphrase_state == CUSTOM_PASSPHRASE ||
+        passphrase_state == FROZEN_IMPLICIT_PASSPHRASE) {
+      EXPECT_TRUE(nigori.encrypt_everything());
+      EXPECT_TRUE(nigori.keystore_bootstrap().blob().empty());
+      if (passphrase_state == CUSTOM_PASSPHRASE) {
+        EXPECT_EQ(sync_pb::NigoriSpecifics::CUSTOM_PASSPHRASE,
+                  nigori.passphrase_state());
+      } else {
+        EXPECT_EQ(sync_pb::NigoriSpecifics::FROZEN_IMPLICIT_PASSPHRASE,
+                  nigori.passphrase_state());
+      }
+    } else {
+      EXPECT_FALSE(nigori.encrypt_everything());
+      EXPECT_FALSE(nigori.keystore_bootstrap().blob().empty());
+      EXPECT_EQ(sync_pb::NigoriSpecifics::KEYSTORE_PASSPHRASE,
+                nigori.passphrase_state());
+      Cryptographer keystore_cryptographer(&encryptor_);
+      KeyParams params = {"localhost", "dummy", kKeystoreKey};
+      keystore_cryptographer.AddKey(params);
+      EXPECT_TRUE(keystore_cryptographer.CanDecryptUsingDefaultKey(
+          nigori.keystore_bootstrap()));
+    }
+
+    Cryptographer temp_cryptographer(&encryptor_);
+    KeyParams params = {"localhost", "dummy", passphrase};
+    temp_cryptographer.AddKey(params);
+    EXPECT_TRUE(temp_cryptographer.CanDecryptUsingDefaultKey(
+        nigori.encryption_keybag()));
+  }
+
  protected:
   TestUserShare test_user_share_;
   FakeEncryptor encryptor_;
   scoped_ptr<SyncEncryptionHandlerImpl> encryption_handler_;
   StrictMock<SyncEncryptionHandlerObserverMock> observer_;
   TestIdFactory ids_;
   MessageLoop message_loop_;
 };
 
 // Verify that the encrypted types are being written to and read from the
@@ skipping 226 matching lines @@
 
   // Set up the current encryption state (containing both keys and encrypt
   // everything).
   sync_pb::NigoriSpecifics current_nigori_specifics;
   GetCryptographer()->AddKey(old_key);
   GetCryptographer()->AddKey(current_key);
   GetCryptographer()->Encrypt(
       our_encrypted_specifics,
       our_encrypted_specifics.mutable_encrypted());
   GetCryptographer()->GetKeys(
-      current_nigori_specifics.mutable_encrypted());
+      current_nigori_specifics.mutable_encryption_keybag());
   current_nigori_specifics.set_encrypt_everything(true);
 
   EXPECT_CALL(*observer(), OnCryptographerStateChanged(_));
   EXPECT_CALL(*observer(), OnEncryptedTypesChanged(
       HasModelTypes(ModelTypeSet::All()), true));
   {
     // Update the encryption handler.
     WriteTransaction trans(FROM_HERE, user_share());
     encryption_handler()->ApplyNigoriUpdate(
         current_nigori_specifics,
         trans.GetWrappedTrans());
   }
   Mock::VerifyAndClearExpectations(observer());
 
   // Now set up the old nigori specifics and apply it on top.
   // Has an old set of keys, and no encrypted types.
   sync_pb::NigoriSpecifics old_nigori;
-  other_cryptographer.GetKeys(old_nigori.mutable_encrypted());
+  other_cryptographer.GetKeys(old_nigori.mutable_encryption_keybag());
 
   EXPECT_CALL(*observer(), OnCryptographerStateChanged(_));
   {
     // Update the encryption handler.
     WriteTransaction trans(FROM_HERE, user_share());
     encryption_handler()->ApplyNigoriUpdate(
         old_nigori,
         trans.GetWrappedTrans());
   }
   EXPECT_TRUE(GetCryptographer()->is_ready());
   EXPECT_FALSE(GetCryptographer()->has_pending_keys());
 
   // Encryption handler should have posted a task to overwrite the old
   // specifics.
   PumpLoop();
 
   {
     // The cryptographer should be able to decrypt both sets of keys and still
     // be encrypting with the newest, and the encrypted types should be the
     // most recent.
     // In addition, the nigori node should match the current encryption state.
     ReadTransaction trans(FROM_HERE, user_share());
     ReadNode nigori_node(&trans);
-    ASSERT_EQ(nigori_node.InitByTagLookup(ModelTypeToRootTag(NIGORI)),
-              BaseNode::INIT_OK);
+    ASSERT_EQ(nigori_node.InitByTagLookup(kNigoriTag), BaseNode::INIT_OK);
     const sync_pb::NigoriSpecifics& nigori = nigori_node.GetNigoriSpecifics();
     EXPECT_TRUE(GetCryptographer()->CanDecryptUsingDefaultKey(
         our_encrypted_specifics.encrypted()));
     EXPECT_TRUE(GetCryptographer()->CanDecrypt(
         other_encrypted_specifics.encrypted()));
-    EXPECT_TRUE(GetCryptographer()->CanDecrypt(nigori.encrypted()));
+    EXPECT_TRUE(GetCryptographer()->CanDecrypt(nigori.encryption_keybag()));
     EXPECT_TRUE(nigori.encrypt_everything());
     EXPECT_TRUE(
-        GetCryptographer()->CanDecryptUsingDefaultKey(nigori.encrypted()));
+        GetCryptographer()->CanDecryptUsingDefaultKey(
+            nigori.encryption_keybag()));
   }
   EXPECT_TRUE(encryption_handler()->EncryptEverythingEnabled());
 }
 
 // Ensure setting the keystore key works, updates the bootstrap token, and
 // doesn't modify the cryptographer.
 TEST_F(SyncEncryptionHandlerImplTest, SetKeystoreUpdatedBoostrapToken) {
   WriteTransaction trans(FROM_HERE, user_share());
   EXPECT_CALL(*observer(), OnBootstrapTokenUpdated(_, _)).Times(0);
   EXPECT_FALSE(GetCryptographer()->is_initialized());
   EXPECT_TRUE(encryption_handler()->NeedKeystoreKey(trans.GetWrappedTrans()));
   EXPECT_FALSE(encryption_handler()->SetKeystoreKey("",
                                                     trans.GetWrappedTrans()));
   EXPECT_TRUE(encryption_handler()->NeedKeystoreKey(trans.GetWrappedTrans()));
   Mock::VerifyAndClearExpectations(observer());
 
-  const char kValidKey[] = "keystore_key";
-  EXPECT_CALL(*observer(),
-              OnBootstrapTokenUpdated(kValidKey, KEYSTORE_BOOTSTRAP_TOKEN));
-  EXPECT_TRUE(encryption_handler()->SetKeystoreKey(kValidKey,
+  EXPECT_CALL(*observer(),
+              OnBootstrapTokenUpdated(kKeystoreKey, KEYSTORE_BOOTSTRAP_TOKEN));
+  EXPECT_TRUE(encryption_handler()->SetKeystoreKey(kKeystoreKey,
                                                    trans.GetWrappedTrans()));
   EXPECT_FALSE(encryption_handler()->NeedKeystoreKey(trans.GetWrappedTrans()));
   EXPECT_FALSE(GetCryptographer()->is_initialized());
 }
 
+// Ensure GetKeystoreBootstrap only updates the keystore bootstrap if it
+// wasn't already set properly. Otherwise, the bootstrap should remain the
+// same.
+TEST_F(SyncEncryptionHandlerImplTest, GetKeystoreBootstrap) {
+  const char kCurKey[] = "cur";
+  sync_pb::EncryptedData encrypted;
+  Cryptographer other_cryptographer(GetCryptographer()->encryptor());
+  KeyParams cur_key = {"localhost", "dummy", kCurKey};
+  other_cryptographer.AddKey(cur_key);
+  EXPECT_TRUE(other_cryptographer.is_ready());
+  EXPECT_TRUE(encryption_handler()->GetKeystoreBootstrapKey(
+      other_cryptographer,
+      kKeystoreKey,
+      &encrypted));
+  std::string serialized = encrypted.SerializeAsString();
+  EXPECT_TRUE(encryption_handler()->GetKeystoreBootstrapKey(
+      other_cryptographer,
+      kKeystoreKey,
+      &encrypted));
+  EXPECT_EQ(serialized, encrypted.SerializeAsString());
+}
+
+// Test that we don't attempt to migrate while an implicit passphrase is pending
+// and that once we do decrypt pending keys we migrate the nigori. Once
+// migrated, we should be in keystore passphrase state.
+TEST_F(SyncEncryptionHandlerImplTest, MigrateOnDecryptImplicitPass) {
+  const char kOtherKey[] = "other";
+  {
+    EXPECT_CALL(*observer(),
+                OnBootstrapTokenUpdated(_, KEYSTORE_BOOTSTRAP_TOKEN));
+    ReadTransaction trans(FROM_HERE, user_share());
+    encryption_handler()->SetKeystoreKey(kKeystoreKey, trans.GetWrappedTrans());
+    Mock::VerifyAndClearExpectations(observer());
+  }
+  EXPECT_FALSE(encryption_handler()->MigratedToKeystore());
+
+  {
+    WriteTransaction trans(FROM_HERE, user_share());
+    WriteNode nigori_node(&trans);
+    ASSERT_EQ(nigori_node.InitByTagLookup(kNigoriTag), BaseNode::INIT_OK);
+    Cryptographer other_cryptographer(GetCryptographer()->encryptor());
+    KeyParams other_key = {"localhost", "dummy", kOtherKey};
+    other_cryptographer.AddKey(other_key);
+
+    sync_pb::NigoriSpecifics nigori;
+    other_cryptographer.GetKeys(nigori.mutable_encryption_keybag());
+    nigori.set_frozen_keybag(false);
+    nigori.set_encrypt_everything(false);
+    EXPECT_CALL(*observer(),
+                OnCryptographerStateChanged(_));
+    EXPECT_CALL(*observer(),
+                OnPassphraseRequired(_, _));
+    encryption_handler()->ApplyNigoriUpdate(nigori, trans.GetWrappedTrans());
+    nigori_node.SetNigoriSpecifics(nigori);
+  }
+  // Run any tasks posted via AppplyNigoriUpdate.
+  PumpLoop();
+  EXPECT_FALSE(encryption_handler()->MigratedToKeystore());
+  Mock::VerifyAndClearExpectations(observer());
+
+  EXPECT_CALL(*observer(),
+              OnCryptographerStateChanged(_));
+  EXPECT_CALL(*observer(),
+              OnPassphraseAccepted());
+  EXPECT_CALL(*observer(),
+              OnPassphraseStateChanged(KEYSTORE_PASSPHRASE));
+  EXPECT_CALL(*observer(),
+              OnBootstrapTokenUpdated(_, PASSPHRASE_BOOTSTRAP_TOKEN));
+  EXPECT_CALL(*observer(),
+              OnEncryptionComplete());
+  EXPECT_FALSE(encryption_handler()->MigratedToKeystore());
+  encryption_handler()->SetDecryptionPassphrase(kOtherKey);
+  EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
+  EXPECT_EQ(KEYSTORE_PASSPHRASE, encryption_handler()->GetPassphraseState());
+  VerifyMigratedNigori(KEYSTORE_PASSPHRASE, kOtherKey);
+}
+
+// Test that we don't attempt to migrate while a custom passphrase is pending,
+// and that once we do decrypt pending keys we migrate the nigori. Once
+// migrated, we should be in custom passphrase state with encrypt everything.
+TEST_F(SyncEncryptionHandlerImplTest, MigrateOnDecryptCustomPass) {
+  const char kOtherKey[] = "other";
+  {
+    EXPECT_CALL(*observer(),
+                OnBootstrapTokenUpdated(_, KEYSTORE_BOOTSTRAP_TOKEN));
+    ReadTransaction trans(FROM_HERE, user_share());
+    encryption_handler()->SetKeystoreKey(kKeystoreKey, trans.GetWrappedTrans());
+    Mock::VerifyAndClearExpectations(observer());
+  }
+  EXPECT_FALSE(encryption_handler()->MigratedToKeystore());
+
+  {
+    WriteTransaction trans(FROM_HERE, user_share());
+    WriteNode nigori_node(&trans);
+    ASSERT_EQ(nigori_node.InitByTagLookup(kNigoriTag), BaseNode::INIT_OK);
+    Cryptographer other_cryptographer(GetCryptographer()->encryptor());
+    KeyParams other_key = {"localhost", "dummy", kOtherKey};
+    other_cryptographer.AddKey(other_key);
+
+    sync_pb::NigoriSpecifics nigori;
+    other_cryptographer.GetKeys(nigori.mutable_encryption_keybag());
+    nigori.set_frozen_keybag(true);
+    nigori.set_encrypt_everything(false);
+    EXPECT_CALL(*observer(),
+                OnCryptographerStateChanged(_));
+    EXPECT_CALL(*observer(),
+                OnPassphraseRequired(_, _));
+    EXPECT_CALL(*observer(),
+                OnPassphraseStateChanged(CUSTOM_PASSPHRASE));
+    encryption_handler()->ApplyNigoriUpdate(nigori, trans.GetWrappedTrans());
+    nigori_node.SetNigoriSpecifics(nigori);
+  }
+  // Run any tasks posted via AppplyNigoriUpdate.
+  PumpLoop();
+  EXPECT_FALSE(encryption_handler()->MigratedToKeystore());
+  Mock::VerifyAndClearExpectations(observer());
+
+  EXPECT_CALL(*observer(),
+              OnCryptographerStateChanged(_));
+  EXPECT_CALL(*observer(),
+              OnPassphraseAccepted());
+  EXPECT_CALL(*observer(),
+              OnBootstrapTokenUpdated(_, PASSPHRASE_BOOTSTRAP_TOKEN));
+  EXPECT_CALL(*observer(),
+              OnEncryptedTypesChanged(_, true));
+  EXPECT_CALL(*observer(),
+              OnEncryptionComplete()).Times(2);
+  EXPECT_FALSE(encryption_handler()->MigratedToKeystore());
+  encryption_handler()->SetDecryptionPassphrase(kOtherKey);
+  EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
+  EXPECT_EQ(CUSTOM_PASSPHRASE, encryption_handler()->GetPassphraseState());
+  VerifyMigratedNigori(CUSTOM_PASSPHRASE, kOtherKey);
+}
+
+// Test that we trigger a migration when we set the keystore key, had an
+// implicit passphrase, and did not have encrypt everything. We should switch
+// to KEYSTORE_PASSPHRASE.
+TEST_F(SyncEncryptionHandlerImplTest, MigrateOnKeystoreKeyAvailableImplicit) {
+  const char kCurKey[] = "cur";
+  KeyParams current_key = {"localhost", "dummy", kCurKey};
+  GetCryptographer()->AddKey(current_key);
+  EXPECT_CALL(*observer(),
+              OnCryptographerStateChanged(_));
+  EXPECT_CALL(*observer(),
+              OnEncryptedTypesChanged(_, false));
+  EXPECT_CALL(*observer(),
+              OnEncryptionComplete());
+  encryption_handler()->Init();
+  Mock::VerifyAndClearExpectations(observer());
+
+  {
+    ReadTransaction trans(FROM_HERE, user_share());
+    // Once we provide a keystore key, we should perform the migration.
+    EXPECT_CALL(*observer(),
+                OnBootstrapTokenUpdated(_, KEYSTORE_BOOTSTRAP_TOKEN));
+    encryption_handler()->SetKeystoreKey(kKeystoreKey, trans.GetWrappedTrans());
+  }
+  EXPECT_CALL(*observer(),
+              OnPassphraseStateChanged(KEYSTORE_PASSPHRASE));
+  // The actual migration gets posted, so run all pending tasks.
+  PumpLoop();
+  EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
+  EXPECT_EQ(KEYSTORE_PASSPHRASE,
+            encryption_handler()->GetPassphraseState());
+  EXPECT_FALSE(encryption_handler()->EncryptEverythingEnabled());
+  VerifyMigratedNigori(KEYSTORE_PASSPHRASE, kCurKey);
+}
+
+// Test that we trigger a migration when we set the keystore key, had an
+// implicit passphrase, and encrypt everything enabled. We should switch to
+// FROZEN_IMPLICIT_PASSPHRASE.
+TEST_F(SyncEncryptionHandlerImplTest,
+       MigrateOnKeystoreKeyAvailableFrozenImplicit) {
+  const char kCurKey[] = "cur";
+  KeyParams current_key = {"localhost", "dummy", kCurKey};
+  GetCryptographer()->AddKey(current_key);
+  EXPECT_CALL(*observer(),
+              OnCryptographerStateChanged(_));
+  EXPECT_CALL(*observer(),
+              OnEncryptedTypesChanged(_, false));
+  EXPECT_CALL(*observer(),
+              OnEncryptionComplete());
+  encryption_handler()->Init();
+  Mock::VerifyAndClearExpectations(observer());
+
+  EXPECT_CALL(*observer(),
+              OnEncryptedTypesChanged(_, true));
+  EXPECT_CALL(*observer(),
+              OnEncryptionComplete());
+  encryption_handler()->EnableEncryptEverything();
+
+  {
+    ReadTransaction trans(FROM_HERE, user_share());
+    // Once we provide a keystore key, we should perform the migration.
+    EXPECT_CALL(*observer(),
+                OnBootstrapTokenUpdated(_, KEYSTORE_BOOTSTRAP_TOKEN));
+    encryption_handler()->SetKeystoreKey(kKeystoreKey, trans.GetWrappedTrans());
+  }
+  EXPECT_CALL(*observer(),
+              OnPassphraseStateChanged(FROZEN_IMPLICIT_PASSPHRASE));
+  // The actual migration gets posted, so run all pending tasks.
+  PumpLoop();
+  EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
+  EXPECT_EQ(FROZEN_IMPLICIT_PASSPHRASE,
+            encryption_handler()->GetPassphraseState());
+  EXPECT_TRUE(encryption_handler()->EncryptEverythingEnabled());
+  VerifyMigratedNigori(FROZEN_IMPLICIT_PASSPHRASE, kCurKey);
+}
+
+// Test that we trigger a migration when we set the keystore key, had a
+// custom passphrase, and encrypt everything enabled. The passphrase state
+// should remain as CUSTOM_PASSPHRASE, and encrypt everything stay the same.
+TEST_F(SyncEncryptionHandlerImplTest,
+       MigrateOnKeystoreKeyAvailableCustomWithEncryption) {
+  const char kCurKey[] = "cur";
+  EXPECT_CALL(*observer(),
+              OnCryptographerStateChanged(_)).Times(2);
+  EXPECT_CALL(*observer(),
+              OnPassphraseRequired(_, _));
+  EXPECT_CALL(*observer(),
+              OnPassphraseAccepted());
+  EXPECT_CALL(*observer(),
+              OnEncryptedTypesChanged(_, false));
+  EXPECT_CALL(*observer(),
+              OnEncryptionComplete());
+  EXPECT_CALL(*observer(),
+              OnPassphraseStateChanged(CUSTOM_PASSPHRASE));
+  EXPECT_CALL(*observer(),
+              OnBootstrapTokenUpdated(_, PASSPHRASE_BOOTSTRAP_TOKEN));
+  encryption_handler()->Init();
+  encryption_handler()->SetEncryptionPassphrase(kCurKey, true);
+  Mock::VerifyAndClearExpectations(observer());
+
+  EXPECT_CALL(*observer(),
+              OnEncryptedTypesChanged(_, true));
+  EXPECT_CALL(*observer(),
+              OnEncryptionComplete());
+  encryption_handler()->EnableEncryptEverything();
+  Mock::VerifyAndClearExpectations(observer());
+
+  {
+    ReadTransaction trans(FROM_HERE, user_share());
+    // Once we provide a keystore key, we should perform the migration.
+    EXPECT_CALL(*observer(),
+                OnBootstrapTokenUpdated(_, KEYSTORE_BOOTSTRAP_TOKEN));
+    encryption_handler()->SetKeystoreKey(kKeystoreKey, trans.GetWrappedTrans());
+  }
+  // The actual migration gets posted, so run all pending tasks.
+  PumpLoop();
+  EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
+  EXPECT_EQ(CUSTOM_PASSPHRASE,
+            encryption_handler()->GetPassphraseState());
+  EXPECT_TRUE(encryption_handler()->EncryptEverythingEnabled());
+  VerifyMigratedNigori(CUSTOM_PASSPHRASE, kCurKey);
+}
+
+// Test that we trigger a migration when we set the keystore key, had a
+// custom passphrase, and did not have encrypt everything. The passphrase state
+// should remain as CUSTOM_PASSPHRASE, and encrypt everything should be enabled.
+TEST_F(SyncEncryptionHandlerImplTest,
+       MigrateOnKeystoreKeyAvailableCustomNoEncryption) {
+  const char kCurKey[] = "cur";
+  EXPECT_CALL(*observer(),
+              OnCryptographerStateChanged(_)).Times(2);
+  EXPECT_CALL(*observer(),
+              OnPassphraseRequired(_, _));
+  EXPECT_CALL(*observer(),
+              OnPassphraseAccepted());
+  EXPECT_CALL(*observer(),
+              OnEncryptedTypesChanged(_, false));
+  EXPECT_CALL(*observer(),
+              OnEncryptionComplete());
+  EXPECT_CALL(*observer(),
+              OnPassphraseStateChanged(CUSTOM_PASSPHRASE));
+  EXPECT_CALL(*observer(),
+              OnBootstrapTokenUpdated(_, PASSPHRASE_BOOTSTRAP_TOKEN));
+  encryption_handler()->Init();
+  encryption_handler()->SetEncryptionPassphrase(kCurKey, true);
+  Mock::VerifyAndClearExpectations(observer());
+
+  {
+    ReadTransaction trans(FROM_HERE, user_share());
+    // Once we provide a keystore key, we should perform the migration.
+    EXPECT_CALL(*observer(),
+                OnBootstrapTokenUpdated(_, KEYSTORE_BOOTSTRAP_TOKEN));
+    encryption_handler()->SetKeystoreKey(kKeystoreKey, trans.GetWrappedTrans());
+  }
+  EXPECT_CALL(*observer(),
+              OnEncryptedTypesChanged(_, true));
+  EXPECT_CALL(*observer(),
+              OnEncryptionComplete());
+  // The actual migration gets posted, so run all pending tasks.
+  PumpLoop();
+  EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
+  EXPECT_EQ(CUSTOM_PASSPHRASE,
+            encryption_handler()->GetPassphraseState());
+  EXPECT_TRUE(encryption_handler()->EncryptEverythingEnabled());
+  VerifyMigratedNigori(CUSTOM_PASSPHRASE, kCurKey);
+}
+
+// Test that we can handle receiving a migrated nigori node in the
+// KEYSTORE_PASS state, and use the keystore bootstrap to decrypt the keybag.
+TEST_F(SyncEncryptionHandlerImplTest, ReceiveMigratedNigoriKeystorePass) {
+  const char kCurKey[] = "cur";
+  sync_pb::EncryptedData encrypted;
+  Cryptographer other_cryptographer(GetCryptographer()->encryptor());
+  KeyParams cur_key = {"localhost", "dummy", kCurKey};
+  other_cryptographer.AddKey(cur_key);
+  EXPECT_TRUE(other_cryptographer.is_ready());
+  EXPECT_TRUE(encryption_handler()->GetKeystoreBootstrapKey(
+      other_cryptographer,
+      kKeystoreKey,
+      &encrypted));
+  EXPECT_FALSE(encryption_handler()->MigratedToKeystore());
+  EXPECT_FALSE(GetCryptographer()->is_ready());
+  EXPECT_NE(encryption_handler()->GetPassphraseState(), KEYSTORE_PASSPHRASE);
+
+  // Now build a nigori node with the generated keystore bootstrap token and
+  // initialize the encryption handler with it. The cryptographer should be
+  // bootstrapped properly to decrypt both kCurKey and kKeystoreKey.
+  {
+    WriteTransaction trans(FROM_HERE, user_share());
+    WriteNode nigori_node(&trans);
+    ASSERT_EQ(nigori_node.InitByTagLookup(kNigoriTag), BaseNode::INIT_OK);
+    sync_pb::NigoriSpecifics nigori;
+    nigori.mutable_keystore_bootstrap()->CopyFrom(encrypted);
+    other_cryptographer.GetKeys(nigori.mutable_encryption_keybag());
+    nigori.set_frozen_keybag(true);
+    nigori.set_keystore_migration_time(1);
+    nigori.set_passphrase_state(sync_pb::NigoriSpecifics::KEYSTORE_PASSPHRASE);
+
+    EXPECT_CALL(*observer(),
+                OnBootstrapTokenUpdated(_, PASSPHRASE_BOOTSTRAP_TOKEN));
+    EXPECT_CALL(*observer(),
+                OnBootstrapTokenUpdated(_, KEYSTORE_BOOTSTRAP_TOKEN));
+    EXPECT_CALL(*observer(),
+                OnPassphraseStateChanged(KEYSTORE_PASSPHRASE));
+    EXPECT_CALL(*observer(),
+                OnCryptographerStateChanged(_)).Times(2);
+    encryption_handler()->SetKeystoreKey(kKeystoreKey, trans.GetWrappedTrans());
+    encryption_handler()->ApplyNigoriUpdate(nigori, trans.GetWrappedTrans());
+    nigori_node.SetNigoriSpecifics(nigori);
+  }
+  // Run any tasks posted via AppplyNigoriUpdate.
+  PumpLoop();
+  Mock::VerifyAndClearExpectations(observer());
+
+  EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
+  EXPECT_TRUE(GetCryptographer()->is_ready());
+  EXPECT_EQ(encryption_handler()->GetPassphraseState(), KEYSTORE_PASSPHRASE);
+  EXPECT_FALSE(encryption_handler()->EncryptEverythingEnabled());
+  VerifyMigratedNigoriWithTimestamp(1, KEYSTORE_PASSPHRASE, kCurKey);
+
+  // Check that the cryptographer still encrypts with the current key.
+  sync_pb::EncryptedData current_encrypted;
+  other_cryptographer.EncryptString("string", &current_encrypted);
+  EXPECT_TRUE(GetCryptographer()->CanDecryptUsingDefaultKey(current_encrypted));
+
+  // Check that the cryptographer can decrypt keystore key based encryption.
+  Cryptographer keystore_cryptographer(GetCryptographer()->encryptor());
+  KeyParams keystore_key =  {"localhost", "dummy", kKeystoreKey};
+  keystore_cryptographer.AddKey(keystore_key);
+  sync_pb::EncryptedData keystore_encrypted;
+  keystore_cryptographer.EncryptString("string", &keystore_encrypted);
+  EXPECT_TRUE(GetCryptographer()->CanDecrypt(keystore_encrypted));
+}
+
+// Test that we handle receiving migrated nigori's with
+// FROZEN_IMPLICIT_PASSPHRASE state. We should be in a pending key state until
+// we supply the pending frozen implicit passphrase key.
+TEST_F(SyncEncryptionHandlerImplTest, ReceiveMigratedNigoriFrozenImplicitPass) {
+  const char kCurKey[] = "cur";
+  sync_pb::EncryptedData encrypted;
+  Cryptographer other_cryptographer(GetCryptographer()->encryptor());
+  KeyParams cur_key = {"localhost", "dummy", kCurKey};
+  other_cryptographer.AddKey(cur_key);
+  EXPECT_FALSE(encryption_handler()->MigratedToKeystore());
+
+  {
+    EXPECT_CALL(*observer(),
+                OnBootstrapTokenUpdated(_, KEYSTORE_BOOTSTRAP_TOKEN));
+    ReadTransaction trans(FROM_HERE, user_share());
+    encryption_handler()->SetKeystoreKey(kKeystoreKey, trans.GetWrappedTrans());
+  }
+  EXPECT_FALSE(encryption_handler()->MigratedToKeystore());
+
+  {
+    EXPECT_CALL(*observer(),
+                OnPassphraseStateChanged(FROZEN_IMPLICIT_PASSPHRASE));
+    EXPECT_CALL(*observer(),
+                OnPassphraseRequired(_, _));
+    EXPECT_CALL(*observer(),
+                OnCryptographerStateChanged(_));
+    EXPECT_CALL(*observer(),
+                OnEncryptedTypesChanged(_, true));
+    WriteTransaction trans(FROM_HERE, user_share());
+    WriteNode nigori_node(&trans);
+    ASSERT_EQ(nigori_node.InitByTagLookup(kNigoriTag), BaseNode::INIT_OK);
+    sync_pb::NigoriSpecifics nigori;
+    nigori.set_frozen_keybag(true);
+    nigori.set_passphrase_state(
+        sync_pb::NigoriSpecifics::FROZEN_IMPLICIT_PASSPHRASE);
+    nigori.set_keystore_migration_time(1);
+    nigori.set_encrypt_everything(true);
+    other_cryptographer.GetKeys(nigori.mutable_encryption_keybag());
+    encryption_handler()->ApplyNigoriUpdate(nigori, trans.GetWrappedTrans());
+    nigori_node.SetNigoriSpecifics(nigori);
+  }
+  // Run any tasks posted via AppplyNigoriUpdate.
+  PumpLoop();
+  Mock::VerifyAndClearExpectations(observer());
+
+  EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
+  EXPECT_EQ(FROZEN_IMPLICIT_PASSPHRASE,
+            encryption_handler()->GetPassphraseState());
+  EXPECT_TRUE(GetCryptographer()->has_pending_keys());
+  EXPECT_TRUE(encryption_handler()->EncryptEverythingEnabled());
+
+  EXPECT_CALL(*observer(),
+              OnBootstrapTokenUpdated(_, PASSPHRASE_BOOTSTRAP_TOKEN));
+  EXPECT_CALL(*observer(),
+              OnCryptographerStateChanged(_));
+  EXPECT_CALL(*observer(),
+              OnEncryptionComplete());
+  EXPECT_CALL(*observer(),
+              OnPassphraseAccepted());
+  encryption_handler()->SetDecryptionPassphrase(kCurKey);
+  EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
+  EXPECT_TRUE(GetCryptographer()->is_ready());
+  VerifyMigratedNigoriWithTimestamp(1, FROZEN_IMPLICIT_PASSPHRASE, kCurKey);
+
+  // Check that the cryptographer still encrypts with the current key.
+  sync_pb::EncryptedData current_encrypted;
+  other_cryptographer.EncryptString("string", &current_encrypted);
+  EXPECT_TRUE(GetCryptographer()->CanDecryptUsingDefaultKey(current_encrypted));
+
+  // Check that the cryptographer can decrypt keystore key based encryption.
+  Cryptographer keystore_cryptographer(GetCryptographer()->encryptor());
+  KeyParams keystore_key =  {"localhost", "dummy", kKeystoreKey};
+  keystore_cryptographer.AddKey(keystore_key);
+  sync_pb::EncryptedData keystore_encrypted;
+  keystore_cryptographer.EncryptString("string", &keystore_encrypted);
+  EXPECT_TRUE(GetCryptographer()->CanDecrypt(keystore_encrypted));
+}
+
+// Test that we handle receiving migrated nigori's with
+// CUSTOM_PASSPHRASE state. We should be in a pending key state until we
+// provide the custom passphrase key.
+TEST_F(SyncEncryptionHandlerImplTest, ReceiveMigratedNigoriCustomPass) {
+  const char kKeystoreKey[] = "keystore_key";
+  const char kCurKey[] = "cur";
+  sync_pb::EncryptedData encrypted;
+  Cryptographer other_cryptographer(GetCryptographer()->encryptor());
+  KeyParams cur_key = {"localhost", "dummy", kCurKey};
+  other_cryptographer.AddKey(cur_key);
+  EXPECT_FALSE(encryption_handler()->MigratedToKeystore());
+
+  {
+    EXPECT_CALL(*observer(),
+                OnBootstrapTokenUpdated(_, KEYSTORE_BOOTSTRAP_TOKEN));
+    ReadTransaction trans(FROM_HERE, user_share());
+    encryption_handler()->SetKeystoreKey(kKeystoreKey,
+                                         trans.GetWrappedTrans());
+  }
+  EXPECT_FALSE(encryption_handler()->MigratedToKeystore());
+
+  {
+    EXPECT_CALL(*observer(),
+                OnPassphraseStateChanged(CUSTOM_PASSPHRASE));
+    EXPECT_CALL(*observer(),
+                OnPassphraseRequired(_, _));
+    EXPECT_CALL(*observer(),
+                OnCryptographerStateChanged(_));
+    EXPECT_CALL(*observer(),
+                OnEncryptedTypesChanged(_, true));
+    WriteTransaction trans(FROM_HERE, user_share());
+    WriteNode nigori_node(&trans);
+    ASSERT_EQ(nigori_node.InitByTagLookup(kNigoriTag), BaseNode::INIT_OK);
+    sync_pb::NigoriSpecifics nigori;
+    nigori.set_frozen_keybag(true);
+    nigori.set_passphrase_state(sync_pb::NigoriSpecifics::CUSTOM_PASSPHRASE);
+    nigori.set_keystore_migration_time(1);
+    nigori.set_encrypt_everything(true);
+    other_cryptographer.GetKeys(nigori.mutable_encryption_keybag());
+    encryption_handler()->ApplyNigoriUpdate(nigori, trans.GetWrappedTrans());
+    nigori_node.SetNigoriSpecifics(nigori);
+  }
+  // Run any tasks posted via AppplyNigoriUpdate.
+  PumpLoop();
+  Mock::VerifyAndClearExpectations(observer());
+
+  EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
+  EXPECT_EQ(CUSTOM_PASSPHRASE, encryption_handler()->GetPassphraseState());
+  EXPECT_TRUE(GetCryptographer()->has_pending_keys());
+  EXPECT_TRUE(encryption_handler()->EncryptEverythingEnabled());
+
+  EXPECT_CALL(*observer(),
+              OnBootstrapTokenUpdated(_, PASSPHRASE_BOOTSTRAP_TOKEN));
+  EXPECT_CALL(*observer(),
+              OnCryptographerStateChanged(_));
+  EXPECT_CALL(*observer(),
+              OnEncryptionComplete());
+  EXPECT_CALL(*observer(),
+              OnPassphraseAccepted());
+  encryption_handler()->SetDecryptionPassphrase(kCurKey);
+  EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
+  EXPECT_TRUE(GetCryptographer()->is_ready());
+  VerifyMigratedNigoriWithTimestamp(1, CUSTOM_PASSPHRASE, kCurKey);
+
+  // Check that the cryptographer still encrypts with the current key.
+  sync_pb::EncryptedData current_encrypted;
+  other_cryptographer.EncryptString("string", &current_encrypted);
+  EXPECT_TRUE(GetCryptographer()->CanDecryptUsingDefaultKey(current_encrypted));
+
+  // Check that the cryptographer can decrypt keystore key based encryption.
+  Cryptographer keystore_cryptographer(GetCryptographer()->encryptor());
+  KeyParams keystore_key =  {"localhost", "dummy", kKeystoreKey};
+  keystore_cryptographer.AddKey(keystore_key);
+  sync_pb::EncryptedData keystore_encrypted;
+  keystore_cryptographer.EncryptString("string", &keystore_encrypted);
+  EXPECT_TRUE(GetCryptographer()->CanDecrypt(keystore_encrypted));
+}
+
+// Test that if we have a migrated nigori with a custom passphrase, then receive
+// and old implicit passphrase nigori, we properly overwrite it with the current
+// state.
+TEST_F(SyncEncryptionHandlerImplTest, ReceiveUnmigratedNigoriAfterMigration) {
+  const char kOldKey[] = "old";
+  const char kCurKey[] = "cur";
+  sync_pb::EncryptedData encrypted;
+  KeyParams old_key = {"localhost", "dummy", kOldKey};
+  KeyParams cur_key = {"localhost", "dummy", kCurKey};
+  GetCryptographer()->AddKey(old_key);
+  GetCryptographer()->AddKey(cur_key);
+
+  // Build a migrated nigori with full encryption.
+  {
+    WriteTransaction trans(FROM_HERE, user_share());
+    WriteNode nigori_node(&trans);
+    ASSERT_EQ(nigori_node.InitByTagLookup(kNigoriTag), BaseNode::INIT_OK);
+    sync_pb::NigoriSpecifics nigori;
+    GetCryptographer()->GetKeys(nigori.mutable_encryption_keybag());
+    nigori.set_frozen_keybag(true);
+    nigori.set_keystore_migration_time(1);
+    nigori.set_passphrase_state(sync_pb::NigoriSpecifics::CUSTOM_PASSPHRASE);
+    nigori.set_encrypt_everything(true);
+    nigori_node.SetNigoriSpecifics(nigori);
+  }
+
+  EXPECT_CALL(*observer(),
+              OnPassphraseStateChanged(CUSTOM_PASSPHRASE));
+  EXPECT_CALL(*observer(),
+              OnCryptographerStateChanged(_));
+  EXPECT_CALL(*observer(),
+              OnEncryptedTypesChanged(_, true)).Times(2);
+  EXPECT_CALL(*observer(),
+              OnEncryptionComplete());
+  encryption_handler()->Init();
+  EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
+  EXPECT_TRUE(GetCryptographer()->is_ready());
+  EXPECT_EQ(encryption_handler()->GetPassphraseState(), CUSTOM_PASSPHRASE);
+  EXPECT_TRUE(encryption_handler()->EncryptEverythingEnabled());
+  VerifyMigratedNigoriWithTimestamp(1, CUSTOM_PASSPHRASE, kCurKey);
+
+  {
+    EXPECT_CALL(*observer(),
+                OnBootstrapTokenUpdated(_, KEYSTORE_BOOTSTRAP_TOKEN));
+    ReadTransaction trans(FROM_HERE, user_share());
+    encryption_handler()->SetKeystoreKey(kKeystoreKey, trans.GetWrappedTrans());
+  }
+  Mock::VerifyAndClearExpectations(observer());
+
+  // Now build an old unmigrated nigori node with old encrypted types. We should
+  // properly overwrite it with the migrated + encrypt everything state.
+  EXPECT_CALL(*observer(),
+              OnCryptographerStateChanged(_));
+  {
+    Cryptographer other_cryptographer(GetCryptographer()->encryptor());
+    other_cryptographer.AddKey(old_key);
+    WriteTransaction trans(FROM_HERE, user_share());
+    WriteNode nigori_node(&trans);
+    ASSERT_EQ(nigori_node.InitByTagLookup(kNigoriTag), BaseNode::INIT_OK);
+    sync_pb::NigoriSpecifics nigori;
+    other_cryptographer.GetKeys(nigori.mutable_encryption_keybag());
+    nigori.set_frozen_keybag(false);
+    nigori.set_encrypt_everything(false);
+    encryption_handler()->ApplyNigoriUpdate(nigori, trans.GetWrappedTrans());
+    nigori_node.SetNigoriSpecifics(nigori);
+  }
+  PumpLoop();
+
+  // Verify we're still migrated and have proper encryption state.
+  EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
+  EXPECT_TRUE(GetCryptographer()->is_ready());
+  EXPECT_EQ(encryption_handler()->GetPassphraseState(), CUSTOM_PASSPHRASE);
+  EXPECT_TRUE(encryption_handler()->EncryptEverythingEnabled());
+  VerifyMigratedNigoriWithTimestamp(1, CUSTOM_PASSPHRASE, kCurKey);
+}
+
+// Test that if we have a migrated nigori with a custom passphrase, then receive
+// a migrated nigori with a keystore passphrase, we properly overwrite it with
+// the current state.
+TEST_F(SyncEncryptionHandlerImplTest, ReceiveOldMigratedNigori) {
+  const char kOldKey[] = "old";
+  const char kCurKey[] = "cur";
+  sync_pb::EncryptedData encrypted;
+  KeyParams old_key = {"localhost", "dummy", kOldKey};
+  KeyParams cur_key = {"localhost", "dummy", kCurKey};
+  KeyParams keystore_key = {"localhost", "dummy", kKeystoreKey};
+  GetCryptographer()->AddKey(old_key);
+  GetCryptographer()->AddKey(cur_key);
+
+  // Build a migrated nigori with full encryption.
+  {
+    WriteTransaction trans(FROM_HERE, user_share());
+    WriteNode nigori_node(&trans);
+    ASSERT_EQ(nigori_node.InitByTagLookup(kNigoriTag), BaseNode::INIT_OK);
+    sync_pb::NigoriSpecifics nigori;
+    GetCryptographer()->GetKeys(nigori.mutable_encryption_keybag());
+    nigori.set_frozen_keybag(true);
+    nigori.set_keystore_migration_time(1);
+    nigori.set_passphrase_state(sync_pb::NigoriSpecifics::CUSTOM_PASSPHRASE);
+    nigori.set_encrypt_everything(true);
+    nigori_node.SetNigoriSpecifics(nigori);
+  }
+
+  EXPECT_CALL(*observer(),
+              OnPassphraseStateChanged(CUSTOM_PASSPHRASE));
+  EXPECT_CALL(*observer(),
+              OnCryptographerStateChanged(_));
+  EXPECT_CALL(*observer(),
+              OnEncryptedTypesChanged(_, true)).Times(2);
+  EXPECT_CALL(*observer(),
+              OnEncryptionComplete());
+  encryption_handler()->Init();
+  EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
+  EXPECT_TRUE(GetCryptographer()->is_ready());
+  EXPECT_EQ(encryption_handler()->GetPassphraseState(), CUSTOM_PASSPHRASE);
+  EXPECT_TRUE(encryption_handler()->EncryptEverythingEnabled());
+  VerifyMigratedNigoriWithTimestamp(1, CUSTOM_PASSPHRASE, kCurKey);
+
+  {
+    EXPECT_CALL(*observer(),
+                OnBootstrapTokenUpdated(_, KEYSTORE_BOOTSTRAP_TOKEN));
+    ReadTransaction trans(FROM_HERE, user_share());
+    encryption_handler()->SetKeystoreKey(kKeystoreKey, trans.GetWrappedTrans());
+  }
+  Mock::VerifyAndClearExpectations(observer());
+
+  // Now build an old keystore nigori node with old encrypted types. We should
+  // properly overwrite it with the migrated + encrypt everything state.
+  EXPECT_CALL(*observer(),
+              OnCryptographerStateChanged(_));
+  {
+    WriteTransaction trans(FROM_HERE, user_share());
+    WriteNode nigori_node(&trans);
+    ASSERT_EQ(nigori_node.InitByTagLookup(kNigoriTag), BaseNode::INIT_OK);
+    sync_pb::NigoriSpecifics nigori;
+    Cryptographer other_cryptographer(GetCryptographer()->encryptor());
+    other_cryptographer.AddKey(old_key);
+    std::string keystore_bootstrap;
+    other_cryptographer.GetBootstrapToken(&keystore_bootstrap);
+    other_cryptographer.GetKeys(nigori.mutable_encryption_keybag());
+    other_cryptographer.AddKey(keystore_key);
+    other_cryptographer.EncryptString(keystore_bootstrap,
+                                      nigori.mutable_keystore_bootstrap());
+    nigori.set_frozen_keybag(true);
+    nigori.set_encrypt_everything(false);
+    nigori.set_passphrase_state(sync_pb::NigoriSpecifics::KEYSTORE_PASSPHRASE);
+    nigori.set_keystore_migration_time(1);
+    encryption_handler()->ApplyNigoriUpdate(nigori, trans.GetWrappedTrans());
+    nigori_node.SetNigoriSpecifics(nigori);
+  }
+  PumpLoop();
+
+  // Verify we're still migrated and have proper encryption state.
+  EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
+  EXPECT_TRUE(GetCryptographer()->is_ready());
+  EXPECT_EQ(encryption_handler()->GetPassphraseState(), CUSTOM_PASSPHRASE);
+  EXPECT_TRUE(encryption_handler()->EncryptEverythingEnabled());
+  VerifyMigratedNigoriWithTimestamp(1, CUSTOM_PASSPHRASE, kCurKey);
+}
+
+// Test that if we receive the keystore key after receiving a migrated nigori
+// node, we properly use the keystore bootstrap to decrypt the keybag.
+TEST_F(SyncEncryptionHandlerImplTest, SetKeystoreAfterReceivingMigratedNigori) {
+  const char kCurKey[] = "cur";
+  sync_pb::EncryptedData encrypted;
+  Cryptographer other_cryptographer(GetCryptographer()->encryptor());
+  KeyParams cur_key = {"localhost", "dummy", kCurKey};
+  other_cryptographer.AddKey(cur_key);
+  EXPECT_TRUE(other_cryptographer.is_ready());
+  EXPECT_TRUE(encryption_handler()->GetKeystoreBootstrapKey(
+      other_cryptographer,
+      kKeystoreKey,
+      &encrypted));
+  EXPECT_FALSE(encryption_handler()->MigratedToKeystore());
+  EXPECT_FALSE(GetCryptographer()->is_ready());
+  EXPECT_NE(encryption_handler()->GetPassphraseState(), KEYSTORE_PASSPHRASE);
+
+  // Now build a nigori node with the generated keystore bootstrap token and
+  // initialize the encryption handler with it. The cryptographer should be
+  // bootstrapped properly to decrypt both kCurKey and kKeystoreKey.
+  {
+    WriteTransaction trans(FROM_HERE, user_share());
+    WriteNode nigori_node(&trans);
+    ASSERT_EQ(nigori_node.InitByTagLookup(kNigoriTag), BaseNode::INIT_OK);
+    sync_pb::NigoriSpecifics nigori;
+    nigori.mutable_keystore_bootstrap()->CopyFrom(encrypted);
+    other_cryptographer.GetKeys(nigori.mutable_encryption_keybag());
+    nigori.set_frozen_keybag(true);
+    nigori.set_keystore_migration_time(1);
+    nigori.set_passphrase_state(sync_pb::NigoriSpecifics::KEYSTORE_PASSPHRASE);
+
+    EXPECT_CALL(*observer(),
+                OnPassphraseStateChanged(KEYSTORE_PASSPHRASE));
+    EXPECT_CALL(*observer(),
+                OnCryptographerStateChanged(_));
+    EXPECT_CALL(*observer(),
+                OnPassphraseRequired(_, _));
+    encryption_handler()->ApplyNigoriUpdate(nigori, trans.GetWrappedTrans());
+    nigori_node.SetNigoriSpecifics(nigori);
+  }
+  // Run any tasks posted via AppplyNigoriUpdate.
+  PumpLoop();
+  EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
+  EXPECT_TRUE(GetCryptographer()->has_pending_keys());
+  EXPECT_EQ(encryption_handler()->GetPassphraseState(), KEYSTORE_PASSPHRASE);
+  EXPECT_FALSE(encryption_handler()->EncryptEverythingEnabled());
+  Mock::VerifyAndClearExpectations(observer());
+
+  EXPECT_CALL(*observer(),
+              OnCryptographerStateChanged(_));
+  EXPECT_CALL(*observer(),
+              OnBootstrapTokenUpdated(_, PASSPHRASE_BOOTSTRAP_TOKEN));
+  {
+    EXPECT_CALL(*observer(),
+                OnBootstrapTokenUpdated(_, KEYSTORE_BOOTSTRAP_TOKEN));
+    ReadTransaction trans(FROM_HERE, user_share());
+    encryption_handler()->SetKeystoreKey(kKeystoreKey, trans.GetWrappedTrans());
+  }
+  PumpLoop();
+  EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
+  EXPECT_TRUE(GetCryptographer()->is_ready());
+  EXPECT_EQ(encryption_handler()->GetPassphraseState(), KEYSTORE_PASSPHRASE);
+  EXPECT_FALSE(encryption_handler()->EncryptEverythingEnabled());
+  VerifyMigratedNigoriWithTimestamp(1, KEYSTORE_PASSPHRASE, kCurKey);
+
+  // Check that the cryptographer still encrypts with the current key.
+  sync_pb::EncryptedData current_encrypted;
+  other_cryptographer.EncryptString("string", &current_encrypted);
+  EXPECT_TRUE(GetCryptographer()->CanDecryptUsingDefaultKey(current_encrypted));
+
+  // Check that the cryptographer can decrypt keystore key based encryption.
+  Cryptographer keystore_cryptographer(GetCryptographer()->encryptor());
+  KeyParams keystore_key =  {"localhost", "dummy", kKeystoreKey};
+  keystore_cryptographer.AddKey(keystore_key);
+  sync_pb::EncryptedData keystore_encrypted;
+  keystore_cryptographer.EncryptString("string", &keystore_encrypted);
+  EXPECT_TRUE(GetCryptographer()->CanDecrypt(keystore_encrypted));
+}
+
+// Test that after receiving a migrated nigori and decrypting it using the
+// keystore key, we can then switch to a custom passphrase. The nigori should
+// remain migrated and encrypt everything should be enabled.
+TEST_F(SyncEncryptionHandlerImplTest, SetCustomPassAfterMigration) {
+  const char kOldKey[] = "old";
+  sync_pb::EncryptedData encrypted;
+  Cryptographer other_cryptographer(GetCryptographer()->encryptor());
+  KeyParams cur_key = {"localhost", "dummy", kOldKey};
+  other_cryptographer.AddKey(cur_key);
+  EXPECT_TRUE(other_cryptographer.is_ready());
+  EXPECT_TRUE(encryption_handler()->GetKeystoreBootstrapKey(
+      other_cryptographer,
+      kKeystoreKey,
+      &encrypted));
+
+  // Build a nigori node with the generated keystore bootstrap token and
+  // initialize the encryption handler with it. The cryptographer should be
+  // bootstrapped properly to decrypt both kOldKey and kKeystoreKey.
+  {
+    WriteTransaction trans(FROM_HERE, user_share());
+    WriteNode nigori_node(&trans);
+    ASSERT_EQ(nigori_node.InitByTagLookup(kNigoriTag), BaseNode::INIT_OK);
+    sync_pb::NigoriSpecifics nigori;
+    nigori.mutable_keystore_bootstrap()->CopyFrom(encrypted);
+    other_cryptographer.GetKeys(nigori.mutable_encryption_keybag());
+    nigori.set_frozen_keybag(true);
+    nigori.set_keystore_migration_time(1);
+    nigori.set_passphrase_state(sync_pb::NigoriSpecifics::KEYSTORE_PASSPHRASE);
+    nigori_node.SetNigoriSpecifics(nigori);
+    EXPECT_CALL(*observer(),
+                OnBootstrapTokenUpdated(_, KEYSTORE_BOOTSTRAP_TOKEN));
+    encryption_handler()->SetKeystoreKey(kKeystoreKey, trans.GetWrappedTrans());
+  }
+
+  EXPECT_CALL(*observer(),
+              OnPassphraseStateChanged(KEYSTORE_PASSPHRASE));
+  EXPECT_CALL(*observer(),
+              OnCryptographerStateChanged(_)).Times(2);
+  EXPECT_CALL(*observer(),
+              OnEncryptedTypesChanged(_, false));
+  EXPECT_CALL(*observer(),
+              OnBootstrapTokenUpdated(_, PASSPHRASE_BOOTSTRAP_TOKEN));
+  EXPECT_CALL(*observer(),
+              OnEncryptionComplete());
+  encryption_handler()->Init();
+  EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
+  EXPECT_TRUE(GetCryptographer()->is_ready());
+  EXPECT_EQ(encryption_handler()->GetPassphraseState(), KEYSTORE_PASSPHRASE);
+  EXPECT_FALSE(encryption_handler()->EncryptEverythingEnabled());
+  Mock::VerifyAndClearExpectations(observer());
+
+  const char kNewKey[] = "new_key";
+  EXPECT_CALL(*observer(),
+              OnCryptographerStateChanged(_));
+  EXPECT_CALL(*observer(),
+              OnPassphraseStateChanged(CUSTOM_PASSPHRASE));
+  EXPECT_CALL(*observer(),
+              OnBootstrapTokenUpdated(_, PASSPHRASE_BOOTSTRAP_TOKEN));
+  EXPECT_CALL(*observer(),
+              OnPassphraseAccepted());
+  EXPECT_CALL(*observer(),
+              OnEncryptedTypesChanged(_, true));
+  EXPECT_CALL(*observer(),
+              OnEncryptionComplete()).Times(2);
+  encryption_handler()->SetEncryptionPassphrase(kNewKey, true);
+  EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
+  EXPECT_TRUE(GetCryptographer()->is_ready());
+  EXPECT_EQ(encryption_handler()->GetPassphraseState(), CUSTOM_PASSPHRASE);
+  EXPECT_TRUE(encryption_handler()->EncryptEverythingEnabled());
+  VerifyMigratedNigoriWithTimestamp(1, CUSTOM_PASSPHRASE, kNewKey);
+
+  // Check that the cryptographer can decrypt the old key.
+  sync_pb::EncryptedData old_encrypted;
+  other_cryptographer.EncryptString("string", &old_encrypted);
+  EXPECT_TRUE(GetCryptographer()->CanDecrypt(old_encrypted));
+
+  // Check that the cryptographer can decrypt keystore key based encryption.
+  Cryptographer keystore_cryptographer(GetCryptographer()->encryptor());
+  KeyParams keystore_key =  {"localhost", "dummy", kKeystoreKey};
+  keystore_cryptographer.AddKey(keystore_key);
+  sync_pb::EncryptedData keystore_encrypted;
+  keystore_cryptographer.EncryptString("string", &keystore_encrypted);
+  EXPECT_TRUE(GetCryptographer()->CanDecrypt(keystore_encrypted));
+
+  // Check the the cryptographer is encrypting with the new key.
+  KeyParams new_key = {"localhost", "dummy", kNewKey};
+  Cryptographer new_cryptographer(GetCryptographer()->encryptor());
+  new_cryptographer.AddKey(new_key);
+  sync_pb::EncryptedData new_encrypted;
+  new_cryptographer.EncryptString("string", &new_encrypted);
+  EXPECT_TRUE(GetCryptographer()->CanDecryptUsingDefaultKey(new_encrypted));
+}
+
+// Test that if a client without a keystore key (e.g. one without keystore
+// encryption enabled) receives a migrated nigori and then attempts to set a
+// custom passphrase, it also enables encrypt everything. The nigori node
+// should remain migrated.
+TEST_F(SyncEncryptionHandlerImplTest,
+       SetCustomPassAfterMigrationNoKeystoreKey) {
+  const char kOldKey[] = "old";
+  sync_pb::EncryptedData encrypted;
+  Cryptographer other_cryptographer(GetCryptographer()->encryptor());
+  KeyParams cur_key = {"localhost", "dummy", kOldKey};
+  other_cryptographer.AddKey(cur_key);
+  KeyParams keystore_key = {"localhost", "dummy", kKeystoreKey};
+  other_cryptographer.AddNonDefaultKey(keystore_key);
+  EXPECT_TRUE(other_cryptographer.is_ready());
+  EXPECT_TRUE(encryption_handler()->GetKeystoreBootstrapKey(
+      other_cryptographer,
+      kKeystoreKey,
+      &encrypted));
+
+  // Build a nigori node with the generated keystore bootstrap token and
+  // initialize the encryption handler with it. The cryptographer will have
+  // pending keys until we provide the decryption passphrase.
+  {
+    WriteTransaction trans(FROM_HERE, user_share());
+    WriteNode nigori_node(&trans);
+    ASSERT_EQ(nigori_node.InitByTagLookup(kNigoriTag), BaseNode::INIT_OK);
+    sync_pb::NigoriSpecifics nigori;
+    nigori.mutable_keystore_bootstrap()->CopyFrom(encrypted);
+    other_cryptographer.GetKeys(nigori.mutable_encryption_keybag());
+    nigori.set_frozen_keybag(true);
+    nigori.set_keystore_migration_time(1);
+    nigori.set_passphrase_state(sync_pb::NigoriSpecifics::KEYSTORE_PASSPHRASE);
+    nigori_node.SetNigoriSpecifics(nigori);
+  }
+
+  EXPECT_CALL(*observer(),
+              OnPassphraseRequired(_, _));
+  EXPECT_CALL(*observer(),
+              OnPassphraseStateChanged(KEYSTORE_PASSPHRASE));
+  EXPECT_CALL(*observer(),
+              OnCryptographerStateChanged(_));
+  EXPECT_CALL(*observer(),
+              OnEncryptedTypesChanged(_, false));
+  encryption_handler()->Init();
+  EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
+  EXPECT_TRUE(GetCryptographer()->has_pending_keys());
+  EXPECT_EQ(encryption_handler()->GetPassphraseState(), KEYSTORE_PASSPHRASE);
+  EXPECT_FALSE(encryption_handler()->EncryptEverythingEnabled());
+  Mock::VerifyAndClearExpectations(observer());
+
+  EXPECT_CALL(*observer(),
+              OnPassphraseAccepted());
+  EXPECT_CALL(*observer(),
+              OnCryptographerStateChanged(_));
+  EXPECT_CALL(*observer(),
+              OnBootstrapTokenUpdated(_, PASSPHRASE_BOOTSTRAP_TOKEN));
+  EXPECT_CALL(*observer(),
+              OnEncryptionComplete());
+  encryption_handler()->SetDecryptionPassphrase(kOldKey);
+  EXPECT_TRUE(GetCryptographer()->is_ready());
+  EXPECT_FALSE(encryption_handler()->EncryptEverythingEnabled());
+  Mock::VerifyAndClearExpectations(observer());
+
+  const char kNewKey[] = "new_key";
+  EXPECT_CALL(*observer(),
+              OnCryptographerStateChanged(_));
+  EXPECT_CALL(*observer(),
+              OnPassphraseStateChanged(CUSTOM_PASSPHRASE));
+  EXPECT_CALL(*observer(),
+              OnBootstrapTokenUpdated(_, PASSPHRASE_BOOTSTRAP_TOKEN));
+  EXPECT_CALL(*observer(),
+              OnPassphraseAccepted());
+  EXPECT_CALL(*observer(),
+              OnEncryptedTypesChanged(_, true));
+  EXPECT_CALL(*observer(),
+              OnEncryptionComplete()).Times(2);
+  encryption_handler()->SetEncryptionPassphrase(kNewKey, true);
+  EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
+  EXPECT_TRUE(GetCryptographer()->is_ready());
+  EXPECT_EQ(encryption_handler()->GetPassphraseState(), CUSTOM_PASSPHRASE);
+  EXPECT_TRUE(encryption_handler()->EncryptEverythingEnabled());
+  VerifyMigratedNigoriWithTimestamp(1, CUSTOM_PASSPHRASE, kNewKey);
+
+  // Check that the cryptographer can decrypt the old key.
+  sync_pb::EncryptedData old_encrypted;
+  other_cryptographer.EncryptString("string", &old_encrypted);
+  EXPECT_TRUE(GetCryptographer()->CanDecrypt(old_encrypted));
+
+  // Check that the cryptographer can still decrypt keystore key based
+  // encryption (should have been extracted from the encryption keybag).
+  Cryptographer keystore_cryptographer(GetCryptographer()->encryptor());
+  keystore_cryptographer.AddKey(keystore_key);
+  sync_pb::EncryptedData keystore_encrypted;
+  keystore_cryptographer.EncryptString("string", &keystore_encrypted);
+  EXPECT_TRUE(GetCryptographer()->CanDecrypt(keystore_encrypted));
+
+  // Check the the cryptographer is encrypting with the new key.
+  KeyParams new_key = {"localhost", "dummy", kNewKey};
+  Cryptographer new_cryptographer(GetCryptographer()->encryptor());
+  new_cryptographer.AddKey(new_key);
+  sync_pb::EncryptedData new_encrypted;
+  new_cryptographer.EncryptString("string", &new_encrypted);
+  EXPECT_TRUE(GetCryptographer()->CanDecryptUsingDefaultKey(new_encrypted));
+}
+
+// Test that if a client without a keystore key (e.g. one without keystore
+// encryption enabled) receives a migrated nigori and then attempts to set a
+// new implicit passphrase, we do not modify the nigori node (the implicit
+// passphrase is dropped).
+TEST_F(SyncEncryptionHandlerImplTest,
+       SetImplicitPassAfterMigrationNoKeystoreKey) {
+  const char kOldKey[] = "old";
+  sync_pb::EncryptedData encrypted;
+  Cryptographer other_cryptographer(GetCryptographer()->encryptor());
+  KeyParams cur_key = {"localhost", "dummy", kOldKey};
+  other_cryptographer.AddKey(cur_key);
+  KeyParams keystore_key = {"localhost", "dummy", kKeystoreKey};
+  other_cryptographer.AddNonDefaultKey(keystore_key);
+  EXPECT_TRUE(other_cryptographer.is_ready());
+  EXPECT_TRUE(encryption_handler()->GetKeystoreBootstrapKey(
+      other_cryptographer,
+      kKeystoreKey,
+      &encrypted));
+
+  // Build a nigori node with the generated keystore bootstrap token and
+  // initialize the encryption handler with it. The cryptographer will have
+  // pending keys until we provide the decryption passphrase.
+  {
+    WriteTransaction trans(FROM_HERE, user_share());
+    WriteNode nigori_node(&trans);
+    ASSERT_EQ(nigori_node.InitByTagLookup(kNigoriTag), BaseNode::INIT_OK);
+    sync_pb::NigoriSpecifics nigori;
+    nigori.mutable_keystore_bootstrap()->CopyFrom(encrypted);
+    other_cryptographer.GetKeys(nigori.mutable_encryption_keybag());
+    nigori.set_frozen_keybag(true);
+    nigori.set_keystore_migration_time(1);
+    nigori.set_passphrase_state(sync_pb::NigoriSpecifics::KEYSTORE_PASSPHRASE);
+    nigori_node.SetNigoriSpecifics(nigori);
+  }
+
+  EXPECT_CALL(*observer(),
+              OnPassphraseRequired(_, _));
+  EXPECT_CALL(*observer(),
+              OnPassphraseStateChanged(KEYSTORE_PASSPHRASE));
+  EXPECT_CALL(*observer(),
+              OnCryptographerStateChanged(_));
+  EXPECT_CALL(*observer(),
+              OnEncryptedTypesChanged(_, false));
+  encryption_handler()->Init();
+  EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
+  EXPECT_TRUE(GetCryptographer()->has_pending_keys());
+  EXPECT_EQ(encryption_handler()->GetPassphraseState(), KEYSTORE_PASSPHRASE);
+  EXPECT_FALSE(encryption_handler()->EncryptEverythingEnabled());
+  Mock::VerifyAndClearExpectations(observer());
+
+  EXPECT_CALL(*observer(),
+              OnPassphraseAccepted());
+  EXPECT_CALL(*observer(),
+              OnCryptographerStateChanged(_));
+  EXPECT_CALL(*observer(),
+              OnBootstrapTokenUpdated(_, PASSPHRASE_BOOTSTRAP_TOKEN));
+  EXPECT_CALL(*observer(),
+              OnEncryptionComplete());
+  encryption_handler()->SetDecryptionPassphrase(kOldKey);
+  EXPECT_TRUE(GetCryptographer()->is_ready());
+  EXPECT_FALSE(encryption_handler()->EncryptEverythingEnabled());
+  Mock::VerifyAndClearExpectations(observer());
+
+  // Should get dropped on the floor silently.
+  const char kNewKey[] = "new_key";
+  encryption_handler()->SetEncryptionPassphrase(kNewKey, false);
+  EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
+  EXPECT_TRUE(GetCryptographer()->is_ready());
+  EXPECT_EQ(encryption_handler()->GetPassphraseState(), KEYSTORE_PASSPHRASE);
+  EXPECT_FALSE(encryption_handler()->EncryptEverythingEnabled());
+  VerifyMigratedNigoriWithTimestamp(1, KEYSTORE_PASSPHRASE, kOldKey);
+
+  // Check that the cryptographer can decrypt the old key.
+  sync_pb::EncryptedData old_encrypted;
+  other_cryptographer.EncryptString("string", &old_encrypted);
+  EXPECT_TRUE(GetCryptographer()->CanDecryptUsingDefaultKey(old_encrypted));
+
+  // Check that the cryptographer can still decrypt keystore key based
+  // encryption (due to extracting the keystore key from the encryption keybag).
+  Cryptographer keystore_cryptographer(GetCryptographer()->encryptor());
+  keystore_cryptographer.AddKey(keystore_key);
+  sync_pb::EncryptedData keystore_encrypted;
+  keystore_cryptographer.EncryptString("string", &keystore_encrypted);
+  EXPECT_TRUE(GetCryptographer()->CanDecrypt(keystore_encrypted));
+
+  // Check the the cryptographer does not have the new key.
+  KeyParams new_key = {"localhost", "dummy", kNewKey};
+  Cryptographer new_cryptographer(GetCryptographer()->encryptor());
+  new_cryptographer.AddKey(new_key);
+  sync_pb::EncryptedData new_encrypted;
+  new_cryptographer.EncryptString("string", &new_encrypted);
+  EXPECT_FALSE(GetCryptographer()->CanDecryptUsingDefaultKey(new_encrypted));
+}
+
+// Test that if a client without a keystore key (e.g. one without keystore
+// encryption enabled) receives a migrated nigori in keystore passphrase state
+// and then attempts to enable encrypt everything, we switch to a custom
+// passphrase. The nigori should remain migrated.
+TEST_F(SyncEncryptionHandlerImplTest,
+       MigrateOnEncryptEverythingKeystorePassphrase) {
+  const char kCurKey[] = "cur";
+  sync_pb::EncryptedData encrypted;
+  Cryptographer other_cryptographer(GetCryptographer()->encryptor());
+  KeyParams cur_key = {"localhost", "dummy", kCurKey};
+  other_cryptographer.AddKey(cur_key);
+  KeyParams keystore_key = {"localhost", "dummy", kKeystoreKey};
+  other_cryptographer.AddNonDefaultKey(keystore_key);
+  EXPECT_TRUE(other_cryptographer.is_ready());
+  EXPECT_TRUE(encryption_handler()->GetKeystoreBootstrapKey(
+      other_cryptographer,
+      kKeystoreKey,
+      &encrypted));
+
+  // Build a nigori node with the generated keystore bootstrap token and
+  // initialize the encryption handler with it. The cryptographer will have
+  // pending keys until we provide the decryption passphrase.
+  {
+    WriteTransaction trans(FROM_HERE, user_share());
+    WriteNode nigori_node(&trans);
+    ASSERT_EQ(nigori_node.InitByTagLookup(kNigoriTag), BaseNode::INIT_OK);
+    sync_pb::NigoriSpecifics nigori;
+    nigori.mutable_keystore_bootstrap()->CopyFrom(encrypted);
+    other_cryptographer.GetKeys(nigori.mutable_encryption_keybag());
+    nigori.set_frozen_keybag(true);
+    nigori.set_keystore_migration_time(1);
+    nigori.set_passphrase_state(sync_pb::NigoriSpecifics::KEYSTORE_PASSPHRASE);
+    nigori_node.SetNigoriSpecifics(nigori);
+  }
+  EXPECT_CALL(*observer(),
+              OnPassphraseRequired(_, _));
+  EXPECT_CALL(*observer(),
+              OnPassphraseStateChanged(KEYSTORE_PASSPHRASE));
+  EXPECT_CALL(*observer(),
+              OnCryptographerStateChanged(_));
+  EXPECT_CALL(*observer(),
+              OnEncryptedTypesChanged(_, false));
+  encryption_handler()->Init();
+  EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
+  EXPECT_TRUE(GetCryptographer()->has_pending_keys());
+  EXPECT_EQ(encryption_handler()->GetPassphraseState(), KEYSTORE_PASSPHRASE);
+  EXPECT_FALSE(encryption_handler()->EncryptEverythingEnabled());
+  Mock::VerifyAndClearExpectations(observer());
+
+  EXPECT_CALL(*observer(),
+              OnPassphraseAccepted());
+  EXPECT_CALL(*observer(),
+              OnCryptographerStateChanged(_));
+  EXPECT_CALL(*observer(),
+              OnBootstrapTokenUpdated(_, PASSPHRASE_BOOTSTRAP_TOKEN));
+  EXPECT_CALL(*observer(),
+              OnEncryptionComplete());
+  encryption_handler()->SetDecryptionPassphrase(kCurKey);
+  Mock::VerifyAndClearExpectations(observer());
+
+  EXPECT_CALL(*observer(),
+              OnPassphraseStateChanged(FROZEN_IMPLICIT_PASSPHRASE));
+  EXPECT_CALL(*observer(),
+              OnEncryptionComplete());
+  EXPECT_CALL(*observer(),
+              OnEncryptedTypesChanged(_, true));
+  encryption_handler()->EnableEncryptEverything();
+  Mock::VerifyAndClearExpectations(observer());
+
+  EXPECT_TRUE(encryption_handler()->MigratedToKeystore());
+  EXPECT_TRUE(GetCryptographer()->is_ready());
+  EXPECT_EQ(FROZEN_IMPLICIT_PASSPHRASE,
+            encryption_handler()->GetPassphraseState());
+  EXPECT_TRUE(encryption_handler()->EncryptEverythingEnabled());
+  VerifyMigratedNigoriWithTimestamp(1, FROZEN_IMPLICIT_PASSPHRASE, kCurKey);
+
+  // Check that the cryptographer is encrypting using the frozen current key.
+  sync_pb::EncryptedData current_encrypted;
+  other_cryptographer.EncryptString("string", &current_encrypted);
+  EXPECT_TRUE(GetCryptographer()->CanDecryptUsingDefaultKey(current_encrypted));
+
+  // Check that the cryptographer can still decrypt keystore key based
+  // encryption (due to extracting the keystore key from the encryption keybag).
+  Cryptographer keystore_cryptographer(GetCryptographer()->encryptor());
+  keystore_cryptographer.AddKey(keystore_key);
+  sync_pb::EncryptedData keystore_encrypted;
+  keystore_cryptographer.EncryptString("string", &keystore_encrypted);
+  EXPECT_TRUE(GetCryptographer()->CanDecrypt(keystore_encrypted));
+}
+
 }  // namespace syncer