Merge 108893 - [Sync] Don't commit items we know are not ready.

Items whose version does not match the server version or who require
(re)encryption are filtered out from the set of commit id's.

BUG=100660
TEST=sync_integration_tests, sync_unit_tests


Review URL: http://codereview.chromium.org/8400035

TBR=zea@chromium.org
Review URL: http://codereview.chromium.org/8505036

git-svn-id: svn://svn.chromium.org/chrome/branches/912/src@109306 0039d316-1c4b-4281-b951-d872f2087c98

5 files changed, 262 insertions, 129 deletions

diff --git a/chrome/browser/sync/engine/get_commit_ids_command.cc b/chrome/browser/sync/engine/get_commit_ids_command.cc
index 89fc309..4bfc5e00 100644
--- a/chrome/browser/sync/engine/get_commit_ids_command.cc
+++ b/chrome/browser/sync/engine/get_commit_ids_command.cc
@@ -24,7 +24,8 @@ using sessions::SyncSession;
 using sessions::StatusController;
 
 GetCommitIdsCommand::GetCommitIdsCommand(int commit_batch_size)
-    : requested_commit_batch_size_(commit_batch_size) {}
+    : requested_commit_batch_size_(commit_batch_size),
+      passphrase_missing_(false) {}
 
 GetCommitIdsCommand::~GetCommitIdsCommand() {}
 
@@ -35,17 +36,21 @@ void GetCommitIdsCommand::ExecuteImpl(SyncSession* session) {
   SyncerUtil::GetUnsyncedEntries(session->write_transaction(),
                                  &all_unsynced_handles);
 
-  Cryptographer *cryptographer =
+  Cryptographer* cryptographer =
       session->context()->directory_manager()->GetCryptographer(
           session->write_transaction());
   if (cryptographer) {
-    FilterEntriesNeedingEncryption(cryptographer->GetEncryptedTypes(),
-                                   session->write_transaction(),
-                                   &all_unsynced_handles);
-  }
+    encrypted_types_ = cryptographer->GetEncryptedTypes();
+    passphrase_missing_ = cryptographer->has_pending_keys();
+  };
+  // We filter out all unready entries from the set of unsynced handles to
+  // ensure we don't trigger useless sync cycles attempting to retry due to
+  // there being work to do. (see ScheduleNextSync in sync_scheduler)
+  FilterUnreadyEntries(session->write_transaction(),
+                       &all_unsynced_handles);
+
   StatusController* status = session->status_controller();
   status->set_unsynced_handles(all_unsynced_handles);
-
   BuildCommitIds(status->unsynced_handles(), session->write_transaction(),
                  session->routing_info());
 
@@ -58,35 +63,62 @@ void GetCommitIdsCommand::ExecuteImpl(SyncSession* session) {
   status->set_commit_set(*ordered_commit_set_.get());
 }
 
-// We create a new list of unsynced handles which omits all handles to entries
-// that require encryption but are written in plaintext. If any were found we
-// overwrite |unsynced_handles| with this new list, else no change is made.
-// Static.
-void GetCommitIdsCommand::FilterEntriesNeedingEncryption(
-    const syncable::ModelTypeSet& encrypted_types,
+namespace {
+
+// An entry ready for commit is defined as one not in conflict (SERVER_VERSION
+// == BASE_VERSION || SERVER_VERSION == 0) and not requiring encryption
+// (any entry containing an encrypted datatype while the cryptographer requires
+// a passphrase is not ready for commit.)
+bool IsEntryReadyForCommit(const syncable::ModelTypeSet& encrypted_types,
+                           bool passphrase_missing,
+                           const syncable::Entry& entry) {
+  if (!entry.Get(syncable::IS_UNSYNCED))
+    return false;
+
+  if (entry.Get(syncable::SERVER_VERSION) > 0 &&
+      (entry.Get(syncable::SERVER_VERSION) >
+       entry.Get(syncable::BASE_VERSION))) {
+    // The local and server versions don't match. The item must be in
+    // conflict, so there's no point in attempting to commit.
+    DCHECK(entry.Get(syncable::IS_UNAPPLIED_UPDATE));  // In conflict.
+    // TODO(zea): switch this to DVLOG once it's clear bug 100660 is fixed.
+    VLOG(1) << "Excluding entry from commit due to version mismatch "
+            << entry;
+    return false;
+  }
+
+  if (encrypted_types.count(entry.GetModelType()) > 0 &&
+      (passphrase_missing ||
+       syncable::EntryNeedsEncryption(encrypted_types, entry))) {
+    // This entry requires encryption but is not properly encrypted (possibly
+    // due to the cryptographer not being initialized or the user hasn't
+    // provided the most recent passphrase).
+    // TODO(zea): switch this to DVLOG once it's clear bug 100660 is fixed.
+    VLOG(1) << "Excluding entry from commit due to lack of encryption "
+            << entry;
+    return false;
+  }
+
+  return true;
+}
+
+}  // namespace
+
+void GetCommitIdsCommand::FilterUnreadyEntries(
     syncable::BaseTransaction* trans,
     syncable::Directory::UnsyncedMetaHandles* unsynced_handles) {
-  bool removed_handles = false;
   syncable::Directory::UnsyncedMetaHandles::iterator iter;
   syncable::Directory::UnsyncedMetaHandles new_unsynced_handles;
   new_unsynced_handles.reserve(unsynced_handles->size());
-  // TODO(zea): If this becomes a bottleneck, we should merge this loop into the
-  // AddCreatesAndMoves and AddDeletes loops.
   for (iter = unsynced_handles->begin();
        iter != unsynced_handles->end();
        ++iter) {
     syncable::Entry entry(trans, syncable::GET_BY_HANDLE, *iter);
-    if (syncable::EntryNeedsEncryption(encrypted_types, entry)) {
-      // This entry requires encryption but is not encrypted (possibly due to
-      // the cryptographer not being initialized). Don't add it to our new list
-      // of unsynced handles.
-      removed_handles = true;
-    } else {
+    if (IsEntryReadyForCommit(encrypted_types_, passphrase_missing_, entry))
       new_unsynced_handles.push_back(*iter);
-    }
   }
-  if (removed_handles)
-    *unsynced_handles = new_unsynced_handles;
+  if (new_unsynced_handles.size() != unsynced_handles->size())
+    unsynced_handles->swap(new_unsynced_handles);
 }
 
 void GetCommitIdsCommand::AddUncommittedParentsAndTheirPredecessors(
@@ -117,6 +149,8 @@ void GetCommitIdsCommand::AddUncommittedParentsAndTheirPredecessors(
 
 bool GetCommitIdsCommand::AddItem(syncable::Entry* item,
                                   OrderedCommitSet* result) {
+  if (!IsEntryReadyForCommit(encrypted_types_, passphrase_missing_, *item))
+    return false;
   int64 item_handle = item->Get(syncable::META_HANDLE);
   if (result->HaveCommitItem(item_handle) ||
       ordered_commit_set_->HaveCommitItem(item_handle)) {
diff --git a/chrome/browser/sync/engine/get_commit_ids_command.h b/chrome/browser/sync/engine/get_commit_ids_command.h
index 86024e1..8f41f2f 100644
--- a/chrome/browser/sync/engine/get_commit_ids_command.h
+++ b/chrome/browser/sync/engine/get_commit_ids_command.h
@@ -29,13 +29,6 @@ class GetCommitIdsCommand : public SyncerCommand {
   // SyncerCommand implementation.
   virtual void ExecuteImpl(sessions::SyncSession* session);
 
-  // Filter |unsynced_handles| to exclude all handles to entries that require
-  // encryption but are in plaintext.
-  static void FilterEntriesNeedingEncryption(
-      const syncable::ModelTypeSet& encrypted_types,
-      syncable::BaseTransaction* trans,
-      syncable::Directory::UnsyncedMetaHandles* unsynced_handles);
-
   // Builds a vector of IDs that should be committed.
   void BuildCommitIds(const vector<int64>& unsynced_handles,
                       syncable::WriteTransaction* write_transaction,
@@ -114,6 +107,14 @@ class GetCommitIdsCommand : public SyncerCommand {
   };
 
  private:
+  // Removes all entries not ready for commit from |unsynced_handles|.
+  // An entry is considered unready for commit if it's in conflict or requires
+  // (re)encryption. Any datatype requiring encryption while the cryptographer
+  // is missing a passphrase is considered unready for commit.
+  void FilterUnreadyEntries(
+      syncable::BaseTransaction* trans,
+      syncable::Directory::UnsyncedMetaHandles* unsynced_handles);
+
   void AddUncommittedParentsAndTheirPredecessors(
       syncable::BaseTransaction* trans,
       syncable::Id parent_id,
@@ -144,6 +145,8 @@ class GetCommitIdsCommand : public SyncerCommand {
   scoped_ptr<sessions::OrderedCommitSet> ordered_commit_set_;
 
   int requested_commit_batch_size_;
+  bool passphrase_missing_;
+  syncable::ModelTypeSet encrypted_types_;
 
   DISALLOW_COPY_AND_ASSIGN(GetCommitIdsCommand);
 };
diff --git a/chrome/browser/sync/engine/syncer_unittest.cc b/chrome/browser/sync/engine/syncer_unittest.cc
index 241526c..9985120 100644
--- a/chrome/browser/sync/engine/syncer_unittest.cc
+++ b/chrome/browser/sync/engine/syncer_unittest.cc
@@ -551,54 +551,145 @@ TEST_F(SyncerTest, GetCommitIdsCommandTruncates) {
   DoTruncationTest(dir, unsynced_handle_view, expected_order);
 }
 
-TEST_F(SyncerTest, GetCommitIdsFilterEntriesNeedingEncryption) {
+TEST_F(SyncerTest, GetCommitIdsFiltersUnreadyEntries) {
   ScopedDirLookup dir(syncdb_.manager(), syncdb_.name());
   ASSERT_TRUE(dir.good());
-  int64 handle_x = CreateUnsyncedDirectory("X", ids_.MakeLocal("x"));
-  int64 handle_b = CreateUnsyncedDirectory("B", ids_.MakeLocal("b"));
-  int64 handle_c = CreateUnsyncedDirectory("C", ids_.MakeLocal("c"));
-  int64 handle_e = CreateUnsyncedDirectory("E", ids_.MakeLocal("e"));
-  int64 handle_f = CreateUnsyncedDirectory("F", ids_.MakeLocal("f"));
+  KeyParams key_params = {"localhost", "dummy", "foobar"};
   sync_pb::EncryptedData encrypted;
   sync_pb::EntitySpecifics encrypted_bookmark;
   encrypted_bookmark.mutable_encrypted();
   AddDefaultExtensionValue(syncable::BOOKMARKS, &encrypted_bookmark);
+  mock_server_->AddUpdateDirectory(1, 0, "A", 10, 10);
+  mock_server_->AddUpdateDirectory(2, 0, "B", 10, 10);
+  mock_server_->AddUpdateDirectory(3, 0, "C", 10, 10);
+  mock_server_->AddUpdateDirectory(4, 0, "D", 10, 10);
+  SyncShareAsDelegate();
+  // Server side change will put A in conflict.
+  mock_server_->AddUpdateDirectory(1, 0, "A", 20, 20);
   {
+    // Mark bookmarks as encrypted and set the cryptographer to have pending
+    // keys.
     WriteTransaction wtrans(FROM_HERE, UNITTEST, dir);
-    MutableEntry entry_x(&wtrans, GET_BY_HANDLE, handle_x);
-    MutableEntry entry_b(&wtrans, GET_BY_HANDLE, handle_b);
-    MutableEntry entry_c(&wtrans, GET_BY_HANDLE, handle_c);
-    MutableEntry entry_e(&wtrans, GET_BY_HANDLE, handle_e);
-    MutableEntry entry_f(&wtrans, GET_BY_HANDLE, handle_f);
-    entry_x.Put(SPECIFICS, encrypted_bookmark);
-    entry_x.Put(NON_UNIQUE_NAME, kEncryptedString);
-    entry_b.Put(SPECIFICS, DefaultBookmarkSpecifics());
-    entry_c.Put(SPECIFICS, DefaultBookmarkSpecifics());
-    entry_e.Put(SPECIFICS, encrypted_bookmark);
-    entry_e.Put(NON_UNIQUE_NAME, kEncryptedString);
-    entry_f.Put(SPECIFICS, DefaultPreferencesSpecifics());
-  }
-
-  syncable::ModelTypeSet encrypted_types;
-  encrypted_types.insert(syncable::BOOKMARKS);
-  syncable::Directory::UnsyncedMetaHandles unsynced_handles;
-  unsynced_handles.push_back(handle_x);
-  unsynced_handles.push_back(handle_b);
-  unsynced_handles.push_back(handle_c);
-  unsynced_handles.push_back(handle_e);
-  unsynced_handles.push_back(handle_f);
-  // The unencrypted bookmarks should be removed from the list.
-  syncable::Directory::UnsyncedMetaHandles expected_handles;
-  expected_handles.push_back(handle_x);  // Was encrypted.
-  expected_handles.push_back(handle_e);  // Was encrypted.
-  expected_handles.push_back(handle_f);  // Does not require encryption.
-  {
+    browser_sync::Cryptographer other_cryptographer;
+    other_cryptographer.AddKey(key_params);
+    sync_pb::EntitySpecifics specifics;
+    sync_pb::NigoriSpecifics* nigori =
+        specifics.MutableExtension(sync_pb::nigori);
+    other_cryptographer.GetKeys(nigori->mutable_encrypted());
+    nigori->set_encrypt_bookmarks(true);
+    syncdb_.manager()->GetCryptographer(&wtrans)->Update(*nigori);
+
+    // In conflict but properly encrypted.
+    MutableEntry A(&wtrans, GET_BY_ID, ids_.FromNumber(1));
+    ASSERT_TRUE(A.good());
+    A.Put(IS_UNSYNCED, true);
+    A.Put(SPECIFICS, encrypted_bookmark);
+    A.Put(NON_UNIQUE_NAME, kEncryptedString);
+    // Not in conflict and properly encrypted.
+    MutableEntry B(&wtrans, GET_BY_ID, ids_.FromNumber(2));
+    ASSERT_TRUE(B.good());
+    B.Put(IS_UNSYNCED, true);
+    B.Put(SPECIFICS, encrypted_bookmark);
+    B.Put(NON_UNIQUE_NAME, kEncryptedString);
+    // Unencrypted specifics.
+    MutableEntry C(&wtrans, GET_BY_ID, ids_.FromNumber(3));
+    ASSERT_TRUE(C.good());
+    C.Put(IS_UNSYNCED, true);
+    C.Put(NON_UNIQUE_NAME, kEncryptedString);
+    // Unencrypted non_unique_name.
+    MutableEntry D(&wtrans, GET_BY_ID, ids_.FromNumber(4));
+    ASSERT_TRUE(D.good());
+    D.Put(IS_UNSYNCED, true);
+    D.Put(SPECIFICS, encrypted_bookmark);
+    D.Put(NON_UNIQUE_NAME, "not encrypted");
+  }
+  SyncShareAsDelegate();
+  {
+    // We remove any unready entries from the status controller's unsynced
+    // handles, so this should remain 0 even though the entries didn't commit.
+    ASSERT_EQ(0U, session_->status_controller()->unsynced_handles().size());
+    // Nothing should have commited due to bookmarks being encrypted and
+    // the cryptographer having pending keys. A would have been resolved
+    // as a simple conflict, but still be unsynced until the next sync cycle.
+    ReadTransaction rtrans(FROM_HERE, dir);
+    Entry entryA(&rtrans, syncable::GET_BY_ID, ids_.FromNumber(1));
+    ASSERT_TRUE(entryA.good());
+    EXPECT_TRUE(entryA.Get(IS_UNSYNCED));
+    Entry entryB(&rtrans, syncable::GET_BY_ID, ids_.FromNumber(2));
+    ASSERT_TRUE(entryB.good());
+    EXPECT_TRUE(entryB.Get(IS_UNSYNCED));
+    Entry entryC(&rtrans, syncable::GET_BY_ID, ids_.FromNumber(3));
+    ASSERT_TRUE(entryC.good());
+    EXPECT_TRUE(entryC.Get(IS_UNSYNCED));
+    Entry entryD(&rtrans, syncable::GET_BY_ID, ids_.FromNumber(4));
+    ASSERT_TRUE(entryD.good());
+    EXPECT_TRUE(entryD.Get(IS_UNSYNCED));
+
+    // Resolve the pending keys.
+    syncdb_.manager()->GetCryptographer(&rtrans)->DecryptPendingKeys(
+        key_params);
+  }
+  SyncShareAsDelegate();
+  {
+    ASSERT_EQ(0U, session_->status_controller()->unsynced_handles().size());
+    // All properly encrypted and non-conflicting items should commit. "A" was
+    // conflicting, but last sync cycle resolved it as simple conflict, so on
+    // this sync cycle it committed succesfullly.
+    ReadTransaction rtrans(FROM_HERE, dir);
+    // Committed successfully.
+    Entry entryA(&rtrans, syncable::GET_BY_ID, ids_.FromNumber(1));
+    ASSERT_TRUE(entryA.good());
+    EXPECT_FALSE(entryA.Get(IS_UNSYNCED));
+    EXPECT_FALSE(entryA.Get(IS_UNAPPLIED_UPDATE));
+    // Committed successfully.
+    Entry entryB(&rtrans, syncable::GET_BY_ID, ids_.FromNumber(2));
+    ASSERT_TRUE(entryB.good());
+    EXPECT_FALSE(entryB.Get(IS_UNSYNCED));
+    EXPECT_FALSE(entryB.Get(IS_UNAPPLIED_UPDATE));
+    // Was not properly encrypted.
+    Entry entryC(&rtrans, syncable::GET_BY_ID, ids_.FromNumber(3));
+    ASSERT_TRUE(entryC.good());
+    EXPECT_TRUE(entryC.Get(IS_UNSYNCED));
+    EXPECT_FALSE(entryC.Get(IS_UNAPPLIED_UPDATE));
+    // Was not properly encrypted.
+    Entry entryD(&rtrans, syncable::GET_BY_ID, ids_.FromNumber(4));
+    ASSERT_TRUE(entryD.good());
+    EXPECT_TRUE(entryD.Get(IS_UNSYNCED));
+    EXPECT_FALSE(entryD.Get(IS_UNAPPLIED_UPDATE));
+  }
+  {
+    // Fix the remaining items.
     WriteTransaction wtrans(FROM_HERE, UNITTEST, dir);
-    GetCommitIdsCommand::FilterEntriesNeedingEncryption(
-        encrypted_types,
-        &wtrans,
-        &unsynced_handles);
-    EXPECT_EQ(expected_handles, unsynced_handles);
+    MutableEntry C(&wtrans, GET_BY_ID, ids_.FromNumber(3));
+    ASSERT_TRUE(C.good());
+    C.Put(SPECIFICS, encrypted_bookmark);
+    C.Put(NON_UNIQUE_NAME, kEncryptedString);
+    MutableEntry D(&wtrans, GET_BY_ID, ids_.FromNumber(4));
+    ASSERT_TRUE(D.good());
+    D.Put(SPECIFICS, encrypted_bookmark);
+    D.Put(NON_UNIQUE_NAME, kEncryptedString);
+  }
+  SyncShareAsDelegate();
+  {
+    ASSERT_EQ(0U, session_->status_controller()->unsynced_handles().size());
+    // None should be unsynced anymore.
+    ReadTransaction rtrans(FROM_HERE, dir);
+    Entry entryA(&rtrans, syncable::GET_BY_ID, ids_.FromNumber(1));
+    ASSERT_TRUE(entryA.good());
+    EXPECT_FALSE(entryA.Get(IS_UNSYNCED));
+    EXPECT_FALSE(entryA.Get(IS_UNAPPLIED_UPDATE));
+    Entry entryB(&rtrans, syncable::GET_BY_ID, ids_.FromNumber(2));
+    ASSERT_TRUE(entryB.good());
+    EXPECT_FALSE(entryB.Get(IS_UNSYNCED));
+    EXPECT_FALSE(entryB.Get(IS_UNAPPLIED_UPDATE));
+    Entry entryC(&rtrans, syncable::GET_BY_ID, ids_.FromNumber(3));
+    ASSERT_TRUE(entryC.good());
+    EXPECT_FALSE(entryC.Get(IS_UNSYNCED));
+    EXPECT_FALSE(entryC.Get(IS_UNAPPLIED_UPDATE));
+    Entry entryD(&rtrans, syncable::GET_BY_ID, ids_.FromNumber(4));
+    ASSERT_TRUE(entryD.good());
+    EXPECT_FALSE(entryD.Get(IS_UNSYNCED));
+    EXPECT_FALSE(entryD.Get(IS_UNAPPLIED_UPDATE));
   }
 }
 
@@ -2814,52 +2905,13 @@ TEST_F(SyncerTest, WeMovedSomethingIntoAFolderServerHasDeleted) {
   saw_syncer_event_ = false;
 }
 
-class FolderMoveDeleteRenameTest : public SyncerTest {
- public:
-  FolderMoveDeleteRenameTest() : done_(false) {}
-
-  static const int64 bob_id_number = 1;
-  static const int64 fred_id_number = 2;
-
-  void MoveBobIntoID2Runner() {
-    if (!done_) {
-      MoveBobIntoID2();
-      done_ = true;
-    }
-  }
-
- protected:
-  void MoveBobIntoID2() {
-    ScopedDirLookup dir(syncdb_.manager(), syncdb_.name());
-    CHECK(dir.good());
-
-    WriteTransaction trans(FROM_HERE, UNITTEST, dir);
-    Entry alice(&trans, GET_BY_ID,
-                TestIdFactory::FromNumber(fred_id_number));
-    CHECK(alice.good());
-    EXPECT_TRUE(!alice.Get(IS_DEL));
-    EXPECT_TRUE(alice.Get(SYNCING)) << "Expected to be called mid-commit.";
-    MutableEntry bob(&trans, GET_BY_ID,
-                     TestIdFactory::FromNumber(bob_id_number));
-    CHECK(bob.good());
-    bob.Put(IS_UNSYNCED, true);
-
-    bob.Put(SYNCING, false);
-    bob.Put(PARENT_ID, alice.Get(ID));
-  }
-
-  bool done_;
-};
-
-TEST_F(FolderMoveDeleteRenameTest,
+TEST_F(SyncerTest,
        WeMovedSomethingIntoAFolderServerHasDeletedAndWeRenamed) {
   ScopedDirLookup dir(syncdb_.manager(), syncdb_.name());
   CHECK(dir.good());
 
-  const syncable::Id bob_id = TestIdFactory::FromNumber(
-      FolderMoveDeleteRenameTest::bob_id_number);
-  const syncable::Id fred_id = TestIdFactory::FromNumber(
-      FolderMoveDeleteRenameTest::fred_id_number);
+  const syncable::Id bob_id = TestIdFactory::FromNumber(1);
+  const syncable::Id fred_id = TestIdFactory::FromNumber(2);
 
   mock_server_->AddUpdateDirectory(bob_id, TestIdFactory::root(),
       "bob", 1, 10);
@@ -2873,18 +2925,18 @@ TEST_F(FolderMoveDeleteRenameTest,
     fred.Put(IS_UNSYNCED, true);
     fred.Put(SYNCING, false);
     fred.Put(NON_UNIQUE_NAME, "Alice");
+
+    // Move Bob within Fred (now Alice).
+    MutableEntry bob(&trans, GET_BY_ID, bob_id);
+    CHECK(bob.good());
+    bob.Put(IS_UNSYNCED, true);
+    bob.Put(SYNCING, false);
+    bob.Put(PARENT_ID, fred_id);
   }
   mock_server_->AddUpdateDirectory(fred_id, TestIdFactory::root(),
       "fred", 2, 20);
   mock_server_->SetLastUpdateDeleted();
   mock_server_->set_conflict_all_commits(true);
-  // This test is a little brittle. We want to move the item into the folder
-  // such that we think we're dealing with a simple conflict, but in reality
-  // it's actually a conflict set.
-  mock_server_->SetMidCommitCallback(
-      NewCallback<FolderMoveDeleteRenameTest>(this,
-          &FolderMoveDeleteRenameTest::MoveBobIntoID2Runner));
-  SyncShareAsDelegate();
   SyncShareAsDelegate();
   SyncShareAsDelegate();
   {
diff --git a/chrome/browser/sync/test/integration/two_client_bookmarks_sync_test.cc b/chrome/browser/sync/test/integration/two_client_bookmarks_sync_test.cc
index 8f6059e..259a2f9 100644
--- a/chrome/browser/sync/test/integration/two_client_bookmarks_sync_test.cc
+++ b/chrome/browser/sync/test/integration/two_client_bookmarks_sync_test.cc
@@ -5,6 +5,7 @@
 #include "base/rand_util.h"
 #include "chrome/browser/profiles/profile.h"
 #include "chrome/browser/sync/profile_sync_service_harness.h"
+#include "chrome/browser/sync/sessions/session_state.h"
 #include "chrome/browser/sync/test/integration/bookmarks_helper.h"
 #include "chrome/browser/sync/test/integration/sync_test.h"
 
@@ -37,6 +38,7 @@ const std::wstring kGenericURLTitle = L"URL Title";
 const std::wstring kGenericFolderName = L"Folder Name";
 const std::wstring kGenericSubfolderName = L"Subfolder Name";
 const std::wstring kGenericSubsubfolderName = L"Subsubfolder Name";
+const char* kValidPassphrase = "passphrase!";
 
 class TwoClientBookmarksSyncTest : public SyncTest {
  public:
@@ -1786,6 +1788,50 @@ IN_PROC_BROWSER_TEST_F(TwoClientBookmarksSyncTest,
   ASSERT_TRUE(AllModelsMatchVerifier());
 }
 
-// TODO(zea): Add first time sync functionality testing. In particular, when
-// there are encrypted types in first time sync we need to ensure we don't
-// duplicate bookmarks.
+IN_PROC_BROWSER_TEST_F(TwoClientBookmarksSyncTest,
+                       FirstClientEnablesEncryptionWithPassSecondChanges) {
+  ASSERT_TRUE(SetupSync()) << "SetupSync() failed.";
+  ASSERT_TRUE(AllModelsMatchVerifier());
+
+  // Add initial bookmarks.
+  ASSERT_TRUE(AddURL(0, 0, IndexedURLTitle(0), GURL(IndexedURL(0))) != NULL);
+  ASSERT_TRUE(AddURL(0, 1, IndexedURLTitle(1), GURL(IndexedURL(1))) != NULL);
+  ASSERT_TRUE(AddURL(0, 2, IndexedURLTitle(2), GURL(IndexedURL(2))) != NULL);
+  ASSERT_TRUE(GetClient(0)->AwaitMutualSyncCycleCompletion(GetClient(1)));
+  ASSERT_TRUE(AllModelsMatchVerifier());
+
+  // Set a passphrase and enable encryption on Client 0. Client 1 will not
+  // understand the bookmark updates.
+  GetClient(0)->service()->SetPassphrase(kValidPassphrase, true);
+  ASSERT_TRUE(GetClient(0)->AwaitPassphraseAccepted());
+  ASSERT_TRUE(EnableEncryption(0, syncable::BOOKMARKS));
+  ASSERT_TRUE(GetClient(0)->AwaitMutualSyncCycleCompletion(GetClient(1)));
+  ASSERT_TRUE(IsEncrypted(0, syncable::BOOKMARKS));
+  ASSERT_TRUE(IsEncrypted(1, syncable::BOOKMARKS));
+  ASSERT_TRUE(GetClient(1)->service()->IsPassphraseRequired());
+  ASSERT_GT(GetClient(1)->GetLastSessionSnapshot()->
+      num_conflicting_updates, 3);  // The encrypted nodes.
+
+  // Client 1 adds bookmarks between the first two and between the second two.
+  ASSERT_TRUE(AddURL(0, 1, IndexedURLTitle(3), GURL(IndexedURL(3))) != NULL);
+  ASSERT_TRUE(AddURL(0, 3, IndexedURLTitle(4), GURL(IndexedURL(4))) != NULL);
+  EXPECT_FALSE(AllModelsMatchVerifier());
+  EXPECT_FALSE(AllModelsMatch());
+
+  // Set the passphrase. Everything should resolve.
+  GetClient(1)->service()->SetPassphrase(kValidPassphrase, true);
+  ASSERT_TRUE(GetClient(1)->AwaitPassphraseAccepted());
+  ASSERT_TRUE(GetClient(1)->AwaitMutualSyncCycleCompletion(GetClient(0)));
+  EXPECT_TRUE(AllModelsMatchVerifier());
+  EXPECT_TRUE(AllModelsMatch());
+  ASSERT_EQ(0, GetClient(1)->GetLastSessionSnapshot()->
+      num_conflicting_updates);
+
+  // Ensure everything is syncing normally by appending a final bookmark.
+  ASSERT_TRUE(AddURL(1, 5, IndexedURLTitle(5), GURL(IndexedURL(5))) != NULL);
+  ASSERT_TRUE(GetClient(1)->AwaitMutualSyncCycleCompletion(GetClient(0)));
+  EXPECT_TRUE(AllModelsMatchVerifier());
+  EXPECT_TRUE(AllModelsMatch());
+  ASSERT_EQ(0, GetClient(1)->GetLastSessionSnapshot()->
+      num_conflicting_updates);
+}
diff --git a/chrome/browser/sync/test/integration/two_client_sessions_sync_test.cc b/chrome/browser/sync/test/integration/two_client_sessions_sync_test.cc
index f0aa9bb..84c8a19 100644
--- a/chrome/browser/sync/test/integration/two_client_sessions_sync_test.cc
+++ b/chrome/browser/sync/test/integration/two_client_sessions_sync_test.cc
@@ -251,22 +251,20 @@ IN_PROC_BROWSER_TEST_F(TwoClientSessionsSyncTest,
   ScopedWindowMap client1_windows;
   ASSERT_TRUE(OpenTabAndGetLocalWindows(1, GURL(kURL1),
       client1_windows.GetMutable()));
-  ASSERT_TRUE(GetClient(1)->AwaitMutualSyncCycleCompletion(GetClient(0)));
-  ASSERT_EQ(0, GetClient(1)->GetLastSessionSnapshot()->
-      num_blocking_conflicting_updates);
-  ASSERT_EQ(8, GetClient(1)->GetLastSessionSnapshot()->
-      num_conflicting_updates);  // The same encrypted nodes.
 
   // At this point we enter the passphrase, triggering a resync, in which the
   // local changes of client 1 get overwritten for now.
   GetClient(1)->service()->SetPassphrase(kValidPassphrase, true);
   ASSERT_TRUE(GetClient(1)->AwaitPassphraseAccepted());
   ASSERT_TRUE(GetClient(1)->WaitForTypeEncryption(syncable::SESSIONS));
+  ASSERT_EQ(0, GetClient(1)->GetLastSessionSnapshot()->
+      num_conflicting_updates);
 
   ASSERT_TRUE(IsEncrypted(0, syncable::SESSIONS));
   ASSERT_TRUE(IsEncrypted(1, syncable::SESSIONS));
   // The session data from client 1 got overwritten. As a result, client 0
-  // should have no foreign session data.
+  // should have no foreign session data. TODO(zea): update this once bug 76596
+  // is resolved and we don't choose server wins on encryption conflicts.
   SyncedSessionVector sessions0;
   SyncedSessionVector sessions1;
   ASSERT_FALSE(GetSessionData(0, &sessions0));