diff --git a/db/column_family_test.cc b/db/column_family_test.cc
index fddbaf518..1fe7601b1 100644
--- a/db/column_family_test.cc
+++ b/db/column_family_test.cc
@@ -2542,6 +2542,36 @@ TEST_F(ColumnFamilyTest, CompactionSpeedupTwoColumnFamilies) {
   cfd->RecalculateWriteStallConditions(mutable_cf_options);
   ASSERT_EQ(2, dbfull()->BGCompactionsAllowed());
 }
+
+TEST_F(ColumnFamilyTest, LogSyncConflictFlush) {
+  Open();
+  CreateColumnFamiliesAndReopen({"one", "two"});
+
+  Put(0, "", "");
+  Put(1, "foo", "bar");
+
+  rocksdb::SyncPoint::GetInstance()->LoadDependency(
+      {{"DBImpl::SyncWAL:BeforeMarkLogsSynced:1",
+        "ColumnFamilyTest::LogSyncConflictFlush:1"},
+       {"ColumnFamilyTest::LogSyncConflictFlush:2",
+        "DBImpl::SyncWAL:BeforeMarkLogsSynced:2"}});
+
+  rocksdb::SyncPoint::GetInstance()->EnableProcessing();
+
+  std::thread thread([&] { db_->SyncWAL(); });
+
+  TEST_SYNC_POINT("ColumnFamilyTest::LogSyncConflictFlush:1");
+  Flush(1);
+  Put(1, "foo", "bar");
+  Flush(1);
+
+  TEST_SYNC_POINT("ColumnFamilyTest::LogSyncConflictFlush:2");
+
+  thread.join();
+
+  rocksdb::SyncPoint::GetInstance()->DisableProcessing();
+  Close();
+}
 }  // namespace rocksdb
 
 int main(int argc, char** argv) {
diff --git a/db/db_impl.cc b/db/db_impl.cc
index d29df88c1..683006388 100644
--- a/db/db_impl.cc
+++ b/db/db_impl.cc
@@ -2202,6 +2202,9 @@ Status DBImpl::SyncWAL() {
     status = directories_.GetWalDir()->Fsync();
   }
 
+  TEST_SYNC_POINT("DBImpl::SyncWAL:BeforeMarkLogsSynced:1");
+  TEST_SYNC_POINT("DBImpl::SyncWAL:BeforeMarkLogsSynced:2");
+
   {
     InstrumentedMutexLock l(&mutex_);
     MarkLogsSynced(current_log_number, need_log_dir_sync, status);
@@ -2229,7 +2232,8 @@ void DBImpl::MarkLogsSynced(
       ++it;
     }
   }
-  assert(logs_.empty() || (logs_.size() == 1 && !logs_[0].getting_synced));
+  assert(logs_.empty() || logs_[0].number > up_to ||
+         (logs_.size() == 1 && !logs_[0].getting_synced));
   log_sync_cv_.SignalAll();
 }