diff --git a/src/bitcask.erl b/src/bitcask.erl
index e62d534b..ef794b74 100644
--- a/src/bitcask.erl
+++ b/src/bitcask.erl
@@ -1729,15 +1729,21 @@ do_put(Key, Value, #bc_state{write_file = WriteFile} = State,
                     State3 = wrap_write_file(State2),
                     do_put(Key, Value, State3, Retries - 1, already_exists);
                     
-                #bitcask_entry{file_id=OldFileId,offset=OldOffset}
-                  when OldFileId =< WriteFileId ->
-                    PrevTombstone = <<?TOMBSTONE2_STR, OldFileId:32>>,
-                    {ok, WriteFile1, _, _} =
-                        bitcask_fileops:write(WriteFile0, Key, PrevTombstone,
-                                              Tstamp),
-                    State3 = State2#bc_state{write_file = WriteFile1},
+                #bitcask_entry{file_id=OldFileId,offset=OldOffset} ->
+                    State3 =
+                        case OldFileId < WriteFileId of
+                            true ->
+                                PrevTomb = <<?TOMBSTONE2_STR, OldFileId:32>>,
+                                {ok, WriteFile1, _, _} =
+                                    bitcask_fileops:write(WriteFile0, Key,
+                                                          PrevTomb, Tstamp),
+                                State2#bc_state{write_file = WriteFile1};
+                            false ->
+                                State2
+                        end,
                     write_and_keydir_put(State3, Key, Value, Tstamp, Retries,
                                          bitcask_time:tstamp(), OldFileId, OldOffset);
+
                 _ ->
                     State3 = State2#bc_state{write_file = WriteFile0},
                     write_and_keydir_put(State3, Key, Value, Tstamp, Retries,
@@ -3439,6 +3445,31 @@ legacy_tombstones_test2() ->
     bitcask:close(B),
     ?assertEqual([Last], AllFiles3).
 
+update_tombstones_test() ->
+    Dir = "/tmp/bc.update.tombstones",
+    Key = <<"k">>,
+    Data = [{Key, integer_to_binary(N)} || N <- lists:seq(1, 10)],
+    B = init_dataset(Dir, [read_write, {max_file_size, 50000000}], Data),
+    ok = bitcask:close(B),
+    % Re-open to guarantee opening a second file.
+    % An update on the new file requires a tombstone.
+    B2 = bitcask:open(Dir, [read_write, {max_file_size, 50000000}]),
+    ok = bitcask:put(B2, Key, <<"last_val">>),
+    ok = bitcask:close(B2),
+    Files = bitcask:readable_files(Dir),
+    Fds = [begin
+               {ok, Fd} = bitcask_fileops:open_file(File),
+               Fd
+           end || File <- Files],
+    CountF = fun(_K, V, _Tstamp, _, Acc) ->
+                     case bitcask:is_tombstone(V) of
+                         true -> Acc + 1;
+                         false -> Acc
+                     end
+             end,
+    TombCount = bitcask:subfold(CountF, Fds, 0),
+    ?assertEqual(1, TombCount).
+
 make_merge_file(Dir, Seed, Probability) ->
     random:seed(Seed),
     case filelib:is_dir(Dir) of