diff --git a/lib/elixir/lib/code.ex b/lib/elixir/lib/code.ex
index 97fec1c9ce..5a8204e1ea 100644
--- a/lib/elixir/lib/code.ex
+++ b/lib/elixir/lib/code.ex
@@ -1634,13 +1634,19 @@ defmodule Code do
         nil
 
       :proceed ->
-        loaded =
-          Module.ParallelChecker.verify(fn ->
-            :elixir_compiler.string(charlist, file, fn _, _ -> :ok end)
-          end)
+        try do
+          loaded =
+            Module.ParallelChecker.verify(fn ->
+              :elixir_compiler.string(charlist, file, fn _, _ -> :ok end)
+            end)
 
-        :elixir_code_server.cast({:required, file})
-        loaded
+          :elixir_code_server.cast({:required, file})
+          loaded
+        catch
+          kind, reason ->
+            :elixir_code_server.call({:release, file})
+            :erlang.raise(kind, reason, __STACKTRACE__)
+        end
     end
   end
 
diff --git a/lib/elixir/src/elixir_code_server.erl b/lib/elixir/src/elixir_code_server.erl
index e2baa51c33..bb563d6e4a 100644
--- a/lib/elixir/src/elixir_code_server.erl
+++ b/lib/elixir/src/elixir_code_server.erl
@@ -59,6 +59,9 @@ handle_call({acquire, Path}, From, Config) ->
 handle_call(required, _From, Config) ->
   {reply, [F || {F, true} <- maps:to_list(Config#elixir_code_server.required)], Config};
 
+handle_call({release, Path}, _From, Config) ->
+  {reply, ok, release(Path, Config)};
+
 handle_call(retrieve_compiler_module, _From, Config) ->
   case Config#elixir_code_server.mod_pool of
     {Used, [Mod | Unused], Counter} ->
@@ -140,6 +143,20 @@ terminate(_Reason, _Config) ->
 code_change(_Old, Config, _Extra) ->
   {ok, Config}.
 
+release(Path, Config) ->
+  Current = Config#elixir_code_server.required,
+  case maps:find(Path, Current) of
+    {ok, []} ->
+      Released = maps:remove(Path, Current),
+      Config#elixir_code_server{required=Released};
+    {ok, [Next | Waiting]} ->
+      _ = gen_server:reply(Next, proceed),
+      Released = maps:put(Path, Waiting, Current),
+      Config#elixir_code_server{required=Released};
+    error ->
+      Config
+  end.
+
 compiler_module(I) ->
   list_to_atom("elixir_compiler_" ++ integer_to_list(I)).
 
diff --git a/lib/elixir/test/elixir/code_test.exs b/lib/elixir/test/elixir/code_test.exs
index 18d024511d..036c516401 100644
--- a/lib/elixir/test/elixir/code_test.exs
+++ b/lib/elixir/test/elixir/code_test.exs
@@ -514,6 +514,25 @@ defmodule CodeTest do
     Code.unrequire_files([fixture_path("code_sample.exs")])
   end
 
+  test "require_file/1 releases the file when compilation fails" do
+    path = tmp_path("bad_require_#{System.unique_integer([:positive])}.ex")
+
+    try do
+      File.write!(path, ~s|raise "boom"|)
+
+      assert_raise RuntimeError, "boom", fn ->
+        Code.require_file(path)
+      end
+
+      assert_raise RuntimeError, "boom", fn ->
+        Code.require_file(path)
+      end
+    after
+      File.rm(path)
+      Code.unrequire_files([path])
+    end
+  end
+
   test "string_to_quoted!/2 errors take lines/columns/indentation into account" do
     assert_exception(
       SyntaxError,