diff --git a/libol-tests.vcxproj b/libol-tests.vcxproj
index 911a266f..24351d8f 100644
--- a/libol-tests.vcxproj
+++ b/libol-tests.vcxproj
@@ -22,6 +22,7 @@
   </ItemGroup>
   <ItemGroup>
     <ClCompile Include="test\echo-server.c" />
+    <ClCompile Include="test\test-callback-stack.c" />
     <ClCompile Include="test\test-fail-always.c" />
     <ClCompile Include="test\test-pass-always.c" />
     <ClCompile Include="test\test-ping-pong.c" />
diff --git a/ol-win.c b/ol-win.c
index b46c2469..a45c95a1 100644
--- a/ol-win.c
+++ b/ol-win.c
@@ -285,7 +285,10 @@ ol_handle* ol_tcp_handle_new(ol_close_cb close_cb, void* data) {
 
 
 int ol_close_error(ol_handle* handle, ol_err e) {
+  ol_req *req;
+
   if (handle->_.flags & OL_HANDLE_CLOSING)
+
     return 0;
 
   handle->_.error = e;
@@ -293,17 +296,21 @@ int ol_close_error(ol_handle* handle, ol_err e) {
   switch (handle->type) {
     case OL_TCP:
       closesocket(handle->_.socket);
-      if (handle->_.reqs_pending != 0) {
-        /* Cannot free the handle right now because there are queued */
-        /* operations. Close the socket, wait for for all packets to come */
-        /* out, then have ol_poll call close_cb. */
-        handle->_.flags |= OL_HANDLE_CLOSING;
-      } else {
-        /* There are no pending operations. Call the close callback now. */
-        handle->_.flags |= OL_HANDLE_CLOSED;
-        if (handle->close_cb)
-          handle->close_cb(handle, e);
+      if (handle->_.reqs_pending == 0) {
+        /* If there are no operations queued for this socket, queue one */
+        /* manually, so ol_poll will call close_cb. */
+        req = (ol_req*)malloc(sizeof(*req));
+        req->handle = handle;
+        req->type = OL_CLOSE;
+        req->_.flags = 0;
+        if (!PostQueuedCompletionStatus(ol_iocp_, 0, (ULONG_PTR)handle, &req->_.overlapped))
+          ol_fatal_error(GetLastError(), "PostQueuedCompletionStatus");
+        req->_.flags |= OL_REQ_PENDING;
+        handle->_.reqs_pending++;
       }
+
+      /* After all packets to come out, ol_poll will call close_cb. */
+      handle->_.flags |= OL_HANDLE_CLOSING;
       return 0;
 
     default:
@@ -588,7 +595,6 @@ void ol_poll() {
       handle->_.flags |= OL_HANDLE_CLOSED;
       if (handle->close_cb)
         handle->close_cb(handle, handle->_.error);
-      ol_refs_--;
     }
     return;
   }
@@ -649,6 +655,10 @@ void ol_poll() {
         free(req);
       }
       return;
+
+    case OL_CLOSE:
+      /* Should never get here */
+      assert(0);
   }
 }
 
diff --git a/ol-win.h b/ol-win.h
index edaad484..138516f5 100644
--- a/ol-win.h
+++ b/ol-win.h
@@ -28,5 +28,4 @@ typedef struct {
   unsigned int flags;
   unsigned int reqs_pending;
   ol_err error;
-} ol_handle_private;
-
+} ol_handle_private;
\ No newline at end of file
diff --git a/ol.h b/ol.h
index 141d007e..cc959f6a 100644
--- a/ol.h
+++ b/ol.h
@@ -52,7 +52,8 @@ typedef enum {
   OL_ACCEPT,
   OL_READ,
   OL_WRITE,
-  OL_SHUTDOWN
+  OL_SHUTDOWN,
+  OL_CLOSE
 } ol_req_type;
 
 
diff --git a/test/test-callback-stack.c b/test/test-callback-stack.c
new file mode 100644
index 00000000..9e89b96c
--- /dev/null
+++ b/test/test-callback-stack.c
@@ -0,0 +1,32 @@
+#include "../ol.h"
+#include "test.h"
+
+
+int nested = 0;
+int close_cb_called = 0;
+
+
+void close_cb(ol_handle *handle, ol_err e) {
+  assert("ol_close error" && e == 0);
+  assert("ol_close_cb not called from a fresh stack" && nested == 0);
+  close_cb_called++;
+  ol_free(handle);
+}
+
+
+TEST_IMPL(close_cb_stack) {
+  ol_handle *handle;
+
+  ol_init();
+  handle = ol_tcp_handle_new(&close_cb, NULL);
+
+  nested++;
+  ol_close(handle);
+  nested--;
+
+  ol_run();
+
+  assert("ol_close_cb not called exactly once" && close_cb_called);
+
+  return 0;
+}
\ No newline at end of file
diff --git a/test/test-list.h b/test/test-list.h
index 28714fd3..28530a18 100644
--- a/test/test-list.h
+++ b/test/test-list.h
@@ -1,5 +1,6 @@
 TEST_DECLARE (echo_server)
 TEST_DECLARE (ping_pong)
+TEST_DECLARE (close_cb_stack);
 TEST_DECLARE (pass_always)
 TEST_DECLARE (fail_always)
 
@@ -7,6 +8,8 @@ TEST_LIST_START
   TEST_ENTRY  (ping_pong)
   TEST_HELPER (ping_pong, echo_server)
 
+  TEST_ENTRY  (close_cb_stack)
+
   TEST_ENTRY  (fail_always)
 
   TEST_ENTRY  (pass_always)