diff --git a/dlls/winhttp/session.c b/dlls/winhttp/session.c
index 2fae530cfd2..3dbbad37265 100644
--- a/dlls/winhttp/session.c
+++ b/dlls/winhttp/session.c
@@ -98,6 +98,8 @@ static void session_destroy( object_header_t *hdr )
 
     TRACE("%p\n", session);
 
+    if (session->unload_event) SetEvent( session->unload_event );
+
     LIST_FOR_EACH_SAFE( item, next, &session->cookie_cache )
     {
         domain = LIST_ENTRY( item, domain_t, entry );
@@ -199,6 +201,10 @@ static BOOL session_set_option( object_header_t *hdr, DWORD option, LPVOID buffe
     case WINHTTP_OPTION_CONFIGURE_PASSPORT_AUTH:
         FIXME("WINHTTP_OPTION_CONFIGURE_PASSPORT_AUTH: 0x%x\n", *(DWORD *)buffer);
         return TRUE;
+    case WINHTTP_OPTION_UNLOAD_NOTIFY_EVENT:
+        TRACE("WINHTTP_OPTION_UNLOAD_NOTIFY_EVENT: %p\n", *(HANDLE *)buffer);
+        session->unload_event = *(HANDLE *)buffer;
+        return TRUE;
     default:
         FIXME("unimplemented option %u\n", option);
         set_last_error( ERROR_INVALID_PARAMETER );
diff --git a/dlls/winhttp/tests/notification.c b/dlls/winhttp/tests/notification.c
index e14af6d03ea..5db8fe384ce 100644
--- a/dlls/winhttp/tests/notification.c
+++ b/dlls/winhttp/tests/notification.c
@@ -158,9 +158,9 @@ static void setup_test( struct info *info, enum api function, unsigned int line
 
 static void test_connection_cache( void )
 {
-    HANDLE ses, con, req;
+    HANDLE ses, con, req, event;
     DWORD size, status;
-    BOOL ret;
+    BOOL ret, unload = TRUE;
     struct info info, *context = &info;
 
     info.test  = cache_test;
@@ -171,6 +171,14 @@ static void test_connection_cache( void )
     ses = WinHttpOpen( user_agent, 0, NULL, NULL, 0 );
     ok(ses != NULL, "failed to open session %u\n", GetLastError());
 
+    event = CreateEventW( NULL, FALSE, FALSE, NULL );
+    ret = WinHttpSetOption( ses, WINHTTP_OPTION_UNLOAD_NOTIFY_EVENT, &event, sizeof(event) );
+    if (!ret)
+    {
+        win_skip("Unload event not supported\n");
+        unload = FALSE;
+    }
+
     WinHttpSetStatusCallback( ses, check_notification, WINHTTP_CALLBACK_FLAG_ALL_NOTIFICATIONS, 0 );
 
     ret = WinHttpSetOption( ses, WINHTTP_OPTION_CONTEXT_VALUE, &context, sizeof(struct info *) );
@@ -236,15 +244,33 @@ static void test_connection_cache( void )
     setup_test( &info, winhttp_close_handle, __LINE__ );
     WinHttpCloseHandle( req );
     WinHttpCloseHandle( con );
+
+    if (unload)
+    {
+        status = WaitForSingleObject( event, 0 );
+        ok(status == WAIT_TIMEOUT, "got %08x\n", status);
+    }
+
     WinHttpCloseHandle( ses );
 
     Sleep(2000); /* make sure connection is evicted from cache */
+    if (unload)
+    {
+        status = WaitForSingleObject( event, 0 );
+        ok(status == WAIT_OBJECT_0, "got %08x\n", status);
+    }
 
     info.index = 0;
 
     ses = WinHttpOpen( user_agent, 0, NULL, NULL, 0 );
     ok(ses != NULL, "failed to open session %u\n", GetLastError());
 
+    if (unload)
+    {
+        ret = WinHttpSetOption( ses, WINHTTP_OPTION_UNLOAD_NOTIFY_EVENT, &event, sizeof(event) );
+        ok(ret, "failed to set unload option\n");
+    }
+
     WinHttpSetStatusCallback( ses, check_notification, WINHTTP_CALLBACK_FLAG_ALL_NOTIFICATIONS, 0 );
 
     ret = WinHttpSetOption( ses, WINHTTP_OPTION_CONTEXT_VALUE, &context, sizeof(struct info *) );
@@ -311,9 +337,23 @@ static void test_connection_cache( void )
 done:
     WinHttpCloseHandle( req );
     WinHttpCloseHandle( con );
+
+    if (unload)
+    {
+        status = WaitForSingleObject( event, 0 );
+        ok(status == WAIT_TIMEOUT, "got %08x\n", status);
+    }
+
     WinHttpCloseHandle( ses );
 
     Sleep(2000); /* make sure connection is evicted from cache */
+    if (unload)
+    {
+        status = WaitForSingleObject( event, 0 );
+        ok(status == WAIT_OBJECT_0, "got %08x\n", status);
+    }
+
+    CloseHandle( event );
 }
 
 static const struct notification redirect_test[] =
@@ -433,9 +473,9 @@ static const struct notification async_test[] =
 
 static void test_async( void )
 {
-    HANDLE ses, con, req;
+    HANDLE ses, con, req, event;
     DWORD size, status;
-    BOOL ret;
+    BOOL ret, unload = TRUE;
     struct info info, *context = &info;
     char buffer[1024];
 
@@ -447,6 +487,14 @@ static void test_async( void )
     ses = WinHttpOpen( user_agent, 0, NULL, NULL, WINHTTP_FLAG_ASYNC );
     ok(ses != NULL, "failed to open session %u\n", GetLastError());
 
+    event = CreateEventW( NULL, FALSE, FALSE, NULL );
+    ret = WinHttpSetOption( ses, WINHTTP_OPTION_UNLOAD_NOTIFY_EVENT, &event, sizeof(event) );
+    if (!ret)
+    {
+        win_skip("Unload event not supported\n");
+        unload = FALSE;
+    }
+
     WinHttpSetStatusCallback( ses, check_notification, WINHTTP_CALLBACK_FLAG_ALL_NOTIFICATIONS, 0 );
 
     ret = WinHttpSetOption( ses, WINHTTP_OPTION_CONTEXT_VALUE, &context, sizeof(struct info *) );
@@ -501,9 +549,22 @@ static void test_async( void )
     setup_test( &info, winhttp_close_handle, __LINE__ );
     WinHttpCloseHandle( req );
     WinHttpCloseHandle( con );
+
+    if (unload)
+    {
+        status = WaitForSingleObject( event, 0 );
+        ok(status == WAIT_TIMEOUT, "got %08x\n", status);
+    }
     WinHttpCloseHandle( ses );
 
     WaitForSingleObject( info.wait, INFINITE );
+
+    if (unload)
+    {
+        status = WaitForSingleObject( event, 2000 );
+        ok(status == WAIT_OBJECT_0, "got %08x\n", status);
+    }
+    CloseHandle( event );
     CloseHandle( info.wait );
 }
 
diff --git a/dlls/winhttp/winhttp_private.h b/dlls/winhttp/winhttp_private.h
index 6a7dd3e439a..b3e28d2c18b 100644
--- a/dlls/winhttp/winhttp_private.h
+++ b/dlls/winhttp/winhttp_private.h
@@ -110,6 +110,7 @@ typedef struct
     LPWSTR proxy_username;
     LPWSTR proxy_password;
     struct list cookie_cache;
+    HANDLE unload_event;
 } session_t;
 
 typedef struct