diff --git a/dlls/winhttp/request.c b/dlls/winhttp/request.c
index a56572d38c..f610ddef94 100644
--- a/dlls/winhttp/request.c
+++ b/dlls/winhttp/request.c
@@ -909,53 +909,68 @@ static BOOL secure_proxy_connect( request_t *request )
 #define INET6_ADDRSTRLEN 46
 #endif
 
+static WCHAR *addr_to_str( const struct sockaddr *addr )
+{
+    char buf[INET6_ADDRSTRLEN];
+    const void *src;
+
+    switch (addr->sa_family)
+    {
+    case AF_INET:
+        src = &((struct sockaddr_in *)addr)->sin_addr;
+        break;
+    case AF_INET6:
+        src = &((struct sockaddr_in6 *)addr)->sin6_addr;
+        break;
+    default:
+        WARN("unsupported address family %d\n", addr->sa_family);
+        return NULL;
+    }
+    if (!inet_ntop( addr->sa_family, src, buf, sizeof(buf) )) return NULL;
+    return strdupAW( buf );
+}
+
 static BOOL open_connection( request_t *request )
 {
     connect_t *connect;
-    const void *addr;
-    char address[INET6_ADDRSTRLEN];
-    WCHAR *addressW;
+    WCHAR *addressW = NULL;
     INTERNET_PORT port;
     socklen_t slen;
+    struct sockaddr *saddr;
+    DWORD len;
 
     if (netconn_connected( &request->netconn )) return TRUE;
 
     connect = request->connect;
     port = connect->serverport ? connect->serverport : (request->hdr.flags & WINHTTP_FLAG_SECURE ? 443 : 80);
+    saddr = (struct sockaddr *)&connect->sockaddr;
+    slen = sizeof(struct sockaddr);
 
-    send_callback( &request->hdr, WINHTTP_CALLBACK_STATUS_RESOLVING_NAME, connect->servername, strlenW(connect->servername) + 1 );
-
-    slen = sizeof(connect->sockaddr);
-    if (!netconn_resolve( connect->servername, port, (struct sockaddr *)&connect->sockaddr, &slen, request->resolve_timeout )) return FALSE;
-    switch (connect->sockaddr.ss_family)
+    if (!connect->resolved)
     {
-    case AF_INET:
-        addr = &((struct sockaddr_in *)&connect->sockaddr)->sin_addr;
-        break;
-    case AF_INET6:
-        addr = &((struct sockaddr_in6 *)&connect->sockaddr)->sin6_addr;
-        break;
-    default:
-        WARN("unsupported address family %d\n", connect->sockaddr.ss_family);
-        return FALSE;
+        len = strlenW( connect->servername ) + 1;
+        send_callback( &request->hdr, WINHTTP_CALLBACK_STATUS_RESOLVING_NAME, connect->servername, len );
+
+        if (!netconn_resolve( connect->servername, port, saddr, &slen, request->resolve_timeout )) return FALSE;
+        connect->resolved = TRUE;
+
+        if (!(addressW = addr_to_str( saddr ))) return FALSE;
+        len = strlenW( addressW ) + 1;
+        send_callback( &request->hdr, WINHTTP_CALLBACK_STATUS_NAME_RESOLVED, addressW, len );
     }
-    inet_ntop( connect->sockaddr.ss_family, addr, address, sizeof(address) );
-    addressW = strdupAW( address );
-
-    send_callback( &request->hdr, WINHTTP_CALLBACK_STATUS_NAME_RESOLVED, addressW, strlenW(addressW) + 1 );
-
-    TRACE("connecting to %s:%u\n", address, port);
+    if (!addressW && !(addressW = addr_to_str( saddr ))) return FALSE;
+    TRACE("connecting to %s:%u\n", debugstr_w(addressW), port);
 
     send_callback( &request->hdr, WINHTTP_CALLBACK_STATUS_CONNECTING_TO_SERVER, addressW, 0 );
 
-    if (!netconn_create( &request->netconn, connect->sockaddr.ss_family, SOCK_STREAM, 0 ))
+    if (!netconn_create( &request->netconn, saddr->sa_family, SOCK_STREAM, 0 ))
     {
         heap_free( addressW );
         return FALSE;
     }
     netconn_set_timeout( &request->netconn, TRUE, request->send_timeout );
     netconn_set_timeout( &request->netconn, FALSE, request->recv_timeout );
-    if (!netconn_connect( &request->netconn, (struct sockaddr *)&connect->sockaddr, slen, request->connect_timeout ))
+    if (!netconn_connect( &request->netconn, saddr, slen, request->connect_timeout ))
     {
         netconn_close( &request->netconn );
         heap_free( addressW );
diff --git a/dlls/winhttp/session.c b/dlls/winhttp/session.c
index 110de8089f..0f9e78279a 100644
--- a/dlls/winhttp/session.c
+++ b/dlls/winhttp/session.c
@@ -423,7 +423,7 @@ BOOL set_server_for_hostname( connect_t *connect, LPCWSTR server, INTERNET_PORT
                 session->proxy_server, colon - session->proxy_server - 1 ))
             {
                 heap_free( connect->servername );
-                connect->sockaddr.ss_family = 0xffff;
+                connect->resolved = FALSE;
                 if (!(connect->servername = heap_alloc(
                     (colon - session->proxy_server + 1) * sizeof(WCHAR) )))
                 {
@@ -445,7 +445,7 @@ BOOL set_server_for_hostname( connect_t *connect, LPCWSTR server, INTERNET_PORT
                 session->proxy_server ))
             {
                 heap_free( connect->servername );
-                connect->sockaddr.ss_family = 0xffff;
+                connect->resolved = FALSE;
                 if (!(connect->servername = strdupW( session->proxy_server )))
                 {
                     ret = FALSE;
@@ -458,7 +458,7 @@ BOOL set_server_for_hostname( connect_t *connect, LPCWSTR server, INTERNET_PORT
     else if (server)
     {
         heap_free( connect->servername );
-        connect->sockaddr.ss_family = 0xffff;
+        connect->resolved = FALSE;
         if (!(connect->servername = strdupW( server )))
         {
             ret = FALSE;
diff --git a/dlls/winhttp/tests/notification.c b/dlls/winhttp/tests/notification.c
index 7ceede75a3..84a35692b8 100644
--- a/dlls/winhttp/tests/notification.c
+++ b/dlls/winhttp/tests/notification.c
@@ -135,6 +135,16 @@ static const struct notification cache_test[] =
     { winhttp_close_handle,     WINHTTP_CALLBACK_STATUS_CLOSING_CONNECTION, 0, 1 },
     { winhttp_close_handle,     WINHTTP_CALLBACK_STATUS_CONNECTION_CLOSED, 0, 1 },
     { winhttp_close_handle,     WINHTTP_CALLBACK_STATUS_HANDLE_CLOSING, 0, 1 },
+    { winhttp_open_request,     WINHTTP_CALLBACK_STATUS_HANDLE_CREATED, 0 },
+    { winhttp_send_request,     WINHTTP_CALLBACK_STATUS_CONNECTING_TO_SERVER, 0 },
+    { winhttp_send_request,     WINHTTP_CALLBACK_STATUS_CONNECTED_TO_SERVER, 0 },
+    { winhttp_send_request,     WINHTTP_CALLBACK_STATUS_SENDING_REQUEST, 0 },
+    { winhttp_send_request,     WINHTTP_CALLBACK_STATUS_REQUEST_SENT, 0 },
+    { winhttp_receive_response, WINHTTP_CALLBACK_STATUS_RECEIVING_RESPONSE, 0 },
+    { winhttp_receive_response, WINHTTP_CALLBACK_STATUS_RESPONSE_RECEIVED, 0 },
+    { winhttp_close_handle,     WINHTTP_CALLBACK_STATUS_CLOSING_CONNECTION, 0, 1 },
+    { winhttp_close_handle,     WINHTTP_CALLBACK_STATUS_CONNECTION_CLOSED, 0, 1 },
+    { winhttp_close_handle,     WINHTTP_CALLBACK_STATUS_HANDLE_CLOSING, 0, 1 },
     { winhttp_close_handle,     WINHTTP_CALLBACK_STATUS_HANDLE_CLOSING, 1, 1 },
     { winhttp_close_handle,     WINHTTP_CALLBACK_STATUS_HANDLE_CLOSING, 1, 1 }
 };
@@ -188,6 +198,32 @@ static void test_connection_cache( void )
     ok(ret, "failed unexpectedly %u\n", GetLastError());
     ok(status == 200, "request failed unexpectedly %u\n", status);
 
+    setup_test( &info, winhttp_close_handle, __LINE__ );
+    WinHttpCloseHandle( req );
+
+    setup_test( &info, winhttp_open_request, __LINE__ );
+    req = WinHttpOpenRequest( con, NULL, NULL, NULL, NULL, NULL, 0 );
+    ok(req != NULL, "failed to open a request %u\n", GetLastError());
+
+    ret = WinHttpSetOption( req, WINHTTP_OPTION_CONTEXT_VALUE, &context, sizeof(struct info *) );
+    ok(ret, "failed to set context value %u\n", GetLastError());
+
+    setup_test( &info, winhttp_send_request, __LINE__ );
+    ret = WinHttpSendRequest( req, NULL, 0, NULL, 0, 0, 0 );
+    ok(ret, "failed to send request %u\n", GetLastError());
+
+    setup_test( &info, winhttp_receive_response, __LINE__ );
+    ret = WinHttpReceiveResponse( req, NULL );
+    ok(ret, "failed to receive response %u\n", GetLastError());
+
+    size = sizeof(status);
+    ret = WinHttpQueryHeaders( req, WINHTTP_QUERY_STATUS_CODE | WINHTTP_QUERY_FLAG_NUMBER, NULL, &status, &size, NULL );
+    ok(ret, "failed unexpectedly %u\n", GetLastError());
+    ok(status == 200, "request failed unexpectedly %u\n", status);
+
+    setup_test( &info, winhttp_close_handle, __LINE__ );
+    WinHttpCloseHandle( req );
+
     setup_test( &info, winhttp_close_handle, __LINE__ );
     WinHttpCloseHandle( req );
     WinHttpCloseHandle( con );
@@ -229,6 +265,29 @@ static void test_connection_cache( void )
     ok(ret, "failed unexpectedly %u\n", GetLastError());
     ok(status == 200, "request failed unexpectedly %u\n", status);
 
+    setup_test( &info, winhttp_close_handle, __LINE__ );
+    WinHttpCloseHandle( req );
+
+    setup_test( &info, winhttp_open_request, __LINE__ );
+    req = WinHttpOpenRequest( con, NULL, NULL, NULL, NULL, NULL, 0 );
+    ok(req != NULL, "failed to open a request %u\n", GetLastError());
+
+    ret = WinHttpSetOption( req, WINHTTP_OPTION_CONTEXT_VALUE, &context, sizeof(struct info *) );
+    ok(ret, "failed to set context value %u\n", GetLastError());
+
+    setup_test( &info, winhttp_send_request, __LINE__ );
+    ret = WinHttpSendRequest( req, NULL, 0, NULL, 0, 0, 0 );
+    ok(ret, "failed to send request %u\n", GetLastError());
+
+    setup_test( &info, winhttp_receive_response, __LINE__ );
+    ret = WinHttpReceiveResponse( req, NULL );
+    ok(ret, "failed to receive response %u\n", GetLastError());
+
+    size = sizeof(status);
+    ret = WinHttpQueryHeaders( req, WINHTTP_QUERY_STATUS_CODE | WINHTTP_QUERY_FLAG_NUMBER, NULL, &status, &size, NULL );
+    ok(ret, "failed unexpectedly %u\n", GetLastError());
+    ok(status == 200, "request failed unexpectedly %u\n", status);
+
     setup_test( &info, winhttp_close_handle, __LINE__ );
     WinHttpCloseHandle( req );
     WinHttpCloseHandle( con );
diff --git a/dlls/winhttp/winhttp_private.h b/dlls/winhttp/winhttp_private.h
index fbd5032e17..7105553a21 100644
--- a/dlls/winhttp/winhttp_private.h
+++ b/dlls/winhttp/winhttp_private.h
@@ -119,6 +119,7 @@ typedef struct
     INTERNET_PORT hostport;
     INTERNET_PORT serverport;
     struct sockaddr_storage sockaddr;
+    BOOL resolved;
 } connect_t;
 
 typedef struct