diff --git a/src/common/http_downloader.cpp b/src/common/http_downloader.cpp
index 9180b20b1..e0f898a9a 100644
--- a/src/common/http_downloader.cpp
+++ b/src/common/http_downloader.cpp
@@ -110,7 +110,7 @@ void HTTPDownloader::LockedPollRequests(std::unique_lock<std::mutex>& lock)
       m_pending_http_requests.erase(m_pending_http_requests.begin() + index);
       lock.unlock();
 
-      req->callback(-1, std::string(), Request::Data());
+      req->callback(HTTP_STATUS_TIMEOUT, std::string(), Request::Data());
 
       CloseRequest(req);
 
diff --git a/src/common/http_downloader.h b/src/common/http_downloader.h
index 8da450cc3..f9eb01f10 100644
--- a/src/common/http_downloader.h
+++ b/src/common/http_downloader.h
@@ -18,7 +18,10 @@ class HTTPDownloader
 public:
   enum : s32
   {
-    HTTP_OK = 200
+    HTTP_STATUS_CANCELLED = -3,
+    HTTP_STATUS_TIMEOUT = -2,
+    HTTP_STATUS_ERROR = -1,
+    HTTP_STATUS_OK = 200
   };
 
   struct Request
diff --git a/src/common/http_downloader_winhttp.cpp b/src/common/http_downloader_winhttp.cpp
index 18d381bec..3af53abab 100644
--- a/src/common/http_downloader_winhttp.cpp
+++ b/src/common/http_downloader_winhttp.cpp
@@ -90,7 +90,7 @@ void CALLBACK HTTPDownloaderWinHttp::HTTPStatusCallback(HINTERNET hRequest, DWOR
     {
       const WINHTTP_ASYNC_RESULT* res = reinterpret_cast<const WINHTTP_ASYNC_RESULT*>(lpvStatusInformation);
       Log_ErrorPrintf("WinHttp async function %p returned error %u", res->dwResult, res->dwError);
-      req->status_code = -1;
+      req->status_code = HTTP_STATUS_ERROR;
       req->state.store(Request::State::Complete);
       return;
     }
@@ -100,7 +100,7 @@ void CALLBACK HTTPDownloaderWinHttp::HTTPStatusCallback(HINTERNET hRequest, DWOR
       if (!WinHttpReceiveResponse(hRequest, nullptr))
       {
         Log_ErrorPrintf("WinHttpReceiveResponse() failed: %u", GetLastError());
-        req->status_code = -1;
+        req->status_code = HTTP_STATUS_ERROR;
         req->state.store(Request::State::Complete);
       }
 
@@ -115,7 +115,7 @@ void CALLBACK HTTPDownloaderWinHttp::HTTPStatusCallback(HINTERNET hRequest, DWOR
                                WINHTTP_HEADER_NAME_BY_INDEX, &req->status_code, &buffer_size, WINHTTP_NO_HEADER_INDEX))
       {
         Log_ErrorPrintf("WinHttpQueryHeaders() for status code failed: %u", GetLastError());
-        req->status_code = -1;
+        req->status_code = HTTP_STATUS_ERROR;
         req->state.store(Request::State::Complete);
         return;
       }
@@ -153,7 +153,7 @@ void CALLBACK HTTPDownloaderWinHttp::HTTPStatusCallback(HINTERNET hRequest, DWOR
       if (!WinHttpQueryDataAvailable(hRequest, nullptr) && GetLastError() != ERROR_IO_PENDING)
       {
         Log_ErrorPrintf("WinHttpQueryDataAvailable() failed: %u", GetLastError());
-        req->status_code = -1;
+        req->status_code = HTTP_STATUS_ERROR;
         req->state.store(Request::State::Complete);
       }
 
@@ -179,7 +179,7 @@ void CALLBACK HTTPDownloaderWinHttp::HTTPStatusCallback(HINTERNET hRequest, DWOR
           GetLastError() != ERROR_IO_PENDING)
       {
         Log_ErrorPrintf("WinHttpReadData() failed: %u", GetLastError());
-        req->status_code = -1;
+        req->status_code = HTTP_STATUS_ERROR;
         req->state.store(Request::State::Complete);
       }
 
@@ -197,7 +197,7 @@ void CALLBACK HTTPDownloaderWinHttp::HTTPStatusCallback(HINTERNET hRequest, DWOR
       if (!WinHttpQueryDataAvailable(hRequest, nullptr) && GetLastError() != ERROR_IO_PENDING)
       {
         Log_ErrorPrintf("WinHttpQueryDataAvailable() failed: %u", GetLastError());
-        req->status_code = -1;
+        req->status_code = HTTP_STATUS_ERROR;
         req->state.store(Request::State::Complete);
       }
 
@@ -239,7 +239,7 @@ bool HTTPDownloaderWinHttp::StartRequest(HTTPDownloader::Request* request)
   if (!WinHttpCrackUrl(url_wide.c_str(), static_cast<DWORD>(url_wide.size()), 0, &uc))
   {
     Log_ErrorPrintf("WinHttpCrackUrl() failed: %u", GetLastError());
-    req->callback(-1, std::string(), req->data);
+    req->callback(HTTP_STATUS_ERROR, std::string(), req->data);
     delete req;
     return false;
   }
@@ -251,7 +251,7 @@ bool HTTPDownloaderWinHttp::StartRequest(HTTPDownloader::Request* request)
   if (!req->hConnection)
   {
     Log_ErrorPrintf("Failed to start HTTP request for '%s': %u", req->url.c_str(), GetLastError());
-    req->callback(-1, std::string(), req->data);
+    req->callback(HTTP_STATUS_ERROR, std::string(), req->data);
     delete req;
     return false;
   }
@@ -284,7 +284,7 @@ bool HTTPDownloaderWinHttp::StartRequest(HTTPDownloader::Request* request)
   if (!result && GetLastError() != ERROR_IO_PENDING)
   {
     Log_ErrorPrintf("WinHttpSendRequest() failed: %u", GetLastError());
-    req->status_code = -1;
+    req->status_code = HTTP_STATUS_ERROR;
     req->state.store(Request::State::Complete);
   }
 
diff --git a/src/core/achievements.cpp b/src/core/achievements.cpp
index e31e41d81..ffd12d019 100644
--- a/src/core/achievements.cpp
+++ b/src/core/achievements.cpp
@@ -307,7 +307,7 @@ void Achievements::DownloadImage(std::string url, std::string cache_filename)
 {
   auto callback = [cache_filename](s32 status_code, std::string content_type,
                                    Common::HTTPDownloader::Request::Data data) {
-    if (status_code != Common::HTTPDownloader::HTTP_OK)
+    if (status_code != Common::HTTPDownloader::HTTP_STATUS_OK)
       return;
 
     if (!FileSystem::WriteBinaryFile(cache_filename.c_str(), data.data(), data.size()))
@@ -616,7 +616,10 @@ void Achievements::ClientServerCall(const rc_api_request_t* request, rc_client_s
   Common::HTTPDownloader::Request::Callback hd_callback =
     [callback, callback_data](s32 status_code, std::string content_type, Common::HTTPDownloader::Request::Data data) {
       rc_api_server_response_t rr;
-      rr.http_status_code = status_code;
+      rr.http_status_code = (status_code <= 0) ? (status_code == Common::HTTPDownloader::HTTP_STATUS_CANCELLED ?
+                                                    RC_API_SERVER_RESPONSE_CLIENT_ERROR :
+                                                    RC_API_SERVER_RESPONSE_RETRYABLE_CLIENT_ERROR) :
+                                                 status_code;
       rr.body_length = data.size();
       rr.body = reinterpret_cast<const char*>(data.data());
 
diff --git a/src/core/game_list.cpp b/src/core/game_list.cpp
index 2e279d631..7c8c69ce4 100644
--- a/src/core/game_list.cpp
+++ b/src/core/game_list.cpp
@@ -1169,7 +1169,7 @@ bool GameList::DownloadCovers(const std::vector<std::string>& url_templates, boo
     downloader->CreateRequest(
       std::move(url), [use_serial, &save_callback, entry_path = std::move(entry_path), filename = std::move(filename)](
                         s32 status_code, std::string content_type, Common::HTTPDownloader::Request::Data data) {
-        if (status_code != Common::HTTPDownloader::HTTP_OK || data.empty())
+        if (status_code != Common::HTTPDownloader::HTTP_STATUS_OK || data.empty())
           return;
 
         std::unique_lock lock(s_mutex);