diff --git a/modules/juce_core/native/juce_win32_Network.cpp b/modules/juce_core/native/juce_win32_Network.cpp
index a62c407c95..5c58ec2eb3 100644
--- a/modules/juce_core/native/juce_win32_Network.cpp
+++ b/modules/juce_core/native/juce_win32_Network.cpp
@@ -343,6 +343,35 @@ private:
         InternetSetOption (sessionHandle, option, &timeOutMs, sizeof (timeOutMs));
     }
 
+    void sendHTTPRequest (INTERNET_BUFFERS& buffers, WebInputStream::Listener* listener)
+    {
+        if (! HttpSendRequestEx (request, &buffers, 0, HSR_INITIATE, 0))
+            return;
+
+        int totalBytesSent = 0;
+
+        while (totalBytesSent < postData.getSize())
+        {
+            auto bytesToSend = jmin (1024, (int) postData.getSize() - totalBytesSent);
+            DWORD bytesSent = 0;
+
+            if (bytesToSend == 0
+                || ! InternetWriteFile (request, static_cast<const char*> (postData.getData()) + totalBytesSent,
+                                        (DWORD) bytesToSend, &bytesSent))
+            {
+                return;
+            }
+
+            totalBytesSent += bytesSent;
+
+            if (listener != nullptr
+                && ! listener->postDataSendProgress (owner, totalBytesSent, (int) postData.getSize()))
+            {
+                return;
+            }
+        }
+    }
+
     void openHTTPConnection (URL_COMPONENTS& uc, const String& address, WebInputStream::Listener* listener)
     {
         const TCHAR* mimeTypes[] = { _T("*/*"), nullptr };
@@ -365,43 +394,29 @@ private:
         if (request != 0)
         {
             INTERNET_BUFFERS buffers = { 0 };
-            buffers.dwStructSize = sizeof (INTERNET_BUFFERS);
-            buffers.lpcszHeader = headers.toWideCharPointer();
+            buffers.dwStructSize    = sizeof (INTERNET_BUFFERS);
+            buffers.lpcszHeader     = headers.toWideCharPointer();
             buffers.dwHeadersLength = (DWORD) headers.length();
-            buffers.dwBufferTotal = (DWORD) postData.getSize();
+            buffers.dwBufferTotal   = (DWORD) postData.getSize();
 
-            if (HttpSendRequestEx (request, &buffers, 0, HSR_INITIATE, 0))
+            auto sendRequestAndTryEnd = [this, &buffers, &listener]() -> bool
             {
-                int bytesSent = 0;
+                sendHTTPRequest (buffers, listener);
 
-                for (;;)
-                {
-                    const int bytesToDo = jmin (1024, (int) postData.getSize() - bytesSent);
-                    DWORD bytesDone = 0;
+                if (HttpEndRequest (request, 0, 0, 0))
+                    return true;
 
-                    if (bytesToDo > 0
-                         && ! InternetWriteFile (request,
-                                                 static_cast<const char*> (postData.getData()) + bytesSent,
-                                                 (DWORD) bytesToDo, &bytesDone))
-                    {
-                        break;
-                    }
-
-                    if (bytesToDo == 0 || (int) bytesDone < bytesToDo)
-                    {
-                        if (HttpEndRequest (request, 0, 0, 0))
-                            return;
+                return false;
+            };
 
-                        break;
-                    }
+            auto closed = sendRequestAndTryEnd();
 
-                    bytesSent += bytesDone;
+            // N.B. this is needed for some authenticated HTTP connections
+            if (! closed && GetLastError() == ERROR_INTERNET_FORCE_RETRY)
+                closed = sendRequestAndTryEnd();
 
-                    if (listener != nullptr
-                          && ! listener->postDataSendProgress (owner, bytesSent, (int) postData.getSize()))
-                        break;
-                }
-            }
+            if (closed)
+                return;
         }
 
         closeConnection();