Windows Live Writer (WLW) image upload errors happen because the software relies on the deprecated Google Picasa Web Albums API to host and publish images. When Google retired Picasa, the authentication protocols and server upload paths used by Windows Live Writer were broken or permanently changed.
The core issue stems from Windows Live Writer trying to contact a server that no longer accepts uploads through that specific tool, resulting in Server Error 500 or authentication prompt loops. 1. Upgrade to Open Live Writer (OLW)
Windows Live Writer is officially abandoned software. The open-source community created an exact, updated replacement that handles modern Google security requirements. Download the update: Download and install Open Live Writer.
Import settings: It features the exact same interface and can import your existing blog accounts and draft folders automatically. 2. Configure a Custom Image Upload Location (FTP)
If you continue to get image upload errors even inside the updated Open Live Writer, you can bypass the Picasa/Google Photos API entirely by hosting images via your own server. Open your Live Writer software. Navigate to Weblog > Edit Weblog Settings. Click on the Images tab on the left sidebar.
Change your image publishing target from the default blog provider to an FTP Server.
Enter your website’s FTP credentials and folder directory. Live Writer will now seamlessly upload your images directly to your web host instead of Google’s broken servers. 3. Switch to Direct Uploads on the Web Interface
Because third-party blogging tools face heavy API limitations with Google, uploading photos manually via your browser guarantees full image quality and reliability. Broken Images with Blogger, Picasa, and WLW – Joe Cheng
Download and run this tool to repair your old posts. You must save the .exe to your hard drive, not run it right from the browser, WordPress.com
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