I recently moved a few web sites running WordPress from an Ubuntu host to a Windows Server 2008 host and have spent the last few hours trying to figure out why I couldn’t upload pictures through Windows Live Writer. Once I got past a recent upgrade bug everything seemed to be working except the files weren’t being written to disk.

Out of sheer desperation I came across the following options screen.

See the issue?

Turns out that at some point WordPress wrote the full *nix path to that option and didn’t error when it couldn’t find the path!