There are whole slew of blog posts and technical articles on configuring IIS and windows permissions to enable file uploads in WordPress sites. I’ve read them before and had cause to re-visit them over the last couple of days as I struggled to get uploads working on this site. Whenever I attempt to upload a file, the site would just site their until an HTTP timeout message appeared. No HTTP 500, just a PHP timeout error.

My IIS and folder permissions were correct as were all the paths in php.ini. As I was testing tweaks or configuration changes, I could see the temporary files being written in the PHP temp folder. In other words, the actual PHP upload was working. Something was blocking the copying of these files to the WordPress site. Was it WordPress itself or a Windows permission?

To compound my confusion, WordPress’ own update functionality was working without a hitch, so this meant the site had the correct write permissions at least on the wp-content folder.

After several hours of fustration I found the problem and it wasn’t with IIS, PHP or Windows. It was with a WordPress setting. I eventually wandered over to WordPress’ Settings > Media and the uploads folder path contained a reference to a W drive. I have absolutely no idea where this has come from. This site has never been on a server with a W drive. However, once set back to the default of wp-content/uploads, file uploads worked again.