I just started working with WordPress and i found out that uploads weren’t working 
. After making sure that the webserver user was granted upload permission (chown webservuser wordpressdir/wp_contents/uploads) and confirming the file paths it was still broken. While “Googling” for a solution, i found a nice plugin called Filosofo Old-Style Upload plugin that enables what they call ‘old-style’ uploading. I’m starting fresh with WordPress 2.3.3, so i don’t know about ‘old-style’ WordPress, but i do know that i want to have control over what I upload and where I upload it.
Anyways, i found the problem causing the “Is its parent directory writable by the server?” message. It was caused by PHP safe mode, so beware to check for php safe mode to be off if you want file uploads to your filesystem to work. My current hosting provider (servage.net) has PHP safe mode enabled by default.
I guess it would be a nice feature if on the upload page a warning would appear to tell you that due to PHP safe mode, file uploads might not be allowed, or is there a better way?
) and see if you are not the only one with the problem and if there might be a solution at hand. Luckily, most of the time, there *is* a solution at hand, in this case thanks to other fellow WordPress users, like Andrew: