Unable to create directory uploads/yyyy/mm. Is its parent writable by server?

So I’ve messed with changing groups, permissions, owners, etc. and I cannot figure this out for the life of me! I’m using Ubuntu LTS 12.04 with nginx and php5-fpm with Vagrant/VirtualBox. WordPress is up and running fine but I cannot upload anything, even plugins. I’m also using the latest version of Bedrock and Roots (downloaded fresh today: 3/4/14).

Saving permissions works fine though… I say this because usually if that’s not writable it’s definitely a permissions issue, so I’m not even sure at this point.

I’ve attempted to use chown, chgrp, usermod, chmod, etc. but this is still what my /web/app/ directory looks like:

$ ls -l
total 0
drwxr-xr-x 1 vagrant vagrant 102 Mar  4 17:15 mu-plugins/
drwxr-xr-x 1 vagrant vagrant 306 Mar  4 19:58 plugins/
drwxr-xr-x 1 vagrant vagrant 136 Mar  4 17:17 themes/
drwxr-xr-x 1 vagrant vagrant  68 Mar  4 21:04 uploads/

I’ve tried changing it to be user and group root and also nginx but it stays vagrant. Any ideas?

As a side note, when I uncheck the “Organize my uploads into month- and year-based folders” in Settings > Media , the error becomes:
“image.jpg” has failed to upload due to an error
The uploaded file could not be moved to uploads.

You can’t manually change permissions in your Vagrant shared folder (since it’s managed by Vagrant). That’s why you’re always seeing it was vagrant:vagrant. Check out this question for the solution http://stackoverflow.com/questions/13169154/cannot-change-permissions-of-folders-within-vagrant-home-folder

You need to change your shared folder options in your Vagrantfile to set the group as your nginx user (www-data maybe?).

Ah yes, that makes perfect sense! I completely forgot about that line

I actually wound up going back and redoing my manifest (I was using puPHPet to do this) and setting my Shared Folder Type from Default to NFS, which seems to have fixed it for some reason. My fresh install is able to upload images now.

Thanks for the help!

NFS is better in general if you can use it. Way faster as well.