[Plugin: Grand Flagallery] Cannot Create Directory

I am having problems with this plugin and any other gallery plugin telling me I am unable to create sub directories and it tells me to check my permissions. My permissions for the wp-content folder are 777 and I can upload pictures to my media with the Default WordPress media feature.

I am using v3.14 and have uploaded it and re-uploaded and made sure all the files were present. As far as I can tell I’ve done everything correctly.

My clients web server provider is web.com and it is a Windows server (as far as I know this is probably the worst combination)

I manually made the default directory for it as it said it could not make it (wp-content/flagallery)

I would greatly appreciate any help as I am bashing my head against a wall at this point.