Add Media to a Post fails (Tries to upload to 2014/04 folder)

When adding images through the Media Library>Add New button images work fine, and are uploaded to the correct file ( uploads/2016/02 currently )

But if I try to upload an image from inside a post (using the add media button above the text input form, then hitting upload) the image fails, and WP sends this error:
The uploaded file could not be moved to wp-content/uploads/2014/04.

2014/04 is almost 2 years ago, why would it try to put it there?

Any Ideas? Its not stopping me from finishing the work I need to do, as I am able to upload all the files to media library first, then select the already uploaded files in media library when creating the post or page.