@epicalex RIght now the file upload is limited to files uploaded a part of the entry data. We don't currently have a Post Image upload field. However, we are working on one and will be introducing a Post Image upload field with Version 1.1 of Gravity Forms.

This will allow a user to submit a form that creates a post and uploads an image that is then associated with that post as a gallery item in the media library.

You could then allow multiple photos to be uploaded by placing multiple photo uploads fields on your form. In the future we will implement the ability to upload multiple images from one field, but for now we are just working on getting the first iteration of the Post Image field up and running in the next release.

The demo is available here: