More than one image field

The File Upload and Post Image field only supports one file at a time. So if you want multiple files you would have to add multiple fields to your form.

This is default behavior of the PHP file uploader and browsers restrict things to only one can be selected.

We do plan on supporting multiple files per upload in a future update but will have to incorporate Flash and/or more advanced jQuery to make it possible.

The issue isn't as simple as implementing a multi-file upload field to Gravity Forms, you then have to tell Gravity Forms how to handle and process those multiple files and where they should be stored and displayed in the entry data. So it isn't a simple customization and would require core changes to Gravity Forms.

It is a feature that we are going to be adding to the plugin, but it's more complex than it sounds so we have to change Gravity Forms to handle multiple files at once from one field before we can add the field itself.