Upload file and fill in fields in one step; or trigger a rule when a file is uploaded I want to make use of the Media module and the File entity module to upload files, in particular images, to my site without having to attach them to a node. Solely uploading images works like a charm, as the Media module automatically places an "add file" link within the navigation menu.

I also added a couple of fields to my image file type. Unfortunately, the Media module doesn't allow me to choose the image file and fill in the fields at the same time, and then submit. Instead, I have to upload the file, go back to the file, click on edit and fill in the fields afterwards, which in my opinion is pretty annoying.

I am not sure if this issue can be resolved somehow. If it can not be, this could be a workaround:

When I upload a file, a rule is triggered that sends me to the edit page. This way uploading the image and filling in the fields somewhat forms a unit.

However, the Rules module does not offer to react on file uploads.

Does anyone have an idea how to get around this issue?
So I believe that uploading and editing files works correctly with the latest dev release of the media module when using a file field or image field.

Like you said when you go to file/add it is using the file_entity module which I believe they are discussing adding upload and editing here http://drupal.org/node/1553114.