Might be related to http://drupal.org/node/1110308.

Problem

Steps:
- Create a new content type
- Create a new node
- Add File field with widget Image FUpload (Storage mode: Multiple images, Number of values: 5)
- Edit node:
... add 2 images to the queue
... click 'Upload images'
... click 'Next step'
... click 'Done editing'

Result:
- No images added.

It looks to me like the files aren't "sticking" because the code calls on $node->{file_field_name} before saving the node, which will come up null on nodes that were created before the field was added to the content type.

Proposed resolution

Maybe there's a better way, but the following patch populates the node with this info using field_file_load(). Works for me.