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This page contains a list of common problems and solutions when using FileField. If you experience a problem that is not listed here, do not post a comment. Post an issue to the FileField issue queue.
When the field is set to "Unlimited" values, I'm only able to upload exactly 21, 25, or some other number of images. See Increase the number of allowed files.
This problem generally has two solutions. If you can upload exactly 21 images, this is probably because of bug in the CCK "Add another field" button. Upgrade to CCK 2.2 (Drupal 6) or higher where this problem is fixed.