This is due to caching, which happens at several levels:
The first three affect all users looking at your repository. The last is only visible to you -- if other people report seeing the updated thumbnail but you only see the old version, then it's your own browser caching the image, and not a problem - just clear your cache.
Cloudflare's cache is automatically purged at regular intervals. The Drupal cache and Islandora Imagecache do the same, but might occasionally need some manual nudging. Your browser's cache can only be cleared by you. In general, if you update a thumbnail and you don't see the new version appear right away, it's usually just a matter of waiting for the caches to update themselves.
To confirm that your thumbnail update went through: Manage your object, go to Datastreams, and look at the TN datastream. Click the TN link, and you should see the most recent version of the thumbnail. You can also click the number in the Versions column, to review the current and previous versions.
If your thumbnails aren't updating after a long wait: Clear the caches manually.
After doing this, you may need to clear your own browser's cache before the updated thumbnails will be visible to you.