There was a problem uploading files to s3 through Paperclip with # characters in the name (s3 doesn’t like # characters). There’s a fix on Paperclip trunk, but that hasn’t been packaged into a gem. Perhaps the Paperclip people could be convinced to cut a release?
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One team is seeing files on s3 disappear occasionally. They’re using v2 of the s3 api, where the s3 gem uses v1. The team has now turned on s3 logging (which is off by default) – which they recommend everyone turn on as a general good practice.