discordcr
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upload_file actually does require a file name
https://github.com/shardlab/discordcr/blob/df22ea8f9499756949dfa16ed629bd1724b77e05/src/discordcr/rest.cr#L430-L431
Not sure where the issue lies, but trying to send a IO without a filename, resulted in discord dropping the upload altogether. Further investigation required.