If you replaced the .dll's of a running ioFTPD I'd at least restart ioFTPD to see if that changes anything. If it doesn't replace the old ones from the zip file and see if things work again...
Are you running a zipscript like ioNiNJA or is this a plain ioFTPD install? The .jpg's aren't always handled by zipscripts and I didn't see one rejecting anything, so I can't tell. In general ioFTPD deletes an uploaded file if it encounters an error from any post processing done by zipscripts so that's where I'd look first.
Enable the 'Log_OpenSSL_Transfer_Errors' in the config file and logs/Debug.log will include any errors returned by the library which might give us a clue what's going on if it turns out to be a .dll issue. I would not have expected the transfer to negotiate a cipher and actually transfer bytes if it was an OpenSSL error though.
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