We’ve 2022.09 version of Mailcow installed on our server and we are having some troubles with file attachments when replying messages. We use only IMAP, no POP3 server and SMTP is relayed thru Mailgun.

The attached files get corrupted when replying a message, but if we attach the exact same file in a new mail, the file is sent correctly.

Even the files saved in “Sent” folder gets corrupted when we try to open it, but this doesn’t occur when we write a new mail.

Any suggestions about how to get this fixed?

Any relevant logs from postfix container?

What email client is being used in this situation?

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    aaronsmith
    The client is Windows 10 Email app version 16005.14326.20970.0

    I didn’t see anything different in Postfix log, here it is (email addressess changed):

    12/10/2022 22:10:20 info 25FB380A2D: removed
    12/10/2022 22:10:20 info 25FB380A2D: to=<XXX@xxx.com.br>, relay=smtp.mailgun.org[34.150.216.144]:587, delay=8.1, delays=6.9/0.08/0.56/0.52, dsn=2.0.0, status=sent (250 Great success)
    12/10/2022 22:10:19 info Trusted TLS connection established to smtp.mailgun.org[34.150.216.144]:587: TLSv1.3 with cipher TLS_AES_128_GCM_SHA256 (128/128 bits) key-exchange X25519 server-signature RSA-PSS (2048 bits) server-digest SHA256
    12/10/2022 22:10:18 info 25FB380A2D: from=<XXX@ttt.com.br>, size=1231822, nrcpt=1 (queue active)
    12/10/2022 22:10:18 info disconnect from mailcowdockerized-sogo-mailcow-1.mailcowdockerized_mailcow-network[172.22.1.248] ehlo=1 auth=1 mail=1 rcpt=1 data=1 quit=1 commands=6
    12/10/2022 22:10:14 info 25FB380A2D: message-id=<>
    12/10/2022 22:10:14 info 25FB380A2D: replace: header Received: from 7000d0f85d88 (mailcowdockerized-sogo-mailcow-1.mailcowdockerized_mailcow-network [172.22.1.248])??(Authenticated sender: XXX@ttt.com.br)??by mail.trezzuri.com.br (Postcow from mailcowdockerized-sogo-mailcow-1.mailcowdockerized_mailcow-network[172.22.1.248]; from=<XXX@ttt.com.br> to=<XXX@xxx.com.br> proto=ESMTP helo=<7000d0f85d88>: Received: from [127.0.0.1] (localhost [127.0.0.1]) by localhost (Mailerdaemon) with ESMTPA id 25FB380A2D??for <XXX@xxx.com.br>; Wed, 12 Oct 2022 22:10:11 -0300 (-03)
    12/10/2022 22:10:14 info 25FB380A2D: client=mailcowdockerized-sogo-mailcow-1.mailcowdockerized_mailcow-network[172.22.1.248], sasl_method=PLAIN, sasl_username=XXX@ttt.com.br

      I’ll have to test this scenario myself. But meanwhile, might be worth opening an issue in GitHub to see if there’s a bug.

      You might also want to try another email client, and/or the Mailcow UI client to see if the same thing happens or not. That will help isolate the scope to determine if the problem is with the email client software or mailcow itself.

        aaronsmith
        I tried with Sogo webmail and MS Outlook 2013, for both it worked correctly.

        So it seems to be something with Windows 10 Email app.

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