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check if login mail is successful

Thanks to all for the help I should check via wireshark, if the login with my mail went well, in practice I have a machine where user and password are stored, which sends mail, but for days you can't connect. more to the mail server. I would like to see the stream as this machine connects to the mail server in order to understand why it can no longer send mails, how can I do to sniff the flow of mail Thank you.