msmtp: authentication failed (method PLAIN) msmtp: server message: 535 5.7.8 Error: authentication failed: msmtp: could not send mail (account test from /home/user/.msmtprc) I have no idea how this is happening, since using msmtp and starttls with gmail works fine. I'm trying to get notifications working through my regular gmail account and I can't seem to get it working. Error-3: SASL authentication failed; server smtp.gmail.com Username and Password not accepted If you are getting below error: Jul 31 16:36:10 server.example.com postfix/smtp[3263]: 712322046F: SASL authentication failed; server smtp.gmail.com[74.125.200.108] said: 535-5.7.8 Username and Password not accepted . For gmail (which is the only place I've run into the issue that started this thread), ... For example, I tried sasl:gssapi:cram-md5:login, and mutt briefly flashed that it couldn't use cram-md5 before successfully sending a message. Follow-Ups: . This information might be about you, your preferences or your device and is mostly used to make the site work as you expect it to. Re: Mutt: SSL Certificate check ... SASL authentication failed. TO verify that it wasn't a firewall issue from my OMV box I rannc -zv smtp.gmail.com 465with results ofDNS fwd/rev mismatch:… Turns out I didn't have mutt compiled with the sasl use flag. That certificate is authenticated by a root certificate from COMODO. I'm having problem sending email with mutt using gmail with IMAP. However, it’s been way too long and once again I remember that the setup of the surrounding environment takes more time than a lot of the coding effort. -- Mutt: SSL Certificate check (certificate 2 of 2 in chain) SASL authentication failed ===== My interpretation is that mutt, or SASL on behalf of mutt, got a certificate from websitewelcome. Sending emails with postfix and gmail - SASL authentication failed: NotionCommotion: Linux - Newbie: 1: 05-26-2017 03:13 PM: mutt sasl authentication failed: sycamorex: Linux - Software: 3: 10-15-2010 06:28 PM I recently decided to restart the eudyptula challenge, because my life is too easy and I miss the passive aggressive pithy comments that take weeks to arrive from supposedly impossible to anger scripts. I've got arch up and running with a minimalist setup, trying to use mutt with gmail via imap. mutt authenticating plain, raspberrypi# msmtp --host=smtp.sina.com --serverinfo SMTP server at smtp.sina.com (xk-6-242-a8.bta.net.cn [202.108.6.242]), port 25: smtp-5-121.smtpsmail.fmail.xd.sinanode.com ESMTP Capabilities: STARTTLS: Support for TLS encryption via the STARTTLS command AUTH: Supported authentication methods: PLAIN LOGIN This server might … I'm using postfix to send email via gmail with an application's password (two step-validation activated). 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