I am using gmail as SMTP server (via ssmtp mail transfer agent in Ubuntu 12.04) for sending outgoing mails from my server. But the problem is that Google often blocks authentication attempts by my machine. Sometimes it works without problems but sometimes it gives this message :

Authorization failed (534 5.7.9 https://support.google.com/mail/bin/answer.py?answer=78754 kn10sm96120374oeb.0 - gsmtp)

How could fix this issue permanently ? I created a separate account that is meant to be used only for sending mails by this machine.

  • please state the reason of downvotes as well. – Rajat Gupta Mar 19 '14 at 18:49

Use your own SMTP server?

Sorry. That's probably not what you want to hear. But Google is telling you that you're hitting their SMTP server often enough that they assume something hinky is going on.

As to whether or not using GMail as the official SMTP server for your entire server is hinky or not, well. There are stated use limits which I assume you're not hitting, but if I were you I'd take those messages as meaning that I was hitting the limits of what they considered appropriate free use.

  • First I am not using Google apps for Business, I am using the simple gmail account just like my free personal gmail account & I am very sure I am not reaching the limits anyway. I started to see these messages from day 1 when I configured a newly created free gmail account to send emails from server. Actually these emails are just sent to my personal account & some other administrators for server administration purposes only. Even when I first configured this setup I was seeing similar messages, so I am sure this is not due to any limits reached. – Rajat Gupta Mar 19 '14 at 18:26
  • Moreover a weird thing was that I fixed this first time, by changing my password from moderately complex to simple one, otherwise this wasn't just working (this is unbelievable but very true). – Rajat Gupta Mar 19 '14 at 18:27
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    Are you seriously arguing with me that because you're not giving Google money, the limits don't apply to you? I believe you when you say that you're not sending 500 emails a day, but the error message you linked means, "You're connecting to us too often." Like I said, I suspect Google is trying to tell you that you're overusing their service. If you disagree, you can always open a ticket with them and argue with them about it. – Katherine Villyard Mar 19 '14 at 18:37
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    that was not meant to be an argument or to prove you wrong, I just tried to describe my complete situation to you. Thank you. – Rajat Gupta Mar 19 '14 at 18:51

Gmail is not designed to be an SMTP server for your website.

http://mandrill.com/, http://sendgrid.com/, http://aws.amazon.com/ses/, and others all have generous free tiers and are specifically designed for this sort of thing. Consider using them.

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