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After upgrading CiviCRM from 4.6 to 4.7.14 I was not able to send (test) emails via SMTP. I got the following error:

authentication failure [SMTP: STARTTLS failed (code: 220, response: 2.0.0 Ready to start TLS)]

After replacing some code in /packages/Net/SMTP.php like Matt suggested I'm now receiving the error:

authentication failure [SMTP: Invalid response code received from SMTP server while sending email. This is often caused by a misconfiguration in Outbound Email settings. Please verify the settings at Administer CiviCRM >> Global Settings >> Outbound Email (SMTP). (code: 535, response: 5.7.8 Error: authentication failed: authentication failure)]

Maillog says:

Dec 21 11:19:55 rs0815 postfix/smtpd[31606]: warning: SASL authentication failure: client response doesn't match what we generated Dec 21 11:19:55 rs0815 postfix/smtpd[31606]: warning: rs0815.rs.example.de[123.123.123.123]: SASL DIGEST-MD5 authentication failed: authentication failure

I doesn't make a difference if I use PHP 5.5 or 5.6.

Any idea what could cause this?

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  • Can you provide more information? E.g. are you prefixing your outgoing mail address with "ssl://"? In Civi 4.7 you should remove that since it's technically incorrect; see github.com/civicrm/civicrm-packages/pull/66
    – Jon G - Megaphone Tech
    Dec 20 '16 at 21:21
  • The SMTP-server is not prefixed with "ssl://", besides it is suggested in the input help: "If the server uses SSL, add 'ssl://' to the beginning of the server name[...]". It's just like smtp.example.com and port 25 with an authentication.
    – Philipp Michael
    Dec 21 '16 at 7:59
  • I've checked the log, see my updated question.
    – Philipp Michael
    Dec 21 '16 at 10:24
  • Hi Philipp, are you also the administrator of the SMTP server. The log suggests it is postfix. Maybe the post unix.stackexchange.com/questions/204515/… offers some help. But it involves altering the configuration of postfix.
    – Kainuk - CiviCooP
    Jan 22 '17 at 11:38
  • It's now working, but I don't know why. I didn't do anything conscious. So I'm still interested in a solution of this problem.
    – Philipp Michael
    Feb 10 '17 at 11:54
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I had this very same problem with SMTP and couldn't find a solution with the configuration, although I didn't change the code you mention. I found a workaround by choosing mail() instead of SMTP in Administer>system settings>outbound email, since when I've had no problems. The default option should apparently work fine on linux systems, if that is appropriate.

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  • Yes, I can send mails with the mail() function but I wan't to use a specific smtp server. So unfortunately this is no option.
    – Philipp Michael
    Dec 21 '16 at 13:23

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