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Updated to FreePBX 13, Sendmail working, Extension Emails are not

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@knotworking wrote:

I upgraded my old FreePBX 2.10 (Asterisk 11) to 13, did a system backup, installed a fresh copy of FreePBX 13 + Asterisk 13 on a new drive and restored the backup from the previous system. Everything is working except voicemail emails. I am using sendmail with gmail as my proxy smtp, emails from fail2ban and emails sent from the command line all go out and are delivered without issue. I’ve set sendmail to it’s highest debug setting, but nothing of use is going to the log.

When I leave a voicemail at an extension, here’s the mail log for that voicemail:
Feb 23 13:04:23 pbx sendmail[30765]: x1NI4N9g030765: from=asterisk, size=12236, class=0, nrcpts=0, msgid=Asterisk-15-2109133094-754-6948@pbx.mywatch.changeip.net, relay=asterisk@localhost
Feb 23 13:04:23 pbx sendmail[30768]: x1NI4Nhj030768: from=asterisk, size=285, class=0, nrcpts=0, msgid=201902231804.x1NI4Nhj030768@pbx.mywatch.changeip.net, relay=asterisk@localhost

Sending an email from the command line (or when the system sends an email), the log is this:

Feb 23 13:07:51 pbx sendmail[31056]: x1NI7p2v031056: from=root, size=223, class=0, nrcpts=1, msgid=201902231807.x1NI7p2v031056@pbx.mywatch.changeip.net, relay=root@localhost
Feb 23 13:07:51 pbx sendmail[31057]: x1NI7pAm031057: from=root@pbx.mywatch.changeip.net, size=502, class=0, nrcpts=1, msgid=201902231807.x1NI7p2v031056@pbx.mywatch.changeip.net, proto=ESMTP, daemon=MTA, relay=pbx.local [127.0.0.1]
Feb 23 13:07:51 pbx sendmail[31056]: x1NI7p2v031056: to={REMOVED}, ctladdr=root (0/0), delay=00:00:00, xdelay=00:00:00, mailer=relay, pri=30223, relay=[127.0.0.1] [127.0.0.1], dsn=2.0.0, stat=Sent (x1NI7pAm031057 Message accepted for delivery)
Feb 23 13:07:51 pbx sendmail[31059]: STARTTLS=client, relay=smtp.gmail.com, version=TLSv1/SSLv3, verify=FAIL, cipher=ECDHE-RSA-AES128-GCM-SHA256, bits=128/128
Feb 23 13:07:53 pbx sendmail[31059]: x1NI7pAm031057: to=<{REMOVED}>, delay=00:00:02, xdelay=00:00:02, mailer=relay, pri=120502, relay=smtp.gmail.com [74.125.141.108], dsn=2.0.0, stat=Sent (OK 1550945274 t17sm1196489vke.26 - gsmtp)

I’ve spent several days trying to figure this one out. I su-ed from root to asterisk, thinking sendmail might have not like asterisk trying to send emails, but I sent a command line test email with no problems. I’ve tweaked so many things, I’m at the point where I feel like I need to look into the core files, but me editing core files has never been a good thing.

Does anybody have any tips or direction they could point me in?

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