Postfix SSL/TLS Wrong Version for GMail Notifications?

    Hi All,


    I'm wondering if anyone else has seen the following log messages when trying to configure Notifications using GMail (email address have been obfuscated but everything else was left alone):

    Code
    Apr  4 10:15:03 Jingleheimer-NAS postfix/pickup[19578]: EE9D2461ABD: uid=0 from=<root>

    Apr  4 10:15:03 Jingleheimer-NAS postfix/cleanup[10178]: EE9D2461ABD: message-id=<20200404141503.EE9D2461ABD@Jingleheimer-NAS.local>

    Apr  4 10:15:03 Jingleheimer-NAS postfix/qmgr[19579]: EE9D2461ABD: from=<mysendingemail@gmail.com>, size=459, nrcpt=2 (queue active)

    Apr  4 10:15:04 Jingleheimer-NAS postfix/pipe[10182]: EE9D2461ABD: to=<openmediavault-notification@localhost.localdomain>, relay=omvnotificationfilter, delay=0.08, delays=0.03/0.02/0/0.03, dsn=2.0.0, status=sent (delivered via omvnotificationfilter service)

    Apr  4 10:15:04 Jingleheimer-NAS postfix/smtp[10181]: connect to smtp.gmail.com[2607:f8b0:400d:c01::6c]:587: Network is unreachable

    Apr  4 10:15:04 Jingleheimer-NAS postfix/smtp[10181]: SSL_connect error to smtp.gmail.com[209.85.144.109]:587: -1

    Apr  4 10:15:04 Jingleheimer-NAS postfix/smtp[10181]: warning: TLS library problem: error:1408F10B:SSL routines:ssl3_get_record:wrong version number:../ssl/record/ssl3_record.c:332:

    Apr  4 10:15:04 Jingleheimer-NAS postfix/smtp[10181]: EE9D2461ABD: to=<myreceivingemail@gmail.com>, relay=smtp.gmail.com[209.85.144.109]:587, delay=0.18, delays=0.03/0.05/0.1/0, dsn=4.7.5, status=deferred (Cannot start TLS: handshake failure)

    Some other tidbits:

    • Clean install of OMV 5.3.9 (installed using the OMV ISO)
    • The sending email ("mysendingemail@gmail.com" above) has 2-factor turned on so I am using an App Password instead of my normal authentication
    • I get the same log message in another installation of OMV 5 in a VM running on my desktop (but same network)
    • I doubt my local firewall is blocking SMTP traffic as I am using the same email / configuration to send notifications with other services (i.e. Shinobi, running on a different device but same network, is able to successfully send SMTP emails without issue)
    • IPv6 is showing as disabled under the Network UI for the network interface and I believe its disabled in my router as well.
    • I've tried limiting the Postfix SSL version with "smtp_tls_protocols=!SSLv2,!SSLv3" in /etc/postfix/main.cf following another forum post about SSLv3 being insecure. No luck.

    I'm struggling to figure out what is cause and what is effect in the log messages. I suspect its a postfix SSL library issue but the "Network is unreachable" could also be the culprit rather then effect. Any ideas?

    Im new to OMV and had problems getting notifications from OMV to my gmail. What I found out is not to use SSL/TLS but STARTTLS. I also set up 2 step auth and used the app password instead of my usual login password. I also made sure my network connection had a DNS....I used 8.8.8.8. Hope this helps!

    I don't recall the error messages, but I also found getting notifications working (for the first time I'd done this) frustrating. I also ended up using STARTTLS, which as I understand it just adds a negotiation phase before transitioning to SSL/TLS. In my case I wanted emails going to a yahoo account, so I assumed that was a factor in SSL/TLS not working.


    I found all the instructions and videos out there on setting up notifications lacking on important details.

    OMV 5.3.9 set up for RAID5 with (3) WD Red 4TB using repurposed Asus P8P67 i5-2500K 16GB

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