I want to thank all who replied and close the loop...

I upgraded the server's monit version to 5.25.1 (latest in the repos at the time) and syntax was deemed OK.  I looked through the release notes and didn't find any mention of this from v5.14 (the version I was originally using) forward, but I guess it was fixed at some point.

I have not tested the backup mailserver yet (maybe I'll purposely change my credentials on the primary to test that).

This pseudo-example is apparently syntactically correct:

set mailserver smtp.domain1.com port 587
username [email protected] password "xxxxxxxxxxxxxxxx",
smtp.domain2.com port 465
username admin2 password "yyyyyyyyyyy"
using SSL
with timeout 10 seconds



On 5/29/2018 9:24 PM, Gee Fitz wrote:
Something like this?

set mailserver example.com <http://example.com> port 587 username "user" password "password" using tlsv1, example2.com <http://example2.com> port 25 username "user2" password "password2" using tlsv1 with timeout 30 seconds,
localhost

On Tue, May 29, 2018 at 10:08 PM, <[email protected] <mailto:[email protected]>> wrote:

    I do use postfix. I read the SASL info, but I didn't notice a way
    to configure multiple defaults. I can look at that again.  (One
    thing I'm trying to monitor is postfix! 🙂)

    Still, if monit supports multiple mailhosts and it supports smtp
    auth, it should support multiple mailhosts each with auth.



    -----Original Message-----
    From: Gee Fitz <[email protected] <mailto:[email protected]>>
    To: This is the general mailing list for monit
    <[email protected] <mailto:[email protected]>>
    Sent: Tue, 29 May 2018 9:02 PM
    Subject: Re: multiple email servers with authentication

    Well. You'll have more luck doing that in postfix or whatever you
    use to relay email. Did you look at ssmtp?

    http://www.scottro.net/qnd/qnd-ssmtp.html
    <http://www.scottro.net/qnd/qnd-ssmtp.html>

    Can't remember if it supports multiple auth or protocols.

    On Tue, May 29, 2018 at 9:51 PM, <[email protected]
    <mailto:[email protected]>> wrote:

        I tried something similar (I moved the timeout to the one
        clause at the end). That didn't work. So it's not only
        "probably" not that syntax, it's definitely not that syntax.

        And I read the docs. As you noticed, it does NOT document how
        to supply the auth and protocol per server, which is a very
        common requirement.

        I should have commented that I'm currently running v5.14.


        -----Original Message-----
        From: Gee Fitz <[email protected] <mailto:[email protected]>>
        To: This is the general mailing list for monit
        <[email protected] <mailto:[email protected]>>
        Sent: Tue, 29 May 2018 8:37 PM
        Subject: Re: multiple email servers with authentication

        Documentation clearly says

        -- Example (setting two mail servers for failover):
        set mailserver smtp.gmail.com <http://smtp.gmail.com>,
        smtp.other.host

        So it's probably

        set mailserver smtp.domain1.com <http://smtp.domain1.com> port
        587, smtp.domain2.com <http://smtp.domain2.com> port 465
        etcetera


        On Tue, May 29, 2018 at 5:55 PM, AJ Weber <[email protected]
        <mailto:[email protected]>> wrote:

            I am attempting to configure multiple (backup)
            mailserver's. Each has a unique username and password, and
            in fact, each has different ports, protocols, etc.

            I have tried this:

            set mailserver smtp.domain1.com <http://smtp.domain1.com>
            port 587
            username [email protected] <mailto:[email protected]>
            password "xxxxxxxxxx"
            with timeout 30 seconds,
            smtp.domain2.com <http://smtp.domain2.com> port 465
            username otheruser password "yyyyyyyyyyyyyyyyyy"
            using SSL with timeout 30 seconds

            This results in a configuration syntax error.

            Can someone help me figure out how to configure my
            mailservers?

            Thanks!

            -AJ


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