#1251 ✓resolved
Jack Carr

Cannot Send Email

Reported by Jack Carr | August 29th, 2015 @ 03:04 AM

Hi,
I'm a registered user.
My SMTP settings work in the Postbox application, but not in Mailmate.

Upon attempting to send email, this error is returned:
Failed connecting to host (smtp.adonsa.net:465).
“error:02002040:system library:connect:Host is down” “error:20073067:BIO routines:CONN_STATE:connect error”

Tip: Open the Activity Viewer (⌥⌘0) before retrying. The SMTP log file might provide additional information.

I'll much appreciate knowing how to resolve the above 3 errors.

Thanks,
Jack

Comments and changes to this ticket

  • benny

    benny August 29th, 2015 @ 12:39 PM

    Some users have reported issues with using port 465. I don't know why there's recently been an increase in such problems, but you can try two things:

    • Fetch the latest test release in which I've changed the handling of port 465. Hold down ⌥ when clicking “Check Now” in the Software Update preferences pane.
    • Change the account settings to use port 587 which also works for this server (port 465 is a non-standard port).

    The latter probably works, but I'd like to know if the first suggestion also works.

  • Jack Carr

    Jack Carr August 29th, 2015 @ 02:15 PM

    Hi Benny,
    Thanks for your fast reply.

    The errors persisted in spite of installing the upgrade,
    and in spite of trying port 587.

    Given my lack of adequate SMTP understanding, i tried
    many settings, SSL on or off, my username there or omitted,
    password omitted, tried prefacing with smtp. and mail.

    I went back to the postbox application, and email sending worked as it should there.

    I appreciate your efforts.
    At the same time, I'm trying to get smart on SMTP procedures.

    Thanks,
    Jack

  • benny

    benny August 29th, 2015 @ 04:05 PM

    That's strange. And you get the same type of error no matter what?

    Try this:

    • Open the Activity Viewer (⌥⌘0) in MailMate.
    • Try again with various SMTP settings.
    • Use “Help ▸ Send Server Logs” to send me log files of your attempts.

    I'll review it and see if I can spot any problems.

  • Jack Carr

    Jack Carr August 30th, 2015 @ 03:43 AM

    Hi Benny,
    Log file was sent separately to mm-feedback@freron.com
    Subject: Ticket 1251 Log file.

    I had to use a webmail application, as mailmate
    returned the same errors.
    Thanks, Jack

  • benny

    benny August 30th, 2015 @ 12:48 PM

    I can only see an attempt to connect on port 2525. This might not work well with MailMate. I strongly suggest trying the standard port 587 which also appears to work for this server when I try to connect manually.

    You can also use port 2525 like this: 2525p. This forces MailMate to connect to the port using the correct method. This only works in recent test versions of MailMate (which you have now).

  • Jack Carr

    Jack Carr August 30th, 2015 @ 02:53 PM

    Hi Benny,
    Thanks for working this during the weekend.

    Okay, it's on me now, to find the cause.
    I rebooted into the Safe mode, and MailMate worked fine with 2525p (and probably other SSLs)

    I have 24 startups, one of which is probably interfering with MailMate.
    So, i have to do a lot of restarts and process of elimination
    (like Conflict Catcher used to do), to narrow down the startup that's not playing nice with MailMate.

    Ostensibly, "Protected Memory" is supposed to prevent this sort of thing from ever happening.

    Here's the list of startups I'll be disabling/enabling in order to
    narrow down the offending one.

    Autodistract, Caffine, Deskovery, Overflow, IconXpritservice, Alarm Clock Pro, Dropbox, Smart Scroll, TotalFinder, Keyboard Maestro Engine, HazelHelper, CMA, finderpop-daemon, WindowMizer, SwitchResX Daemon, 1Password Startup, QRecall, Paste, Paste Helper, Cookie, Stock + Pro. plus Little Snitch which begins upon bootup.

    Please don't close this out yet, I'll keep you informed as I work thru these startups.

    Thanks,
    Jack

  • benny

    benny August 30th, 2015 @ 02:55 PM

    Are you sure it didn't work in non-safe mode with 2525p? I would have expected that.

  • Jack Carr

    Jack Carr August 30th, 2015 @ 03:00 PM

    Hi Benny,
    Addendum,

    Situation persisted with 2525p when booted into the unsafe mode.
    I went thru all possibilities and combinations, so something
    is not playing nice with Mailmate.

    Ditto when I tried appending the p to 587 and 465 while unsafe.

    I hope to be bringing the cause to you
    Thanks

    Jack

  • benny

    benny August 30th, 2015 @ 03:18 PM

    Port 465 is an IMAP port and usually should not be used with p. SMTP standard ports are 25 and 587.

    What happen in the Terminal if you do this (in safe/unsafe mode):

    telnet mail.adonsa.net 587
    

    If it works then you'll get a response like this:

    Trying 50.22.11.17...  
    Connected to mail.adonsa.net.  
    Escape character is '^]'.  
    220-bancroft.accountservergroup.com ESMTP Exim 4.85 [#2](/projects/58672/tickets/2 "Ticket #2") Sun, 30 Aug 2015 10:16:19 -0500  
    220-We do not authorize the use of this system to transport unsolicited,  
    220 and/or bulk e-mail.
    

    You can then write quit to close the connection.

  • Jack Carr

    Jack Carr August 30th, 2015 @ 05:00 PM

    Hi Bennie,
    Here's the telenet results:

    ============While booted UNSAFE =========== $ telnet mail.adonsa.net 587 Trying 50.22.11.17...
    Connected to mail.adonsa.net.
    Escape character is '^]'.
    220-bancroft.accountservergroup.com ESMTP Exim 4.85 #2 Sun, 30 Aug 2015 11:42:16 -0500
    220-We do not authorize the use of this system to transport unsolicited,
    220 and/or bulk e-mail.

    $ telnet mail.adonsa.net 2525 Trying 50.22.11.17...
    Connected to mail.adonsa.net.
    Escape character is '^]'.
    220-bancroft.accountservergroup.com ESMTP Exim 4.85 #2 Sun, 30 Aug 2015 11:45:34 -0500
    220-We do not authorize the use of this system to transport unsolicited,
    220 and/or bulk e-mail.

    $ telnet mail.adonsa.net 465 Trying 50.22.11.17...
    Connected to mail.adonsa.net.
    Escape character is '^]'.

    ============== While booted SAFE-mode ==========

    $ telnet mail.adonsa.net 587 Trying 50.22.11.17...
    Connected to mail.adonsa.net.
    Escape character is '^]'.
    220-bancroft.accountservergroup.com ESMTP Exim 4.85 #2 Sun, 30 Aug 2015 11:50:48 -0500
    220-We do not authorize the use of this system to transport unsolicited,
    220 and/or bulk e-mail.

    $ telnet mail.adonsa.net 2525 Trying 50.22.11.17...
    Connected to mail.adonsa.net.
    Escape character is '^]'.
    220-bancroft.accountservergroup.com ESMTP Exim 4.85 #2 Sun, 30 Aug 2015 11:51:46 -0500
    220-We do not authorize the use of this system to transport unsolicited,
    220 and/or bulk e-mail.

    $ telnet mail.adonsa.net 465 Trying 50.22.11.17...
    Connected to mail.adonsa.net.
    Escape character is '^]'.

  • Jack Carr

    Jack Carr August 30th, 2015 @ 05:01 PM

    Correction

    Benny

    Sorry for misspelling

  • Jack Carr

    Jack Carr August 30th, 2015 @ 06:11 PM

    Benny,
    Found it, and it's entirely my fault.
    I humbly apologize for putting you thru this knee jerk.

    I should have done this first

    I went thru my Little Snitch settings, and discovered
    i had set Mailmate to Deny all outgoing connections.

    No wonder it wouldn't work.
    I'm hanging my head in shame for screwing up like a PC user.

    Please close the case file on this.
    Thanks for indulging my chain of screwups.
    Jack

  • benny

    benny August 30th, 2015 @ 06:14 PM

    • State changed from “new” to “resolved”

    :-)

  • Alex Veer
  • Alex Veer
  • Alex Veer

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