1 2 Previous Next 16 Replies Latest reply: Nov 19, 2012 7:29 AM by MrHoffman
Paul Cezanne Level 1 Level 1 (10 points)
Wow, this one is killing me. I have a Mini with Snow Leopard Server running mail. I use CRAM-MD5 authentication and SSL connections for both IMAP and SMTP.

I HAD to get a Windows 7 netbook to run QuickBooks and Office (not my choice), so now I'm trying to connect either the Outlook 2010 client or a Thunderbird client with one of my accounts so QuickBooks can send invoices, etc...

I was able to connect to IMAP with both clients using the SSL connection. I can't remember the level of authentication that worked for Thunderbird, but I had to drop to PLAIN for Outlook to work.

Now the hair-pulling problem... The SMTP authentication and connection methods don't work for either client. NONE of them in any combination. Even dropping SSL and going to PLAIN don't work.

Does anyone have any idea what this is all about?

Thanks.

MacBook Pro, Mac OS X (10.6.4), MacMini Server - latest Snow Leopard
  • 1. Re: No SMTP Authentication for Thunderbird or Outlook?
    MrHoffman Level 6 Level 6 (12,465 points)
    What are the exact error message(s)?

    How is the local network configured?

    Are you even able to connect to the mail server via telnet?

    If you're getting to the mail server, can you connect to port 25? (eg: using telnet to connect to port 25)

    If you can connect into port 25 via telnet, is it responding like a mail server?

    If you've connected to port 25 and it's a mail server, what (other) ports are you connecting to?

    Are you using authenticated connections for sending? Port 587, etc.

    If you're connecting, what sort of relevant "stuff" might be present in the mail server logs after a failure?

    Can you connect from that Windows 7 box and clients to another IMAP or POP3 server elsewhere?

    I'd also encourage you to pursue this with the Microsoft Windows and Microsoft office forums and folks; Windows is the most central part of this, and you're here connecting to a standard IMAP or POP3 server. Which means this is primarily with the client platform, and secondarily with the server. You could, for instance, be connecting that Windows box to most any platform.
  • 2. Re: No SMTP Authentication for Thunderbird or Outlook?
    Paul Cezanne Level 1 Level 1 (10 points)
    What are the exact error message(s)?

    +No error messages - just no connection. Just says not able to connect. With Thunderbird, it the error log on the client says the server doesn't support TLS. The server's SMTP log says "fatal, too many errors, program terminated"+

    How is the local network configured?

    +Can you be more specific?+

    Are you even able to connect to the mail server via telnet?

    +I don't use telnet - don't even know what it is.+

    If you're getting to the mail server, can you connect to port 25? (eg: using telnet to connect to port 25)

    +Yes, I can connect to port 25 with the clients if I drop to PLAIN. I know this because the Outlook client says it's connected but the authentication won't occur - it just keeps asking for the password over and over. I think is particularly odd in the case where I've dropped to PLAIN+

    If you can connect into port 25 via telnet, is it responding like a mail server?

    +No responses+

    If you've connected to port 25 and it's a mail server, what (other) ports are you connecting to?

    +Not sure what you're asking. With another service?+

    Are you using authenticated connections for sending? Port 587, etc.

    +As I already indicated, those don't work.+

    If you're connecting, what sort of relevant "stuff" might be present in the mail server logs after a failure?

    +See the log messages I mentioned above.+

    Can you connect from that Windows 7 box and clients to another IMAP or POP3 server elsewhere?

    +Don't know - don't have one.+

    I'd also encourage you to pursue this with the Microsoft Windows and Microsoft office forums and folks; Windows is the most central part of this, and you're here connecting to a standard IMAP or POP3 server. Which means this is primarily with the client platform, and secondarily with the server. You could, for instance, be connecting that Windows box to most any platform.

    +I'll certainly follow up with their forums. This seems, however, like it might be a pretty common problem and it's certainly relevant for this forum. Maybe someone else on the forum could help? Thanks.+
  • 3. Re: No SMTP Authentication for Thunderbird or Outlook?
    Paul Cezanne Level 1 Level 1 (10 points)
    Solved it. Use STARTTLS in the Thunderbird Client, not SSL/TLS, even if you are using SSL on Snow Leopard Server Mail.

    I have not solved the Outlook issue.
  • 4. Re: No SMTP Authentication for Thunderbird or Outlook?
    aliaspc Level 1 Level 1 (0 points)
    Paul, I'm getting a similar message from Outlook 2010 on my new iMac saying cannot connect with outgoing server. Server requires authentication. Is this in anyway similar to your issue? I can receive email from my Verizon ISP mail server using Outlook but cannot send. Have searched Microsoft Outlook Q&A, and found suggestion to try different ports, but those efforts failed as well.
  • 5. Re: No SMTP Authentication for Thunderbird or Outlook?
    UptimeJeff Level 4 Level 4 (3,390 points)
    The outlook issue is probably a helo restriction.
    Look in main.cf

    Change
    smtpdhelorestrictions = rejectinvalid_helohostname rejectnon_fqdn_helohostname

    to this
    smtpdhelorestrictions = permitsaslauthenticated permit_mynetworks rejectinvalid_helohostname rejectnon_fqdn_helohostname


    In Outlook, use port 587/TLS (not ssl)
  • 6. Re: No SMTP Authentication for Outlook or Outllok Express?
    AlvaroL Level 1 Level 1 (0 points)
    I do have a similar problem, and it is a helo command rejected. The exact message is:

    The message was not sent, one of the destinations was rejected by the server. Your e-mail address is "alvaro@ledific.com". Subject 'test', Account: 'mail.incontrol.com.ec', Server: 'mail.incontrol.com.ec', Protocol: SMTP, Server answer: '504 5.5.2 <ALVARO>: Helo command rejected: need fully-qualified hostname', Port: 25, Security (SSL): No, Server error: 504, Error number: 0x800CCC79.

    All my Macs work fine, but PCs with Windows (XP,7,Vista) receive mails but can´t send e-mails.

    If this is something I have to change on main.cf, where can I find this file?

    I am using a Mac Mini as a server with the latest Snow Leopard version
  • 7. Re: No SMTP Authentication for Outlook or Outllok Express?
    UptimeJeff Level 4 Level 4 (3,390 points)
    do this, open Terminal and copy/paste this:


    sudo postconf -e "smtpdhelorestrictions = permitsaslauthenticated permit_mynetworks rejectinvalid_helohostname rejectnon_fqdn_helohostname"



    sudo postfix reload



    that should fix it
  • 8. Re: No SMTP Authentication for Thunderbird or Outlook?
    jlisburn Level 1 Level 1 (0 points)
    I'm having continued problems with this issue and none of the solutions listed helps me out. Some Windows/Outlook clients can connect and some can't. Al have different combos of Windows and Outlook versions and their doesn't seem to be a common thread.
    Windows 7 Outlook 2003 - no go
    Windows 7 Outlook 2007 - 2 good, one no go
    Windows 7 Outlok 2010 - fine
    Windows Vista Outlok 2007 - fine
    ??????
  • 9. Re: No SMTP Authentication for Thunderbird or Outlook?
    Paul Cezanne Level 1 Level 1 (10 points)
    What were your settings for Win7 and Outlook 2010? I still can't get that to work.
  • 10. Re: No SMTP Authentication for Thunderbird or Outlook?
    Paul Cezanne Level 1 Level 1 (10 points)
    Still not answered
  • 11. Re: No SMTP Authentication for Thunderbird or Outlook?
    Jeff Donovan Level 2 Level 2 (170 points)
    im not sure what the settings are but im working on a similar issue.

    definitely use STARTTLS on either port 25 or 587
    you can test your connection by telneting to it:587

    verify that tls is enabled in your master.cf

    ** STMPS port 465 is disabled by default in osx server main.cf. you can uncomment the lines to allow SASL.

    you can also try
    brokensasl_authclients = yes
    # this is to support outlook and other clients

    gl

    iof anyone knows how i can get sasl to read ldap for passwd im all ears.
  • 12. Re: No SMTP Authentication for Thunderbird or Outlook?
    MO_Mule Level 1 Level 1 (5 points)
    UptimeJeff

    Thank you for that, that worked perfectly. That was the answer for me, and probably answered this thread, but I didn't start it...
  • 13. Re: No SMTP Authentication for Thunderbird or Outlook?
    Paul Cezanne Level 1 Level 1 (10 points)
    The brokensasl_authclients = yes setting allows an obsolete version of the AUTH command to work, which may allow some Microsoft clients to work.

    See http://www.postfix.org/postconf.5.html

    Basically, it's making the server work in a non-standard way so that something that's broken can work. Not the best approach when trying to keep a secure server.

    Is a real fix even available? Seems to me the latest version of Outlook (that's actually been around for a while) connecting to Snow Leopard Server is not exactly an unexpected circumstance.
  • 14. Re: No SMTP Authentication for Outlook or Outllok Express?
    jpawelchak Level 1 Level 1 (0 points)

    Is the following correct? why does "= permitsaslauth..." look funny to me?

     

     

    sudo postconf -e "smtpdhelorestrictions = permitsaslauthenticated permit_mynetworks rejectinvalid_helohostname rejectnon_fqdn_helohostname"


     


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