10.10.4 Cannot connect to non-GMail SMTP server over SSL.

Discussion in 'OS X Yosemite (10.10)' started by SuperTango, Jul 4, 2015.

  1. SuperTango macrumors newbie

    Joined:
    Aug 23, 2011
    #1
    I am an email administrator who maintains a small group of 3 different Linux (CentOS 5) based email servers. Since the 10.10.4 upgrade, none of my users can connect to the SMTP servers over SSL (either port 465 or 587). Using the connection doctor, it always says:

    SMTP: Could not connect to this SMTP server. Check your network connection and that you entered the correct information about the Account preferences. Also verify that the server supports SSL. If it does not, deselect the "Use SSL" checkbox in the Advanced tab of the Account preferences.

    This has been working fine for years, so I know it should be working.

    The SMTP logs on the mac show:

    Jul 4 16:23:45 mac-client.example.com Mail[36498] <Debug>: [0x600000765880] >> STARTTLS (0 additional bytes)
    Jul 4 16:23:45 mac-client.example.com Mail[36498] <Debug>: [0x608000b6b280] << 250-outbound.example.com Hello c-24-6-61-6.hsd1.ca.comcast.net [24.6.61.6], pleased to meet you

    Jul 4 16:23:45 mac-client.example.com Mail[36498] <Debug>: [0x608000b6b280] << 250-ENHANCEDSTATUSCODES

    Jul 4 16:23:45 mac-client.example.com Mail[36498] <Debug>: [0x608000b6b280] << 250-PIPELINING

    Jul 4 16:23:45 mac-client.example.com Mail[36498] <Debug>: [0x608000b6b280] << 250-8BITMIME

    Jul 4 16:23:45 mac-client.example.com Mail[36498] <Debug>: [0x608000b6b280] << 250-SIZE

    Jul 4 16:23:45 mac-client.example.com Mail[36498] <Debug>: [0x608000b6b280] << 250-DSN

    Jul 4 16:23:45 mac-client.example.com Mail[36498] <Debug>: [0x608000b6b280] << 250-ETRN

    Jul 4 16:23:45 mac-client.example.com Mail[36498] <Debug>: [0x608000b6b280] << 250-STARTTLS

    Jul 4 16:23:45 mac-client.example.com Mail[36498] <Debug>: [0x608000b6b280] << 250-DELIVERBY

    Jul 4 16:23:45 mac-client.example.com Mail[36498] <Debug>: [0x608000b6b280] << 250 HELP

    Jul 4 16:23:45 mac-client.example.com Mail[36498] <Debug>: [0x608000b6b280] >> STARTTLS (0 additional bytes)
    Jul 4 16:23:45 mac-client.example.com Mail[36498] <Debug>: [0x600000765880] << 220 2.0.0 (18 additional bytes)
    Jul 4 16:23:45 mac-client.example.com Mail[36498] <Debug>: [0x608000b6b280] << 220 2.0.0 (18 additional bytes)
    Jul 4 16:23:54 mac-client.example.com Mail[36498] <Debug>: Could not connect: <MFSMTPConnection: 0x608000b6b280> (Disconnected) account: A{SMTP - 210E3607-5A77-4B94-9492-8EFD802C9A44} (Error Domain=NSPOSIXErrorDomain Code=60 "The operation couldn’t be completed. Operation timed out")
    Jul 4 16:23:54 mac-client.example.com Mail[36498] <Debug>: Could not connect: <MFSMTPConnection: 0x6100007660c0> (Disconnected) account: A{SMTP - 4C0C8CBD-5978-4717-8762-8A3B0DB2BC86} (Error Domain=NSOSStatusErrorDomain Code=-9850 "The operation couldn’t be completed. (OSStatus error -9850.)")
    Jul 4 16:23:54 mac-client.example.com Mail[36498] <Debug>: Could not connect: <MFSMTPConnection: 0x610000371700> (Disconnected) account: A{SMTP - de0db566-bf54-4bea-80df-0dd8425e082e} (Error Domain=NSOSStatusErrorDomain Code=-9850 "The operation couldn’t be completed. (OSStatus error -9850.)")

    The server logs show:

    Jul 4 16:36:05 server sendmail[14474]: STARTTLS=server, error: accept failed=0, SSL_error=5, errno=0, retry=-1
    Jul 4 16:36:05 server sendmail[14474]: t64Na5CS014474: client [X.X.X.X] did not issue MAIL/EXPN/VRFY/ETRN during connection to MSA

    we have the Logjam updates and such setup for our servers, and the mac clients can connect to IMAP (using certs issued by the same CA). Anyone have any ideas?

    Thanks.
     
  2. Queen6 macrumors 603

    Queen6

    Joined:
    Dec 11, 2008
    Location:
    Enjoying Better Things
  3. SuperTango thread starter macrumors newbie

    Joined:
    Aug 23, 2011
    #3
    993 is IMAPS (which is working fine).
     
  4. Queen6 macrumors 603

    Queen6

    Joined:
    Dec 11, 2008
    Location:
    Enjoying Better Things
    #4
    My bad, drilled through all the settings SMTP is on 465 with no issue

    Q-6
     

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