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.
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.
