Submission port doesn't support TLS?

[BasharTeg]

I have my toaster all setup and it is working nicely, except when I attempt to use SSL/TLS while submitting emails to Submission from remote.  The SMTP AUTH works properly, so I am able to send emails unencrypted from remote.  But when I enable SSL on an Outlook Express client, it says "Your server has unexpectedly terminated the connection."

I did a tcpdump of the transaction and the only thing I can make of it is the server saying 502 unimplemented.  I tried telnetting to the submission port and typing STARTTLS, and that seems to work fine.  Any ideas?

tcpdump: listening on em0
15:38:32.330270 24-52-213-117.crlsca.adelphia.net.64033 > 192.168.0.5.submission: S 3237078104:3237078104(0) win 16384 <mss 1380,nop,nop,sackOK> (DF)
0x0000   4500 0030 0502 4000 6506 626f 1834 d575        E..0..@.e.bo.4.u
0x0010   c0a8 0005 fa21 024b c0f1 e458 ca22 1325        .....!.K...X.".%
0x0020   7002 4000 1619 0000 0204 0564 0101 0402        p.@........d....
15:38:32.330302 192.168.0.5.submission > 24-52-213-117.crlsca.adelphia.net.64033: S 1385805897:1385805897(0) ack 3237078105 win 57344 <mss 1460> (DF)
0x0000   4500 002c 246e 4000 4006 6807 c0a8 0005        E..,$n@.>@.h.....
0x0010   1834 d575 024b fa21 5299 b849 c0f1 e459        .4.u.K.!R..I...Y
0x0020   6012 e000 ae75 0000 0204 05b4                  `....u......
15:38:32.370991 24-52-213-117.crlsca.adelphia.net.64033 > 192.168.0.5.submission: . ack 1 win 16560 (DF)
0x0000   4500 0028 0503 4000 6506 6276 1834 d575        E..(..@.e.bv.4.u
0x0010   c0a8 0005 fa21 024b c0f1 e459 5299 b84a        .....!.K...YR..J
0x0020   5010 40b0 1431 0000 0000 0000 0000             P.@..1........
15:38:32.374582 192.168.0.5.submission > 24-52-213-117.crlsca.adelphia.net.64033: P 1:34(33) ack 1 win 57960 (DF)
0x0000   4500 0049 2471 4000 4006 67e7 c0a8 0005        E..I$q@.>@.g.....
0x0010   1834 d575 024b fa21 5299 b84a c0f1 e459        .4.u.K.!R..J...Y
0x0020   5018 e268 ae92 0000 3232 3020 6d61 696c        P..h....220.mail
0x0030   2e66 7265 6564 6f6d 766f 6963 652e 636f        .freedomvoice.co
0x0040   6d20 4553 4d54 500d 0a                         m.ESMTP..
15:38:32.379864 24-52-213-117.crlsca.adelphia.net.64033 > 192.168.0.5.submission: P 1:103(102) ack 1 win 16560 (DF)
0x0000   4500 008e 0504 4000 6506 620f 1834 d575        E.....@.e.b..4.u
0x0010   c0a8 0005 fa21 024b c0f1 e459 5299 b84a        .....!.K...YR..J
0x0020   5018 40b0 4ef9 0000 1603 0100 6101 0000        P.@.N.......a...
0x0030   5d03 0140 c5de faf1 163f 7687 0abd a4dc        ]..@.....?v.....
0x0040   7391 d57d 1261 0c71 5b4c be19 b806 fb71        s..}.a.q[L.....q
0x0050   4175                                           Au
15:38:32.415842 24-52-213-117.crlsca.adelphia.net.64033 > 192.168.0.5.submission: F 103:103(0) ack 34 win 16527 (DF)
0x0000   4500 0028 0505 4000 6506 6274 1834 d575        E..(..@.e.bt.4.u
0x0010   c0a8 0005 fa21 024b c0f1 e4bf 5299 b86b        .....!.K....R..k
0x0020   5011 408f 13ca 0000 0000 0000 0000             P.@...........
15:38:32.415858 192.168.0.5.submission > 24-52-213-117.crlsca.adelphia.net.64033: P 34:90(56) ack 104 win 57960 (DF)
0x0000   4500 0060 2472 4000 4006 67cf c0a8 0005        E..`$r@.>@.g.....
0x0010   1834 d575 024b fa21 5299 b86b c0f1 e4c0        .4.u.K.!R..k....
0x0020   5018 e268 aea9 0000 3530 3220 756e 696d        P..h....502.unim
0x0030   706c 656d 656e 7465 6420 2823 352e 352e        plemented.(#5.5.
0x0040   3129 0d0a 3530 3220 756e 696d 706c 656d        1)..502.unimplem
0x0050   656e                                           en
15:38:32.415888 192.168.0.5.submission > 24-52-213-117.crlsca.adelphia.net.64033: F 90:90(0) ack 104 win 57960 (DF)
0x0000   4500 0028 2473 4000 4006 6806 c0a8 0005        E..($s@.>@.h.....
0x0010   1834 d575 024b fa21 5299 b8a3 c0f1 e4c0        .4.u.K.!R.......
0x0020   5011 e268 ae71 0000                            P..h.q..
15:38:32.423719 24-52-213-117.crlsca.adelphia.net.64034 > 192.168.0.5.submission: S 3237166437:3237166437(0) win 16384 <mss 1380,nop,nop,sackOK> (DF)
0x0000   4500 0030 0506 4000 6506 626b 1834 d575        E..0..@.e.bk.4.u
0x0010   c0a8 0005 fa22 024b c0f3 3d65 a5f5 3c88        .....".K..=e..<.
0x0020   7002 4000 b7d3 0000 0204 0564 0101 0402        p.@........d....
15:38:32.423754 192.168.0.5.submission > 24-52-213-117.crlsca.adelphia.net.64034: S 1106908436:1106908436(0) ack 3237166438 win 57344 <mss 1460> (DF)
0x0000   4500 002c 2474 4000 4006 6801 c0a8 0005        E..,$t@.>@.h.....
0x0010   1834 d575 024b fa22 41fa 1514 c0f3 3d66        .4.u.K."A.....=f
0x0020   6012 e000 ae75 0000 0204 05b4                  `....u......
15:38:32.459941 24-52-213-117.crlsca.adelphia.net.64033 > 192.168.0.5.submission: R 3237078208:3237078208(0) win 0 (DF)
0x0000   4500 0028 0507 4000 6506 6272 1834 d575        E..(..@.e.br.4.u
0x0010   c0a8 0005 fa21 024b c0f1 e4c0 ca22 1325        .....!.K.....".%
0x0020   5004 0000 8222 0000 0000 0000 0000             P...."........
15:38:32.471560 24-52-213-117.crlsca.adelphia.net.64034 > 192.168.0.5.submission: . ack 1 win 16560 (DF)
0x0000   4500 0028 0509 4000 6506 6270 1834 d575        E..(..@.e.bp.4.u
0x0010   c0a8 0005 fa22 024b c0f3 3d66 41fa 1515        .....".K..=fA...
0x0020   5010 40b0 6ef6 0000 0000 0000 0000             P.@.n.........
15:38:32.474946 192.168.0.5.submission > 24-52-213-117.crlsca.adelphia.net.64034: P 1:34(33) ack 1 win 57960 (DF)
0x0000   4500 0049 2477 4000 4006 67e1 c0a8 0005        E..I$w@.>@.g.....
0x0010   1834 d575 024b fa22 41fa 1515 c0f3 3d66        .4.u.K."A.....=f
0x0020   5018 e268 ae92 0000 3232 3020 6d61 696c        P..h....220.mail
0x0030   2e66 7265 6564 6f6d 766f 6963 652e 636f        .freedomvoice.co
0x0040   6d20 4553 4d54 500d 0a                         m.ESMTP..
15:38:32.476685 24-52-213-117.crlsca.adelphia.net.64034 > 192.168.0.5.submission: F 1:1(0) ack 1 win 16560 (DF)
0x0000   4500 0028 050a 4000 6506 626f 1834 d575        E..(..@.e.bo.4.u
0x0010   c0a8 0005 fa22 024b c0f3 3d66 41fa 1515        .....".K..=fA...
0x0020   5011 40b0 6ef5 0000 0000 0000 0000             P.@.n.........
15:38:32.476707 192.168.0.5.submission > 24-52-213-117.crlsca.adelphia.net.64034: . ack 2 win 57960 (DF)
0x0000   4500 0028 2478 4000 4006 6801 c0a8 0005        E..($x@.>@.h.....
0x0010   1834 d575 024b fa22 41fa 1536 c0f3 3d67        .4.u.K."A..6..=g
0x0020   5010 e268 ae71 0000                            P..h.q..
15:38:32.476729 192.168.0.5.submission > 24-52-213-117.crlsca.adelphia.net.64034: F 34:34(0) ack 2 win 57960 (DF)
0x0000   4500 0028 2479 4000 4006 6800 c0a8 0005        E..($y@.>@.h.....
0x0010   1834 d575 024b fa22 41fa 1536 c0f3 3d67        .4.u.K."A..6..=g
0x0020   5011 e268 ae71 0000                            P..h.q..
15:38:32.518409 24-52-213-117.crlsca.adelphia.net.64034 > 192.168.0.5.submission: R 3237166439:3237166439(0) win 0 (DF)
0x0000   4500 0028 050c 4000 6506 626d 1834 d575        E..(..@.e.bm.4.u
0x0010   c0a8 0005 fa22 024b c0f3 3d67 a5f5 3c88        .....".K..=g..<.
0x0020   5004 0000 2443 0000 0000 0000 0000             P...$C........

[matt]

I use it that way every day, using Mail.app on MacOS X. I know plenty of folks have "issues" to resolve before everything "just works" when using Outlook, and even then they end up with sporadic issues.

Matt