From owner-freebsd-questions@FreeBSD.ORG Sat Mar 30 10:14:48 2013 Return-Path: Delivered-To: freebsd-questions@freebsd.org Received: from mx1.freebsd.org (mx1.FreeBSD.org [8.8.178.115]) by hub.freebsd.org (Postfix) with ESMTP id 05932568 for ; Sat, 30 Mar 2013 10:14:48 +0000 (UTC) (envelope-from mexas@bristol.ac.uk) Received: from dirg.bris.ac.uk (dirg.bris.ac.uk [137.222.10.102]) by mx1.freebsd.org (Postfix) with ESMTP id C100FB0E for ; Sat, 30 Mar 2013 10:14:47 +0000 (UTC) Received: from ncsc.bris.ac.uk ([137.222.10.41]) by dirg.bris.ac.uk with esmtp (Exim 4.72) (envelope-from ) id 1ULso9-00070z-PG for freebsd-questions@freebsd.org; Sat, 30 Mar 2013 10:14:45 +0000 Received: from cpc2-aztw9-0-0-cust169.18-1.cable.virginmedia.com ([77.97.103.170] helo=zzz.men.bris.ac.uk) by ncsc.bris.ac.uk with esmtpsa (TLSv1:AES256-SHA:256) (Exim 4.72) (envelope-from ) id 1ULso9-0000FP-0k for freebsd-questions@freebsd.org; Sat, 30 Mar 2013 10:14:45 +0000 Received: from zzz.men.bris.ac.uk (localhost [127.0.0.1]) by zzz.men.bris.ac.uk (8.14.6/8.14.6) with ESMTP id r2UAEiRa081672 for ; Sat, 30 Mar 2013 10:14:44 GMT (envelope-from mexas@zzz.men.bris.ac.uk) Received: (from mexas@localhost) by zzz.men.bris.ac.uk (8.14.6/8.14.6/Submit) id r2UAEi1W081669 for freebsd-questions@freebsd.org; Sat, 30 Mar 2013 10:14:44 GMT (envelope-from mexas) Date: Sat, 30 Mar 2013 10:14:44 GMT From: Anton Shterenlikht Message-Id: <201303301014.r2UAEi1W081669@zzz.men.bris.ac.uk> To: freebsd-questions@freebsd.org Subject: Re: Operation timed out with smtp.gmail.com - please help In-Reply-To: <20130329153619.69c5b4dd@scorpio> X-BeenThere: freebsd-questions@freebsd.org X-Mailman-Version: 2.1.14 Precedence: list Reply-To: mexas@bristol.ac.uk List-Id: User questions List-Unsubscribe: , List-Archive: List-Post: List-Help: List-Subscribe: , X-List-Received-Date: Sat, 30 Mar 2013 10:14:48 -0000 Date: Fri, 29 Mar 2013 15:36:19 -0400 From: Jerry To: FreeBSD Subject: Re: Operation timed out with smtp.gmail.com - please help On Fri, 29 Mar 2013 18:32:34 GMT Anton Shterenlikht articulated: > Please help debug sendmail / smtp.gmail config. > > My University just switched to gmail (dickheads) > and I'm trying to figure out how to set it up. > > It used to work ok with the University smtp auth > server. Now I get in /var/log/maillog: > > sm-mta[72300]: r2TI0vQc072134: to=, > ctladdr= (1001/1001), > delay=00:20:01, xdelay=00:00:00, mailer=relay, pri=210424, > relay=smtp.gmail.com, dsn=4.0.0, > stat=Deferred: Operation timed out with smtp.gmail.com > > I switched the firewall off completely. > > I have: > > # cat /etc/mail/auth/client-info > AuthInfo:smtp.gmail.com "U:root" "I:mexas@bristol.ac.uk" "P:xxxxx" > # > > and this in /etc/mail/freebsd.mc: > > define(`confAUTH_MECHANISMS', `GSSAPI DIGEST-MD5 CRAM-MD5 LOGIN')dnl > define(`SMART_HOST', `smtp.gmail.com')dnl > > I rebuilt (run make under /etc/mail. This just > renames freebsd.mc to .mc, and freebsd.submit.mc > to .submit.mc) and restarted sendmail. > > I also use: > > MASQUERADE_AS(`bristol.ac.uk') > MASQUERADE_DOMAIN(`bristol.ac.uk') > > to use the university domain instead of > may xxxx.men.bris.ac.uk, which is not > acceptable. Try this at the command line: openssl s_client -connect smtp.gmail.com:25 -starttls smtp If it times out, change the port number to 587 and try it again. If you cannot make a connect using either port number then you have a firewall problem. Thank you, I get: $ openssl s_client -connect smtp.gmail.com:25 -starttls smtp connect: Operation timed out connect:errno=60 $ $ openssl s_client -connect smtp.gmail.com:587 -starttls smtp CONNECTED(00000003) depth=1 C = US, O = Google Inc, CN = Google Internet Authority verify error:num=20:unable to get local issuer certificate verify return:0 --- Certificate chain 0 s:/C=US/ST=California/L=Mountain View/O=Google Inc/CN=smtp.gmail.com i:/C=US/O=Google Inc/CN=Google Internet Authority 1 s:/C=US/O=Google Inc/CN=Google Internet Authority i:/C=US/O=Equifax/OU=Equifax Secure Certificate Authority --- Server certificate -----BEGIN CERTIFICATE----- MIIDgDCCAumgAwIBAgIKO3T/ewAAAABoqDANBgkqhkiG9w0BAQUFADBGMQswCQYD VQQGEwJVUzETMBEGA1UEChMKR29vZ2xlIEluYzEiMCAGA1UEAxMZR29vZ2xlIElu dGVybmV0IEF1dGhvcml0eTAeFw0xMjA5MTIxMTU3NTBaFw0xMzA2MDcxOTQzMjda MGgxCzAJBgNVBAYTAlVTMRMwEQYDVQQIEwpDYWxpZm9ybmlhMRYwFAYDVQQHEw1N b3VudGFpbiBWaWV3MRMwEQYDVQQKEwpHb29nbGUgSW5jMRcwFQYDVQQDEw5zbXRw LmdtYWlsLmNvbTCBnzANBgkqhkiG9w0BAQEFAAOBjQAwgYkCgYEAv0UvQmjW1y96 cOK6AdQVEYPRd3ZQ9UhxkKfuVaYS9riOESFkWxkz+b3Ts/EOA5SY8axkaJS7Qa/v N7laztYY8tTkx9Ml+eCY4xh0fFq9z4/WWADGqTY5I0wvqjZr+jBuYGulK1fU4ZUS QpuZMMO9x7Bmr5LVP9C5r2qnoqtMtJUCAwEAAaOCAVEwggFNMB0GA1UdJQQWMBQG CCsGAQUFBwMBBggrBgEFBQcDAjAdBgNVHQ4EFgQUaCtARMZ9urIDfdpR6v1AkQsr 44owHwYDVR0jBBgwFoAUv8Aw6/VDET5nup6R+/xq2uNrEiQwWwYDVR0fBFQwUjBQ oE6gTIZKaHR0cDovL3d3dy5nc3RhdGljLmNvbS9Hb29nbGVJbnRlcm5ldEF1dGhv cml0eS9Hb29nbGVJbnRlcm5ldEF1dGhvcml0eS5jcmwwZgYIKwYBBQUHAQEEWjBY MFYGCCsGAQUFBzAChkpodHRwOi8vd3d3LmdzdGF0aWMuY29tL0dvb2dsZUludGVy bmV0QXV0aG9yaXR5L0dvb2dsZUludGVybmV0QXV0aG9yaXR5LmNydDAMBgNVHRMB Af8EAjAAMBkGA1UdEQQSMBCCDnNtdHAuZ21haWwuY29tMA0GCSqGSIb3DQEBBQUA A4GBADSkwmtEUhy/AhX2sIULT0Q5S9OlfKxbyE8hEc8nxls3jbk5yKZYd35Bzyy8 raoUPFuD3IH+zP/FGj5LPQirjnJLUvuFDsiM4eowPUthQad9SGWWdz6hCx8HpEUZ 1ssGnwb3HX34e9RH57v9LdtVUPdFYQsBJ36miGPylWk6r0xx -----END CERTIFICATE----- subject=/C=US/ST=California/L=Mountain View/O=Google Inc/CN=smtp.gmail.com issuer=/C=US/O=Google Inc/CN=Google Internet Authority --- No client certificate CA names sent --- SSL handshake has read 2317 bytes and written 476 bytes --- New, TLSv1/SSLv3, Cipher is ECDHE-RSA-RC4-SHA Server public key is 1024 bit Secure Renegotiation IS supported Compression: NONE Expansion: NONE SSL-Session: Protocol : TLSv1.2 Cipher : ECDHE-RSA-RC4-SHA Session-ID: 8CAF4204FADB72F58FA6334A62F65B7182EF06F3C9AD8042FD44B9F726E8C9D5 Session-ID-ctx: Master-Key: 45312AE23341AAFA1414BDDD30740E4FB40655986FD410A606CD351206BBAC5E5496F77DDF4DBE32B0E9B7E7FFA1057 Key-Arg : None PSK identity: None PSK identity hint: None SRP username: None TLS session ticket lifetime hint: 100800 (seconds) TLS session ticket: 0000 - 63 53 11 b3 92 0d 59 63-15 90 58 10 84 f2 f7 6a cS....Yc..X....j 0010 - 7c 7c 62 96 c5 3d cb 52-ca 32 2d 97 de 51 10 6d ||b..=.R.2-..Q.m 0020 - d2 97 ca 69 f8 cf 3d 6e-c9 60 73 3a 49 3a 4a 74 ...i..=n.`s:I:Jt 0030 - 88 ee 2c b0 75 4d 5b 61-56 a4 fe e3 42 56 7c 2d ..,.uM[aV...BV|- 0040 - 70 db e2 d7 5d 84 bd 88-06 7c c2 96 19 53 d0 58 p...]....|...S.X 0050 - f9 6a fb dd 3a 7b 73 3e-f9 bc 6d b1 ac 6a 63 13 .j..:{s>..m..jc. 0060 - 64 b8 be 1f b8 fd 05 da-7d 87 63 a4 53 6e 3a 55 d.......}.c.Sn:U 0070 - fe 73 f6 05 63 9a c6 c9-da cb 6c 4e ce 1d 1f a1 .s..c.....lN.... 0080 - 07 12 0b c7 d1 ce 71 5a-f1 2c b4 a9 20 32 e2 64 ......qZ.,.. 2.d 0090 - 49 fd 77 41 I.wA Start Time: 1364638180 Timeout : 300 (sec) Verify return code: 20 (unable to get local issuer certificate) --- 250 ENHANCEDSTATUSCODES ^C $ The university IT support page: http://www.bristol.ac.uk/it-services/applications/email/gmail/manual-config-gmail.html actually says that port 465 SSL should be used, so I also tried: $ openssl s_client -connect smtp.gmail.com:465 -starttls smtp CONNECTED(00000003) ^C $ Not sure what to make of this. Is the port set by sendmail config files? Many thanks for your help Anton