Aloha,

I have set up sendmail on a linux server. It sends through Time Warner's external MTA server via define(`SMART_HOST', `smtp-server.hawaii.rr.com'). The system works except for certain email recipients. Three of the four clients on the machine send emails to certain recipients, maillog confirms that is was sent but it never shows up in the recipients email. What makes this perplexing the 4 client on the machine is able to sent to the same email address and it show up in the recipients email. The system has been running well for over 3 years. I just don't know where to look to figure out what is happening. Any suggests are very much appreciated. If anyone wish to see the maillog send me an email.

cheers,
Hal

Hi,

You should post here the relevant part of /var/log/maillog masking sensitive data (email addresses, IPs etc)
Also run the following command for both a working and a non-working email and see what you get:
Regards

1 members found this post helpful.

Troubleshooting email servers can be a real challenge. This is what I would do, but I am sure there are plenty of ways to nail this down :


Telnet into the remote mail server, and send an email using each of your clients email address in the 'from' field in successive emails. The remote server should tell you why a particular email has failed.

If the remote server accepts all emails, perhaps ask the recipients to check their junk mail folders before claiming they did not get the email.

There are plenty of " how - to's " to be found doing a search on "testing sendmail with telnet".

Keep us posted !

Thank you for your reply and request.

MAILLOG --- email sent from sandi to hrichman, hrichman never recieved it

Jul 29 18:48:43 pq-server sendmail[2523]: NOQUEUE: connect from cpe-XX-X-XXX-XX.XXX.XX.XX.XX [XX.XX.XXX.XX]
Jul 29 18:48:43 pq-server sendmail[2523]: AUTH: available mech=DIGEST-MD5 ANONYMOUS LOGIN CRAM-MD5 PLAIN GSSAPI, allowed mech=EXTERNAL GSSAPI DIGEST-MD5 CRAM-MD5 LOGIN PLAIN
Jul 29 18:48:43 pq-server sendmail[2523]: r6U4mhkF002523: Milter: no active filter
Jul 29 18:48:43 pq-server sendmail[2523]: r6U4mhkF002523: --- 220 localhost6.localdomain6 ESMTP Sendmail 8.14.4/8.14.4; Mon, 29 Jul 2013 18:48:43 -1000
Jul 29 18:48:43 pq-server sendmail[2523]: r6U4mhkF002523: <-- EHLO halPC
Jul 29 18:48:43 pq-server sendmail[2523]: r6U4mhkF002523: --- 250-localhost6.localdomain6 Hello cpe-XX-X-XXX-XX.hawaii.res.rr.com [XX.X.XXX.XX], pleased to meet you
Jul 29 18:48:43 pq-server sendmail[2523]: r6U4mhkF002523: --- 250-ENHANCEDSTATUSCODES
Jul 29 18:48:43 pq-server sendmail[2523]: r6U4mhkF002523: --- 250-PIPELINING
Jul 29 18:48:43 pq-server sendmail[2523]: r6U4mhkF002523: --- 250-8BITMIME
Jul 29 18:48:43 pq-server sendmail[2523]: r6U4mhkF002523: --- 250-SIZE
Jul 29 18:48:43 pq-server sendmail[2523]: r6U4mhkF002523: --- 250-DSN
Jul 29 18:48:43 pq-server sendmail[2523]: r6U4mhkF002523: --- 250-AUTH GSSAPI DIGEST-MD5 CRAM-MD5 LOGIN PLAIN
Jul 29 18:48:43 pq-server sendmail[2523]: r6U4mhkF002523: --- 250-STARTTLS
Jul 29 18:48:43 pq-server sendmail[2523]: r6U4mhkF002523: --- 250-DELIVERBY
Jul 29 18:48:43 pq-server sendmail[2523]: r6U4mhkF002523: --- 250 HELP
Jul 29 18:48:43 pq-server sendmail[2523]: r6U4mhkF002523: <-- AUTH DIGEST-MD5
Jul 29 18:48:43 pq-server sendmail[2523]: r6U4mhkF002523: --- 334 bm9uY2U9ImVZdWtaa296TTBYRGMxUkFnVUVLVElUd2t2T0I2VDV1VDBHUFZ2K3VKT1E9IixyZWFsbT0ibG9jYWxob3N0Ni5sb2Nh bGRvbWFpbjYiLHFvcD0iYXV0aCxhdXRoLWludCxhdXRoLWNvbmYiLGNpcGhlcj0icmM0LTQwLHJjNC01NixyYzQsZGVzLDNkZXMi LG1heGJ1Zj04MTkyLGNoYXJzZXQ9dXRmLTgsYWxnb3JpdGhtPW1kNS1zZXNz
Jul 29 18:48:43 pq-server sendmail[2523]: r6U4mhkF002523: --- 535 5.7.0 authentication failed
Jul 29 18:48:43 pq-server sendmail[2523]: r6U4mhkF002523: AUTH failure (DIGEST-MD5): authentication failure (-13) SASL(-13): authentication failure: realm changed: authentication aborted, relay=cpe-XX-X-XXX-XX.XXX.XX.XX.XX [XX.X.XXX.XX]
Jul 29 18:48:43 pq-server sendmail[2523]: r6U4mhkF002523: <-- AUTH LOGIN
Jul 29 18:48:43 pq-server sendmail[2523]: r6U4mhkF002523: --- 334 VXNlcm5hbWU6
Jul 29 18:48:43 pq-server sendmail[2523]: r6U4mhkF002523: --- 334 UGFzc3dvcmQ6
Jul 29 18:48:43 pq-server sendmail[2523]: r6U4mhkF002523: --- 235 2.0.0 OK Authenticated
Jul 29 18:48:43 pq-server sendmail[2523]: AUTH=server, relay=cpe-XX-X-XXX-XX.XXX.XX.XX.XX [XX.X.XXX.XX], authid=sandi, mech=LOGIN, bits=0
Jul 29 18:48:43 pq-server sendmail[2523]: r6U4mhkF002523: <-- MAIL FROM: <sandi@XXX.com>
Jul 29 18:48:43 pq-server sendmail[2523]: r6U4mhkF002523: --- 250 2.1.0 <sandi@XXX.com>... Sender ok
Jul 29 18:48:43 pq-server sendmail[2523]: r6U4mhkF002523: <-- RCPT TO: <hrichman@XXX>
Jul 29 18:48:43 pq-server sendmail[2523]: r6U4mhkF002523: --- 250 2.1.5 <hrichman@XXX>... Recipient ok
Jul 29 18:48:43 pq-server sendmail[2523]: r6U4mhkF002523: <-- DATA
Jul 29 18:48:43 pq-server sendmail[2523]: r6U4mhkF002523: --- 354 Enter mail, end with "." on a line by itself
Jul 29 18:48:44 pq-server sendmail[2523]: r6U4mhkF002523: from=<sandi@XXX.com>, size=2375, class=0, nrcpts=1, msgid=<00aa01ce8ce0$d52640e0$7f72c2a0$@com>, proto=ESMTP, daemon=MTA, relay=cpe-XX-X-XXX-XX.XXX.XX.XX.XX [XX.X.XXX.XX]
Jul 29 18:48:44 pq-server sendmail[2523]: r6U4mhkF002523: --- 050 <hrichman@XXX>... queued
Jul 29 18:48:44 pq-server sendmail[2523]: r6U4mhkF002523: to=<hrichman@XXX>, delay=00:00:01, mailer=relay, pri=32375, stat=queued
Jul 29 18:48:44 pq-server sendmail[2523]: r6U4mhkF002523: --- 250 2.0.0 r6U4mhkF002523 Message accepted for delivery
Jul 29 18:48:45 pq-server MailScanner[1863]: New Batch: Scanning 1 messages, 2903 bytes
Jul 29 18:48:45 pq-server MailScanner[1863]: Virus and Content Scanning: Starting
Jul 29 18:48:45 pq-server MailScanner[2526]: Unrar command /usr/bin/unrar does not exist or is not executable, please either install it or remove the setting from MailScanner.conf
Jul 29 18:48:46 pq-server MailScanner[1863]: Expired 4 records from the SpamAssassin cache
Jul 29 18:48:46 pq-server sendmail[2523]: r6U4mhkG002523: <-- QUIT
Jul 29 18:48:46 pq-server sendmail[2523]: r6U4mhkG002523: --- 221 2.0.0 localhost6.localdomain6 closing connection
Jul 29 18:48:47 pq-server MailScanner[1863]: Uninfected: Delivered 1 messages
Jul 29 18:48:47 pq-server sendmail[2529]: STARTTLS: ClientCertFile missing
Jul 29 18:48:47 pq-server sendmail[2529]: STARTTLS: ClientKeyFile missing
Jul 29 18:48:47 pq-server sendmail[2529]: STARTTLS: CRLFile missing
Jul 29 18:48:47 pq-server sendmail[2529]: STARTTLS=client, init=1
Jul 29 18:48:47 pq-server MailScanner[1863]: Deleted 1 messages from processing-database
Jul 29 18:48:47 pq-server sendmail[2530]: r6U4mhkF002523: SMTP outgoing connect on [192.168.1.101]
Jul 29 18:48:48 pq-server sendmail[2530]: r6U4mhkF002523: to=<hrichman@XXX>, ctladdr=<sandi@XXX.com> (514/514), delay=00:00:05, xdelay=00:00:01, mailer=relay, pri=122375, relay=smtp-server.XXX.XX.com. [XX.XX.XX.XX], dsn=2.0.0, stat=Sent (OK 51/5B-18468-8F647F15)
Jul 29 18:48:48 pq-server sendmail[2530]: r6U4mhkF002523: done; delay=00:00:05, ntries=1

MAILLOG --- email sent from kelly to hrichman, hrichman recieved email

Jul 29 18:48:55 pq-server sendmail[2531]: NOQUEUE: connect from cpe-XX-X-XXX-XX.XXX.XX.XX.XX [XX.X.XXX.XX]
Jul 29 18:48:55 pq-server sendmail[2531]: AUTH: available mech=DIGEST-MD5 ANONYMOUS LOGIN CRAM-MD5 PLAIN GSSAPI, allowed mech=EXTERNAL GSSAPI DIGEST-MD5 CRAM-MD5 LOGIN PLAIN
Jul 29 18:48:55 pq-server sendmail[2531]: r6U4mt3C002531: Milter: no active filter
Jul 29 18:48:55 pq-server sendmail[2531]: r6U4mt3C002531: --- 220 localhost6.localdomain6 ESMTP Sendmail 8.14.4/8.14.4; Mon, 29 Jul 2013 18:48:55 -1000
Jul 29 18:48:55 pq-server sendmail[2531]: r6U4mt3C002531: <-- EHLO halPC
Jul 29 18:48:55 pq-server sendmail[2531]: r6U4mt3C002531: --- 250-localhost6.localdomain6 Hello cpe-XX-X-XXX-XX.hawaii.res.rr.com [XX.X.XXX.XX], pleased to meet you
Jul 29 18:48:55 pq-server sendmail[2531]: r6U4mt3C002531: --- 250-ENHANCEDSTATUSCODES
Jul 29 18:48:55 pq-server sendmail[2531]: r6U4mt3C002531: --- 250-PIPELINING
Jul 29 18:48:55 pq-server sendmail[2531]: r6U4mt3C002531: --- 250-8BITMIME
Jul 29 18:48:55 pq-server sendmail[2531]: r6U4mt3C002531: --- 250-SIZE
Jul 29 18:48:55 pq-server sendmail[2531]: r6U4mt3C002531: --- 250-DSN
Jul 29 18:48:55 pq-server sendmail[2531]: r6U4mt3C002531: --- 250-AUTH GSSAPI DIGEST-MD5 CRAM-MD5 LOGIN PLAIN
Jul 29 18:48:55 pq-server sendmail[2531]: r6U4mt3C002531: --- 250-STARTTLS
Jul 29 18:48:55 pq-server sendmail[2531]: r6U4mt3C002531: --- 250-DELIVERBY
Jul 29 18:48:55 pq-server sendmail[2531]: r6U4mt3C002531: --- 250 HELP
Jul 29 18:48:55 pq-server sendmail[2531]: r6U4mt3C002531: <-- AUTH DIGEST-MD5
Jul 29 18:48:55 pq-server sendmail[2531]: r6U4mt3C002531: --- 334 bm9uY2U9IkUzTW9BTzgrN0liMElJa2drY2gvZEhid2dkTHF1ZGNTL080cGZRR0NVTFk9IixyZWFsbT0ibG9jYWxob3N0Ni5sb2Nh bGRvbWFpbjYiLHFvcD0iYXV0aCxhdXRoLWludCxhdXRoLWNvbmYiLGNpcGhlcj0icmM0LTQwLHJjNC01NixyYzQsZGVzLDNkZXMi LG1heGJ1Zj04MTkyLGNoYXJzZXQ9dXRmLTgsYWxnb3JpdGhtPW1kNS1zZXNz
Jul 29 18:48:55 pq-server sendmail[2531]: r6U4mt3C002531: --- 535 5.7.0 authentication failed
Jul 29 18:48:55 pq-server sendmail[2531]: r6U4mt3C002531: AUTH failure (DIGEST-MD5): authentication failure (-13) SASL(-13): authentication failure: realm changed: authentication aborted, relay=cpe-XX-X-XXX-XX.XXX.XX.XX.XX [XX.X.XXX.XX]
Jul 29 18:48:55 pq-server sendmail[2531]: r6U4mt3C002531: <-- AUTH LOGIN
Jul 29 18:48:55 pq-server sendmail[2531]: r6U4mt3C002531: --- 334 VXNlcm5hbWU6
Jul 29 18:48:55 pq-server sendmail[2531]: r6U4mt3C002531: --- 334 UGFzc3dvcmQ6
Jul 29 18:48:55 pq-server sendmail[2531]: r6U4mt3C002531: --- 235 2.0.0 OK Authenticated
Jul 29 18:48:55 pq-server sendmail[2531]: AUTH=server, relay=cpe-XX-X-XXX-XX.XXX.XX.XX.XX [XX.X.XXX.XX], authid=kelly, mech=LOGIN, bits=0
Jul 29 18:48:55 pq-server sendmail[2531]: r6U4mt3C002531: <-- MAIL FROM: <kelly@XXX.com>
Jul 29 18:48:55 pq-server sendmail[2531]: r6U4mt3C002531: --- 250 2.1.0 <kelly@XXX.com>... Sender ok
Jul 29 18:48:55 pq-server sendmail[2531]: r6U4mt3C002531: <-- RCPT TO: <hrichman@XXX>
Jul 29 18:48:55 pq-server sendmail[2531]: r6U4mt3C002531: --- 250 2.1.5 <hrichman@XXX>... Recipient ok
Jul 29 18:48:55 pq-server sendmail[2531]: r6U4mt3C002531: <-- DATA
Jul 29 18:48:55 pq-server sendmail[2531]: r6U4mt3C002531: --- 354 Enter mail, end with "." on a line by itself
Jul 29 18:48:55 pq-server sendmail[2531]: r6U4mt3C002531: from=<kelly@XXX.com>, size=2377, class=0, nrcpts=1, msgid=<00af01ce8ce0$dc469820$94d3c860$@com>, proto=ESMTP, daemon=MTA, relay=cpe-XX-X-XXX-XX.XXX.XX.XX.XX [XX.X.XXX.XX]
Jul 29 18:48:55 pq-server sendmail[2531]: r6U4mt3C002531: --- 050 <hrichman@XXX>... queued
Jul 29 18:48:55 pq-server sendmail[2531]: r6U4mt3C002531: to=<hrichman@XXX>, delay=00:00:00, mailer=relay, pri=32377, stat=queued
Jul 29 18:48:56 pq-server sendmail[2531]: r6U4mt3C002531: --- 250 2.0.0 r6U4mt3C002531 Message accepted for delivery
Jul 29 18:48:56 pq-server dovecot: imap-login: Login: user=<kelly>, method=PLAIN, rip=XX.X.XXX.XX, lip=192.168.1.101, mpid=2536, TLS
Jul 29 18:48:58 pq-server sendmail[2531]: r6U4mt3D002531: <-- QUIT
Jul 29 18:48:58 pq-server sendmail[2531]: r6U4mt3D002531: --- 221 2.0.0 localhost6.localdomain6 closing connection
Jul 29 18:48:58 pq-server MailScanner[860]: New Batch: Scanning 1 messages, 2905 bytes
Jul 29 18:48:58 pq-server MailScanner[860]: Virus and Content Scanning: Starting
Jul 29 18:48:59 pq-server MailScanner[2539]: Unrar command /usr/bin/unrar does not exist or is not executable, please either install it or remove the setting from MailScanner.conf
Jul 29 18:49:00 pq-server MailScanner[860]: Uninfected: Delivered 1 messages
Jul 29 18:49:00 pq-server sendmail[2542]: STARTTLS: ClientCertFile missing
Jul 29 18:49:00 pq-server sendmail[2542]: STARTTLS: ClientKeyFile missing
Jul 29 18:49:00 pq-server sendmail[2542]: STARTTLS: CRLFile missing
Jul 29 18:49:00 pq-server sendmail[2542]: STARTTLS=client, init=1
Jul 29 18:49:00 pq-server MailScanner[860]: Deleted 1 messages from processing-database
Jul 29 18:49:00 pq-server MailScanner[860]: MailScanner child dying of old age
Jul 29 18:49:00 pq-server MailScanner[2544]: MailScanner E-Mail Virus Scanner version 4.84.3 starting...
Jul 29 18:49:00 pq-server sendmail[2543]: r6U4mt3C002531: SMTP outgoing connect on [192.168.1.101]
Jul 29 18:49:00 pq-server MailScanner[2544]: Reading configuration file /etc/MailScanner/MailScanner.conf
Jul 29 18:49:00 pq-server MailScanner[2544]: Reading configuration file /etc/MailScanner/conf.d/README
Jul 29 18:49:00 pq-server MailScanner[2544]: Read 873 hostnames from the phishing whitelist
Jul 29 18:49:00 pq-server MailScanner[2544]: Read 3966 hostnames from the phishing blacklists
Jul 29 18:49:00 pq-server MailScanner[2544]: Using SpamAssassin results cache
Jul 29 18:49:00 pq-server MailScanner[2544]: Connected to SpamAssassin cache database
Jul 29 18:49:00 pq-server MailScanner[2544]: Enabling SpamAssassin auto-whitelist functionality...
Jul 29 18:49:01 pq-server sendmail[2543]: r6U4mt3C002531: to=<hrichman@XXX>, ctladdr=<kelly@XXX.com> (503/503), delay=00:00:06, xdelay=00:00:01, mailer=relay, pri=122377, relay=smtp-server.XXX.com. [XX.XX.XX.XX], dsn=2.0.0, stat=Sent (OK F2/19-02415-40747F15)
Jul 29 18:49:01 pq-server sendmail[2543]: r6U4mt3C002531: done; delay=00:00:06, ntries=1
Jul 29 18:49:02 pq-server MailScanner[2544]: I have found clamavmodule scanners installed, and will use them all by default.
Jul 29 18:49:07 pq-server MailScanner[2544]: Connected to Processing Attempts Database
Jul 29 18:49:07 pq-server MailScanner[2544]: Found 0 messages in the Processing Attempts Database
Jul 29 18:49:07 pq-server MailScanner[2544]: Using locktype = posix
Jul 29 18:49:40 pq-server dovecot: imap(kelly): Disconnected: Logged out bytes=2615/463


the results of sendmail -bv <email address>

first for sandi

[active@pq-server ~]# sendmail -bv sandi@XXX.com
\sandi... deliverable: mailer local, user \sandi
sandy... deliverable: mailer local, user sandy
spq@XXX.com... deliverable: mailer relay, host smtp-server.hawaii.rr.com, user spq@XXX.com

second for kelly
[active@pq-server ~]# sendmail -bv kelly@XXX.com
kelly@XXX.com... deliverable: mailer local, user kelly

The only difference I can spot between those 2 logs, is that the 2nd user (the one that can send out mail) is authenticated against dovecot also.
So I guess there is pop (and/or imap) before smtp involved to relay mail.

Aloha,

Both users use IMAP and both should be authenticated. Also to be clear both accounts can successfully send emails. It is just that some email address fail to be delivered to recipient but only for Sandi. The email address that fails delivery from sandi is successfully delivered from kelly. I tried to telnet into the external MTA but it would not let me. If an email is not received by the recipient and no error is generated in either maillog or in a reply to the sender from the external MTA... where might I look for the error. There should be some trail somewhere but I am at lost as to where.

Thank you all for taking the time to consider this problem and any suggestions are greatly appreciated.

cheers,
Hal

Check the mail queue at your side to see if mail is stuck there.
Ask the recipient to see if the mail has finished in the spam folder. If possible ask the admin of the smarthost to see what happens with the mail in question.

Regards