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Old 07-18-2005, 04:12 PM   #1
LQ Newbie
Registered: Dec 2004
Distribution: RHEL 3/4, Fedora 3, dynebolic, Knoppix
Posts: 23

Rep: Reputation: 15
sendmail: stat=Deferred: Connection timed out with

Recently, we've upgraded our firewalls here at work and two of our boxes have been unable to send mail locally. Keep in mind that there is a route between the intranet (running sendmail) and the mail server (groupwise gwia).

Basically, any mail from our intranet or listserve have been able to send mail outside our network to the likes of yahoo, google, hotmail, etc. However, sending mail to our internal mail server is not working (this handles all mail for our domain). This has caused our not-for-profit clients to go crazy, but I've been forwarding a lot of it manually. So here's the issue. Whenever sendmail attempts to send out mail to our mail server we get the following error:

Jul 18 12:15:22 intranet sendmail[22904]: j6DK10iR032416: to=<>, ctladdr=<root@localhost.localdomain> (0/0), delay=4+21:14:22, xdelay=00:00:00, mailer=esmtp, pri=12900444,, dsn=4.0.0, stat=Deferred: Connection timed out with

Jul 18 12:15:22 intranet sendmail[22904]: j6DJ4q9X031388: to=<>, ctladdr=<apache@localhost.localdomain> (48/48), delay=4+22:10:30, xdelay=00:00:00, mailer=esmtp, pri=13080949,, dsn=4.0.0, stat=Deferred: Connection timed out with

So, being the inquisitive guy I am, I checked the /etc/hosts file (btw this is RH EL 4) and everything seems to be setup correctly (this was working before): s-intranet localhost.localdomain localhost s-intranet email

My is also the same as it was before the upgrade:

dnl #
dnl # This is the sendmail macro config file for m4. If you make changes to
dnl # /etc/mail/, you will need to regenerate the
dnl # /etc/mail/ file by confirming that the sendmail-cf package is
dnl # installed and then performing a
dnl #
dnl # make -C /etc/mail
dnl #
VERSIONID(`setup for Red Hat Linux')dnl
dnl #
dnl # default logging level is 9, you might want to set it higher to
dnl # debug the configuration
dnl #
dnl define(`confLOG_LEVEL', `9')dnl
dnl #
dnl # Uncomment and edit the following line if your outgoing mail needs to
dnl # be sent out through an external mail server:
dnl #
dnl define(`SMART_HOST',`')
dnl #
dnl define(`confAUTO_REBUILD')dnl
define(`confTO_CONNECT', `1m')dnl
define(`ALIAS_FILE', `/etc/aliases')dnl
define(`STATUS_FILE', `/var/log/mail/statistics')dnl
define(`UUCP_MAILER_MAX', `2000000')dnl
define(`confUSERDB_SPEC', `/etc/mail/userdb.db')dnl
define(`confPRIVACY_FLAGS', `authwarnings,novrfy,noexpn,restrictqrun')dnl
define(`confAUTH_OPTIONS', `A')dnl
dnl #
dnl # The following allows relaying if the user authenticates, and disallows
dnl # plaintext authentication (PLAIN/LOGIN) on non-TLS links
dnl #
dnl define(`confAUTH_OPTIONS', `A p')dnl
dnl #
dnl # PLAIN is the preferred plaintext authentication method and used by
dnl # Mozilla Mail and Evolution, though Outlook Express and other MUAs do
dnl # use LOGIN. Other mechanisms should be used if the connection is not
dnl # guaranteed secure.
dnl #
dnl #
dnl # Rudimentary information on creating certificates for sendmail TLS:
dnl # make -C /usr/share/ssl/certs usage
dnl # or use the included script
dnl #
dnl define(`confCACERT_PATH',`/usr/share/ssl/certs')
dnl define(`confCACERT',`/usr/share/ssl/certs/ca-bundle.crt')
dnl define(`confSERVER_CERT',`/usr/share/ssl/certs/sendmail.pem')
dnl define(`confSERVER_KEY',`/usr/share/ssl/certs/sendmail.pem')
dnl #
dnl # This allows sendmail to use a keyfile that is shared with OpenLDAP's
dnl # slapd, which requires the file to be readble by group ldap
dnl #
dnl define(`confDONT_BLAME_SENDMAIL',`groupreadablekeyfile')dnl
dnl #
dnl define(`confTO_QUEUEWARN', `4h')dnl
dnl define(`confTO_QUEUERETURN', `5d')dnl
dnl define(`confQUEUE_LA', `12')dnl
dnl define(`confREFUSE_LA', `18')dnl
define(`confTO_IDENT', `0')dnl
dnl FEATURE(delay_checks)dnl
FEATURE(`mailertable',`hash -o /etc/mail/mailertable.db')dnl
FEATURE(`virtusertable',`hash -o /etc/mail/virtusertable.db')dnl
dnl #
dnl # The -t option will retry delivery if e.g. the user runs over his quota.
dnl #
FEATURE(local_procmail,`',`procmail -t -Y -a $h -d $u')dnl
FEATURE(`access_db',`hash -T<TMPF> -o /etc/mail/access.db')dnl
dnl #
dnl # The following causes sendmail to only listen on the IPv4 loopback address
dnl # and not on any other network devices. Remove the loopback
dnl # address restriction to accept email from the internet or intranet.
dnl #
dnl DAEMON_OPTIONS(`Port=smtp,Addr=, Name=MTA')dnl
dnl #
dnl # The following causes sendmail to additionally listen to port 587 for
dnl # mail from MUAs that authenticate. Roaming users who can't reach their
dnl # preferred sendmail daemon due to port 25 being blocked or redirected find
dnl # this useful.
dnl #
# dnl DAEMON_OPTIONS(`Port=submission, Name=MSA, M=Ea')dnl
dnl #
dnl # The following causes sendmail to additionally listen to port 465, but
dnl # starting immediately in TLS mode upon connecting. Port 25 or 587 followed
dnl # by STARTTLS is preferred, but roaming clients using Outlook Express can't
dnl # do STARTTLS on ports other than 25. Mozilla Mail can ONLY use STARTTLS
dnl # and doesn't support the deprecated smtps; Evolution <1.1.1 uses smtps
dnl # when SSL is enabled-- STARTTLS support is available in version 1.1.1.
dnl #
dnl # For this to work your OpenSSL certificates must be configured.
dnl #
dnl DAEMON_OPTIONS(`Port=smtps, Name=TLSMTA, M=s')dnl
dnl #
dnl # The following causes sendmail to additionally listen on the IPv6 loopback
dnl # device. Remove the loopback address restriction listen to the network.
dnl #
dnl DAEMON_OPTIONS(`[ort=smtp,Addr=::1, Name=MTA-v6, Family=inet6')dnl
dnl #
dnl # enable both ipv6 and ipv4 in sendmail:
dnl #
dnl DAEMON_OPTIONS(`Name=MTA-v4, Family=inet, Name=MTA-v6, Family=inet6')
dnl #
dnl # We strongly recommend not accepting unresolvable domains if you want to
dnl # protect yourself from spam. However, the laptop and users on computers
dnl # that do not have 24x7 DNS do need this.
dnl #
dnl #
dnl FEATURE(`relay_based_on_MX')dnl
dnl FEATURE(`relay_entire_domain)dnl
dnl (`confBIND_OPTS', `WorkAroundBrokenAAAA')dnl
dnl #
dnl # Also accept email sent to "localhost.localdomain" as local email.
dnl #
dnl #
dnl # The following example makes mail from this host and any additional
dnl # specified domains appear to be sent from
dnl #
dnl MASQUERADE_AS(`')dnl
dnl #
dnl # masquerade not just the headers, but the envelope as well
dnl #
dnl FEATURE(masquerade_envelope)dnl
dnl #
dnl # masquerade not just, but @* as well
dnl #
dnl FEATURE(masquerade_entire_domain)dnl
dnl #
dnl MASQUERADE_DOMAIN(localhost)dnl
dnl MASQUERADE_DOMAIN(localhost.localdomain)dnl
dnl MASQUERADE_DOMAIN(mydomain.lan)dnl

My next guess was that the firewall was blocking traffic on port 25. So, I telnet into the Groupwise box from the Intranet:

telnet 25
mail from:
rcpt to:

And low and behold I receive a message from the Intranet a few minutes later. This is extremely weird. I wrote a small perl script to call the sendmail command, but that mail never gets processed.

Restart the box you say, after scheduling down time, I restarted the server to no avail. The same problem persists. I've googled and searched through LinuxQuestions and although individuals have had similar problems I can't solve the problem. I think that maybe ICMP traffic between the two is being blocked, hence the (Connection timed out message). However I can't say for sure as our network guy is being most uncooperative saying the problem resides with our Red Hat Boxes.

Any questions, comments, suggestions, help would be most welcome.

Thanks !
Old 07-19-2005, 11:04 AM   #2
LQ Newbie
Registered: Dec 2004
Distribution: RHEL 3/4, Fedora 3, dynebolic, Knoppix
Posts: 23

Original Poster
Rep: Reputation: 15
I figured it out. How lame. I went back and looked over my mail logs from the past few days and from time to time there was a reverse DNS lookup to 172.31.5 the DMZ address of our email server. Performing a dig on returns the email address on the DMZ, which the intranet used to be a part of.

So, I figured that sendmail was also performing a reverse dns lookup on Adding a DNS record for the local email remedied this problem. I'd have to look at the RFC for telnet as well, but it did not work when I used the DMZ address (telnet 25), but it worked with:

telnet 25
telnet 25

Interesting, I should have figured that out earlier. DNS!!!

I've learned a few things and thats all that matters. Thanks LQ!!


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