# Sendmail: "Relaying denied. Proper authentication required."



## oskare100

Hello,
I can't figure out how to be able to send mails using sendmail. I've a dovecot/sendmail installation and I can recieve mails OK but when I try to send mail I get the error message "Relaying denied. Proper authentication required."

Example from maillog:
Oct 2 18:10:08 localhost sendmail[2196]: l92GA4UC002196: ruleset=check_rcpt, arg1=<[email protected]>, relay=rl-nvt-kaxx.xxxxxx.xxx [000.000.000.000], reject=  550 5.7.1 <[email protected]>... Relaying denied. Proper authentication required .
Oct 2 18:10:08 localhost sendmail[2196]: l92GA4UC002196: from=<[email protected]>, size=0, class=0, nrcpts=0, proto=SMTP, daemon=MTA, relay=rl-nvt-kaxx.xxxxxx.xxx [000.000.000.000]

Here is my sendmail.mc:
divert(-1)dnl
dnl #
dnl # This is the sendmail macro config file for m4. If you make changes to
dnl # /etc/mail/sendmail.mc, you will need to regenerate the
dnl # /etc/mail/sendmail.cf file by confirming that the sendmail-cf package is
dnl # installed and then performing a
dnl #
dnl # make -C /etc/mail
dnl #
include(`/usr/share/sendmail-cf/m4/cf.m4')dnl
VERSIONID(`setup for linux')dnl
OSTYPE(`linux')dnl
dnl #
dnl # Do not advertize sendmail version.
dnl #
dnl define(`confSMTP_LOGIN_MSG', `$j Sendmail; $b')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 #
define(`SMART_HOST', `smtp.myisp.com')dnl
dnl #
define(`confDEF_USER_ID', ``8:12'')dnl
dnl define(`confAUTO_REBUILD')dnl
define(`confTO_CONNECT', `1m')dnl
define(`confTRY_NULL_MX_LIST', `True')dnl
define(`confDONT_PROBE_INTERFACES', `True')dnl
define(`PROCMAIL_MAILER_PATH', `/usr/bin/procmail')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
TRUST_AUTH_MECH(`LOGIN PLAIN')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 # Please remember that saslauthd needs to be running for AUTH.
dnl #
TRUST_AUTH_MECH(`EXTERNAL DIGEST-MD5 CRAM-MD5 LOGIN PLAIN')dnl
define(`confAUTH_MECHANISMS', `EXTERNAL GSSAPI DIGEST-MD5 CRAM-MD5 LOGIN PLAIN')dnl
dnl #
dnl # Rudimentary information on creating certificates for sendmail TLS:
dnl # cd /usr/share/ssl/certs; make sendmail.pem
dnl # Complete usage:
dnl # make -C /usr/share/ssl/certs usage
dnl #
dnl define(`confCACERT_PATH', `/etc/pki/tls/certs')dnl
dnl define(`confCACERT', `/etc/pki/tls/certs/ca-bundle.crt')dnl
dnl define(`confSERVER_CERT', `/etc/pki/tls/certs/sendmail.pem')dnl
dnl define(`confSERVER_KEY', `/etc/pki/tls/certs/sendmail.pem')dnl
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(`no_default_msa', `dnl')dnl
FEATURE(`smrsh', `/usr/sbin/smrsh')dnl
FEATURE(`mailertable', `hash -o /etc/mail/mailertable.db')dnl
FEATURE(`virtusertable', `hash -o /etc/mail/virtusertable.db')dnl
FEATURE(redirect)dnl
FEATURE(always_add_domain)dnl
FEATURE(use_cw_file)dnl
FEATURE(use_ct_file)dnl
dnl #
dnl # The following limits the number of processes sendmail can fork to accept
dnl # incoming messages or process its message queues to 20.) sendmail refuses
dnl # to accept connections once it has reached its quota of child processes.
dnl #
dnl define(`confMAX_DAEMON_CHILDREN', `20')dnl
dnl #
dnl # Limits the number of new connections per second. This caps the overhead
dnl # incurred due to forking new sendmail processes. May be useful against
dnl # DoS attacks or barrages of spam. (As mentioned below, a per-IP address
dnl # limit would be useful but is not available as an option at this writing.)
dnl #
dnl define(`confCONNECTION_RATE_THROTTLE', `3')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
FEATURE(`blacklist_recipients')dnl
EXPOSED_USER(`root')dnl
dnl FEATURE(`allmasquerade')
dnl #
dnl # For using Cyrus-IMAPd as POP3/IMAP server through LMTP delivery uncomment
dnl # the following 2 definitions and activate below in the MAILER section the
dnl # cyrusv2 mailer.
dnl #
dnl define(`confLOCAL_MAILER', `cyrusv2')dnl
dnl define(`CYRUSV2_MAILER_ARGS', `FILE /var/lib/imap/socket/lmtp')dnl
dnl #
dnl # The following causes sendmail to only listen on the IPv4 loopback address
dnl # 127.0.0.1 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, Name=MTA')
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(`port=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 #
FEATURE(`accept_unresolvable_domains')dnl
dnl #
dnl FEATURE(`relay_based_on_MX')dnl
dnl #
dnl # Also accept email sent to "localhost.localdomain" as local email.
dnl #
LOCAL_DOMAIN(`localhost.localdomain')dnl
dnl #
dnl # The following example makes mail from this host and any additional
dnl # specified domains appear to be sent from mydomain.com
dnl #
dnl MASQUERADE_AS(`entisco.com')dnl
dnl #
dnl # masquerade not just the headers, but the envelope as well
dnl #
dnl FEATURE(masquerade_envelope)dnl
dnl #
dnl # masquerade not just @mydomainalias.com, but @*.mydomainalias.com as well
dnl #
dnl FEATURE(masquerade_entire_domain)dnl
dnl #
dnl MASQUERADE_DOMAIN(localhost)dnl
dnl MASQUERADE_DOMAIN(localhost.localdomain)dnl
dnl MASQUERADE_DOMAIN(mydomainalias.com)dnl
dnl MASQUERADE_DOMAIN(mydomain.lan)dnl
MAILER(smtp)dnl
MAILER(procmail)dnl
dnl MAILER(cyrusv2)dnl

Here is my local-host-names:
mydomain.com

Here is my relay-domains:
mydomain.com

mydomain.com is actually my real domain, and the "xxxx.." parts of the IPs and mail addresses has just been changed for this thread. I really need help to solve this, I can't figure out why the server just gives me that error message regardless of what I do.. Please help!

Thanks in advance,
Oskar R


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## lensman3

This is an anit-spam feature of sendmail you have encountered. You have to fool gmail into thinking you are legit....

Uncomment the lines:
FEATURE(masquerade_envelope)dnl
FEATURE(masquerade_entire_domain)dnl

Up at the top change the line to the gmal dns name. Mine is comcast.com. This tells sendmail somehow that email you send is from gmail and not a rogue spammer. 
define(`SMART_HOST',`smtp.comcast.net')dnl

I also had to define this name. I use my reverse DNS name so that comcast is happy and can prove that I "am a person of quality" and not some spammer. I think that my sendmail actually tells the comcast.com's sendmail daemon that this is my domain name.
define(`confDOMAIN_NAME', `q-ww-xxx-yyy-zzz.xxxx.xx.comcast.net')dnl

When that is done, run "make" and restart sendmail. You will also have to install the "development " version of the sendmail macros as well as the m4 assembler routine.

I also had to modify the file "access" in "/etc/mail" to indicate who had permission to use email in my domain. If you get this wrong, every email spammer in China will be using you as their gateway. It also tends to make your ISP mad too!!!

A hack that is helpful for debugging is: "telnet gmail.com 25" . Sendmail uses port 25 for its communication. This will connect you to the sendmail daemon and you can type in commands and see the responses. Type in "help" and you see which command sendmail expects. Look at EXPN, VRFY, and HELP. Different sendmail servers have different commands turned on or locked out. Especially the phishing commands.


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