Jtdylktuy

I need to send emails to different recipients (many), from my gmail account, the same message for each, but different attachments. So I looked into command line mail clients and stumbled upon this tutorial about setting up sendmail for gmail.

I get errors at the 'install sendmail' and make stages that I need help for.

Subsidiary question: how to get sendmail.mc to be reset to default (the one you see below is copy pasted from one I found online)? removing/installing sendmail doesn't do it.

# apt-get install sendmail sendmail-base sendmail-bin sendmail-cf sendmail-doc

Reading package lists... Done

Building dependency tree       

Reading state information... Done

sendmail-base is already the newest version (8.15.2-3).

sendmail-base set to manually installed.

sendmail-bin is already the newest version (8.15.2-3).

sendmail-bin set to manually installed.

sendmail-cf is already the newest version (8.15.2-3).

sendmail-cf set to manually installed.

sendmail-doc is already the newest version (8.15.2-3).

The following additional packages will be installed:

  procmail sensible-mda

Suggested packages:

  rmail

The following NEW packages will be installed:

  procmail sendmail sensible-mda

0 upgraded, 3 newly installed, 0 to remove and 7 not upgraded.

1 not fully installed or removed.

Need to get 0 B/151 kB of archives.

After this operation, 792 kB of additional disk space will be used.

Do you want to continue? [Y/n] Y

Selecting previously unselected package procmail.

(Reading database ... 259644 files and directories currently installed.)

Preparing to unpack .../procmail_3.22-25ubuntu0.16.04.1_amd64.deb ...

Unpacking procmail (3.22-25ubuntu0.16.04.1) ...

Selecting previously unselected package sensible-mda.

Preparing to unpack .../sensible-mda_8.15.2-3_amd64.deb ...

Unpacking sensible-mda (8.15.2-3) ...

Selecting previously unselected package sendmail.

Preparing to unpack .../sendmail_8.15.2-3_all.deb ...

Unpacking sendmail (8.15.2-3) ...

Processing triggers for man-db (2.7.5-1) ...

Setting up sendmail-bin (8.15.2-3) ...

Saving old /etc/mail/sendmail.cf as /etc/mail/sendmail.cf.old ...

Updating sendmail environment ...

Reading configuration from /etc/mail/sendmail.conf.

Validating configuration.

Writing configuration to /etc/mail/sendmail.conf.

Writing /etc/cron.d/sendmail.

Reading configuration from /etc/mail/sendmail.conf.

Validating configuration.

Writing configuration to /etc/mail/sendmail.conf.

Writing /etc/cron.d/sendmail.

Could not open /etc/mail/databases(No such file or directory), creating it.

Could not open /usr/share/sendmail-cf/m4/cf.m4(No such file or directory)

Reading configuration from /etc/mail/sendmail.conf.

Validating configuration.

Creating /etc/mail/databases...



Checking filesystem, this may take some time - it will not hang!

  ...   Done.



Checking for installed MDAs...

Adding link for newly extant program (procmail)

sasl2-bin not installed, not configuring sendmail support.



To enable sendmail SASL2 support at a later date, invoke "/usr/share/sendmail/update_auth"





Creating/Updating SSL(for TLS) information

Creating /etc/mail/tls/starttls.m4...

You already have sendmail certificates





*** *** *** WARNING *** WARNING *** WARNING *** WARNING *** *** ***



Everything you need to support STARTTLS (encrypted mail transmission

and user authentication via certificates) is installed and configured

but is *NOT* being used.



To enable sendmail to use STARTTLS, you need to:

1) Add this line to /etc/mail/sendmail.mc and optionally

   to /etc/mail/submit.mc:

  include(`/etc/mail/tls/starttls.m4')dnl

2) Run sendmailconfig

3) Restart sendmail



Checking {sendmail,submit}.mc and related databases...

Reading configuration from /etc/mail/sendmail.conf.

Validating configuration.

Creating /etc/mail/databases...

Could not open /usr/share/sendmail-cf/m4/cf.m4(No such file or directory)

Reading configuration from /etc/mail/sendmail.conf.

Validating configuration.

Creating /etc/mail/databases...

Could not open /usr/share/sendmail-cf/m4/cf.m4(No such file or directory)

Reading configuration from /etc/mail/sendmail.conf.

Validating configuration.

Creating /etc/mail/Makefile...

Reading configuration from /etc/mail/sendmail.conf.

Validating configuration.

Writing configuration to /etc/mail/sendmail.conf.

Writing /etc/cron.d/sendmail.

Disabling HOST statistics file(/var/lib/sendmail/host_status).

Creating /etc/mail/sendmail.cf...

m4:/etc/mail/sendmail.mc:10: cannot open `/usr/share/sendmail-cf/m4/cf.m4': No such file or directory



Creating /etc/mail/submit.cf...

Informational: confCR_FILE file empty: /etc/mail/relay-domains

Informational: confCT_FILE file empty: /etc/mail/trusted-users

Informational: confUSERDB_SPEC file empty: /etc/mail/userdb.db

Updating /etc/mail/access...

Updating /etc/mail/authinfo/gmail...

Informational: mailertable file empty: /etc/mail/mailertable

Informational: use_ct_file file empty: /etc/mail/trusted-users

Informational: virtusertable file empty: /etc/mail/virtusertable

Updating /etc/aliases...

WARNING: local host name (yogurt) is not qualified; see cf/README: WHO AM I?

newaliases: cannot open /etc/mail/aliases: No such file or directory



Warning: These messages were issued while creating sendmail.cf

    make sure they are benign before starting sendmail!



Errors in generating sendmail.cf

m4:/etc/mail/sendmail.mc:10: cannot open `/usr/share/sendmail-cf/m4/cf.m4': No such file or directory



Job for sendmail.service failed because the control process exited with error code. See "systemctl status sendmail.service" and "journalctl -xe" for details.

invoke-rc.d: initscript sendmail, action "start" failed.

● sendmail.service - LSB: powerful, efficient, and scalable Mail Transport Agent

   Loaded: loaded (/etc/init.d/sendmail; bad; vendor preset: enabled)

   Active: failed (Result: exit-code) since Sat 2018-06-09 12:32:49 EDT; 5ms ago

     Docs: man:systemd-sysv-generator(8)

  Process: 13910 ExecStart=/etc/init.d/sendmail start (code=exited, status=2)



Jun 09 12:32:49 yogurt sendmail[13910]:  * Starting Mail Transport Agent (MTA) sendmail

Jun 09 12:32:49 yogurt sendmail[13910]: Makefile:343: warning: overriding recipe for target '/etc/aliases.db'

Jun 09 12:32:49 yogurt sendmail[13910]: Makefile:340: warning: ignoring old recipe for target '/etc/aliases.db'

Jun 09 12:32:49 yogurt sendmail[13910]: Makefile:395: warning: overriding recipe for target '/etc/aliases'

Jun 09 12:32:49 yogurt sendmail[13910]: Makefile:340: warning: ignoring old recipe for target '/etc/aliases'

Jun 09 12:32:49 yogurt sendmail[13910]: make: *** No rule to make target '/usr/share/sendmail-cf/m4/cf.m4', nee...Stop.

Jun 09 12:32:49 yogurt systemd[1]: sendmail.service: Control process exited, code=exited status=2

Jun 09 12:32:49 yogurt systemd[1]: Failed to start LSB: powerful, efficient, and scalable Mail Transport Agent.

Jun 09 12:32:49 yogurt systemd[1]: sendmail.service: Unit entered failed state.

Jun 09 12:32:49 yogurt systemd[1]: sendmail.service: Failed with result 'exit-code'.

Hint: Some lines were ellipsized, use -l to show in full.

dpkg: error processing package sendmail-bin (--configure):

 subprocess installed post-installation script returned error exit status 1

Setting up procmail (3.22-25ubuntu0.16.04.1) ...

dpkg: dependency problems prevent configuration of sensible-mda:

 sensible-mda depends on sendmail-bin | mail-transport-agent; however:

  Package sendmail-bin is not configured yet.

  Package mail-transport-agent is not installed.

  Package postfix which provides mail-transport-agent is not installed.

  Package sendmail-bin which provides mail-transport-agent is not configured yet.



dpkg: error processing package sensible-mda (--configure):

 dependency problems - leaving unconfigured

No apport report written because the error message indicates its a followup error from a previous failure.

                                                                                                          No apport report written because the error message indicates its a followup error from a previous failure.

                                                                                             dpkg: dependency problems prevent configuration of sendmail:

 sendmail depends on sendmail-bin; however:

  Package sendmail-bin is not configured yet.

 sendmail depends on sensible-mda; however:

  Package sensible-mda is not configured yet.



dpkg: error processing package sendmail (--configure):

 dependency problems - leaving unconfigured

Errors were encountered while processing:

 sendmail-bin

 sensible-mda

 sendmail

E: Sub-process /usr/bin/dpkg returned an error code (1)





# make /etc/init.d/sendmail reload

Makefile:343: warning: overriding recipe for target '/etc/aliases.db'

Makefile:340: warning: ignoring old recipe for target '/etc/aliases.db'

Makefile:395: warning: overriding recipe for target '/etc/aliases'

Makefile:340: warning: ignoring old recipe for target '/etc/aliases'

make: Nothing to be done for '/etc/init.d/sendmail'.

/etc/init.d/sendmail reload

 * Reloading Mail Transport Agent (MTA) sendmail                                                                               Makefile:343: warning: overriding recipe for target '/etc/aliases.db'

Makefile:340: warning: ignoring old recipe for target '/etc/aliases.db'

Makefile:395: warning: overriding recipe for target '/etc/aliases'

Makefile:340: warning: ignoring old recipe for target '/etc/aliases'

make[1]: *** No rule to make target '/usr/share/sendmail-cf/m4/cf.m4', needed by '/etc/mail/databases'.  Stop.

sendmail.mc after update according to tutorial:

# cat 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 #     /etc/mail/make

dnl #

include(`/usr/share/sendmail-cf/m4/cf.m4')dnl

VERSIONID(`setup for linux')dnl

OSTYPE(`debian')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', `[10.0.2.2]')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

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 #

dnl TRUST_AUTH_MECH(`EXTERNAL DIGEST-MD5 CRAM-MD5 LOGIN PLAIN')dnl

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 /etc/pki/tls/certs; make sendmail.pem

dnl # Complete usage:

dnl #     make -C /etc/pki/tls/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')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 #

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,Addr=127.0.0.1, 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(`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(`future-access.com')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(`mydomain.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

divert(-1)

#

# This file is used to configure sendmail for use with Debian systems.

#

divert(0)



define(`_USE_ETC_MAIL_')dnl

include(`/usr/share/sendmail/cf/m4/cf.m4')dnl

VERSIONID(`@(#)sendmail.mc      8.9.3-21 (Debian) 20000309')

OSTYPE(`debian')dnl

DOMAIN(`debian-mta')dnl

dnl # Items controlled by /etc/mail/sendmail.conf - DO NOT TOUCH HERE 

undefine(`confHOST_STATUS_DIRECTORY')dnl        #DAEMON_HOSTSTATS 

dnl # Items controlled by /etc/mail/sendmail.conf - DO NOT TOUCH HERE



define(`confSAFE_FILE_ENV',             `/')dnl



LOCAL_CONFIG



define(`SMART_HOST', `SMTP:smtp.int.radiomaranon.org.pe')dnl



MASQUERADE_AS(radiomaranon.org.pe)dnl

FEATURE(masquerade_envelope)dnl

FEATURE(always_add_domain)dnl

Cwowie.int.radiomaranon.org.pe

CGowie.int.radiomaranon.org.pe

FEATURE(use_cw_file)dnl

FEATURE(use_ct_file)dnl

FEATURE(`nouucp', `reject')dnl



dnl define hosts we relay for

FEATURE(`access_db')dnl

dnl FEATURE(`genericstable', `hash -o /etc/mail/genericstable.db')dnl

dnl FEATURE(`virtusertable', `hash -o /etc/mail/virtusertable.db')dnl

FEATURE(accept_unresolvable_domains)



FEATURE(nocanonify)dnl

define(`confSERVICE_SWITCH_FILE',/etc/mail/service.switch)dnl

define(`confBIND_OPTS',`-AAONLY -DNSRCH -DEFNAMES')dnl

dnl  see 'man resolver'

define(`confDONT_PROBE_INTERFACES', `True')dnl

define(`SMTP_MAILER_FLAGS',`e')dnl



define(`confTO_QUEUEWARN', `2d')dnl

dnl define(`confDIAL_DELAY', `0')dnl

define(`confCON_EXPENSIVE', `True')dnl



define(`confPRIVACY_FLAGS', `needmailhelo,novrfy,noexpn,noreceipts,noverb')dnl



#GMail settings:

define(`SMART_HOST',`[smtp.gmail.com]')dnl

define(`RELAY_MAILER_ARGS', `TCP $h 587')dnl

define(`ESMTP_MAILER_ARGS', `TCP $h 587')dnl

define(`confAUTH_OPTIONS', `A p')dnl

TRUST_AUTH_MECH(`EXTERNAL DIGEST-MD5 CRAM-MD5 LOGIN PLAIN')dnl

define(`confAUTH_MECHANISMS', `EXTERNAL GSSAPI DIGEST-MD5 CRAM-MD5 LOGIN PLAIN')dnl

FEATURE(`authinfo',`hash -o /etc/mail/authinfo/gmail.db')dnl



MAILER_DEFINITIONS

MAILER(local)dnl

MAILER(smtp)dnl

MAILER(procmail)dnl

authinfo:

# echo $PWD

/etc/mail/authinfo

# cat authinfo

AuthInfo: U:root I:myuserid@gmail.com P:mypwd

# cat gmail

AuthInfo: "U:root" "I:myuserid@gmail.com" "P:mypwd"

While I still believe that you should use mailx instead of full-fledged MTA to send emails via gmail (https://www.systutorials.com/1411/sending-email-from-mailx-command-in-linux-using-gmails-smtp/) I will give you example of using sendmail+gmail config.

First if all, you need sasl libplain because SMTP auth is based on SASL and Sendmail uses Cyrus SASL (https://www.cyrusimap.org/sasl/) to implement authentication. Make sure to install it, or you will have "AUTH=client, available mechanisms do not fulfill requirements" in your maillog. You also need openssl because sendmail uses it for TLS, but it should be installed already.

CentOS/RH: yum install cyrus-sasl-plain openssl

Ubuntu: apt-get install libsasl2-modules openssl

So, here is my mc file paired with comments.

divert(-1)dnl

include(`/usr/share/sendmail-cf/m4/cf.m4')dnl centos's specific path, you may have different

VERSIONID(`setup for linux')dnl

OSTYPE(`linux')dnl

define(`confDEF_USER_ID', ``8:12'')dnl

define(`ALIAS_FILE', `/etc/aliases')dnl

define(`confPRIVACY_FLAGS', `authwarnings,novrfy,noexpn,restrictqrun')dnl just to force clients obey SMTP

define(`confAUTH_MECHANISMS', `PLAIN')dnl Gmail is OK with SASL-PLAIN when used with TLS

FEATURE(authinfo)dnl This  feature enables /etc/mail/authinfo

define(`SMART_HOST', `smtp.gmail.com')dnl Always send email to this host instead of MX

define(`confTO_IDENT', `0')dnl disable prehistoric IDENT proto

FEATURE(`no_default_msa', `dnl')dnl MSA (567 port) is good idea, but nobody uses it

FEATURE(nouucp, `nospecial')dnl Nobody needs UUCP these days

FEATURE(nocanonify)dnl We assume that client always provides DQDN

EXPOSED_USER(`root')dnl

DAEMON_OPTIONS(`Port=smtp,Addr=127.0.0.1, Name=MTA')dnl Listen localhost:25

MAILER(smtp)dnl The only mailer I need is SMTP, I do not use local mail

Here is /etc/mail/authinfo (make sure to replace [MY_LOGIN_ON_GMAIL] with your actual login)

AuthInfo: "I:[MY_LOGIN_ON_GMAIL]@gmail.com" "P:[MY_PASSWORD_ON_GMAIL]"

What it means: "Always use AuthInfo for any SMTP connection, using [MY_LOGIN_ON_GMAIL]@gmail.com as login and [MY_PASSWORD_ON_GMAIL]" as password.

You may need to compile this file to hash db (on many OSses you may call make inside of /etc/mail) and convert .mc file to sendmail.cf (command is OS specific, make may work) and restart sendmail (make restart in /etc/mail or ``systemctl restart sendmail'')

Lets try: echo "Hello" | mail -r [MY_LOGIN_ON_GMAIL]@gmail.com -s "Hey, it works" [MY_LOGIN_ON_GMAIL]@gmail.com

-r here is "From".

That is all.

If you have any problems, check /var/log/mail

PS: to check that authinfo ruleset is used by sendmail (which means your changes from mc file are in cf file) use
echo "authinfo test test" | sendmail -bt. You should see your login/pass