Some info from my system. Please tell me if I need to post some more of it.
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# more /var/log/mail/errors.log
Jan 22 17:53:21 localhost sendmail[30867]: q0MGhKxd030867: SYSERR(root): hash map "generics": missing map file /etc/mail/genericstable.db: No such file or directory
How to generate it? Any "sendmail noob" friendly manual?
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# more /var/log/mail/errors.log
Jan 22 20:53:21 localhost sendmail[1838]: q0MItu0w019406: to=<my_hidden_personal.email@gmail.com>, ctladdr=<apache@localhost.localdomain> (490/485), delay=00:57:25, xdelay=00:10:00, mailer=esmtp, pri=210596, relay=alt4.gmail-smtp-in.l.google.com. [209.85.225.26], dsn=4.0.0, stat=Deferred: Connection timed out with alt4.gmail-smtp-in.l.google.com.
It probably needs some authentication?
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# more /etc/mail/access
# Check the /usr/share/doc/sendmail-8.14.4/README.cf file for a description
# of the format of this file. (search for access_db in that file)
# The /usr/share/doc/sendmail-8.14.4/README.cf is part of the sendmail-doc
# package.
#
# by default we allow relaying from localhost...
localhost.localdomain RELAY
localhost RELAY
127.0.0.1 RELAY
I didn't change configuration of sendmail yet. It's not familiar to me at all

Thanks,
Filip.