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So this is an issue I've been struggling with for a while. I figured I'd put it out here to see if maybe anyone has any ideas on how to fix it. The problem is that, for whatever reason, I cannot get phpmail to function. Whenever an email is supposed to be sent it doesn't go. I've checked my logs for: MyBB (tools->email logs, system logs, etc...) and var/spool/mail/ but there's nothing there. Checking /var/logs/maillog reveals this: Mar 16 21:13:38 server sendmail[14968]: u2H1Dcq0014968: from=apache, size=825, class=0, nrcpts=1, msgid=<201603170113.u2H1Dcq0014968@localhost.localdomain>, relay=apache@localhost Mar 16 21:13:38 server postfix/smtpd[14950]: connect from localhost.localdomain[127.0.0.1] Mar 16 21:13:38 server postfix/smtpd[14950]: NOQUEUE: reject: RCPT from localhost.localdomain[127.0.0.1]: 454 4.7.1 <endlessfightforum@gmail>: Relay access denied; from=<apache@localhost.localdomain> to=<endlessfightforum@gmail> proto=ESMTP helo=<localhost.localdomain> Mar 16 21:13:38 server sendmail[14968]: u2H1Dcq0014968: to=endlessfightforum@gmail, ctladdr=apache (48/48), delay=00:00:00, xdelay=00:00:00, mailer=relay, pri=30825, relay=[127.0.0.1] [127.0.0.1], dsn=4.7.1, stat=Deferred: 454 4.7.1 <endlessfightforum@gmail>: Relay access denied Mar 16 21:13:38 server postfix/smtpd[14950]: disconnect from localhost.localdomain[127.0.0.1] I have an MX record set in my DNS directing mail to mail.endlessfight.net. I have a ptr record set up for any reverse DNS lookups (sometimes needed for mail servers). In my /etc/postfix/main.cf I have my $mydomain (endlessfight.net) and $myhostname (mail.endlessfight.net) declared as they should be. So it really shouldn't be setting localhost.localdomain for anything to begin with. But even though it is, I also have a Canonical list set so that anytime it says localhost.localdomain it should instead replace that with endlessfightforum@gmail. (But it doesn't seem to be doing that either.) For some extra technical details... Furthermore I have a Roundcube email installed also and it works just fine. I can send and receive emails with it no problem. So this issue seems isolated to phpmail. So at this point I'm kind of at a loss as to what's wrong. I've considered taking a backup of everything and then reinstalling the OS/Panel to basically wipe the slate clean and start over... But I have no idea if that'd even work or if I'd just end up back where I am now.