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I own a domain whose MX record up until now pointed to a commercial mail server where I had an account for the domain; that was the only account, call it me@myplace.

I now need to add some email accounts, so I set up a mail server of my own and changed the MX record to point to it. However, after doing tests of the smtp relay by sending back and forth to a gmail account (there@gmail.com), I am a bit nervous:

  • If I reply to to a message from the gmail account, everything is fine.

  • If I send a message to the gmail account from the same user name as the only account which existed for the domain before (me@myplace) -- with which the gmail account has a history -- everything is fine.

  • If I send a message to the gmail account using a new user account -- e.g., new@myplace -- everything seems to go through from the remote client, and the smtp server log notes:

    esmtp: id=XXXXXXXXX,from=<new@myplace>,addr=<there@gmail.com>,size=694,success: delivered: gmail-smtp-in.l.google.com
    

    I.e., the gmail server has accepted the message and told my server everything is fine, so my server told the remote client everything is fine. Except the gmail server is lying, because the message is never delivered to there@gmail.com.

I am worried that this is a sign of more serious problems yet to come -- that some commercial mail servers whitelist by relay IP not just domain, and will discard my mail because I am not a whitelisted commercial server, and that they will do it the same way google apparently has done: by cheerily reporting it accepted, meaning I will never get a bounce notice or have anyway of knowing my mail is not being delivered.

So my 2-part question is:

  1. Is this really dishonesty on the part of the gmail server? I.e., it is saying it is accepting mail for delivery which it never intends to deliver? Or is there some ambiguity I've missed?

  2. If so, is it a waste of time for me to try and run my own mail server? Will a lot of commercial servers simply look at the IP of the relay (which matches the domain's MX record) and just silently/dishonestly discard my mail because it's not on a whitelist -- meaning in essence, I have to pay for a whitelisted commercial server if I want email delivered in the modern world?

I have owned this domain for years and it has never been a source of spam, if that matters.

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I've been running my own mailserver for years. Actually, getting on for two decades. I agree that some (piss-poor) providers file-as-junk pretty much any email from anyone except the top-tier providers, but my attitude to correspondents using such accounts is "You picked a provider who doesn't show you all your email. You sort it out." SMTP is designed to be distributed. –  MadHatter Dec 19 '13 at 11:22
    
@MadHatter : Good to know. I'll probably keep the paying for previous provider, since it is only a few dollars/year for the one address, and I can fall back on it for sending without changing the MX if there are problems. But the google issue resolved reasonably (see checkmark) and everything has been fine the past few days, so :) –  goldilocks Dec 20 '13 at 14:58
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2 Answers

up vote 4 down vote accepted
  1. No. All it means is they accepted it, and you passed the first battery of tests. There are further tests that usually take more time, and these tests often happen after the mail is accepted. Neither you, nor the server itself knows if you will pass or fail those tests.

  2. No. However if you jump through all the hoops, proper RDNS, SPF and ensuring you are not an open relay, you'll probably find that your ratio of accepted to not delivered mails drops significantly.

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Re #1 -- yeep, they showed up in the "Spam" box after a few hours (?) -- something I checked initially but then forgot about. Anyway, all seems well now. –  goldilocks Dec 20 '13 at 14:55
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  1. You should do some more reading on SMTP, email and spam filtering/blacklisting.

  2. Servers are not people. They do not lie. If the log shows that the gmail server accepted the email then it accepted it.

  3. Accepting the email and delivering it to the mailbox are two different things. The gmail server accepted the email but may have rejected, purged or filtered it at a later stage of delivering the email to the mailbox of the recipient.

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