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I have my own Exchange Server 2013 (SP1). I am able to receive emails ok but sending emails is not reliable. Emails sent to gmail or seznam.cz (email provider in Czech Republic) is ok.

The problem is sending emails to outlook.com. I guess it is somehow discarded by spam filter but I don't know why. The delivery report says The message was successfully handed off to a different email system. This is as far as we can track it. but email is not delivered and nothing returns back.

This I have already done:

  • set MX record for my domain (aaa.com to mail.aaa.com)
  • set A recored (mail.aaa.com to x.x.x.x)
  • set reverse IP record (x.x.x.x to mail.aaa.com)
  • set TXT record v=spf1 mx a -all
  • removed internal hostnames of outbound emails (link)
  • set FQDN for send connector (mail.aaa.com)
  • set FQDN for FrontendTransport receive connectors (mail.aaa.com)

The mail server is not listed in any blacklist in http://mxtoolbox.com/blacklists.aspx.

Is there anything else I should do? I really don't know where to start looking right now.

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    If your Exchange server lives at a consumer-level ISP, it's possible that it's blocked for that reason. E.G. spamhaus.org/pbl – Katherine Villyard Oct 13 '14 at 19:43
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    If your issue is with Outlook.com then contact them to investigate: smallbusiness.support.microsoft.com/en-US/contact and turn up SMTP logging in Exchange technet.microsoft.com/en-us/library/… to verbose and view those logs to see what the connection details look like while the mail is being sent to Outlook.com. – TheCleaner Oct 13 '14 at 19:50
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    If your mail server is getting a successful SMTP message out, and recipients aren't receiving it, you must ask the people who own the next-hop mailserver. There is literally no other way for you to find out what that mailserver did with what your server gave them. You can guess all day long, and you should (in general) follow best practices and check if you're on DNS RBLs, etc, but it's still just guessing. – mfinni Oct 13 '14 at 20:35
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Adding this as an answer : If your mail server is getting a successful SMTP message out, and recipients aren't receiving it, you must ask the people who own the next-hop mailserver. There is literally no other way for you to find out what that mailserver did with what your server gave them. You can guess all day long, and you should (in general) follow best practices and check if you're on DNS RBLs, etc, but it's still just guessing.

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    ok, I'm going to contact the MS support – Martin Volek Oct 14 '14 at 17:13
  • Don't forget to mark an answer. – mfinni Oct 14 '14 at 23:36
  • I contacted the Outlook.com support. There is actually a form for that exact problem - link. They contected me few hour later that the spam filter will be minigated for that IP address. The emails are now delivered to outlook.com mail boxes. – Martin Volek Oct 15 '14 at 21:00
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I believe that there is no issue with the exchange server. Please check for the mail whether it is being moved to Spam in outlook.com. Try adding the exchange server mail id in outlook.com contact and try re sending the mail.

If you are thinking that exchange server is prompting false message with out sending mail. The check whether you are able to ping the below server from that exchange server machine network.

Incoming mail server: pop3.live.com

Outgoing mail server (SMTP): smtp.live.com

Also try opening the below ports in firewall and check. (For verification purpose mostly not a fix)

SMTP port: 587,995
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    This is not a good answer at all. Any mailserver that is reporting a successful SMTP transmission when there's an actual failure to connect on the TCP port is terrible software, and I've never heard of Exchange doing it. Plus, ping is ICMP - a system can block ICMP and still allow connections on TCP 25 (SMTP), so testing via ping is less than useless, it could actually mislead you if you assume it correlates with SMTP connectivity. – mfinni Oct 13 '14 at 20:38

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