Mails Google and Outlook

OS type and version Ubuntu 20.04
Virtualmin version 7.5


I installed a new virtualmin server yesterday but notice that sometimes things go wrong when sending and receiving mail.

  1. Sending a mail from my server to my outlook email address goes wrong and returns following mail:

  2. Sending from my outlook mailbox to a mailbox on my server works.

  3. Sending a mail from my server to my icloud email address works.

  4. Sending from a Gmail mailbox to a mailbox on my server returns the following mail in the Gmail mailbox:
    In English:
    Message not delivered
    Your message cannot be delivered to because the remote server is configured incorrectly. Please see the technical details below for more information.

  5. Sending from a mailbox on my server to my Gmail mailbox works.

Does anyone know what the problem is?

The block list problem you have to address with your host. Apparently your IP is in a very spammy neighborhood.

Microsoft’s Outlook Deliverability Support is also notoriously obnoxious and hard to deal with, so joining their SNDS / JMRP programs isn’t likely to be useful in terms of getting your IP off their naughty list. (It’s easy, however, so worth a shot anyway.)

The rest are just the usual PTR, SPF, DKIM, and DMARC, the latter three of which you can do in Virtualmin. Your host will have to set up PTR.


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It’s a new VPS that I purchased so only just got the ip too.

But the SPF, DKIM, and DMARC I can do myself in VIrtualmin you said, how and where exactly? To my previous server I didn’t have to do this, there everything worked perfectly right away.
And does that solve the Google mailbox problem then?

I have now set “SPF record enabled” and “DMARC record enabled” to yes in the DNS Options, installed and turned on DKIM in the Email Settings. Is that enough?

But the Gmail mailbox still get a relay access denied error mail.

IP addresses are handed round like confetti and especially the ones that identified as spammer (or worse). VPS providers often don’t seem to care much about cleaning them before re assignment. Once you do get hold of a clean one - keep it. I have had a few bad ones over the years and getting them removed from the multitude of lists can be a nightmare. I often wonder if these list are of any practical use these days.

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You have to have it all in place, including getting off the blocklist and having PTR set up.

The PTR can only be set by the IP owner (the hosting company or data center), so that leaves the blocklist. In this case, the message from Outlook suggests that an entire Class C has been blocklisted; so that too will likely have to go through your provider as well.

Outlook Deliverability Support is generally unhelpful even when you’re talking about a single IP address. In this case, however, they specifically referred you to the ISP; so they’ll have to deal with them.

If you join their SNDS / JMRP program, however, you’ll at least be able to start a case. You can explain that you just got the IP and inherited the bad reputation. It will do no good other than getting a ticket on record. They’ll just respond that they’re still seeing malicious activity from that IP. It wouldn’t matter if the IP were assigned to a toaster. They would still insist that it’s sending spam. It’s a boilerplate reply.

I have a method that’s worked for me, but it wouldn’t work in this instance because it’s not a single IP that’s being blocked. It’s a whole range of IP’s.

My method is to respond to their denial with a notice of my own that I’m blocking all of Microsoft’s IP addresses from all of my servers because about 40 percent of my incoming spam comes from Microsoft-owned addresses (which happens to be true). Then I actually do it, exempting my postmaster address so they can reply. That gets the ticket bumped upstairs and fixed.

It won’t work in this case, however. Your host or data center would have to do it; and it’s doubtful that too many hosts are ballsy enough (or crazy enough) to block all of Microsoft. Besides, if Outlook blocked an entire Class C, then there really was a shitload of spam being sent.

I’ve kept servers that I didn’t need online just because they had clean IP’s. As @Stegan said, once you get a clean IP, hold onto it at all costs. They’re priceless.


1 Like is a good site to test your email. (They give a few free tests each day)

If you do an email test, what score does assign to your email?

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who is the VPS?

Another helpful resource:

They have tools that analyze a zillion aspects of your MX setup (and more), and give hints on what’s working or not. One nice URL:

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Check your IP against spamhouse also check DNS records to be in compliance with dkim… test it with Google as it would work there it will work elsewhere… regards Microsoft spam, check spamhouse and go from there

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