I’m trying to diagnose issues with sending emails to outlook.com (which is used by our corporate as their choice of email currently)
Notoriously all my emails were spam till yesterday for both, google and Microsoft. Turns out that the reason what the digitalocean IP was earlier used by some spammer. We got that fixed by getting IP unlisted everywhere and requesting google and Microsoft to remove it from blacklist as well.
Everything went smooth except for mails reaching in spam for outlook.com.
Here are headers for diagnostics:
https://pastebin.com/EQWaPKvk
headers are reporting something is not right with DKIM but I’m unable to understand what exactly is not working!
Any help would be highly appreciated!
Thanks in advance
That page not available on pastebin,
Looks like it expired!
Here is another link:
https://pastebin.com/EQWaPKvk
OP Updated.
It looks like a DNS error, I wonder if you have bad a DNS configuration or you changed it and your changes didn’t propagate.
TempError (protection.outlook.com: error in processing during lookup of rctngl.xyz: DNS Timeout)
Other people have had similar issues to interesting DNS configurations.
https://social.technet.microsoft.com/Forums/ie/en-US/e6ee0018-ef01-43f3-b8aa-76374184be55/receivedspf-temperror-xxx-error-in-processing-during-lookup-of-xxx-dns-timeout?forum=exchangesvrsecuremessaginglegacy
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I’m using totally stock MIAB, no changes committed so far!
Tested on DKIMvalidator, mail tester etc, none of them report any record issues
I cross verified my DNS from whatsmydns.net as well couldn’t find any difference between the records created by MIAB and the publicly visible records! I wonder what can be the source of problem!
I’d look at your DNS configuration and see if there is something wrong there. I wouldn’t make any assumptions that anything is correct.
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If this is a new box - remember DNS propagation takes UP TO 48 HOURS for a full affect (rarely does it actually take this long).
If this is a box that has been in production awhile, I’d venture to say an issue in a configuration somewhere or at your domain registrar.
I’m aware of this! I started testing email delivery after a week of server being left just as an inbox without any sending.
Any clue about where to look at? DNS is managed by the box itself.
Do you mind sending me your domain via PM? I can run some DNS checks on my end.
I’d start with re-running setup script for MIAB though make sure it completes with no errors.
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Sent! Hoping for something positive. ! 
Please share the result if you handle the issue. Because I also have same problem.
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Check your spam listings for the site using mxtoolbox
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Mxtoolbox says all Green on my domain and even then, the outlook problem persists.
Hey @murgero
Another pastebin! https://pastebin.com/qYcwuAf3
I Still don’t understand why is it giving a timeout on SPF & DMARC …
But I have strong feelings that this failure is the reason why microsoft is blacklisting emails.
This still has the smell of a DNS Configuration error to me.
However I looked at the domain using MXtoolbox and it looked OK to me.
What does http://dkimvalidator.com say? I find that quite useful.
Whats the spec of the MIAB box? Is it grossly underspecced and is struggling? Is it containerised?
DNS timeout for SPF - it’s possible maybe a record for one of your nameservers is bad. Why don’t you delete those and re-add them (this will take 48 hours!
DKIMValidator is happy with records.
DO 2GB RAM + Dual Core CPU
I can confirm the glue records are configured as follows:
ns1 - droplet IP
ns2 - floating IP
Both point to the same droplet.
I sure can do that but is there any positive impact? I could not find an issue with anything.
So DKIM is fine, the spec of your MIAB is twice the hardware of mine.
I know nothing about droplets so can’t comment on that.
I still feel this is a config issue, but since I can’t see it I can’t comment
I haven’t made any config changes. I’m okay sharing anything specific that you may like to look at because I seriously have no clue about where to look at.