Delayed Email from Outlook.com - Any experience?

[Scott Schultz]

Hey, all.

I don't really know exactly where I should be posting about this issue, and I don't really believe it's an Untangle issue at all, but I've exhausted the resources that Microsoft Support is willing to extend me.

My problem is that my employer is intermittently receiving email from outlook.com that's delayed by several hours; sometimes upwards of 10 hours or more, which effectively means the next business day.

Since Microsoft insists that it's not their problem, I'm at least checking whether anyone here has run into this issue before? Googling around about it shows me that other people who almost certainly were NOT running an Untangle firewall have had similar issues and similar fruitless run-arounds with MS support.

I'm of course willing to post logs and email headers if someone thinks that will be constructive. At the moment, I'm kind of fishing for someone to say, "Yeah, we had that problem and when we did X, it went away."

Scott Schultz
Systems Admin
cjhunter.com

[sky-knight]

This happens from time to time with all of the major email providers within their free services. The resolution is always the same...

You have to read the SMTP logs of the receiving mail server to see if there is any indication as to why the delay happens. Only the transmitting service knows for sure. But if you can find attempts at re-sending and the like you can potentially adjust your email reception to cure the delay.

But you're right, this is almost never an Untangle problem. Another thing to keep in mind, a reality that many find ridiculous yet is nonetheless true... Email being delivered within 24 hours is considered "working". SMTP was never meant for instant, or near instant delivery. So in some ways you can say, this is actually working as intended.

As far as Microsoft is concerned, adoption of M365 services has greatly accelerated thanks to COVID. Before COVID the East Coast Azure datacenters were FULL. This overflow is now spreading across the US, and also starting to impact the EU and other areas. As this happens, Microsoft is pulling resources from their unpaid services and putting it into their paid services. This has gotten so bad in some cases that vendors such as myself cannot make full use of our Azure credits via our Microsoft Partner benefit programs. Microsoft literally cannot build data centers fast enough.

So while I haven't seen a delay from any hotmail or equivalent free emails, it wouldn't surprise me if such were happening. Anyone using a free email address for commercial use is honestly... objectively stupid... and this lack of support you're experiencing is why. Residential users... well they get what they get, it's "free".

There is one thing you can do is double check your DNS, SPF, DKIM, and DMARC rules, and make sure your public facing SMTP service is working properly. A lack of any of the above rules will cause a delay from a Google or M365. M365 includes Outlook.com, it's all the same Exchange cluster.

[dwasserman]

The (by default hidden) header of email have the full info about path and time of each hop in the way.

https://mxtoolbox.com/Public/Content/EmailHeaders/