Email Delivery Problems

Office365 seemed to have some issues with our email provider, so we’re going to take a stab at direct delivery. If you experience an issue with receiving emails, please let me know either with a DM or a reply on this thread so I can investigate.


It looks like hotmail/ is junking any mail from us regardless of if we send it through a relay or not. If you’re using one of those services, you’ll likely need to add to your safe mailing list.

Ive been getting the last dozen or so through office365 just fine.

Ted Bass

Yep; that was the main problem I’ve been trying to fix… I do find it amusing that fixing Office365 deliver-ability broke hotmail since they run on the same stack these days.

Oh wow that is odd.

Ted Bass

Anyone up for posting a full header on a message that was junked? I’ve checked mine (gmail), and they are very clean. SPF and DKIM both validate the message. It would be interesting to see what think about it.

Hotmail doesn’t really disclose the reason for marking a message as
Spam, but since it’s a super low number of people I’m probably going to
just hope it clears up on its own and focus on keeping us in Google and
365 inboxes.

A quick survey last night of different MXes, and Google Apps & Gmail are far and above the biggest user base, followed by Office 365 then Barracuda. Most everything else is 1-2 different users each, so I’ll probably only really be proactive with the top 3. I’ve also configured throttling for some of the common problematic recipients (aol, yahoo, hotmail) so hopefully we can keep a decent reputation there and at least make the junk folders but they’re super hostile environments for senders so there’s not a lot I can do.

I do know hotmail doesn’t seem to care whether I use SparkPost or direct delivery, but if there’s demand we can try using Sendgrid to handle those mails.

So we’ve got 6 folks on Outlook/Hotmail MXes and mail is still going to junk even though we’ve earned a 100% senderscore. The only thing I can do to try and improve our inbox positioning is to publish DMARC records which requires us getting DKIM set up on the google apps account.

Or we can publicly shame anyone who’s still using hotmail in 2016 :grin: