PuffyNov 25, 2023
Puffy

Is there anyone from #Microsoft mail team that would be willing to chat to me about an issue we're having delivering to #Office365 / Outlook hosted mailboxes. Even if it's just pointing me in the direction of the right place to report it to.

I'm becoming desperate and getting no where through support channels. #sysadmin #infosec

Nov 25, 2023 at 8:48amWeb
Show threadFrank Berger Nov 25, 2023
@Puffy
Been there, done that, feel you, brother!... sorry to say so, but your peril is their sales channel.. Check if your reverse IP lookup matches the name the MTA uses. Add SPF records if not done, and ensure they match the mails you're sending. Check smtp blacklists. Consider DomainKeys and make sure they work.. I am not with hotmail or outlook or office365, just a sysadmin operating a mailserver for customers wishing that Microsoft would have found their place in the technology graveyard.
Show threadPuffyNov 25, 2023
@foppel Hi Frank, thanks for taking the time to reach out. Unfortunately we have all those things in place, not on any RBLs that we're aware of. As far as I can tell, we're doing everything right but all of a sudden last week we're running into issues and I just can't get any kind of clarity on why this is the case. And of course clients are frustrated and don't understand why we can't just fix the issue, lots of cancellations already unfortunately.
Show threadFrank Berger Nov 25, 2023
@Puffy That sucks brother, I feel for you. As I said, it is their sales pitch to your customers.. check here for some guidelines: https://postmaster.live.com/pm/troubleshooting.aspx#errors
And there is a contact form (which registers as an app on github WTF?) where you might get help? Try it: https://support.microsoft.com/en-us/getsupport?oaspworkflow=start_1.0.0.0&wfname=capsub&productkey=edfsmsbl3 - i wish you all the luck in the world
Troubleshooting