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Ask HN: Is there hope for Microsoft 365 support?

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Re: Ask HN: Is there hope for Microsoft 365 support?

#21
post #19

You have Unified Support and dedicated CSAM assigned to your case? If you're trying to solve this over Basic support...Good luck friend!

I guess only basic since our main provider is Google, not MS.

We do use Azure for small stuff, but too small for any special support channel.

Re: Ask HN: Is there hope for Microsoft 365 support?

#22
post #10

Have you looked at the Exchange Online and Defender portals for clues? Especially in the Message Trace section of Exchange Online? I recently helped troubleshoot a similar issue - we were suddenly getting emails disappearing when sending to M365 customers. No spam or quarantine, just disappearing down a black hole like you described. We sent a test message to a M365 customer who could help run the message trace, and…

Yes, I have. Message Trace is an interesting one. If we send an email without the 25friday.com keywords everything works fine, the message is shown on Message trace as delivered and the recipient gets the email with SCL 1 (all good here). As soon as the very same email is appended with a www.25friday.com, Message Trace still shows the outbound email, also as delivered, but the recipient (if a Microsoft account) never…

Are you sure that it's MS who's blocking? Just think it's weird that they show it as delivered to recipient, sounds like they send the mail and something weird happens after.

Re: Ask HN: Is there hope for Microsoft 365 support?

#23
post #22

Earlier quoted context omitted.

Yes, I have. Message Trace is an interesting one. If we send an email without the 25friday.com keywords everything works fine, the message is shown on Message trace as delivered and the recipient gets the email with SCL 1 (all good here). As soon as the very same email is appended with a www.25friday.com, Message Trace still shows the outbound email, also as delivered, but the recipient (if a Microsoft account) never…

Are you sure that it's MS who's blocking? Just think it's weird that they show it as delivered to recipient, sounds like they send the mail and something weird happens after.

Well, it works fine for every single recipient unless it's a Microsoft one.

If the recipient is using a personal microsoft / outlook / hotmail account the email gets delivered with a spam score of 9.

If the recipient is a MS 365 account, blackhole it is.

We even set up our own MS 365 to prove this.

Re: Ask HN: Is there hope for Microsoft 365 support?

#24

Earlier quoted context omitted.

We don't even have any sort of login on our main page, the redirects we have are mostly around apex domain to www.25friday.com, http to https and the likes.... This is a pure company landing page with the typical business description, career application page, articles etc. We do have subdomains for internal tools of course, but those should not even be publicly accessible (behind an auth proxy).

Outlook also recently changed the default “report message” action in the UI to be “report phishing/malware” instead of “report spam”. This was a terrible design choice; phishing reports from my org’s own user base has increased 4x since the change which is a lot of false positives. So maybe folks mean to “report spam” on your emails but “report phishing” instead…

Could be the reason, but even so, we have really low volume campaigns and mostly to people we actually interact / have a history with. I would assume it would take more than a few accidental hits to trigger this issue.

Re: Ask HN: Is there hope for Microsoft 365 support?

#25
Similar experience. I am IT Director at a medium sized school district (3500 students) and our emails were blocked by Microsoft for a few weeks. Our email domain and up address are not on any blacklist and have an excellent reputation. The mail server has been operating for over 15 years. I was able to get unblocked by emailing Microsoft support opening a case and registering our mail server with Microsoft smart network data services.

“ You are receiving this because you have signed up to be a user of Smart Network Data Services, or a Smart Network Data Services user has requested that this email be sent to this address. Smart Network Data Services is a revolutionary Windows Live Mail initiative, designed to allow everyone who owns IP space to contribute to the fight against spam and protect e-mail as a valued communications, productivity and commerce tool. If you have questions about our privacy policy, please read our privacy statement available at http://privacy.live.com. I

Re: Ask HN: Is there hope for Microsoft 365 support?

#26
post #25

Similar experience. I am IT Director at a medium sized school district (3500 students) and our emails were blocked by Microsoft for a few weeks. Our email domain and up address are not on any blacklist and have an excellent reputation. The mail server has been operating for over 15 years. I was able to get unblocked by emailing Microsoft support opening a case and registering our mail server with Microsoft smart netw…

We also had a look at it, but the problem is that we don't control our mail server as it's Google provided.

Re: Ask HN: Is there hope for Microsoft 365 support?

#28
A tangential note, but after fighting for weeks with office365 and outlook to have basic features working for a small business, I would advise anyone sane of mind to avoid like hell using office365 or exchange for emails/calendar.

On the outside, things look great, looks like to be a good value for the price, but for real, everything is buggy, lot of basic features requires you to manage them with PowerShell commands, there are bugs for years and the support is clueless. For example don't mind using "shared mailbox" or "delegation" without fighting a labyrinth of unexpected behaviors.

For outlook app in itself, you have around 3.5 different versions of it fighting in duel. With the "new" version not necessarily the one to use to have all the paid features, that would be the "classic" version.

With the new or web version, you can't move more than around 100 mails at a time, or more crazy, you can't delete more than 10 contacts in one go...

What amaze me is that all the email/contact/agenda suite looks like semi abandoned when they should make so much money with all the subscription and when everyone is there showing off with billion dollar tech in AI when your basic features are still incomplete and buggies.

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