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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?
#12Use a 3rd party SMTP like sendgrid.
Once you get on a shitlist it's almost impossible to get off of it.
Re: Ask HN: Is there hope for Microsoft 365 support?
#13Have 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 gets the email. We used one of these emails (EML) to create a submission on the defender portal of a false positive, but they always simply disappear with 0 feedback (and the problem still occurring).
We also had a signature with the www.25friday.com link on it and took it out after realising it was causing emails to go to this black hole, so that at least we can still send emails, but we keep having to be careful to never sending any content (or attachment) that somehow mentions the 25friday.com domain.
Re: Ask HN: Is there hope for Microsoft 365 support?
#14Use a 3rd party SMTP like sendgrid. Once you get on a shitlist it's almost impossible to get off of it.
We signed up to MS 365 using a subdomain and try to triage the issue and if anything it only made the issue clearer, that it has nothing to do with the sending domain but pure content filtering.
Re: Ask HN: Is there hope for Microsoft 365 support?
#15MS are notorious for blacklisting IP ranges from providers like Linode, which makes it impossible for a small biz to run its own commercial system. I'm not surprised they also keyword block, because Outlook flags Microsoft's own marketing messages as spam. There really needs to be some kind of global Digital Bill of Rights which provides legal recourse from these giant sclerotic algo-run oligopolies. MS, Meta, Amazon…
> There really needs to be some kind of global Digital Bill of Rights which provides legal recourse from these giant sclerotic algo-run oligopolies
Agreed. I think the problem is mainly that communicating what is wrong in a way that politicians can understand is difficult, and the people who governments hire to make them understand, are not incentivised to do so here (they're typically corporate types, good at ticking boxes, not so good at technology).
Making the EU understand issues such as why Apple's monopoly is a bad thing is easy in comparison, because everybody has a phone and everybody understands "shops". Even so, I'm impressed that went the way it did. I don't have much hope for politicians understanding what MS et al. are doing to mail though.
Re: Ask HN: Is there hope for Microsoft 365 support?
#16In my cynical world view, your options are:
1. Rename the company
2. You (or somebody you know) gets a job at Microsoft in the correct team and removes 25friday from the backlist.
I'm guessing at some point the past, there was a large spam campaign that targeted friday the 25th for some reason.
Re: Ask HN: Is there hope for Microsoft 365 support?
#17On a related note, can we as a community start tarnishing Microsoft et al. for e-mail? Blog posts, about pages, documentation, anything and everything where it's appropriate, we should be stating it as a fact that Microsoft's e-mail solutions are sub-par. Off the top of my head;
"Please bear in mind that if you are using a non-standards compliant e-mail service provider such as Microsoft, e-mail delivery may be effected"
I wasn't even sure if the standard specified what to do with undeliverables, but it turns out that RFC 5321, RFC 3461, and RFC 3464 do. TIL :)
Re: Ask HN: Is there hope for Microsoft 365 support?
#18In my cynical world view, your options are: 1. Rename the company 2. You (or somebody you know) gets a job at Microsoft in the correct team and removes 25friday from the backlist. I'm guessing at some point the past, there was a large spam campaign that targeted friday the 25th for some reason.
Joking aside, we are seriously considering moving all comms to 25friday.nl (which we also own) if we can't find a way around this...
Re: Ask HN: Is there hope for Microsoft 365 support?
#19You have Unified Support and dedicated CSAM assigned to your case? If you're trying to solve this over Basic support...Good luck friend!
Re: Ask HN: Is there hope for Microsoft 365 support?
#20On a related note, can we as a community start tarnishing Microsoft et al. for e-mail? Blog posts, about pages, documentation, anything and everything where it's appropriate, we should be stating it as a fact that Microsoft's e-mail solutions are sub-par. Off the top of my head; "Please bear in mind that if you are using a non-standards compliant e-mail service provider such as Microsoft, e-mail delivery may be effec…
I'd love to but what see in practice is that the bigger the company the more likely it is that they use MS. Which hits double hard since this means our bigger clients are the ones not getting our emails...