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Outlook/Hotmail is no longer blocking my mail server

taoshu.in

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Re: Outlook/Hotmail is no longer blocking my mail server

#221

Post by yonrg »

benmanns wrote: post #202
yonrg wrote: post #147

Earlier quoted context omitted.

Right. When I changed my vps to another hoster, I totally forgot how much trouble it was to get a good reputation in the beginning. But it was really not that much work again. Just unfortunate, because one big Mail provider just discarded instead of rejecting my mails. After this was settled, everything works quite nice again. Important to me is keeping spf, dkim, dmarc and now also mts up to date. See mail-checker.c…

Do you mean a different domain? mail-checker.com Looks like a parked spam domain.

Oh you are right. Sorry for the fauxpas. It is mail-tester.com as corrected below. Thanks for mentioning

Re: Outlook/Hotmail is no longer blocking my mail server

#222

Post by sheikheddy »

csnover wrote: post #152
sheikheddy wrote: post #47

I work on Microsoft's anti-spam team, AMA!

I guess my question is can you please fix your braindead blacklisting? Several times per year—I can practically guarantee it’ll happen sometime in December, and indeed had to deal with this just five days ago—I end up with a bunch of users whose email notifications stop working because Microsoft have started blocking the entire netrange where my server lives. I don’t have control over other Linode customers, guys! I…

My guess is that the effectiveness issue isn’t actually due to SNDS and is probably related to sender reputation having famously high false positive rates. I read a paper a while back which introduced a different algorithm with tighter bounds on regret, I didn’t really understand it tbh, but I can implement it behind a flight and run a data study to see if it works better. The problem is that most graph based stuff doesn’t scale super well because of something-something complexity classes. I think the lady who architected it 5 years ago didn’t do a great job and there’s a bunch of arbitrary config stuff which was put as a placeholder and then became enshrined in stone… but the guy maintaining it rn is really smart so I’ll have him review my half-assed PR when he’s back next week (and idk how long it’ll take to finish the other half of it, shit never ships around here).

About the calendar widget thing… man am I glad I our team doesn’t own that. No one ever touches legacy stuff cause they’re afraid it’ll break or no one will update but the trick is to file it as an accessibility bug since that gets someone to actually prioritize it since it shows up in reports that the execs read. But dude good luck getting that off the backlog, the one engineer we have who is good at UX stuff (i.e, can code with both quality and velocity instead of just one) has her hands full as is.

Re: Outlook/Hotmail is no longer blocking my mail server

#223

Post by sheikheddy »

Dylan16807 wrote: post #177
vel0city wrote: post #174

Earlier quoted context omitted.

> Give most servers "Internet*" access where some ports are missing? Disallow SMTP traffic unless an account has a certain reputation or verified identity related to it? I mean, they don't have to do that, and I would agree the government shouldn't force it to happen. But if someone is constantly causing you problems you shouldn't be required to deal with their shit. If you don't want to behave, expect consequences f…

Personally inviting someone to your party? Surely the analogy to linode is something like an apartment building owner. You wouldn't ban your established friend just because you keep having problems with nearby tenants.

Oh man I think around 2 years ago there was a 3x spike in Europe outbound spam and the fraud team had to disable like 200k+ tenants from some shady cloud VPS. We didn’t have a long term plan for the abuse back then besides playing whack-a-mole, and if we have one now, I haven’t heard of it.

Dumb question, but wtf is the solution even? I’m confused about what you expect us to do. I haven’t thought about the problem much so I might be missing some obvious Pareto improvement.

Re: Outlook/Hotmail is no longer blocking my mail server

#224

Post by sheikheddy »

Dunedan wrote: post #71
sheikheddy wrote: post #47

I work on Microsoft's anti-spam team, AMA!

Why do you put mail servers on your block list which never sent spam? And why do you make it nearly impossible to get unlocked once on that list?

Yo I’m not even gonna apologize about this, it would be so wack if we didn’t do that:

a) if a mail sever looks like it’s gonna send spam, then you gotta block it. I personally have philosophical hang ups about this, like it’d be wrong to sentence someone to prison for crimes they didn’t commit just because a system added up some points and made a prediction with high confidence, but in real life, you absolutely need to be proactive. b) there is literally no way to do this that wont immediately get abused. Trust me we’ve tried. We make it nearly impossible to get unlocked on purpose because if it was easy, then it’d be like 1 innocent person using it and 99 attackers due to the adversarial incentive structures.

Now ofc there’s more nuance here, we really do want to get it wrong less often, and you do pay us so it’s not fair to blame it all on the bad guys, so I’m grateful for the feedback but I think you should give me even more detailed feedback since there’s not much I can do except give a vague high level explanation unless you help me by being specific.

Re: Outlook/Hotmail is no longer blocking my mail server

#225

Post by Dylan16807 »

sheikheddy wrote: post #223
Dylan16807 wrote: post #177

Earlier quoted context omitted.

Personally inviting someone to your party? Surely the analogy to linode is something like an apartment building owner. You wouldn't ban your established friend just because you keep having problems with nearby tenants.

Oh man I think around 2 years ago there was a 3x spike in Europe outbound spam and the fraud team had to disable like 200k+ tenants from some shady cloud VPS. We didn’t have a long term plan for the abuse back then besides playing whack-a-mole, and if we have one now, I haven’t heard of it. Dumb question, but wtf is the solution even? I’m confused about what you expect us to do. I haven’t thought about the problem mu…

Did I accidentally give the impression I have a particularly good solution to spam in mind? I don't.

My main suggestion here is just that an established reputation for a specific IP/domain should override the reputation of the IP block it's inside of.

Re: Outlook/Hotmail is no longer blocking my mail server

#226

Post by sheikheddy »

TonyTrapp wrote: post #209
sheikheddy wrote: post #47

I work on Microsoft's anti-spam team, AMA!

Similar question as my sibling comments. I have rented a server with a static IP address for over ten years now. Nobody else has used this IP during this time. Yet, every few months I have to beg Microsoft to unblock the IP. In the beginning I could do this on my own, but something changed a few years ago and now I have to beg my ISP (netcup) instead to contact Microsoft on behalf of me to temporarily whitelist the d…

Aww man, not joking this actually breaks my heart, something about the way you wrote it makes it sink in how much we’ve failed you. I’m angry at how much of your time we’ve wasted and this experience is completely unacceptable.

…I think this is just a systemic issue beyond my ability to comprehend, let alone solve, and— I hope I’m wrong about this but honestly when I look ahead it seems the future is only going to get worse for people like you. Which I wish I could phrase in a way that was more kind and respectful, it’s not what anyone wants, these unthinking scars inflicted on email as a medium.

But what I can do is make sure that it’s not worse for you, specifically. If I was perfect I’d attack this rot at its core, but I’m not, so I’ll just solve the problem in front of me even though I know it doesn’t scale and hope God forgives me. Get in touch with me directly and I’ll figure out how to make sure you don’t have to jump through those hurdles again.

Re: Outlook/Hotmail is no longer blocking my mail server

#227

Post by sheikheddy »

NorwegianDude wrote: post #215
sheikheddy wrote: post #47

I work on Microsoft's anti-spam team, AMA!

What's the best way to quickly get MS to trust a server/domain? Does MS ignore IP reputation in cases where the domain has a good reputation? How would you go about getting a new domain and an IP address from a public cloud provider working consistently? I've had issues with outlook when it comes to new domains and IPs, but after some time it works. I do however usually have more email than a personal server so what'…

Hmm, oh wow, occasionally I’m reminded that if I flipped sides to run phishing campaigns I’d be totally unstoppable.

There isn’t a quick way, by design. You need to wait a minimum period and meet some predicates, and the organized scammers already know what the period is via empirical testing but I’m not comfortable disclosing details of those predicates for disorganized scammers to use. More so because I’d definitely get into trouble for it than due to any belief in security via obscurity. Cushy job makes you risk averse.

Since I can’t share any of the tricks, some general advice— the main thing that matters is a long track record of good behavior. You can end up in a vicious cycle where you fight the system when it punishes you and then it doubles down on the beatings— this is bizarre and kafkaesque and happens all the time. What you want is for there to be two-way communication, if it’s unbalanced with traffic being broadcast but no one engaging with it, that’s going to be cracked down on sooner than if recipients reply.

Re: Outlook/Hotmail is no longer blocking my mail server

#228

Post by sheikheddy »

Biganon wrote: post #204
sheikheddy wrote: post #47

I work on Microsoft's anti-spam team, AMA!

How do you sleep at night?

I don’t. I have slept in the daytime ever since covid and actually got a move to the east coast approved as a health accommodation after I started routinely missing important afternoon meetings due to my incurable insomnia (mornings are easy when you stay up all night). I still struggle with it, especially since it’s not a consistent offset to my circadian rhythm. There’s data I’ve collected but it’s hard to fit a simple function to it— it’s not like I’m on a 26 hour schedule either. This isn’t due to trauma or addiction, my brain is just an outlier in many dimensions and this is one of them.

Re: Outlook/Hotmail is no longer blocking my mail server

#229

Post by sheikheddy »

Avamander wrote: post #59
currysausage wrote: post #54

Earlier quoted context omitted.

The most pressing question: why does Outlook.com just silently discard some emails?

Not the person you replied to, but as far as I've heard it's done with SmartScreen matches.

This is correct but not the only reason it could be happening.

Re: Outlook/Hotmail is no longer blocking my mail server

#230

Post by sheikheddy »

pbhjpbhj wrote: post #211
sheikheddy wrote: post #47

I work on Microsoft's anti-spam team, AMA!

Why doesn't whitelisting an address ensure one receives messages from it, the address has never sent spam, sends at most a couple of emails a day. But I couldn't receive emails from it, there was no notification or information despite the address being on my whitelist? What's the rationale there?

Huh? This shouldn’t be possible in principle? Don’t quote me on that though, I wish I’d paid more attention to my notes but they’re a mess and haven’t kept up with newer changes, if they were accurate at all in the first place. I’d submit an escalation so support can look into it.
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