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Outlook/Hotmail is no longer blocking my mail server

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

#241

Earlier quoted context omitted.

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.

But why do you consider this good practice? It's (unnecessarily?) frustrating for senders and poses a legal risk for recipients (the sender has the logs to prove that they sent the invoice, while the recipient doesn't have any record).

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

#242
post #71

Earlier quoted context omitted.

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…

Thanks for responding, really appreciated.

> made a prediction with high confidence

Do you somehow track the amount of false positives these predictions generate? How do you tune the prediction to not generate too many false positives?

> but in real life, you absolutely need to be proactive

Why is Microsoft the only provider who needs to do such proactive blocking? Why don't you need to do that for email addresses associated with Office 365?

> 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.

My story is very much the same as for everybody else having the same trouble, including the person whose blog post sparked this discussion: A root server for personal use located in the data center of a mid-sized hoster, running a mail server as part of its duties. In my case the whole mail setup runs on IP-addresses separate from everything else. Mail volume to Microsoft would probably be on average 1-2 emails per month. No issues whatsoever getting emails delivered to other mail providers, only to Microsoft. This whole setup is in place since several years.

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

#243

Earlier quoted context omitted.

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 d…

> I read a paper a while back which introduced a different algorithm with tighter bounds on regret

Got a link or cite for that paper? It sounds interesting.

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

#244

Earlier quoted context omitted.

> - Self hosting is a bit elitist - not for the masses. Is it? Most people, including nomads & unhoused, seem to have smartphones these days (at risk of theft, but arguably easily replaceable). And 4/5G/PublicWifi connectivity in urban areas is so saturated. I wonder, is it reasonable for me to want government investment and legislation (but no other state interference) into some open source server project that we ca…

As a nomad, and someone who does run a self hosted mail server for fun, I don't think that's such a good idea. As mentioned, phones can be stolen or broken or just off. Do I want to increase dependencies on phone further by it being the primary store for all my mails as well? Each platform, which is not using TOTP MFA would still depend on email OTPs and so with a broken phone one completely loses access. With TOTPs…

I suppose I haven't been fully compelled by any of these replies (but I don't have anything compelling in return). Sorry, my lack of knowledge is the failure here (Dunning Kruger effect: I don't see why dynamic IPs / mac addresses / OTP / VPN / encryption are real insurmountable issues here)

Also nomadic, also in tech - And I would happily run a mail server on my phone, sacrifice thickness of phone for the extra necessary battery life, and keep a spare phone somewhere for quick restore/swap (I have a spare old android I keep in case I break my current one, which I can keep at a friend's place, an Airbnb or a subscription locker / safe.

What's the alternative being proposed though, Google et al? Or a home server (I have no home)? Or still free market, but providers are smaller businesses that are more heavily legislated and are watched over by the state to ensure our data is safe? I'm just not sure 'where' my data+computing should be, other than right next to me in my pocket (but then where do my backups go?).

Sorry for the appalling and directionless writing, it's just that everything just seems to circle back to the solution being: *'two small portable battery operated wireless devices that we have control of and the big providers do not have access to; keep one of them on our person and one in another safe place for DR purposes.'*

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

#245

Earlier quoted context omitted.

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 ge…

Appreciated. How can we get in touch?

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

#246
post #243

Earlier quoted context omitted.

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 d…

> I read a paper a while back which introduced a different algorithm with tighter bounds on regret Got a link or cite for that paper? It sounds interesting.

https://arxiv.org/abs/1411.1127

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

#248

Earlier quoted context omitted.

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 ge…

Appreciated. How can we get in touch?

Abdurraheem dot ali at microsoft dot com

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

#249

Earlier quoted context omitted.

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…

Thanks for responding, really appreciated. > made a prediction with high confidence Do you somehow track the amount of false positives these predictions generate? How do you tune the prediction to not generate too many false positives? > but in real life, you absolutely need to be proactive Why is Microsoft the only provider who needs to do such proactive blocking? Why don't you need to do that for email addresses as…

> Why is Microsoft the only provider who needs to do such proactive blocking? Why don't you need to do that for email addresses associated with Office 365?

They're not.

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

#250

Earlier quoted context omitted.

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

But why do you consider this good practice? It's (unnecessarily?) frustrating for senders and poses a legal risk for recipients (the sender has the logs to prove that they sent the invoice, while the recipient doesn't have any record).

Again, not the person you replied to. But some feedback mechanisms take time (so action has to be taken after a 2xx reply) and some indicators are just very very very accurate that leaving them in even just Spam is a way bigger risk. Users have a terrible tendency to dig out malware from Spam folders.
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