20 ms·

Outlook/Hotmail is no longer blocking my mail server

196 points by unclet 3y ago

abberation 3y ago
Wow, Outlook actually tells you they blocked you? My email (custom gmail domain btw) just ends up in the Spam folder of outlook clients with no notification at all.
- jraph 3y ago
  I self host. Over the years, I've had both situations with outlook. I've tried many things. As it happens, I noticed my mails have gone through just fine in the last months, at least to companies using Microsoft services without me doing anything specific, after I threw the towel with Outlook. I did switch VPS providers almost a year ago, though to a provider that I expect to be more filtered (ovh).
- delusional 3y ago
  That's a different issue. You're usually not notified of spam designations, but bounces (where the mail server completely refuses to accept your email) do usually receive a notification. If you're designated as both (for example if you keep sending email that bounces) you'll get blackholed and wont receive any bounce notification either.
  - Sayrus 3y ago
    When I used to self-host my emails, GMail would "accept" mails then drop them. Microsoft was kind enough to tell me they dropped them but getting out of the blacklists was a pain.
  - lucb1e 3y ago
    An advantage of landing in spam is that the user still has a choice and is in control. Rejecting outright is a "lalalala I can't hear youu!!" type of stupid situation that only big providers can get away with, without the users realizing their bigcorp is the one with delivery issues
    - uxp8u61q 3y ago
      As a user, I'm thankful I don't need to sift through hundreds of spam emails a day to find potential false positives. Because that's what you're advocating. You'd apparently like everyone to have a terrible email experience for the sake of your own personal comfort and preference (self hosting your emails). Besides, for something truly important, the people or organisations who need to reach me know how to do so other than via email (phone, chat, postal mail...).
      - Dalewyn 3y ago
        This. Microsoft, Google, et al. aren't doing anything worthy of criticism here; it's the spammers who ruin email for the rest of us who should be facing the music.
        Avamander 3y ago
        Until it's not illegal it's only going to get worse.
        uxp8u61q 3y ago
        Spamming is illegal.
        Avamander 3y ago
        In a lot of jurisdictions it basically isn't. I'd love to see at least a few convictions though, where it is.
    - pm215 3y ago
      Conversely, if you as the sender get a bounce at least you know something went wrong and can try a different way to contact the other person (different email, telephone, text message...) Bouncing is the traditional approach, and the original ethos was "bounce, or defer, or deliver, but don't ever accidentally or deliberately just drop an email on the floor". It depends whether you think of "the user" as the sender or the re cover -- as a (human) sender I'd rather get a bounce than be silently ignored in a spam folder, but as a receiver I prefer the grey-area emails to be accept-but-spamfolder, not bounced...
- BSDobelix 3y ago
  Have you tested with: https://www.mail-tester.com/ https://www.mail-tester.com/
  - TomK32 3y ago
    Thanks, I was missing a DKIM on my mailcow setup. 10/10 now :-)
    - BSDobelix 3y ago
      Excellent!! Have a nice day!
  - Pathogen-David 3y ago
    Another useful tool is https://www.learndmarc.com/ https://www.learndmarc.com/ -- I found the presentation very helpful when I was finally getting on the DMARC train a while back.
    - BSDobelix 3y ago
      True, MECSA is also interesting: https://mecsa.jrc.ec.europa.eu/en/ https://mecsa.jrc.ec.europa.eu/en/
      - yonrg 3y ago
        They made me configure MTS
      - _ache_ 3y ago
        Whoa ! Very nice tool.
      - Pathogen-David 3y ago
        Ooh, thank you for sharing! This has given me a few things I should look into improving with my setup.
albertgoeswoof 3y ago
I run a small transactional email provider (https://mailpace.com https://mailpace.com), our IPs are very rarely added to blocklists- but we are very strict on what we allow through our service, and surprisingly we’ve had no long term delivery issues with any of the big providers. So thanks to the federated/decentralized design of email, is totally possible to be part of the network without any special privileges. We are sending millions of emails every day though, which is quite different to sending a couple hundred personal emails a week. If you’re running this on a cloud host, expect to be blocked by default. However if you can find a small vps provider you’ll have better luck on sending yourself.
- TobyTheDog123 3y ago
  (Unrelated to the OP - but I've been so frustrated by this for so long that it's worth the [flagged]) A product like this is exactly what I've been looking for with pretty great pricing. The one thing that this (and most providers) are missing is making email easy to test. I'm about to launch a product where email is critical, and there's no way to send an example email (with a non-test email address) to your service and see that you receive it, without it being sent to the To address. Better yet, the few providers that do support it charge as if it were a real email, when none of the delivery costs exist on their end (there are infrastructure costs, sure, but there is none of the reputation risk nor need for clean IPs, the reason people use transactional services like these in the first place).
- yonrg 3y ago
  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.com e.g. I still wonder though, why some big mail providers do not do dkim/dmarc? I happen to realize this when I started to fight spam and gave incoming mails without dkim/dmarc a high spam score.
  - 3y ago
tschumacher 3y ago
Maybe the big webmail providers are relying more on machine learning for filtering spam instead of blocking IP ranges these days.
- gumballindie 3y ago
  That would be horribly unreliable. I hope they dont rely on machine learning for such critical infrastructure.
  - mort96 3y ago
    Blocking IP ranges is also horribly unreliable. There is no good way to fight spam in a system like e-mail, just varying levels of terrible ways.
vouaobrasil 3y ago
Running a mail server should be something anyone can do. And while this is cool, there are so many other problems to do it. It's the price we pay of letting big tech companies control so much of the virtual infrastructure: big tech has commoditized the internet so much into a platform for consumerism that it becomes a valuable target for spam. In my opinion, the internet would be much better if none of the big players ever entered it, including Google, Facebook, Yahoo, etc, and it would allow for many more decentralized and valuable commons like email.
- mort96 3y ago
  The basic fact of the matter is that >99% of people will never be interested in hosting their own e-mail server, and that's okay. This means we need organizations to host e-mail for people. In a capitalist system, that means companies, and it leads to consolidation and monopolization. So far, governments have been seemingly uninterested in going after the large e-mail providers for anticompetitive practices; maybe that should change. But as long as those anticompetitive practices only really affect individual hobbyists who wanna host their own e-mail, while business interests are unaffected, I don't see this changing.
  - vouaobrasil 3y ago
    I don't think it just affects hobbyists. It allows affects people who want to use smaller email servers, or even people who WOULD use smaller email servers simply because larger ones did not exist. I think the government SHOULD go after consolidation such as Google, and that traditional anti-trust law is insufficient to combat the dangers of large tech companies. This is precisely because traditional anti-trust laws only look after large PROPORTIONS. In today's modern economy, due to its size, we have a danger that we've never seen before: large ABSOLUTE size, which was never a problem in history as it is today. Therefore, we need new laws that go after absolute size, as well as large proportions (traditional anti-trust).
  - yobbo 3y ago
    > In a capitalist system, that means companies, and it leads to consolidation and monopolization. No, a "capitalist system" does not lead to consolidation and monopolization.
V__ 3y ago
Is this mira of a U.S. centric problem? I selfhost my mail in Germany, have one at a smaller mail provider and never had problems. It is also not uncommon for companies to either have a local Exchange Server or use the mail service at their hosting provider. If everything is configured correctly, delivery works fine.
- psd1 3y ago
  Your experience may not be typical. I ran mail servers before office 365 was a thing, and I often had to get off block lists. There are stories on HN about it being worse, now that you have to request unblocking from MS and Google. Yours is the first comment that doesn't complain.
  - layer8 3y ago
    Nah, I have the same experience as the GP, and in every HN thread about email self-hosting, there are a number of comments along the lines of “I’ve been self-hosting my email for 10-20 years and never had any problems”. My SME employer also self-hosts without issues. Experiences obviously differ, but it’s unclear where the differences stem from, apart from long-term IP reputation.
  - vel0city 3y ago
    > Yours is the first comment that doesn't complain. It is potentially more of those with problems are more likely to speak up than everyone else just posting "works fine for me" a thousand times over. I haven't had much deliverability problems with self-hosted things. I set it up right, and I get the emails I expected to get. So there's now two of us saying "works fine for me."
- justsomehnguy 3y ago
  Personal anecdote != universal, global experience. > have one at a smaller mail provider a) [hosted] Mail provider b) Server (colo/dedicated/VPS/whatever) provider Choose one. > not uncommon for companies to either have a local Exchange Server Yes and it's PITA to pull it out of the lists of some shitheads, like SpamHaus. Source: guess it
freetanga 3y ago
I think that governments should offer one free email account per citizen for life. Which you could use or not, but is there for you as a digital inbox… which are the options? - Self hosting is a bit elitist - not for the masses. - A paid-for option (proton, tutta,…) would be cataloged as elitist. People perceive email as free. - A free option provided by a Corporate player will gravitate towards monopolies and lack of privacy. - A free for life government issued, easy to recover digital point of contact where all your government interactions are pointed towards would be a great step. You could still have a separate one if you don’t trust big brother, but at least your “recovery” address would be secure for life.
- benbristow 3y ago
  Ah yes, a government owned email service, what could go wrong?
  - lotsofpulp 3y ago
    Nothing? It can exist as a utility alongside other email services.
    - iAMkenough 3y ago
      Nothing can go wrong? In that case, the government should create a public social network as a utility alongside other social media services too.
      - lotsofpulp 3y ago
        Sure, although I think the utility of a communications network capable of receiving and sending documents within a country is very well proven to be a benefit to society, so any comparison to something less battle tested seems unnecessary. It makes no sense that in the physical world, we entrust government with identity verification and transmitting correspondence, but that trust is somehow lost in the digital world.
sheikheddy 3y ago
I work on Microsoft's anti-spam team, AMA!
- currysausage 3y ago
  The most pressing question: why does Outlook.com just silently discard some emails?
  - Avamander 3y ago
    Not the person you replied to, but as far as I've heard it's done with SmartScreen matches.
    - sheikheddy 3y ago
      This is correct but not the only reason it could be happening.
      - currysausage 3y ago
        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).
        Avamander 3y ago
        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.
        currysausage 3y ago
        This was not the cause in my case (no attachments, no URLs, just plain text, as far as I can remember). I know how to send email (ask mail-tester.com). Regardless, there are always better options than silently discarding the whole email: delete attachments, erase everything that looks like a URL, even erase the whole message body, but please tell the recipient that you accepted an email and from whom.
issafram 3y ago
TL;DR emailed Microsoft a few times
brunnock 3y ago
I ran into this issue several years ago. After complaining, MS allowed me to send email to MS properties (hotmail, live.com), but continued to block my email to their Office 365 clients. I now use AWS SES to handle mail delivery. It's free for up to 200 daily messages which is fine for me.
Dunedan 3y ago
After many years of regularly getting blocked by Hotmail and outlook.com, I just decided to reject every incoming email from Hotmail and Outlook with an error message explaining the situation. If they don't allow me to respond to emails sent by their customers, why would I allow them to send me emails in the first place?
- Avamander 3y ago
  You sure showed it to them. /s Did you sign up to their JMRP to figure out what they didn't like or how were they blocking you?
- unclet 3y ago
  If all indie mail servers blocked by Hotmail block mail from the blocker, it will make the big player review their blocking policy.
shaicoleman 3y ago
Outlook/Hotmail blocks DigitalOcean. After half a dozens attempts over the years to delist my IP, and following all the best practices (dedicated fixed IP, SPF, DKIM, DMARC, FCrDNS, zero spam, TLS, etc.) I gave up. Eventually, most people realize that their Outlook/Hotmail email service is defective because they're not receiving emails, and they migrate to another email service.
- Avamander 3y ago
  > Eventually, most people realize that their Outlook/Hotmail email service is defective because they're not receiving emails, and the move to something else. Or people realise that DO's current anti-abuse is very insufficient and will move to something else.
  - shaicoleman 3y ago
    Outlook/Hotmail is the only service that's blocking my emails. I've been with DigitalOcean for 10 years. Beforehand it was just a matter of filling a form and waiting 24 hours to get the IP whitelisted. A few years ago, Microsoft started refusing whitelisting IPs. DigitalOcean on the other hand started blocking SMTP by default for new customers since June/2022 [1], and thus significantly reduced the amount of spam coming out of their network. That said, they're still not doing enough to stop spam from their network, and they're still a source of spam [2]. I can cryptographically prove the identity of the server (and thus its reputation), and there's no justified reason to block mails based only on the network's IP address, while ignoring all the other factors. 1. https://www.digitalocean.com/blog/smtp-restricted-by-default https://www.digitalocean.com/blog/smtp-restricted-by-default 2. https://www.uceprotect.net/en/l3charts.php https://www.uceprotect.net/en/l3charts.php
    - progval 3y ago
      Ah, that explains why I stopped receiving so much spam from DigitalOcean last year. Thanks
    - literalAardvark 3y ago
beretguy 3y ago
What if I don’t have a blog?
huhtenberg 3y ago
We go through this every few months. Here's the recipe - 1. Visit https://olcsupport.office.com/ https://olcsupport.office.com/ and submit the complaint. 2. Wait for the auto-reply, followed by the "Nothing was detected" email. 3. Reply to the latter with "Escalate" in the body. Within a day, they hammer shit in place and the block is removed.
- wolverine876 3y ago
  Do they ever respond? Maybe the block comes and goes, and has nothing to do with attempts to contact Microsoft?
  - seszett 3y ago
    They responded to me when I asked to get unblocked: We have implemented mitigation for your IP (51.15.2.26) and this process may take 24 - 48 hours to replicate completely throughout our system.
    - huhtenberg 3y ago
      Yep, exactly. That's the follow-up we get for the "Escalate" request. The IP's different tho :)
  - jeltz 3y ago
    They have always responded to me when I have contacted them. I have had to contact them twice.
- RankingMember 3y ago
  Really love the modern support experience of no-response, trial-and-error, until suddenly, if you're lucky, the void on other end magically solves the problem. Confidence-inspiring stuff
  - kstrauser 3y ago
    It occurs to me that I make fun of sovereign citizen types, but in tech we have our own set of rituals for getting large organizations to do what we want. While those people are still boneheads, maybe I should be more empathetic about their motivations and why they think that this time it might work.
WarOnPrivacy 3y ago
>When I try to reply his message in my mail client, it received the following error message: > Delivery to xxx@outlook.com failed with error: outlook-com.olc.protection.outlook.com. said:... He got error messages? I get mail silently dropped. MS drops mail from my reputable mail servers - and from rep svs that send mail to MS accts I manage.
spoiledtechie 3y ago
GMail is the worst for email blocking resolutions. They don't have an effective feedback loop built into their system. So when a user does block you, no one is told about it, to be fixed. Therefore lowering your reputation with them over time. How can we as ESPs respond to them appropriately with removal of these people who don't want our emails anymore, if we don't know who the user is? If there are any GMAIL service team members here, I would LOVE to know why a feedback loop was never implemented like the other providers.
- inetknght 3y ago
  > How can we as ESPs respond to them appropriately with removal of these people who don't want our emails anymore, if we don't know who the user is? 1. Don't send spam 2. ??? 3. Profit! Literally _all_ email that I've blocked has been from companies where I uncheck the box "send spam to me" and the company sends it anyway, or where the company thinks "oh this guy bought stuff from us, we can now send our daily/weekly/fuckly marketing spam!" or "we got your email from whatever shady place, and now we're sending you our information because you're in our industry" or stupid shit like that. Gmail does not have a "block everything from this domain feature". I would love to block whole domains from my gmail account. Alas, I run my own email server to achieve it.
  - deleted 3y ago
    [deleted]
- uxp8u61q 3y ago
  Maybe ask yourself why some users end up blocking you altogether. Surely you didn't start sending them newsletters or the like without being completely certain that they wanted to receive them, and you provide a simple, prominent and reliable way to unsubscribe if/when they change their mind, right?
  - basilgohar 3y ago
    There's a block-by-default setup for new email servers. You have to go through the reputation-building process which is not at all clear nor is it always guaranteed to work. Yes, it "works" for most people, but it also has the effect of entrenching the incumbent large email providers and preventing more independent providers from cropping up. The current method is very lazy and collectively punishes a lot of innocent email providers for the crimes of the abusers.
StayTrue 3y ago
I had this problem for years. I would get the block lifted and it would return in short order. I surmise it’s because my mail server runs on a VPS and other users on my subnet are not well behaved (actually I know this for a fact). I solved the problem by paying for a next hop SMTPS server as an upstream smarthost for non-local mails. That means my mails come from a subnet that fronts TONS of other servers/domains. That makes it a bigger headache for MS to block. Sad but there you go. I do not use the external service for inbound. Inbound mails come direct to my server per the MX.
- jbotz 3y ago
  Who do you use for the upstream smarthost?
  - StayTrue 3y ago
    mailgun.com
- deltarholamda 3y ago
  I do the same thing, also with mailgun. It's generally much easier to deal with, especially if you have a fairly low volume of outgoing emails. Mailgun has been very good to me, highly recommended.
throwawaaarrgh 3y ago
> Maybe the fake contact information of my Microsoft Account make them worry that I am not a good guy.
ostensible 3y ago
Why not avoid fighting these windmills by using any of the existing commercial mail relays for sending — like SES or mailchimp?
- dclaw 3y ago
  We shouldn't have to. These companies are fucking ridiculous and blanket ban entire swaths of the internet from sending email.
  - azinman2 3y ago
    We also shouldn’t have to have so much spam, but alas people are crappy. So the common routes get targeted. Welcome to the modern internet.
  - ostensible 3y ago
    Do you have a better solution? You can complain on the forums about how unfair life is, how incompetent companies are, fight every provider to prove your reputation until cows come home,… Or you can pay someone to handle that for you. It’s a no-brainer. The whole discussion is moot. You pay your plumber to plumb, your builder to build, and email delivery company to deliver your emails. Trying to DYI everything is a waste of everyone’s time.
TwoNineFive 3y ago
I run my own mail servers and hotmail and other Microsoft-based email services regularly blocks my mail by source IP on the various domains I run. I've been using the same /29 network for over 15 years now. There's no nearby adjacent networks that are on any blacklists. I monitor blacklists on a regular basis. No marketing. The domains I run are strictly personal and projects. I monitor volume and all kinds of stuff. I know there's nothing like spam or any kind of marketing going outbound. It's astonishing how honest Microsoft is when I send them an email telling them to unblock. They literally just admit that they never had reason to block the domain/IP and they unlist it for a few years and then it goes back on their list. It's become apparent that they blacklist by default. Fortunately I only run into the occasional idiot who uses Hotmail or live.com.
charles_f 3y ago
Side note - the privacy consent is downright aggressive. If you want to remove your consent you have to unselect 100+ checkboxes for each of the partners, whereas accepting is a simple "accept all". I bypassed using reading mode, but darn...

196 points by unclet 3y ago

Wow, Outlook actually tells you they blocked you? My email (custom gmail domain btw) just ends up in the Spam folder of outlook clients with no notification at all.

jraph 3y ago
I self host. Over the years, I've had both situations with outlook. I've tried many things. As it happens, I noticed my mails have gone through just fine in the last months, at least to companies using Microsoft services without me doing anything specific, after I threw the towel with Outlook. I did switch VPS providers almost a year ago, though to a provider that I expect to be more filtered (ovh).
delusional 3y ago
That's a different issue. You're usually not notified of spam designations, but bounces (where the mail server completely refuses to accept your email) do usually receive a notification. If you're designated as both (for example if you keep sending email that bounces) you'll get blackholed and wont receive any bounce notification either.
- Sayrus 3y ago
  When I used to self-host my emails, GMail would "accept" mails then drop them. Microsoft was kind enough to tell me they dropped them but getting out of the blacklists was a pain.
- lucb1e 3y ago
  An advantage of landing in spam is that the user still has a choice and is in control. Rejecting outright is a "lalalala I can't hear youu!!" type of stupid situation that only big providers can get away with, without the users realizing their bigcorp is the one with delivery issues
  - uxp8u61q 3y ago
    As a user, I'm thankful I don't need to sift through hundreds of spam emails a day to find potential false positives. Because that's what you're advocating. You'd apparently like everyone to have a terrible email experience for the sake of your own personal comfort and preference (self hosting your emails). Besides, for something truly important, the people or organisations who need to reach me know how to do so other than via email (phone, chat, postal mail...).
    - Dalewyn 3y ago
      This. Microsoft, Google, et al. aren't doing anything worthy of criticism here; it's the spammers who ruin email for the rest of us who should be facing the music.
      - Avamander 3y ago
        Until it's not illegal it's only going to get worse.
        uxp8u61q 3y ago
        Spamming is illegal.
        Avamander 3y ago
        In a lot of jurisdictions it basically isn't. I'd love to see at least a few convictions though, where it is.
  - pm215 3y ago
    Conversely, if you as the sender get a bounce at least you know something went wrong and can try a different way to contact the other person (different email, telephone, text message...) Bouncing is the traditional approach, and the original ethos was "bounce, or defer, or deliver, but don't ever accidentally or deliberately just drop an email on the floor". It depends whether you think of "the user" as the sender or the re cover -- as a (human) sender I'd rather get a bounce than be silently ignored in a spam folder, but as a receiver I prefer the grey-area emails to be accept-but-spamfolder, not bounced...
BSDobelix 3y ago
Have you tested with: https://www.mail-tester.com/ https://www.mail-tester.com/
- TomK32 3y ago
  Thanks, I was missing a DKIM on my mailcow setup. 10/10 now :-)
  - BSDobelix 3y ago
    Excellent!! Have a nice day!
- Pathogen-David 3y ago
  Another useful tool is https://www.learndmarc.com/ https://www.learndmarc.com/ -- I found the presentation very helpful when I was finally getting on the DMARC train a while back.
  - BSDobelix 3y ago
    True, MECSA is also interesting: https://mecsa.jrc.ec.europa.eu/en/ https://mecsa.jrc.ec.europa.eu/en/
    - yonrg 3y ago
      They made me configure MTS
    - _ache_ 3y ago
      Whoa ! Very nice tool.
    - Pathogen-David 3y ago
      Ooh, thank you for sharing! This has given me a few things I should look into improving with my setup.

albertgoeswoof 3y ago

I run a small transactional email provider (https://mailpace.com https://mailpace.com), our IPs are very rarely added to blocklists- but we are very strict on what we allow through our service, and surprisingly we’ve had no long term delivery issues with any of the big providers. So thanks to the federated/decentralized design of email, is totally possible to be part of the network without any special privileges. We are sending millions of emails every day though, which is quite different to sending a couple hundred personal emails a week. If you’re running this on a cloud host, expect to be blocked by default. However if you can find a small vps provider you’ll have better luck on sending yourself.

TobyTheDog123 3y ago
(Unrelated to the OP - but I've been so frustrated by this for so long that it's worth the [flagged]) A product like this is exactly what I've been looking for with pretty great pricing. The one thing that this (and most providers) are missing is making email easy to test. I'm about to launch a product where email is critical, and there's no way to send an example email (with a non-test email address) to your service and see that you receive it, without it being sent to the To address. Better yet, the few providers that do support it charge as if it were a real email, when none of the delivery costs exist on their end (there are infrastructure costs, sure, but there is none of the reputation risk nor need for clean IPs, the reason people use transactional services like these in the first place).
yonrg 3y ago
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.com e.g. I still wonder though, why some big mail providers do not do dkim/dmarc? I happen to realize this when I started to fight spam and gave incoming mails without dkim/dmarc a high spam score.
- 3y ago

tschumacher 3y ago

Maybe the big webmail providers are relying more on machine learning for filtering spam instead of blocking IP ranges these days.

gumballindie 3y ago
That would be horribly unreliable. I hope they dont rely on machine learning for such critical infrastructure.
- mort96 3y ago
  Blocking IP ranges is also horribly unreliable. There is no good way to fight spam in a system like e-mail, just varying levels of terrible ways.

vouaobrasil 3y ago

Running a mail server should be something anyone can do. And while this is cool, there are so many other problems to do it. It's the price we pay of letting big tech companies control so much of the virtual infrastructure: big tech has commoditized the internet so much into a platform for consumerism that it becomes a valuable target for spam. In my opinion, the internet would be much better if none of the big players ever entered it, including Google, Facebook, Yahoo, etc, and it would allow for many more decentralized and valuable commons like email.

mort96 3y ago
The basic fact of the matter is that >99% of people will never be interested in hosting their own e-mail server, and that's okay. This means we need organizations to host e-mail for people. In a capitalist system, that means companies, and it leads to consolidation and monopolization. So far, governments have been seemingly uninterested in going after the large e-mail providers for anticompetitive practices; maybe that should change. But as long as those anticompetitive practices only really affect individual hobbyists who wanna host their own e-mail, while business interests are unaffected, I don't see this changing.
- vouaobrasil 3y ago
  I don't think it just affects hobbyists. It allows affects people who want to use smaller email servers, or even people who WOULD use smaller email servers simply because larger ones did not exist. I think the government SHOULD go after consolidation such as Google, and that traditional anti-trust law is insufficient to combat the dangers of large tech companies. This is precisely because traditional anti-trust laws only look after large PROPORTIONS. In today's modern economy, due to its size, we have a danger that we've never seen before: large ABSOLUTE size, which was never a problem in history as it is today. Therefore, we need new laws that go after absolute size, as well as large proportions (traditional anti-trust).
- yobbo 3y ago
  > In a capitalist system, that means companies, and it leads to consolidation and monopolization. No, a "capitalist system" does not lead to consolidation and monopolization.

V__ 3y ago

Is this mira of a U.S. centric problem? I selfhost my mail in Germany, have one at a smaller mail provider and never had problems. It is also not uncommon for companies to either have a local Exchange Server or use the mail service at their hosting provider. If everything is configured correctly, delivery works fine.

psd1 3y ago
Your experience may not be typical. I ran mail servers before office 365 was a thing, and I often had to get off block lists. There are stories on HN about it being worse, now that you have to request unblocking from MS and Google. Yours is the first comment that doesn't complain.
- layer8 3y ago
  Nah, I have the same experience as the GP, and in every HN thread about email self-hosting, there are a number of comments along the lines of “I’ve been self-hosting my email for 10-20 years and never had any problems”. My SME employer also self-hosts without issues. Experiences obviously differ, but it’s unclear where the differences stem from, apart from long-term IP reputation.
- vel0city 3y ago
  > Yours is the first comment that doesn't complain. It is potentially more of those with problems are more likely to speak up than everyone else just posting "works fine for me" a thousand times over. I haven't had much deliverability problems with self-hosted things. I set it up right, and I get the emails I expected to get. So there's now two of us saying "works fine for me."
justsomehnguy 3y ago
Personal anecdote != universal, global experience. > have one at a smaller mail provider a) [hosted] Mail provider b) Server (colo/dedicated/VPS/whatever) provider Choose one. > not uncommon for companies to either have a local Exchange Server Yes and it's PITA to pull it out of the lists of some shitheads, like SpamHaus. Source: guess it

freetanga 3y ago

I think that governments should offer one free email account per citizen for life. Which you could use or not, but is there for you as a digital inbox… which are the options? - Self hosting is a bit elitist - not for the masses. - A paid-for option (proton, tutta,…) would be cataloged as elitist. People perceive email as free. - A free option provided by a Corporate player will gravitate towards monopolies and lack of privacy. - A free for life government issued, easy to recover digital point of contact where all your government interactions are pointed towards would be a great step. You could still have a separate one if you don’t trust big brother, but at least your “recovery” address would be secure for life.

benbristow 3y ago
Ah yes, a government owned email service, what could go wrong?
- lotsofpulp 3y ago
  Nothing? It can exist as a utility alongside other email services.
  - iAMkenough 3y ago
    Nothing can go wrong? In that case, the government should create a public social network as a utility alongside other social media services too.
    - lotsofpulp 3y ago
      Sure, although I think the utility of a communications network capable of receiving and sending documents within a country is very well proven to be a benefit to society, so any comparison to something less battle tested seems unnecessary. It makes no sense that in the physical world, we entrust government with identity verification and transmitting correspondence, but that trust is somehow lost in the digital world.

sheikheddy 3y ago

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

currysausage 3y ago
The most pressing question: why does Outlook.com just silently discard some emails?
- Avamander 3y ago
  Not the person you replied to, but as far as I've heard it's done with SmartScreen matches.
  - sheikheddy 3y ago
    This is correct but not the only reason it could be happening.
    - currysausage 3y ago
      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).
      - Avamander 3y ago
        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.
        currysausage 3y ago
        This was not the cause in my case (no attachments, no URLs, just plain text, as far as I can remember). I know how to send email (ask mail-tester.com). Regardless, there are always better options than silently discarding the whole email: delete attachments, erase everything that looks like a URL, even erase the whole message body, but please tell the recipient that you accepted an email and from whom.

issafram 3y ago

TL;DR emailed Microsoft a few times

brunnock 3y ago

I ran into this issue several years ago. After complaining, MS allowed me to send email to MS properties (hotmail, live.com), but continued to block my email to their Office 365 clients. I now use AWS SES to handle mail delivery. It's free for up to 200 daily messages which is fine for me.

Dunedan 3y ago

After many years of regularly getting blocked by Hotmail and outlook.com, I just decided to reject every incoming email from Hotmail and Outlook with an error message explaining the situation. If they don't allow me to respond to emails sent by their customers, why would I allow them to send me emails in the first place?

Avamander 3y ago
You sure showed it to them. /s Did you sign up to their JMRP to figure out what they didn't like or how were they blocking you?
unclet 3y ago
If all indie mail servers blocked by Hotmail block mail from the blocker, it will make the big player review their blocking policy.

shaicoleman 3y ago

Outlook/Hotmail blocks DigitalOcean. After half a dozens attempts over the years to delist my IP, and following all the best practices (dedicated fixed IP, SPF, DKIM, DMARC, FCrDNS, zero spam, TLS, etc.) I gave up. Eventually, most people realize that their Outlook/Hotmail email service is defective because they're not receiving emails, and they migrate to another email service.

Avamander 3y ago
> Eventually, most people realize that their Outlook/Hotmail email service is defective because they're not receiving emails, and the move to something else. Or people realise that DO's current anti-abuse is very insufficient and will move to something else.
- shaicoleman 3y ago
  Outlook/Hotmail is the only service that's blocking my emails. I've been with DigitalOcean for 10 years. Beforehand it was just a matter of filling a form and waiting 24 hours to get the IP whitelisted. A few years ago, Microsoft started refusing whitelisting IPs. DigitalOcean on the other hand started blocking SMTP by default for new customers since June/2022 [1], and thus significantly reduced the amount of spam coming out of their network. That said, they're still not doing enough to stop spam from their network, and they're still a source of spam [2]. I can cryptographically prove the identity of the server (and thus its reputation), and there's no justified reason to block mails based only on the network's IP address, while ignoring all the other factors. 1. https://www.digitalocean.com/blog/smtp-restricted-by-default https://www.digitalocean.com/blog/smtp-restricted-by-default 2. https://www.uceprotect.net/en/l3charts.php https://www.uceprotect.net/en/l3charts.php
  - progval 3y ago
    Ah, that explains why I stopped receiving so much spam from DigitalOcean last year. Thanks
  - literalAardvark 3y ago

beretguy 3y ago

What if I don’t have a blog?

huhtenberg 3y ago

We go through this every few months. Here's the recipe - 1. Visit https://olcsupport.office.com/ https://olcsupport.office.com/ and submit the complaint. 2. Wait for the auto-reply, followed by the "Nothing was detected" email. 3. Reply to the latter with "Escalate" in the body. Within a day, they hammer shit in place and the block is removed.

wolverine876 3y ago
Do they ever respond? Maybe the block comes and goes, and has nothing to do with attempts to contact Microsoft?
- seszett 3y ago
  They responded to me when I asked to get unblocked: We have implemented mitigation for your IP (51.15.2.26) and this process may take 24 - 48 hours to replicate completely throughout our system.
  - huhtenberg 3y ago
    Yep, exactly. That's the follow-up we get for the "Escalate" request. The IP's different tho :)
- jeltz 3y ago
  They have always responded to me when I have contacted them. I have had to contact them twice.
RankingMember 3y ago
Really love the modern support experience of no-response, trial-and-error, until suddenly, if you're lucky, the void on other end magically solves the problem. Confidence-inspiring stuff
- kstrauser 3y ago
  It occurs to me that I make fun of sovereign citizen types, but in tech we have our own set of rituals for getting large organizations to do what we want. While those people are still boneheads, maybe I should be more empathetic about their motivations and why they think that this time it might work.

WarOnPrivacy 3y ago

>When I try to reply his message in my mail client, it received the following error message: > Delivery to xxx@outlook.com failed with error: outlook-com.olc.protection.outlook.com. said:... He got error messages? I get mail silently dropped. MS drops mail from my reputable mail servers - and from rep svs that send mail to MS accts I manage.

spoiledtechie 3y ago

GMail is the worst for email blocking resolutions. They don't have an effective feedback loop built into their system. So when a user does block you, no one is told about it, to be fixed. Therefore lowering your reputation with them over time. How can we as ESPs respond to them appropriately with removal of these people who don't want our emails anymore, if we don't know who the user is? If there are any GMAIL service team members here, I would LOVE to know why a feedback loop was never implemented like the other providers.

inetknght 3y ago
> How can we as ESPs respond to them appropriately with removal of these people who don't want our emails anymore, if we don't know who the user is? 1. Don't send spam 2. ??? 3. Profit! Literally _all_ email that I've blocked has been from companies where I uncheck the box "send spam to me" and the company sends it anyway, or where the company thinks "oh this guy bought stuff from us, we can now send our daily/weekly/fuckly marketing spam!" or "we got your email from whatever shady place, and now we're sending you our information because you're in our industry" or stupid shit like that. Gmail does not have a "block everything from this domain feature". I would love to block whole domains from my gmail account. Alas, I run my own email server to achieve it.
- deleted 3y ago
  [deleted]
uxp8u61q 3y ago
Maybe ask yourself why some users end up blocking you altogether. Surely you didn't start sending them newsletters or the like without being completely certain that they wanted to receive them, and you provide a simple, prominent and reliable way to unsubscribe if/when they change their mind, right?
- basilgohar 3y ago
  There's a block-by-default setup for new email servers. You have to go through the reputation-building process which is not at all clear nor is it always guaranteed to work. Yes, it "works" for most people, but it also has the effect of entrenching the incumbent large email providers and preventing more independent providers from cropping up. The current method is very lazy and collectively punishes a lot of innocent email providers for the crimes of the abusers.

StayTrue 3y ago

I had this problem for years. I would get the block lifted and it would return in short order. I surmise it’s because my mail server runs on a VPS and other users on my subnet are not well behaved (actually I know this for a fact). I solved the problem by paying for a next hop SMTPS server as an upstream smarthost for non-local mails. That means my mails come from a subnet that fronts TONS of other servers/domains. That makes it a bigger headache for MS to block. Sad but there you go. I do not use the external service for inbound. Inbound mails come direct to my server per the MX.

jbotz 3y ago
Who do you use for the upstream smarthost?
- StayTrue 3y ago
  mailgun.com
deltarholamda 3y ago
I do the same thing, also with mailgun. It's generally much easier to deal with, especially if you have a fairly low volume of outgoing emails. Mailgun has been very good to me, highly recommended.

throwawaaarrgh 3y ago

> Maybe the fake contact information of my Microsoft Account make them worry that I am not a good guy.

ostensible 3y ago

Why not avoid fighting these windmills by using any of the existing commercial mail relays for sending — like SES or mailchimp?

dclaw 3y ago
We shouldn't have to. These companies are fucking ridiculous and blanket ban entire swaths of the internet from sending email.
- azinman2 3y ago
  We also shouldn’t have to have so much spam, but alas people are crappy. So the common routes get targeted. Welcome to the modern internet.
- ostensible 3y ago
  Do you have a better solution? You can complain on the forums about how unfair life is, how incompetent companies are, fight every provider to prove your reputation until cows come home,… Or you can pay someone to handle that for you. It’s a no-brainer. The whole discussion is moot. You pay your plumber to plumb, your builder to build, and email delivery company to deliver your emails. Trying to DYI everything is a waste of everyone’s time.

TwoNineFive 3y ago

I run my own mail servers and hotmail and other Microsoft-based email services regularly blocks my mail by source IP on the various domains I run. I've been using the same /29 network for over 15 years now. There's no nearby adjacent networks that are on any blacklists. I monitor blacklists on a regular basis. No marketing. The domains I run are strictly personal and projects. I monitor volume and all kinds of stuff. I know there's nothing like spam or any kind of marketing going outbound. It's astonishing how honest Microsoft is when I send them an email telling them to unblock. They literally just admit that they never had reason to block the domain/IP and they unlist it for a few years and then it goes back on their list. It's become apparent that they blacklist by default. Fortunately I only run into the occasional idiot who uses Hotmail or live.com.

charles_f 3y ago

Side note - the privacy consent is downright aggressive. If you want to remove your consent you have to unselect 100+ checkboxes for each of the partners, whereas accepting is a simple "accept all". I bypassed using reading mode, but darn...