7 ms·

Emails to Outlook.com rejected due to a fault or overzealous blocking rules

190 points by Bender 8mo ago

TonyTrapp 8mo ago
I've had this exact problem for years. My IP addresses have been used for 15+ years for sending e-mail, they are spam-free, but Microsoft keeps blocking them. Every two months or so I have to ask them to unblock the IP again, then I can send mails to Outlook again, until they just random decide to block me again. It's an absolute clown show.
- lucasfin000 8mo ago
  This is the price every small sender pays. The unblock request process is essentially designed to make you give up or move to a large ESP. There's no appeals process, no SLA, no acknowledgment that your reputation data might just be wrong. You're at the mercy of a system that treats false positives as acceptable damage.
Alifatisk 8mo ago
I created my first Outlook account when I was young. Now, 30 years later and its still my primary account. I can't imagine how I would migrate to another email address if Microslop would begin ruining Outlook by forced subscription or something. My digital life is in M$ hands at the moment.
- eviks 8mo ago
  You could start the process now, before the ruin?
- butILoveLife 8mo ago
  I learned this lesson the hard way with OneDrive. Now I only use Windows for legacy software that my customers force on me. Fedora has not just been liberating, but jaw dropping. I actually felt offended that I had wasted so much time on debian-family/ubuntu/mint and windows.
  - BLKNSLVR 8mo ago
    OneDrive was born enshittified. The concept, way back when, was great. I tried to use it, by a previous name, for replicating / distributing data backups and it always worked great... for a few days, maybe weeks. And then something unrecoverable went wrong, and I had to re-set it up essentially from scratch and it worked great... for a few days, maybe weeks. And then something unrecoverable went wrong. In the intervening 15+ years, OneDrive has never made my experience of computing better. It has only ever nagged, slowed, and failed. And that was before Microslop went down the x% AI coding path.
    - pluralmonad 8mo ago
      I personally like when you open any office doc, do nothing to it before closing and you get the scary warning asking if you want to save your document (to onedrive) implying all is lost if you select no. I am sure millions of tech unsavvy people have been conned into sending their data to Bill Gates.
- nicbou 8mo ago
  I would start migrating to an email domain that you control. It will come useful at one point or another.
  - josephg 8mo ago
    Yep this. I migrated from Gmail to my own domain years ago. It was painful. Weirdly enough, I think the longest holdouts were my parents, who were still sending email to my Gmail account a decade after I stopped using the address. I moved my email to Fastmail, and I’ve been very happy ever since. But now that I own the domain, moving to a different provider - if I ever need to - would be trivial.
    - ohyoutravel 8mo ago
      I moved to Fastmail, set it up with Gmail so I received forwarded emails. Years later there’s still a long tail of senders using my Gmail, but I get the emails forwarded, and only actually log in to Gmail every six months or so.
- jraph 8mo ago
  Act now. - create a new email address somewhere else, preferably with your own domain - redirect all your emails to your new account - send an auto reply: "I don't use this email address anymore, and I may not see this email. My new address is XXX" The third point is a lie that nudges people into updating their addressnook a lot faster. If you just silently redirect they might not even notice. But you can explain in a sentence why you are doing this. This redirect+auto reply can be left in place forever.
  - Bender 8mo ago
    Adding that ideally one would only auto-replay to people in their address book at the time so one is not replying to spammers.
- consumer451 8mo ago
  > I can't imagine how I would migrate to another email address Imapsync is your best friend for this, as far as syncing the new account with the old one. https://github.com/imapsync/imapsync https://github.com/imapsync/imapsync https://imapsync.lamiral.info/ https://imapsync.lamiral.info/
wccrawford 8mo ago
It feels like there's quite a lot of spin on this. There's no hint as to how many users were actually affected. It only really seems to mention Estonia, and probably only a region of it. The ISP there claims they haven't received any reports of SPAM. But that sounds wrong. No reports probably means your reporting system is broken. So putting that together, it seems like a small ISP screwed up and let spammers go wild, and Outlook blocked them for it. I can't really fault Outlook for that.
- shevy-java 8mo ago
  > There's no hint as to how many users were actually affected. How many users would you see as the threshold then? Since you stated that there is a spin to this, how many users would go over your defined threshold level?
- cromulent 8mo ago
  The article has hyperlinks in it, e.g. to this: https://learn.microsoft.com/en-us/answers/questions/5786144/all-sending-ips-temporarily-rate-limited-(451-4-7 https://learn.microsoft.com/en-us/answers/questions/5786144/... which comes from an ESP serving millions of users.
- thedanbob 8mo ago
  My org (USA) was affected. I wasn't the primary person dealing with it, but from what I gather one user marked one of our emails as junk, and then suddenly all of our emails to Outlook users started getting blocked.
- jeroenhd 8mo ago
  Someone recently leveraged some kind of automated spam attack against my domain using Zendesk's email servers. For some reason, Zendesk doesn't enforce SPF and DKIM checks when opening new tickets, so I got flooded with "your new account has been registered" and "thank you for filing a ticket" emails. I blocked off Zendesk entirely because they didn't fix their shitty email system. The other newsletter mail services (mailgun/sendgrid/etc.) are just as bad for this. There are plenty of reasons why large email senders could (and should) be on reputation blacklists. None of these email delivery companies seem to care very much about the spam they send until shit hits the fan, and now that it did it seems everyone blames the people maintaining the blacklists.
gzread 8mo ago
Everyone who runs an email server knows Microslop doesn't care about receiving its customer's emails. The best thing you can do is migrate away.
- miohtama 8mo ago
  No worries. If you migrate your email server to Azure(TM) the delivery is guaranteed.
- kijin 8mo ago
  Keep a few throwaway Hotmail/Outlook addresses in your password manager, in case you need to use a Windows PC that demands a Microslop account. That's about the end of their usefulness. Just like Internet Explorer used to be the program you used once -- and only once -- to download a proper browser.
mono442 8mo ago
It's has been like this for a long time. For me hotmail is unusable because some emails just never arrive due to their spam filtering.
shevy-java 8mo ago
[flagged]
- JasonADrury 8mo ago
  Why do you feel the need to pollute HN with terrible slashdot jokes?
- mrweasel 8mo ago
  To be fair, Outlook.com has always been a bit shitty, if you're trying to deliver email to them. Last time it was reasonably good the service was still called Hotmail. The problem is that we've allowed email to be centralized around a few massive providers, who do not care about customer service. If you're large enough, you probably have a contact at Microsoft for Outlook. Everyone else has to yell into the void and sometimes that works.
  - vladvasiliu 8mo ago
    > If you're large enough, you probably have a contact at Microsoft for Outlook. For certain very large values of "large". I work for a company which has several thousand Office365 accounts with MS, many of which are the expensive one. It's nigh impossible to get support from them, you're always supposed to go through some partner, who has no idea what they're talking about. And when you do get someone through MS, it's actually still some kind of useless 3rd party who'll ask you to turn your VM off and on again when you complain that it won't turn off (this is actually a true story we had happen on azure). In the end, after about an hour on the phone, the dude gave up and called for help higher up. It took something like a week to have a freaking VM unstuck and destroyed on Azure. Contrast this with AWS, where we were spending much less at the time, only had the basic free support, and I was with someone on the phone in under five minutes who helped us have our direct connect issue solved in 15 minutes.
dismalpedigree 8mo ago
I’m guessing they connected CoPilot to the inbound filter and it is doing stupid and unexpected things.
mmsc 8mo ago
I wonder if Microsoft actually likes running their free email service still. They wiped a ton of old Hotmail and Live.com emails some years ago (and then allowed new people to register those deleted names). I imagine they don't get much out of it anymore.
- ohyoutravel 8mo ago
  They wiped all the emails from my 25 year old Hotmail account. Pretty weak. I refuse to use Microsoft products except if forced, and do my best to evangelize this position.
  - expedition32 8mo ago
    Most people will never pay for email service. Which leaves you Google, MS or god forbid your own ISP.
- simonw 8mo ago
  I wonder how many accounts on other services were then hijacked using "forgot my password" attacks. UPDATE: After a bit of digging it looks like they started the username recycling policy in 2013, may have quietly stopped doing that in 2018 but formalized no longer doing that in 2021: https://web.archive.org/web/20230627104616/https://www.microsoft.com/en-us/servicesagreement/Updates https://web.archive.org/web/20230627104616/https://www.micro... "Summary of changes to the Microsoft Services Agreement – June 15, 2021 [...] In the Outlook and Office Services sections, we’ve removed the Outlook.com section to clarify that an email address or username is not recycled into our system or assigned to another user."
  - deltoidmaximus 8mo ago
    It's wild to me they ever started doing this in the first place. And in 2013 no less, it isn't like the hijacking risk was some far off concept at that point.
- mrweasel 8mo ago
  It's certainly not free to run and maybe it doesn't really make sense for Microsoft to run Outlook.com anymore, except that it's an easy way to motivate people to having a Microsoft account. Outlook.com certainly has to show up as an expense, one that Microsoft would like to reduce. When you look at what other providers charge for a single email account, it's hard to see Microsoft making money of Outlook.com. There's obviously something to be said for scale, but still, it must cost them something.
arend321 8mo ago
I'm in the privileged position to advise clients to move away from hotmail/live if they want uninterrupted email delivery.
BLKNSLVR 8mo ago
"whatever Microslop is doing" Indirect reference to this recent thread: https://news.ycombinator.com/item?id=47230704 https://news.ycombinator.com/item?id=47230704
joshstrange 8mo ago
Just had a friend reach out yesterday about this issue. His outlook account for 10+ years started having issues receiving emails from his dad and a company he works with. All I could find was that his dad’s email was missing SPF/DMARC but the other email address that was having problems looked like it was configured correctly. I only was able to get a screenshot of the email voice his dad received and it mentioned being on a block list (like in the article).
boesboes 8mo ago
I've stopped diagnosing outlook/hotmail/live delivery issues about 12 years go, they simply do not give a single fuck about their customers. It used to be different, about 18 years ago orso, they had ways to contact them and resolve such issue. fuck big tech :)
Ensorceled 8mo ago
My clients have been experiencing this forever; the logs SAY "temporarily rate limited due to IP reputation." but really the emails are never going to get delivered. I have to get MailChimp or Mailgun to rotate the IPs. It looks like all it takes is one person to mark your email as spam, even by accident. Note that these are mailing lists which they signed up for in MailChimp case OR transactional emails in the Mailgun case. It's only hotmail/outlook that we constantly have this issue with, Google etc. are all fine.
- scandox 8mo ago
  Often these "spam" reports by end users are just accidental clicks as well. Many of the abuse reports we get are like an email from someone's Mum and visibly legitimate. At other times there are users who use the Report Spam function as a kind of inbox management tool - a way of moving mail away so they don't have to see it because Trash or Delete or whatever is just further away from their pointer.
  - pluralmonad 8mo ago
    I tell my friends and family to never click unsubscribe links, unless they had proactively subscribed. Buying something from a company that requires an email does not count. unsolicited marketing emails are spam and should be treated as such. Double so if that company sends marketing emails disguised behind support@company.com.
    - iamacyborg 8mo ago
      > Double so if that company sends marketing emails disguised behind support@company.com That’s typically not a disguise but a clear means of indicating that you can reply to the email
      - pluralmonad 8mo ago
        No, sending marketing from support emails is almost certainly trying to game spam filters. Marketing@company.com would work for the allow replies purpose.
Markoff 8mo ago
As long term Outlook.com user all I can say it's their service is extremely unreliable, my emails are either not delivered at all or end up in junk mail, some emails I don't receive at all or my partners are rate limited sometimes receiving their emails with hours long delays. I assume also their junk filters block some emails and there is no way to avoid it, you repeatedly add senders to safe senders list, even to safe subscriptions and their email still end up marked as junk even after years long communication from same addresses. As backup when something important I write email to recipient from gmail whether they received my email from outlook only to find out my email was never received.
CrzyLngPwd 8mo ago
It's not just Outlook, it's all MS email products as well as Yahoo. These are emails that our customers have specifically requested and we get support tickets blaming us. It's been like this for years.
gus_massa 8mo ago
A few years ago, in my university we have a big problem at the beginning of the semester to contact ~10K students, in particular when they register to our Moodle platform and the server sends them a message. Gmail was usually ok. Yahoo had some max messages per day. But Hotmail/Live/Outlook/whatever just made the messages disappear, no spam folder, no bounce, just disappear. We had some success telling the students to send us a message from their Hotmail/Live/Outlook/whatever address half an hour before registration. This adds our address to some special secret list for that account, and our later messages (usually) reach them. (It may fail. It may fail. IWOMM. YMMV.)
iamcalledrob 8mo ago
I was unable to reach a business this week who host their email on Office 365. Any email I sent would bounce with: 550 5.7.520 Message blocked because it contains content identified as spam. AS(4810)' For context, I was replying to an existing and very mundane email thread. Something is rotten in the state of Outlook
- spogbiper 8mo ago
  outlook.com and Office 365 are very different beasts. with the latter problems are more often something (mis)configured by the customer/administrator of the 365 account rather than microsoft themselves, and there are steps the customer can take to work around the issue. With outlook.com there is nothing the recipient can do.
rbc 8mo ago
This is one of those articles that demonstrates why email should be distributed. Letting Google and Microsoft run email for the planet is just asking for problems. There are some technical demands to running email services, but they are still in reach of the technically inclined individual or organization. If for no other reason, it would help keep the big mail service providers honest.
cute_boi 8mo ago
microslop should start focusing on real world problem than overhyped ai bubble.
deleted 8mo ago
[deleted]
zelphirkalt 8mo ago
It is my experience, that Outlook is not a reliable e-mail service. Sometimes e-mails are not delivered, or only delivered hours later. When they are delivered, even as a paying customer, they are downloaded so slowly, that I had to wait 10 minutes to get all my e-mails, while my 1 EUR per month Posteo provider delivers in seconds. My impression is, that the only reason one would want to have MS as a mail provider is, that they are entrenched in the e-mail provider reputation and delivery game. Other than that, it seems to be an all around bad service. Not even talking about the mail client itself.
- SoftTalker 8mo ago
  The big reason is enterprises buy into O365 and running their email through Outlook instead of on-prem or at another provider is part of that. For the same reason they use Teams over Zoom or Slack or other alternatives.
  - azalemeth 8mo ago
    Exactly. Nobody chooses MS for quality, and those who do choose it are never those who suffer the most for its own decisions.
    - wolvoleo 8mo ago
      Yup. It's really the cheapest not the best. And Microsoft sell directly to our C suite who have white glove IT support that do everything for them so they never see any issues. The old saying of "Microsoft is better at talking to your boss than you are" is certainly true though. Unfortunately.
lousken 8mo ago
I was using outlook for communicating with businesses as it is often what they use. Some of them just could not send a response back to me, so I am not using outlook anymore. Just normal Microslop stuff
bradleyy 8mo ago
Having to explain to customers that they didn't receive an email because Outlook has a multi-stage set of email servers and the inside ones reject due to the edge (antispam) servers is always interesting.
ycombinatornews 8mo ago
Very happy I decided to ditch outlook (and did it) this year after 10+ years. Every other year some part of the system would break, deliverability, authentication or 2FA. More ads, less value. Eh. Another product driven into ground by Microslop
whalesalad 8mo ago
Days since last Microsoft fuckup: 0 (hard-coded)
- tredre3 8mo ago
  BTW your domain is missing SPF and DMARC records.
  - whalesalad 8mo ago
    I got 99 problems but mail delivery ain’t one
crimsonnoodle58 8mo ago
We experienced this exact error this week. Only affected outlook.com users, and not 365 users. Had to supply MS support with proof of ownership of the IP. The whole process took about a week to resolve.
VladVladikoff 8mo ago
This has plagued us for years. We send quite a lot of transactional email (about 150k emails per day), and there have been several times where Microsoft blocked our server. Usually it is because Microsoft has banned an entire netblock, that our server just happens to be sitting in. I have seen them do this to IPs fro Hetzner, Linode, Amazon AWS (SES), etc. And yeah we've signed up for their junk mail reporting service, and we have all our DNS records dialed in perfectly. I even went as far as signing up for Azure, in the hopes that if I sent from a Microsoft IP it might not get blocked. But I didn't make it very far, every step of the way was like watching paint dry while the interface loaded or did something. Once I finally got the thing set up in order to send mail, the API was so molasses slow that it couldn't handle our mail throughput. Meaning it would take about 30 seconds to send each transactional email because of how slow their API is. Well that's only 2880 emails per day, that is not a reasonable send rate at all. I have even lost customers over this mess, it's really hard to explain to them that they can't receive our email because of their provider and not us. Especially when Microsoft has the audacity to return: 250 OK Email Queued (but then not deliver it anyway!) If anyone has any solutions to this mess I am all ears!
- tokyobreakfast 8mo ago
  It's almost certainly because your customers are reporting your emails as spam by moving it into the junk folder which is training their systems. Once enough of your customers do this to cross a certain threshold, you are identified as an undesirable sender and QED.
  - dijit 8mo ago
    It happens at scale. There's like a middle scale where you're not big enough that Microsoft will go out of their way to whitelist you, but you're big enough that your "send to junk" rate is just high in terms of absolute numbers. It's certainly not a ratio, it must be based on absolute numbers because I've seen it too many times across too many companies, and the only ones that get away with it are extremely low volume. Once you have 1,000,000 mails, even a 0.1% mark as spam rate is 1,000 emails. - and some people treat mark as spam as their delete button, certainly more than 0.1% of people. Don't ask me why. EDIT: on inspection; it's worth noting the mechanism is even more insidious than "people mark you as spam". Microsoft also weighs delete-without-opening as a negative signal. So if you're sending transactional mail (receipts, shipping notifications, invoices) and your users get exactly what they wanted, feel satisfied, and bin it without opening. You've just taken a reputation hit for doing your job correctly. The senders most at risk aren't the ones sending rubbish. EDIT2; theres a reply to me that I can’t reply to because its [dead]; though the point is valid so I vouched. To them I say: I agree. But you probably want your receipt, and thats the example I gave (for a reason).
throwaway613746 8mo ago
My company has been massively affected by this over the past month. It sucks having to tell customers "this is on Microsoft's end, we're trying to work through it with them but we don't have an ETA and can't say more than that" because Microsoft support is absolutely useless. The other day we changed some DMARC/SPF records around and that seemed to do the trick but now it appears to just be a coincidence.
msxanadu 8mo ago
A question related to the outlook.com false spam mail problem... Why are incoming emails to outlook.com so large? 15KB minimum for a text email with just a title. Equivalent Gmail to/from Apple Mail is just a couple of KB.
elcritch 8mo ago
For these large services it seems that small companies should be allowed to sue them. Otherwise there’s no incentive for the big providers to care. Similarly for anti-virus. It’s a PITA when Windows or Mac falsely flag a program as a virus when it’s not in their app stores.
- dqv 8mo ago
  Yes, at least in the US, being a litigious freak gets results. Weird trick to get unblocked: follow the standard three-email procedure to sender support, then send a fourth email ccing buscond@microsoft.com telling them to unblock or next step is attorney general. The thing about a lot of attorney generals is they LOVE to smack down a big corporation like Microsoft for the little guy.
LorenPechtel 8mo ago
I'm thinking perhaps they turned on some idiot AI. And they don't want to back down and admit they did it wrong.
aclindsa 8mo ago
Funny, my email server started being blocked on Feb. 23. I assumed it was just me, but maybe they block a bunch of people all at once?
g8oz 8mo ago
Not surprised. Confirmation emails from numerous services have been been unable to get through for me.

190 points by Bender 8mo ago

I've had this exact problem for years. My IP addresses have been used for 15+ years for sending e-mail, they are spam-free, but Microsoft keeps blocking them. Every two months or so I have to ask them to unblock the IP again, then I can send mails to Outlook again, until they just random decide to block me again. It's an absolute clown show.

lucasfin000 8mo ago
This is the price every small sender pays. The unblock request process is essentially designed to make you give up or move to a large ESP. There's no appeals process, no SLA, no acknowledgment that your reputation data might just be wrong. You're at the mercy of a system that treats false positives as acceptable damage.

Alifatisk 8mo ago

I created my first Outlook account when I was young. Now, 30 years later and its still my primary account. I can't imagine how I would migrate to another email address if Microslop would begin ruining Outlook by forced subscription or something. My digital life is in M$ hands at the moment.

eviks 8mo ago
You could start the process now, before the ruin?
butILoveLife 8mo ago
I learned this lesson the hard way with OneDrive. Now I only use Windows for legacy software that my customers force on me. Fedora has not just been liberating, but jaw dropping. I actually felt offended that I had wasted so much time on debian-family/ubuntu/mint and windows.
- BLKNSLVR 8mo ago
  OneDrive was born enshittified. The concept, way back when, was great. I tried to use it, by a previous name, for replicating / distributing data backups and it always worked great... for a few days, maybe weeks. And then something unrecoverable went wrong, and I had to re-set it up essentially from scratch and it worked great... for a few days, maybe weeks. And then something unrecoverable went wrong. In the intervening 15+ years, OneDrive has never made my experience of computing better. It has only ever nagged, slowed, and failed. And that was before Microslop went down the x% AI coding path.
  - pluralmonad 8mo ago
    I personally like when you open any office doc, do nothing to it before closing and you get the scary warning asking if you want to save your document (to onedrive) implying all is lost if you select no. I am sure millions of tech unsavvy people have been conned into sending their data to Bill Gates.
nicbou 8mo ago
I would start migrating to an email domain that you control. It will come useful at one point or another.
- josephg 8mo ago
  Yep this. I migrated from Gmail to my own domain years ago. It was painful. Weirdly enough, I think the longest holdouts were my parents, who were still sending email to my Gmail account a decade after I stopped using the address. I moved my email to Fastmail, and I’ve been very happy ever since. But now that I own the domain, moving to a different provider - if I ever need to - would be trivial.
  - ohyoutravel 8mo ago
    I moved to Fastmail, set it up with Gmail so I received forwarded emails. Years later there’s still a long tail of senders using my Gmail, but I get the emails forwarded, and only actually log in to Gmail every six months or so.
jraph 8mo ago
Act now. - create a new email address somewhere else, preferably with your own domain - redirect all your emails to your new account - send an auto reply: "I don't use this email address anymore, and I may not see this email. My new address is XXX" The third point is a lie that nudges people into updating their addressnook a lot faster. If you just silently redirect they might not even notice. But you can explain in a sentence why you are doing this. This redirect+auto reply can be left in place forever.
- Bender 8mo ago
  Adding that ideally one would only auto-replay to people in their address book at the time so one is not replying to spammers.
consumer451 8mo ago
> I can't imagine how I would migrate to another email address Imapsync is your best friend for this, as far as syncing the new account with the old one. https://github.com/imapsync/imapsync https://github.com/imapsync/imapsync https://imapsync.lamiral.info/ https://imapsync.lamiral.info/

wccrawford 8mo ago

It feels like there's quite a lot of spin on this. There's no hint as to how many users were actually affected. It only really seems to mention Estonia, and probably only a region of it. The ISP there claims they haven't received any reports of SPAM. But that sounds wrong. No reports probably means your reporting system is broken. So putting that together, it seems like a small ISP screwed up and let spammers go wild, and Outlook blocked them for it. I can't really fault Outlook for that.

shevy-java 8mo ago
> There's no hint as to how many users were actually affected. How many users would you see as the threshold then? Since you stated that there is a spin to this, how many users would go over your defined threshold level?
cromulent 8mo ago
The article has hyperlinks in it, e.g. to this: https://learn.microsoft.com/en-us/answers/questions/5786144/all-sending-ips-temporarily-rate-limited-(451-4-7 https://learn.microsoft.com/en-us/answers/questions/5786144/... which comes from an ESP serving millions of users.
thedanbob 8mo ago
My org (USA) was affected. I wasn't the primary person dealing with it, but from what I gather one user marked one of our emails as junk, and then suddenly all of our emails to Outlook users started getting blocked.
jeroenhd 8mo ago
Someone recently leveraged some kind of automated spam attack against my domain using Zendesk's email servers. For some reason, Zendesk doesn't enforce SPF and DKIM checks when opening new tickets, so I got flooded with "your new account has been registered" and "thank you for filing a ticket" emails. I blocked off Zendesk entirely because they didn't fix their shitty email system. The other newsletter mail services (mailgun/sendgrid/etc.) are just as bad for this. There are plenty of reasons why large email senders could (and should) be on reputation blacklists. None of these email delivery companies seem to care very much about the spam they send until shit hits the fan, and now that it did it seems everyone blames the people maintaining the blacklists.

gzread 8mo ago

Everyone who runs an email server knows Microslop doesn't care about receiving its customer's emails. The best thing you can do is migrate away.

miohtama 8mo ago
No worries. If you migrate your email server to Azure(TM) the delivery is guaranteed.
kijin 8mo ago
Keep a few throwaway Hotmail/Outlook addresses in your password manager, in case you need to use a Windows PC that demands a Microslop account. That's about the end of their usefulness. Just like Internet Explorer used to be the program you used once -- and only once -- to download a proper browser.

mono442 8mo ago

It's has been like this for a long time. For me hotmail is unusable because some emails just never arrive due to their spam filtering.

shevy-java 8mo ago

[flagged]

JasonADrury 8mo ago
Why do you feel the need to pollute HN with terrible slashdot jokes?
mrweasel 8mo ago
To be fair, Outlook.com has always been a bit shitty, if you're trying to deliver email to them. Last time it was reasonably good the service was still called Hotmail. The problem is that we've allowed email to be centralized around a few massive providers, who do not care about customer service. If you're large enough, you probably have a contact at Microsoft for Outlook. Everyone else has to yell into the void and sometimes that works.
- vladvasiliu 8mo ago
  > If you're large enough, you probably have a contact at Microsoft for Outlook. For certain very large values of "large". I work for a company which has several thousand Office365 accounts with MS, many of which are the expensive one. It's nigh impossible to get support from them, you're always supposed to go through some partner, who has no idea what they're talking about. And when you do get someone through MS, it's actually still some kind of useless 3rd party who'll ask you to turn your VM off and on again when you complain that it won't turn off (this is actually a true story we had happen on azure). In the end, after about an hour on the phone, the dude gave up and called for help higher up. It took something like a week to have a freaking VM unstuck and destroyed on Azure. Contrast this with AWS, where we were spending much less at the time, only had the basic free support, and I was with someone on the phone in under five minutes who helped us have our direct connect issue solved in 15 minutes.

dismalpedigree 8mo ago

I’m guessing they connected CoPilot to the inbound filter and it is doing stupid and unexpected things.

mmsc 8mo ago

I wonder if Microsoft actually likes running their free email service still. They wiped a ton of old Hotmail and Live.com emails some years ago (and then allowed new people to register those deleted names). I imagine they don't get much out of it anymore.

ohyoutravel 8mo ago
They wiped all the emails from my 25 year old Hotmail account. Pretty weak. I refuse to use Microsoft products except if forced, and do my best to evangelize this position.
- expedition32 8mo ago
  Most people will never pay for email service. Which leaves you Google, MS or god forbid your own ISP.
simonw 8mo ago
I wonder how many accounts on other services were then hijacked using "forgot my password" attacks. UPDATE: After a bit of digging it looks like they started the username recycling policy in 2013, may have quietly stopped doing that in 2018 but formalized no longer doing that in 2021: https://web.archive.org/web/20230627104616/https://www.microsoft.com/en-us/servicesagreement/Updates https://web.archive.org/web/20230627104616/https://www.micro... "Summary of changes to the Microsoft Services Agreement – June 15, 2021 [...] In the Outlook and Office Services sections, we’ve removed the Outlook.com section to clarify that an email address or username is not recycled into our system or assigned to another user."
- deltoidmaximus 8mo ago
  It's wild to me they ever started doing this in the first place. And in 2013 no less, it isn't like the hijacking risk was some far off concept at that point.
mrweasel 8mo ago
It's certainly not free to run and maybe it doesn't really make sense for Microsoft to run Outlook.com anymore, except that it's an easy way to motivate people to having a Microsoft account. Outlook.com certainly has to show up as an expense, one that Microsoft would like to reduce. When you look at what other providers charge for a single email account, it's hard to see Microsoft making money of Outlook.com. There's obviously something to be said for scale, but still, it must cost them something.

arend321 8mo ago

I'm in the privileged position to advise clients to move away from hotmail/live if they want uninterrupted email delivery.

BLKNSLVR 8mo ago

"whatever Microslop is doing" Indirect reference to this recent thread: https://news.ycombinator.com/item?id=47230704 https://news.ycombinator.com/item?id=47230704

joshstrange 8mo ago

Just had a friend reach out yesterday about this issue. His outlook account for 10+ years started having issues receiving emails from his dad and a company he works with. All I could find was that his dad’s email was missing SPF/DMARC but the other email address that was having problems looked like it was configured correctly. I only was able to get a screenshot of the email voice his dad received and it mentioned being on a block list (like in the article).

boesboes 8mo ago

I've stopped diagnosing outlook/hotmail/live delivery issues about 12 years go, they simply do not give a single fuck about their customers. It used to be different, about 18 years ago orso, they had ways to contact them and resolve such issue. fuck big tech :)

Ensorceled 8mo ago

My clients have been experiencing this forever; the logs SAY "temporarily rate limited due to IP reputation." but really the emails are never going to get delivered. I have to get MailChimp or Mailgun to rotate the IPs. It looks like all it takes is one person to mark your email as spam, even by accident. Note that these are mailing lists which they signed up for in MailChimp case OR transactional emails in the Mailgun case. It's only hotmail/outlook that we constantly have this issue with, Google etc. are all fine.

scandox 8mo ago
Often these "spam" reports by end users are just accidental clicks as well. Many of the abuse reports we get are like an email from someone's Mum and visibly legitimate. At other times there are users who use the Report Spam function as a kind of inbox management tool - a way of moving mail away so they don't have to see it because Trash or Delete or whatever is just further away from their pointer.
- pluralmonad 8mo ago
  I tell my friends and family to never click unsubscribe links, unless they had proactively subscribed. Buying something from a company that requires an email does not count. unsolicited marketing emails are spam and should be treated as such. Double so if that company sends marketing emails disguised behind support@company.com.
  - iamacyborg 8mo ago
    > Double so if that company sends marketing emails disguised behind support@company.com That’s typically not a disguise but a clear means of indicating that you can reply to the email
    - pluralmonad 8mo ago
      No, sending marketing from support emails is almost certainly trying to game spam filters. Marketing@company.com would work for the allow replies purpose.

Markoff 8mo ago

As long term Outlook.com user all I can say it's their service is extremely unreliable, my emails are either not delivered at all or end up in junk mail, some emails I don't receive at all or my partners are rate limited sometimes receiving their emails with hours long delays. I assume also their junk filters block some emails and there is no way to avoid it, you repeatedly add senders to safe senders list, even to safe subscriptions and their email still end up marked as junk even after years long communication from same addresses. As backup when something important I write email to recipient from gmail whether they received my email from outlook only to find out my email was never received.

CrzyLngPwd 8mo ago

It's not just Outlook, it's all MS email products as well as Yahoo. These are emails that our customers have specifically requested and we get support tickets blaming us. It's been like this for years.

gus_massa 8mo ago

A few years ago, in my university we have a big problem at the beginning of the semester to contact ~10K students, in particular when they register to our Moodle platform and the server sends them a message. Gmail was usually ok. Yahoo had some max messages per day. But Hotmail/Live/Outlook/whatever just made the messages disappear, no spam folder, no bounce, just disappear. We had some success telling the students to send us a message from their Hotmail/Live/Outlook/whatever address half an hour before registration. This adds our address to some special secret list for that account, and our later messages (usually) reach them. (It may fail. It may fail. IWOMM. YMMV.)

iamcalledrob 8mo ago

I was unable to reach a business this week who host their email on Office 365. Any email I sent would bounce with: 550 5.7.520 Message blocked because it contains content identified as spam. AS(4810)' For context, I was replying to an existing and very mundane email thread. Something is rotten in the state of Outlook

spogbiper 8mo ago
outlook.com and Office 365 are very different beasts. with the latter problems are more often something (mis)configured by the customer/administrator of the 365 account rather than microsoft themselves, and there are steps the customer can take to work around the issue. With outlook.com there is nothing the recipient can do.

rbc 8mo ago

This is one of those articles that demonstrates why email should be distributed. Letting Google and Microsoft run email for the planet is just asking for problems. There are some technical demands to running email services, but they are still in reach of the technically inclined individual or organization. If for no other reason, it would help keep the big mail service providers honest.

cute_boi 8mo ago

microslop should start focusing on real world problem than overhyped ai bubble.

deleted 8mo ago

[deleted]

zelphirkalt 8mo ago

It is my experience, that Outlook is not a reliable e-mail service. Sometimes e-mails are not delivered, or only delivered hours later. When they are delivered, even as a paying customer, they are downloaded so slowly, that I had to wait 10 minutes to get all my e-mails, while my 1 EUR per month Posteo provider delivers in seconds. My impression is, that the only reason one would want to have MS as a mail provider is, that they are entrenched in the e-mail provider reputation and delivery game. Other than that, it seems to be an all around bad service. Not even talking about the mail client itself.

SoftTalker 8mo ago
The big reason is enterprises buy into O365 and running their email through Outlook instead of on-prem or at another provider is part of that. For the same reason they use Teams over Zoom or Slack or other alternatives.
- azalemeth 8mo ago
  Exactly. Nobody chooses MS for quality, and those who do choose it are never those who suffer the most for its own decisions.
  - wolvoleo 8mo ago
    Yup. It's really the cheapest not the best. And Microsoft sell directly to our C suite who have white glove IT support that do everything for them so they never see any issues. The old saying of "Microsoft is better at talking to your boss than you are" is certainly true though. Unfortunately.

lousken 8mo ago

I was using outlook for communicating with businesses as it is often what they use. Some of them just could not send a response back to me, so I am not using outlook anymore. Just normal Microslop stuff

bradleyy 8mo ago

Having to explain to customers that they didn't receive an email because Outlook has a multi-stage set of email servers and the inside ones reject due to the edge (antispam) servers is always interesting.

ycombinatornews 8mo ago

Very happy I decided to ditch outlook (and did it) this year after 10+ years. Every other year some part of the system would break, deliverability, authentication or 2FA. More ads, less value. Eh. Another product driven into ground by Microslop

whalesalad 8mo ago

Days since last Microsoft fuckup: 0 (hard-coded)

tredre3 8mo ago
BTW your domain is missing SPF and DMARC records.
- whalesalad 8mo ago
  I got 99 problems but mail delivery ain’t one

crimsonnoodle58 8mo ago

We experienced this exact error this week. Only affected outlook.com users, and not 365 users. Had to supply MS support with proof of ownership of the IP. The whole process took about a week to resolve.

VladVladikoff 8mo ago

This has plagued us for years. We send quite a lot of transactional email (about 150k emails per day), and there have been several times where Microsoft blocked our server. Usually it is because Microsoft has banned an entire netblock, that our server just happens to be sitting in. I have seen them do this to IPs fro Hetzner, Linode, Amazon AWS (SES), etc. And yeah we've signed up for their junk mail reporting service, and we have all our DNS records dialed in perfectly. I even went as far as signing up for Azure, in the hopes that if I sent from a Microsoft IP it might not get blocked. But I didn't make it very far, every step of the way was like watching paint dry while the interface loaded or did something. Once I finally got the thing set up in order to send mail, the API was so molasses slow that it couldn't handle our mail throughput. Meaning it would take about 30 seconds to send each transactional email because of how slow their API is. Well that's only 2880 emails per day, that is not a reasonable send rate at all. I have even lost customers over this mess, it's really hard to explain to them that they can't receive our email because of their provider and not us. Especially when Microsoft has the audacity to return: 250 OK Email Queued (but then not deliver it anyway!) If anyone has any solutions to this mess I am all ears!

tokyobreakfast 8mo ago
It's almost certainly because your customers are reporting your emails as spam by moving it into the junk folder which is training their systems. Once enough of your customers do this to cross a certain threshold, you are identified as an undesirable sender and QED.
- dijit 8mo ago
  It happens at scale. There's like a middle scale where you're not big enough that Microsoft will go out of their way to whitelist you, but you're big enough that your "send to junk" rate is just high in terms of absolute numbers. It's certainly not a ratio, it must be based on absolute numbers because I've seen it too many times across too many companies, and the only ones that get away with it are extremely low volume. Once you have 1,000,000 mails, even a 0.1% mark as spam rate is 1,000 emails. - and some people treat mark as spam as their delete button, certainly more than 0.1% of people. Don't ask me why. EDIT: on inspection; it's worth noting the mechanism is even more insidious than "people mark you as spam". Microsoft also weighs delete-without-opening as a negative signal. So if you're sending transactional mail (receipts, shipping notifications, invoices) and your users get exactly what they wanted, feel satisfied, and bin it without opening. You've just taken a reputation hit for doing your job correctly. The senders most at risk aren't the ones sending rubbish. EDIT2; theres a reply to me that I can’t reply to because its [dead]; though the point is valid so I vouched. To them I say: I agree. But you probably want your receipt, and thats the example I gave (for a reason).

throwaway613746 8mo ago

My company has been massively affected by this over the past month. It sucks having to tell customers "this is on Microsoft's end, we're trying to work through it with them but we don't have an ETA and can't say more than that" because Microsoft support is absolutely useless. The other day we changed some DMARC/SPF records around and that seemed to do the trick but now it appears to just be a coincidence.

msxanadu 8mo ago

A question related to the outlook.com false spam mail problem... Why are incoming emails to outlook.com so large? 15KB minimum for a text email with just a title. Equivalent Gmail to/from Apple Mail is just a couple of KB.

elcritch 8mo ago

For these large services it seems that small companies should be allowed to sue them. Otherwise there’s no incentive for the big providers to care. Similarly for anti-virus. It’s a PITA when Windows or Mac falsely flag a program as a virus when it’s not in their app stores.

dqv 8mo ago
Yes, at least in the US, being a litigious freak gets results. Weird trick to get unblocked: follow the standard three-email procedure to sender support, then send a fourth email ccing buscond@microsoft.com telling them to unblock or next step is attorney general. The thing about a lot of attorney generals is they LOVE to smack down a big corporation like Microsoft for the little guy.

LorenPechtel 8mo ago

I'm thinking perhaps they turned on some idiot AI. And they don't want to back down and admit they did it wrong.

aclindsa 8mo ago

Funny, my email server started being blocked on Feb. 23. I assumed it was just me, but maybe they block a bunch of people all at once?

g8oz 8mo ago

Not surprised. Confirmation emails from numerous services have been been unable to get through for me.