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.
bradleyy 23 minutes 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.
Ensorceled 7 hours 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.
Arainach 1 hours ago [-]
Agreed. I was an early outlook.com user (was working at MS when it launched, I think internal users got slightly early access allowing me to claim a nicer name than my Gmail) but despite having well over a decade of accounts tied to it got so angry at certain messages never appearing that a couple of years ago I reversed the flow of forwarding and swapped to another account as my primary.
Sounds like it's gotten even worse.
scandox 7 hours 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 6 hours 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 6 hours 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
ycombinatrix 1 hours ago [-]
How is it not a disguise? It means you can't block marketing emails without also blocking the legitimate support emails.
pluralmonad 4 hours 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.
iamacyborg 3 hours ago [-]
> sending marketing from support emails is almost certainly trying to game spam filters
That is not how spam filters work.
pluralmonad 30 minutes ago [-]
If I've interacted with a specific email address, like support@company.com, my email provider will put them in my inbox.
jeroenhd 6 hours ago [-]
"Report spam" is quicker and easier than "unsubscribe".
Gmail added a popup asking the user if they want to unsubscribe when flagging a newsletter with the appropriate unsubscribe headers, so it must be common enough to warrant Gmail developer attention.
Ensorceled 6 hours ago [-]
> Gmail added a popup asking the user if they want to unsubscribe when flagging a newsletter with the appropriate unsubscribe headers
Unfortunately close to 100% of the spam I'm flagging causes this popup now :-/
I'm getting a dozen spam a day now on my Gmail account ... I think they're losing the battle.
1 hours ago [-]
lousken 39 minutes 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
I'm in the privileged position to advise clients to move away from hotmail/live if they want uninterrupted email delivery.
57 minutes ago [-]
ycombinatornews 21 minutes 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
gzread 7 hours 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 6 hours ago [-]
No worries. If you migrate your email server to Azure(TM) the delivery is guaranteed.
kijin 6 hours 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.
CrzyLngPwd 6 hours 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.
wccrawford 7 hours 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.
thedanbob 7 hours 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.
shevy-java 7 hours 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?
jeroenhd 6 hours 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.
jamespo 1 hours ago [-]
This was widespread, I was also affected. I think you can create spoof tickets / accounts over Https with no verification and zendesk don't want to do anything which adds friction.
which comes from an ESP serving millions of users.
joshstrange 7 hours 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).
mmsc 7 hours 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.
simonw 7 hours ago [-]
I wonder how many accounts on other services were then hijacked using "forgot my password" attacks.
"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 6 hours 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 6 hours 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.
john_strinlai 1 hours 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.
it also funnels people into using exchange for work. more like a "marketing expense".
ohyoutravel 7 hours 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 6 hours ago [-]
Most people will never pay for email service. Which leaves you Google, MS or god forbid your own ISP.
shevy-java 7 hours ago [-]
Ever since Microslop, 'xcuse me, Microsoft entered the AI age,
the quality went downhill. Someone should analyse this objectively
since right now this may be more of an impression. But people are
noticeably angrier than they used to be about Microsoft, say, 5
years ago, to today.
mrweasel 7 hours 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.
JasonADrury 7 hours ago [-]
Why do you feel the need to pollute HN with terrible slashdot jokes?
Alifatisk 7 hours 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.
nicbou 7 hours ago [-]
I would start migrating to an email domain that you control. It will come useful at one point or another.
josephg 7 hours 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 7 hours 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.
butILoveLife 7 hours 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 6 hours 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 6 hours 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.
eviks 7 hours ago [-]
You could start the process now, before the ruin?
gus_massa 6 hours 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 1 hours 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
mono442 7 hours 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.
rbc 1 hours 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.
dismalpedigree 7 hours ago [-]
I’m guessing they connected CoPilot to the inbound filter and it is doing stupid and unexpected things.
TonyTrapp 7 hours 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 23 minutes 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.
Markoff 7 hours 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.
boesboes 7 hours 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 :)
cute_boi 58 minutes ago [-]
microslop should start focusing on real world problem than overhyped ai bubble.
Rendered at 19:14:29 GMT+0000 (Coordinated Universal Time) with Vercel.
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.
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.
Sounds like it's gotten even worse.
That’s typically not a disguise but a clear means of indicating that you can reply to the email
That is not how spam filters work.
Gmail added a popup asking the user if they want to unsubscribe when flagging a newsletter with the appropriate unsubscribe headers, so it must be common enough to warrant Gmail developer attention.
Unfortunately close to 100% of the spam I'm flagging causes this popup now :-/
I'm getting a dozen spam a day now on my Gmail account ... I think they're losing the battle.
Indirect reference to this recent thread: https://news.ycombinator.com/item?id=47230704
Eh. Another product driven into ground by Microslop
Just like Internet Explorer used to be the program you used once -- and only once -- to download a proper browser.
These are emails that our customers have specifically requested and we get support tickets blaming us.
It's been like this for years.
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.
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?
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.
https://learn.microsoft.com/en-us/answers/questions/5786144/...
which comes from an ESP serving millions of users.
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).
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.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."
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.
it also funnels people into using exchange for work. more like a "marketing expense".
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.
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.
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.
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.
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.)
Something is rotten in the state of Outlook
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.
fuck big tech :)