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Microsoft Silently Dropping Emails – a Sad but True Story (2020)

221 points by catherd 5y ago

catherd 5y ago
I'm currently having the same experience. Unlike virtually all other email providers, Microsoft does not cooperate if you follow standard email practices. You can follow all their instructions, sign up for their monitoring tools, submit issue reports, try to build "reputation" and if you are self-hosting they will still have a high likelihood of silently dropping your emails after their server tells you it got them, or putting them in the recipients spam even after being marked as an approved sender.
- arthurcolle 5y ago
  Unforgivable. Literally destroying the decentralized nature of one of the last few "decentralized" systems that exists. For shame
  - donmcronald 5y ago
    “Email is so unreliable. Have you tried Teams?” Just ignore that it’s Microsoft breaking a legacy standard to advantage their other products that compete against email. I think they should start fining companies in stock. Dilute the shareholder value by 5% and see how quickly things change.
    - arthurcolle 5y ago
      I like this, let's start a club
    - lostlogin 5y ago
      > Teams Moving back to a full MS stack after 15ish years away from it is so disappointing. I’d assumed things had got better. Their previously good products are now some sort of split personality monster that sort of work together but mostly just exist near each other and have a common logo. Teams is a mushy world between the distant parts. Go on, try change a footer on a “Word” document or move an image. Try and copy a document and change its contents and re-upload. It might work, and it might work most the time. But when it goes wrong it’s devastating.
      - robotnikman 5y ago
        That's basically my experience administering Microsoft 365 at my last job.
      - arthurcolle 5y ago
        It's almost easier centering divs in CSS. And that's saying a lot... Lol!
- MattGaiser 5y ago
  Yep. My Dad's company uses a small hosting provider so he cannot email me @live anymore.
  - catherd 5y ago
    Try adding him to your contact list.
  - kureikain 5y ago
    Try to email your dad first. If you're the one initiate the conversation, then your dad will be able to reply to that same thread. After that, add him to contact list once he responded. The point is to make an attempt of your self initiate the connect to that server.
    - franga2000 5y ago
      Doesn't always work. I've seen Outlook 365 or whatever it is mark a reply as spam. It's rare, but apparently not impossible.
  - account42 5y ago
    Have you considered switching to a better email provider than @live then?
kureikain 5y ago
I run an email forwarding service https://hanami.run https://hanami.run and I used to had this exact problem. They had a dedicated page at https://sendersupport.olc.protection.outlook.com/snds/data.aspx https://sendersupport.olc.protection.outlook.com/snds/data.a... that supposed to be used for these delivery issue. I tried to submit multiple requests from there. Even IPs that aren't sent any email in last 3 months. Then one day the problem just disappears and I was able to send email just fine. Till this day, I still don't know what happen. Another similar service is apple icloud, which I think even much more worse than Hotmail. At least, hotmail give you a portal that you can see some data. With the announcement of apple icloud email service, I imagine people who are self-hosted email gonna have a lot issue with them.
- unclekev 5y ago
  > With the announcement of apple icloud email service, I imagine people who are self-hosted email gonna have a lot issue with them. What announcement? iCloud has had a E-Mail service for over 10 years now. iCloud was doing email back when it was called MobileMe.
  - kureikain 5y ago
    They started to introduce support for custom domain. That means many will switch to them, for the convenience of the ecosystem. So that means one more awkward email providers we have to deal with :)
    - unclekev 5y ago
      Ah understood. Apologies, I misunderstood what you were trying to say. Thanks for clarifying :)
anonydsfsfs 5y ago
Had the exact same experience when I worked at a non-profit: we had a self-hosted Postfix server, and our subscriber emails would get silently dropped. This only ever happened for Outlook.com users, and we had set up SPF, DKIM, and DMARC long ago. We got the same run-around with Microsoft support, and eventually we had to give up and move to using Google's SMTP Relay service.
- donmcronald 5y ago
  It’s tacit collusion between the big providers to force all businesses onto their overpriced cloud services. One Office 365 user costs the same as 50 users at a shared host.
omk 5y ago
>Biggest problem is, that Microsoft always blacklists the whole server! If only one of my customers does something not in line with the secret rules of SmartScreen, emails of all other customers are blocked too. IMHO this is just unprofessional. Why not just block the domain under suspicion and send the adminstrator a message (maybe as part of the JMRP)? The reason for blocking IP originates from a culture set before DKIM. Any IP could shoot out emails for any domain. You don't want to blacklist a domain for an email it did not legitimately author. However, in a post DKIM world, where adoption is above 80% this could be a feasible solution at least for emails carrying a DKIM signature. The domain owner has provided proofs that the IP address is being used by them to send out emails. Flagging emails from a domain and IP could be blocked while allowing other domains from the same IP to operate.
- arthurcolle 5y ago
  This is anti-competitive behavior by definition. What a farce.
paxys 5y ago
Unrelated but if the author is reading this please get rid of the sticky header on that site. It is beyond annoying.
gorbachev 5y ago
The general problem is by no means unique to Microsoft. Misconfigured email servers, with spam filters and SPF/DKIM setups being the most common issues, drop emails far more often people tend to realize.
johnchristopher 5y ago
So, basically, email lacks an ACK mechanism. Couldn't a matrix client with email and asynchronous features be a drop-in replacement for email ? Wouldn't that be a killer product ? SPF, DKIM, and DMARC are not to core to email protocols if I understand correctly. There shouldn't be a way for a matrix a client to delete a message sent to another client to keep with the email usage and expectation. So matrix messages wouldn't necessarily be used as email text messages but attached documents to messages would carry email that a client would store and archive.
- JimDabell 5y ago
  > So, basically, email lacks an ACK mechanism. As the article mentions, Microsoft’s server was telling the sender that it had accepted it. An ACK had taken place. But there’s no point in having an ACK if the recipient lies about it.
  - denysvitali 5y ago
    Tbh queued for delivery doesn't mean the email has been successfully delivered, BUT, the mail server should inform the user if a delivery cannot be performed. Most probably this whole problem realted to silently dropping emails is intended behavior, a type of shadowbanning applied to emails to prevent spammers from knowing their email was blocked. Too bad that this in turn causes huge issues for legitimate users
    - denton-scratch 5y ago
      Not "should"; it's a "MUST". If there is a delivery failure after acceptance of a message, the receiver-SMTP MUST formulate and mail a notification message. This notification MUST be sent using a null ("<>") reverse-path in the envelope. The recipient of this notification MUST be the address from the envelope return path (or the Return-Path: line). And: As discussed in Section 7.8 and Section 7.9 below, dropping mail without notification of the sender is permitted in practice. However, it is extremely dangerous and violates a long tradition and community expectations that mail is either delivered or returned. If silent message-dropping is misused, it could easily undermine confidence in the reliability of the Internet's mail systems. So silent dropping of messages should be considered only in those cases where there is very high confidence that the messages are seriously fraudulent or otherwise inappropriate. https://datatracker.ietf.org/doc/html/rfc5321#section-4.5.4 https://datatracker.ietf.org/doc/html/rfc5321#section-4.5.4 The RFC makes clear the long-standing principle that a mail-server operator is entitled to make his own rules as to what mail he is and isn't willing to accept. But he's NOT allowed to accept it for delivery, and then silently discard it. Hotmail was always awful for this. There are comments up-thread to the effect that Microsoft might be trying to squeeze out self-hosted mailservers. I suspect that was the case in the Hotmail days. Either it worked, and nobody self-hosts any more (FALSE) or it didn't work, and they should have given up. I suspect the same policies are still in place due to corporate inertia.
ternaryoperator 5y ago
I have had the exact same experience. Even put the senders on your whitelist and it makes no difference at all. It means that Office 365 cannot be trusted for handling mail. When it comes time to renew, after two years of putting up with this, I am moving off it.
jimbojet 5y ago
As someone who worked on reputation at Microsoft, it sounds like a bad case of the right hand not talking to the left. Outlook SmartScreen judgment should be available to tier 3 support along with the IP block list check as a primary investigation step. The author should not have needed to go through tier 3 on two tickets before escalating to someone who had visibility into SmartScreen judgments. Hopefully this blog gets some publicity and Microsoft support amends their investigation process, as I’m sure the author is not the only person running into this issue. All opinions are my own and not that of Microsoft.
- anonydsfsfs 5y ago
  I've worked extensively with Microsoft support on deliverability issues, and I don't think it's a case of the right hand not talking to the left, it's a case of support wanting to close out issues as quickly as possible due to misaligned incentives. Microsoft has zero incentive to help small-time senders like the OP, since recipients are much more likely to blame the OP for delivery issues than Microsoft. Plus, Microsoft has no way of knowing for certain whether the OP is legitimate, so if they choose to help them, they might accidentally help a spammer. Therefore, Microsoft support is incentivized to simply ignore complaints like the OP or give them the run-around, which has been my experience. The only part of the article that surprised me is the fact they actually got the issue escalated. I've never succeeded in doing that; talking to Microsoft support is like talking to a brick wall.
  - donmcronald 5y ago
    > talking to Microsoft support is like talking to a brick wall I once had DKIM keys get out of sync with DNS in Office 365. It’s supposed to be handled automatically and that should never happen. Support was as useful as a baby trying to do calculus. It took me 3 days to get the keys rotated and after I understood how it works I realized they should have been able to help me mitigate it right away (dkim keys can be rotated while disabled).
  - vxNsr 5y ago
    > The only part of the article that surprised me is the fact they actually got the issue escalated. I've never succeeded in doing that; talking to Microsoft support is like talking to a brick wall. I’ve found that the best trick with Microsoft is: money talks. If you pay them for support suddenly you should have a much easier time getting things done. Obviously paying MS to fix a problem they caused is abhorrent but sometimes you gotta hold your nose and do it.
techsupporter 5y ago
I had this problem repeatedly with both Google and Microsoft, though never at the same time and never, so far as I could tell, for the same reason. Everything was set up properly. The domains I hosted had IPv4 and IPv6 addresses with forward and reverse DNS matching exactly. SPF was set perfectly, according to multiple test sites. DKIM was always used and always validated, again according to multiple test sites. I even signed up for a DMARC endpoint account at report-uri.com. Didn't matter. Messages would be spontaneously rejected, sometimes in mid-conversation (this happened to my wife quite a lot). Other times, the remote end would claim to accept the message and then it would disappear into the great bit bucket in the sky. It would be like this for a day or two then spontaneously go back to working. I finally gave up and switched entirely over to Fastmail awhile back. No more delivery problems, but no more self-hosting my own e-mail, something I'd done for twenty years prior (my domain is older than Mozilla and Google).
- hardwaresofton 5y ago
  > I finally gave up and switched entirely over to Fastmail awhile back. No more delivery problems, but no more self-hosting my own e-mail, something I'd done for twenty years prior (my domain is older than Mozilla and Google). Can anyone speak to what a provider like Fastmail does behind the scenes that guarantees their delivery? Is it the threat to sue/kick up dirt/raise issues with the appropriate regulatory body if perfectly good emails don't go through? Merely having a seat at some sort of regulatory body or committee?
  - tallanvor 5y ago
    From what I can tell, there are two main reasons companies like Fastmail don't have these problems. The first is that good email providers spend a lot of time maintaining the reputation of the IP addresses they use and shut down bad actors as quickly as possible. The second is that the more people that use the service, the higher percentage of good quality emails being sent, reducing the effect of the occasional bad actor.
  - jraph 5y ago
    I'm self-hosting my mails. Microsoft expects you to send enough mails to consider your mails not as spam. One thing Fastmail does that people who self-host can't is: sending enough mails. I don't know what other measure they may take but this alone probably goes a long way. And yes, this is fucking frustrating. I'm not going to send thousands of mails per months just for the sake of it and don't know how I should do that without spamming. This is so fucked up.
hyldmo 5y ago
Meanwhile, I get so much spam on my hotmail account (from obvious spam addresses too) that I’ve had to switch to gmail. It seems both the false positive and false negative rate is sky-high.
Clewza313 5y ago
> SmartScreen® Filter technology is always adapting and learning more about what is and isn’t unwanted mail, it is not possible for us to offer specific advice about improving your mail content. Translation: "The filtering is based on machine learning. If there are false positives, too bad, even we don't know what's causing them. Try to look less like spam or something?"
- donmcronald 5y ago
  They should be liable for their shitty ML algorithms. It’s extra detrimental to small businesses who get their email dropped for no good reason. Silently dropping email is malicious IMO.
- swiley 5y ago
  ML is the software form of cheap plastic crap that quickly breaks.
adevx 5y ago
This sounds similar to my experience with Microsoft based email (Outlook, Hotmail, Live, custom 365 domains) I eventually decided to route Microsoft hosted emails over Amazon SES instead of a VPS hosted Postfix setup. This did help a bit. The fact that all other email providers work perfectly fine and Microsoft is the problematic one I think signals an issue with their spam filtering.
cyborgx7 5y ago
Oh hey, Microsoft is breaking another open decentralized standard again as they are pushing their own proprietary alternative. But let's keep pretending they changed.
- pteraspidomorph 5y ago
  Speaking as someone who has been running MTAs for more than 15 years - Microsoft has been breaking e-mail for years. They are an order of magnitude more awful than anyone else, and no one should have their e-mail with them for any reason. See also (recent): https://answers.microsoft.com/en-us/outlook_com/forum/all/hotmailoutlook-block-list-s3140-blocks-all-new/699f3a56-406e-4804-97e2-cbe23b9bb01c https://answers.microsoft.com/en-us/outlook_com/forum/all/ho...
  - mnw21cam 5y ago
    It all started with top-posting, and went downhill from there.
  - jiggawatts 5y ago
    This is why IT should unionise, or form a guild. Imagine if this was turned around, and simultaneously a huge chunk of the world instantly black-holed Office 365 outbound email. Then in response to the roaring noise from Redmond, simply send back their canned response of "Not qualified for mitigation. Our investigation has determined that the above IP(s) do not qualify for mitigation." Do that for 24 hours, then 48 hours, and so on until they smarten up. I guarantee you they'll have their CEO breathing down the necks of every moron in the spam filter team until they fix it. Until then? Nothing will happen. Nothing at all. We'll complain on YC News, we'll complain on /r/sysadmin, and a bunch of small businesses will go out of business. Microsoft 365 will continue to grow to consume the world. Email will be rebranded "Teams Mail", and as far as everyone is concerned that will make perfect sense. Either we act, or we live with the consequences of inaction.
    - pas 5y ago
      Collectivist action is great, when it's great. But with it comes all the usual ossification problems. (For a collective to have power others have to give it to them. Either the collective manages to secure a monopoly, like the various professional licensing/accreditation bodies, legal bar association, medical residency programs with fixed number of slots. Or stakeholders - companies, professionals, regulators - have to join the collective and give up at least some of their independence during the process.) Yes, email is kind of important. But it's also pretty shoddy. It always has been. (Confidentiality, integrity, authentication, signed receipt of delivery. All are important for regular business correspondence and by default all were [and still are] hit and miss with email.) This practice of MS of not accepting email might be abuse of market power. But they can easily say their clients signed up for Outlook to have exactly this protection. What would the courts think? Who knows.
pulse7 5y ago
Governments don't like self-hosting, because they need to ask for data every time they need it. For big hosting providers like Google, Microsoft, Fastmail and others they have mails already. So there are incentives to make it harder and harder to self-host...
nonamesleft 5y ago
I started getting this on our transactional mail relay some years ago, hotmail responded with "Not qualified for mitigation", therefore instead of spending pointless effort dealing with these miserable jollems i used o365 to counter it (my organization was already using o365, which also never did this S3150 thing to me) by: Adding a relay user to the o365 then configuring all the domains i needed to send from on the o365 tenant (without changing the MX records naturally). (Using a normal o365 user account to relay is possible for me as our typical customer base is enterprise and education, not random end users) Adding distribution lists as the from-addresses that i needed to send from and gave send-as rights to the relay user, compiled a list of hotmail/outlook domains (which i've had to add to over the years but it is relatively stable for me by now), then configured the outgoing relay server that does all the dkim-stamping to route all outgoing mail to outlook/hotmail domains through o365. When i see a S3150 in the logs i just add another domain to the list, i should probably make this pre-emptive by looking at the target mx records before sending, as its not trivial to make exim resend something that ended in a 5xx. All other mail providers have removed blocks by simply asking, not hotmail. Also all our newsletter-like mail goes through separate services, these are all transactional mails (meeting invites, user account creation, password resets and such).
agent327 5y ago
Despite all the outrage, there is also this: "As far as I know, emails from my business custmers are branded, formatted following best practices, have unsubscribe links and a valid contact footer." In other words, his customers are sending out the type of emails that actually require unsubscribe links. You know, _spam_. So maybe it isn't Microsoft who is the bad guy here?
- anfogoat 5y ago
  Microsoft is telling this guy they received the email for delivery and then silently dropped it. If you're not going to deliver an email you either inform the sender or shutdown your mail servers and remove your MX. > Despite all the outrage Hah! Please, there's hardly any. Certainly nowhere close the outrage this deserves.
  - agent327 5y ago
    Oh please. It was the commercial spammers that destroyed email as a useful communication medium. Not sending all sorts of useless notifications is just another defence mechanism against those a*holes. Once in a while I still get an undeliverable notification for Chinese spam; they just configured my personal email as their return address, and some stupid mail server decided to tell me it couldn't accept the email. Great job guys, now you're spamming innocent bystanders! So yes, telling people that their spam-load was accepted, and then just not delivering it, seems perfectly fine to me. It's a tough world out there, and it was made that way by precisely the kind of people that need "unsubscribe" links in their emails to begin with. I feel no sympathy for him. These days communication uses web forms, Teams, Skype, Facebook, Twitter, or any other electronic mechanism that isn't email. They are all regulated by their respective owners, so they have a slightly better chance of surviving the onslaught of the advertisers. Email works fine for contact with friends and family, but not for spam, and that's how it should be.
    - account42 5y ago
      Backscatter spam only happens with a misconfigured email service. If you are not going to deliver the mail, reply with an error during submission, don't send a automatic notification email to the return address.
markonen 5y ago
These details about the proprietary "SmartScreen" were really useful. We have been sending login code emails via AWS SES and have had a lot of issues with Hotmail/Outlook.com not delivering them. My takeaways: 1) There's a risk that a shared IP system like AWS SES will get blocked by SmartScreen based on emails someone else is sending. 2) We really should look at the contents of our (trivial) transactional emails, too.
KingMachiavelli 5y ago
Even the user side of Microsoft's email is confusing and prone to loosing emails. O365 defaults or at least the recommended settings will just quarantine emails without notifying anyone. I guess Microsoft doesn't trust users to not open emails in the spam folder? I think I have it configured now to alert the recipient and me on quarantined emails but there are at least two relevant dashboard (Exchange and umm Security Center? who knows what the current names are today) that probably have like 35 submenus and 1000+ settings. Running my own email server would be easier. Another thing, a few months ago I noticed a couple incoming emails were not quarantined/blocked but also not delivered. I don't think the issue has reoccurred since but it's just crazy that emails are just lost sometimes.
fogihujy 5y ago
It's common knowledge that Microsoft considers everyone to be spammers until proven innocent. Getting to a point where your mails end up in the recipients' inboxes is a long path -- Microsoft doesn't care if you set everything up perfectly, as spammers can do the same -- and one has to provide them with enough data to learn to trust one's IP's/ranges/domains. Contacting Microsoft means you have to go through a difficult dance through multiple canned replies, multiple escalation requests, and being lucky enough to get someone to actually escalate. Silently dropping emails isn't Microsoft-specific, though. It's quite common to have a Postfix/Amavis setup set to discard spam over a certain spam score threshold.
NazakiAid 5y ago
Had the same problem as well when sending an email to a client of mine who used Hotmail. Had had successful communications with them in the past 1.5 years then suddenly, bam. Was put on the "S3140 block list". Had to use my personal Gmail to send emails to them. Never emailed another person who used Microsoft email services. Was told my email server was sending spam by them (as people had reported emails from the IP as unwanted), so I did a full security check (using logs, trying to find holes, etc), and upgraded software. No problems that I could find. After lots of back and forth, they said my IP was blocked as it was "suspicious" and they unblocked it (how kind of them). The process took a long time, which I could imagine could be devastating to a small business (luckily my client understood as I made sure to tell them how bad Microsoft is).
fleddr 5y ago
I can only confirm that out of all the email providers, Microsoft is the most tedious, non-standard and brutal when it comes to dropping email. I'm coming from the perspective of a community site owner that pushes out email notifications to its members. Nothing spammy, all emails are opted-in and essential for the basic functioning of the community. They may be as simple as "person X liked your post". It's purely functional email. Plain text, no links, images, nothing. The entire site is non-commercial. Further, the domain from which it is sent is well established (14 years old) and never used for sending out spam. It also has implemented all the best practices, like DMARC, SPF, the like. It's not in the gray zone by any stretch of the imagination. It's as clean as it gets. Yet still, as random as the weather, it's always hotmail.com and live.com users complaining about email not arriving. It's not in their spam folder, it's just not there at all. I never face this issue with any other email provider, only Microsoft. There's no help at all regarding what triggers it, other than the standard document listing best practices I'm already following. They do have some tools to analyze issues, but guess what, only available for high volume email pushers. There's also a public tool to check blocklists, some of which are shared between email providers, yet even when not blocked anywhere, you're still blocked at Microsoft. So after all this self-analysis, I've learned to raise the ticket. Admittedly, occasionally they admit it was a false positive, and then lift the ban. But they never fix anything structurally, it's an issue that keeps coming back. It's maddening. Since I'm in the mood of self-pity, I'll add to this Microsoft-specific problem by mentioning that it's hell to push out email in general for small websites. For example, besides the functional email notifications, there's also an opt-in weekly newsletter. It's found deeply within user's personal settings, so those finding this setting and enabling it, surely want it. Within the range of a few hundred to a few thousand subscribers, now you have a signal problem. A handful of users may no longer want the newsletter and do not unsubscribe (which is easily done from the bottom of each email). Instead, they may delete it, report it as spam, block the sender. These are convenient to do from an email client, but the problem is that I never see their desire to unsubscribe. I'd gladly honor it. What happens instead is that in the case of low volume, just a handful of these negative signals may push all of your email into the spam folder. Technically this is incorrect. It's not spam. The user opted in, the contents of the emails are not spammy, and the user never indicated to not want them anymore. But email providers don't care, it's all spam now. To resolve this, I compare last activity on the site with the user's opt-in status, and auto unsubscribe everybody not recently active, regardless of whether they want this. This significantly reduces the chance of users flagging the email as unwanted in their email client. At the same time, now I have users complaining their newsletters aren't coming. Bottom line: you can't win. With the best of intentions, fully wanting to comply with every technical and legal guidance in the book, it still does not work.
aliswe 5y ago
When these long-winded issues arise, you need to call people up. Email clearly isn't working. You'd be surprised (or not) by the difference verbal communication makes, not only do your verbal expressions translate better, but the tone of voice may (or not) instill trust in the person on the other end.
- account42 5y ago
  > Email clearly isn't working. It's working just fine for most people. Email sometimes isn't working for Microsoft customers - but that is entirely Microsoft's doing.
nwellnhof 5y ago
On the opposite side, I found Microsoft Azure to be one of the biggest sources of spam on the internet. I have blocked them completely on my private mail server.
jsilence 5y ago
Hashtag MeeToo
Geee 5y ago
Yeah, these problems are consistent with Microsoft email. I've been using Sendgrid to send emails for our SaaS and some customers who use Microsoft email don't receive transactional messages at all. There's nothing you can do about it. Also, seen this happen with other apps too. Transactional messages don't arrive on Microsoft email addresses.
kseistrup 5y ago
Does setting up MTA-STS have any effect on deliverability? I can see in my webserver logs that both Microsoft and Gmail/Google are checking the MTA-STS settings at regular intervals.
account42 5y ago
Microsoft is also the only server operator that will randomly block me. Since I don't host any customers I have decided to simply not care about them and their customers - if someone using microsoft's email services isn't able to get email from me, it's their problem.
dade_ 5y ago
I had to stop using Office365 for business because it kept doing this same thing. I disabled every spam, and protection I could find, and enlisted the help of support. Some legitimate email would simply never arrive and they couldn’t explain why. It seems there are layers of protection, some with no logging (available to the tenant admin) to troubleshoot, it became a huge waste of time, negating the purpose of using a cloud service. In the end I moved to a different service provider and never had the problem again.
QuadrupleA 5y ago
Had this same issue many times sending via AWS (SES). Spent dozens of hours on it with no help from Microsoft, ultimately Amazon had to sort it out with them. Silently dropping mail (not even to the spam folder) is a maddeningly cryptic action on MS's part, and has squandered massive amounts of developer and system administrator time. If you're in a position to sway anybody from using Outlook.com, Hotmail.com, or Msn.com or Live.com I highly encourage it - MS has made a lot of lives difficult with their email policies, including NerdAdmin's here.
Firehawke 5y ago
I've never hit this with GMail, but I've hit this repeatedly with outlook.com/hotmail.com accounts. There's a persistent 20% chance of any given email to my accounts being dropped silently. It's been enough of a headache that I haven't been able to migrate off GMail and that's frustrating as hell. Especially with important medical emails..
ludditetech 5y ago
Kudos Nerd Admin epic post and work through

221 points by catherd 5y ago

I'm currently having the same experience. Unlike virtually all other email providers, Microsoft does not cooperate if you follow standard email practices. You can follow all their instructions, sign up for their monitoring tools, submit issue reports, try to build "reputation" and if you are self-hosting they will still have a high likelihood of silently dropping your emails after their server tells you it got them, or putting them in the recipients spam even after being marked as an approved sender.

arthurcolle 5y ago
Unforgivable. Literally destroying the decentralized nature of one of the last few "decentralized" systems that exists. For shame
- donmcronald 5y ago
  “Email is so unreliable. Have you tried Teams?” Just ignore that it’s Microsoft breaking a legacy standard to advantage their other products that compete against email. I think they should start fining companies in stock. Dilute the shareholder value by 5% and see how quickly things change.
  - arthurcolle 5y ago
    I like this, let's start a club
  - lostlogin 5y ago
    > Teams Moving back to a full MS stack after 15ish years away from it is so disappointing. I’d assumed things had got better. Their previously good products are now some sort of split personality monster that sort of work together but mostly just exist near each other and have a common logo. Teams is a mushy world between the distant parts. Go on, try change a footer on a “Word” document or move an image. Try and copy a document and change its contents and re-upload. It might work, and it might work most the time. But when it goes wrong it’s devastating.
    - robotnikman 5y ago
      That's basically my experience administering Microsoft 365 at my last job.
    - arthurcolle 5y ago
      It's almost easier centering divs in CSS. And that's saying a lot... Lol!
MattGaiser 5y ago
Yep. My Dad's company uses a small hosting provider so he cannot email me @live anymore.
- catherd 5y ago
  Try adding him to your contact list.
- kureikain 5y ago
  Try to email your dad first. If you're the one initiate the conversation, then your dad will be able to reply to that same thread. After that, add him to contact list once he responded. The point is to make an attempt of your self initiate the connect to that server.
  - franga2000 5y ago
    Doesn't always work. I've seen Outlook 365 or whatever it is mark a reply as spam. It's rare, but apparently not impossible.
- account42 5y ago
  Have you considered switching to a better email provider than @live then?

kureikain 5y ago

I run an email forwarding service https://hanami.run https://hanami.run and I used to had this exact problem. They had a dedicated page at https://sendersupport.olc.protection.outlook.com/snds/data.aspx https://sendersupport.olc.protection.outlook.com/snds/data.a... that supposed to be used for these delivery issue. I tried to submit multiple requests from there. Even IPs that aren't sent any email in last 3 months. Then one day the problem just disappears and I was able to send email just fine. Till this day, I still don't know what happen. Another similar service is apple icloud, which I think even much more worse than Hotmail. At least, hotmail give you a portal that you can see some data. With the announcement of apple icloud email service, I imagine people who are self-hosted email gonna have a lot issue with them.

unclekev 5y ago
> With the announcement of apple icloud email service, I imagine people who are self-hosted email gonna have a lot issue with them. What announcement? iCloud has had a E-Mail service for over 10 years now. iCloud was doing email back when it was called MobileMe.
- kureikain 5y ago
  They started to introduce support for custom domain. That means many will switch to them, for the convenience of the ecosystem. So that means one more awkward email providers we have to deal with :)
  - unclekev 5y ago
    Ah understood. Apologies, I misunderstood what you were trying to say. Thanks for clarifying :)

anonydsfsfs 5y ago

Had the exact same experience when I worked at a non-profit: we had a self-hosted Postfix server, and our subscriber emails would get silently dropped. This only ever happened for Outlook.com users, and we had set up SPF, DKIM, and DMARC long ago. We got the same run-around with Microsoft support, and eventually we had to give up and move to using Google's SMTP Relay service.

donmcronald 5y ago
It’s tacit collusion between the big providers to force all businesses onto their overpriced cloud services. One Office 365 user costs the same as 50 users at a shared host.

omk 5y ago

>Biggest problem is, that Microsoft always blacklists the whole server! If only one of my customers does something not in line with the secret rules of SmartScreen, emails of all other customers are blocked too. IMHO this is just unprofessional. Why not just block the domain under suspicion and send the adminstrator a message (maybe as part of the JMRP)? The reason for blocking IP originates from a culture set before DKIM. Any IP could shoot out emails for any domain. You don't want to blacklist a domain for an email it did not legitimately author. However, in a post DKIM world, where adoption is above 80% this could be a feasible solution at least for emails carrying a DKIM signature. The domain owner has provided proofs that the IP address is being used by them to send out emails. Flagging emails from a domain and IP could be blocked while allowing other domains from the same IP to operate.

arthurcolle 5y ago
This is anti-competitive behavior by definition. What a farce.

paxys 5y ago

Unrelated but if the author is reading this please get rid of the sticky header on that site. It is beyond annoying.

gorbachev 5y ago

The general problem is by no means unique to Microsoft. Misconfigured email servers, with spam filters and SPF/DKIM setups being the most common issues, drop emails far more often people tend to realize.

johnchristopher 5y ago

So, basically, email lacks an ACK mechanism. Couldn't a matrix client with email and asynchronous features be a drop-in replacement for email ? Wouldn't that be a killer product ? SPF, DKIM, and DMARC are not to core to email protocols if I understand correctly. There shouldn't be a way for a matrix a client to delete a message sent to another client to keep with the email usage and expectation. So matrix messages wouldn't necessarily be used as email text messages but attached documents to messages would carry email that a client would store and archive.

JimDabell 5y ago
> So, basically, email lacks an ACK mechanism. As the article mentions, Microsoft’s server was telling the sender that it had accepted it. An ACK had taken place. But there’s no point in having an ACK if the recipient lies about it.
- denysvitali 5y ago
  Tbh queued for delivery doesn't mean the email has been successfully delivered, BUT, the mail server should inform the user if a delivery cannot be performed. Most probably this whole problem realted to silently dropping emails is intended behavior, a type of shadowbanning applied to emails to prevent spammers from knowing their email was blocked. Too bad that this in turn causes huge issues for legitimate users
  - denton-scratch 5y ago
    Not "should"; it's a "MUST". If there is a delivery failure after acceptance of a message, the receiver-SMTP MUST formulate and mail a notification message. This notification MUST be sent using a null ("<>") reverse-path in the envelope. The recipient of this notification MUST be the address from the envelope return path (or the Return-Path: line). And: As discussed in Section 7.8 and Section 7.9 below, dropping mail without notification of the sender is permitted in practice. However, it is extremely dangerous and violates a long tradition and community expectations that mail is either delivered or returned. If silent message-dropping is misused, it could easily undermine confidence in the reliability of the Internet's mail systems. So silent dropping of messages should be considered only in those cases where there is very high confidence that the messages are seriously fraudulent or otherwise inappropriate. https://datatracker.ietf.org/doc/html/rfc5321#section-4.5.4 https://datatracker.ietf.org/doc/html/rfc5321#section-4.5.4 The RFC makes clear the long-standing principle that a mail-server operator is entitled to make his own rules as to what mail he is and isn't willing to accept. But he's NOT allowed to accept it for delivery, and then silently discard it. Hotmail was always awful for this. There are comments up-thread to the effect that Microsoft might be trying to squeeze out self-hosted mailservers. I suspect that was the case in the Hotmail days. Either it worked, and nobody self-hosts any more (FALSE) or it didn't work, and they should have given up. I suspect the same policies are still in place due to corporate inertia.

ternaryoperator 5y ago

I have had the exact same experience. Even put the senders on your whitelist and it makes no difference at all. It means that Office 365 cannot be trusted for handling mail. When it comes time to renew, after two years of putting up with this, I am moving off it.

jimbojet 5y ago

As someone who worked on reputation at Microsoft, it sounds like a bad case of the right hand not talking to the left. Outlook SmartScreen judgment should be available to tier 3 support along with the IP block list check as a primary investigation step. The author should not have needed to go through tier 3 on two tickets before escalating to someone who had visibility into SmartScreen judgments. Hopefully this blog gets some publicity and Microsoft support amends their investigation process, as I’m sure the author is not the only person running into this issue. All opinions are my own and not that of Microsoft.

anonydsfsfs 5y ago
I've worked extensively with Microsoft support on deliverability issues, and I don't think it's a case of the right hand not talking to the left, it's a case of support wanting to close out issues as quickly as possible due to misaligned incentives. Microsoft has zero incentive to help small-time senders like the OP, since recipients are much more likely to blame the OP for delivery issues than Microsoft. Plus, Microsoft has no way of knowing for certain whether the OP is legitimate, so if they choose to help them, they might accidentally help a spammer. Therefore, Microsoft support is incentivized to simply ignore complaints like the OP or give them the run-around, which has been my experience. The only part of the article that surprised me is the fact they actually got the issue escalated. I've never succeeded in doing that; talking to Microsoft support is like talking to a brick wall.
- donmcronald 5y ago
  > talking to Microsoft support is like talking to a brick wall I once had DKIM keys get out of sync with DNS in Office 365. It’s supposed to be handled automatically and that should never happen. Support was as useful as a baby trying to do calculus. It took me 3 days to get the keys rotated and after I understood how it works I realized they should have been able to help me mitigate it right away (dkim keys can be rotated while disabled).
- vxNsr 5y ago
  > The only part of the article that surprised me is the fact they actually got the issue escalated. I've never succeeded in doing that; talking to Microsoft support is like talking to a brick wall. I’ve found that the best trick with Microsoft is: money talks. If you pay them for support suddenly you should have a much easier time getting things done. Obviously paying MS to fix a problem they caused is abhorrent but sometimes you gotta hold your nose and do it.

techsupporter 5y ago

I had this problem repeatedly with both Google and Microsoft, though never at the same time and never, so far as I could tell, for the same reason. Everything was set up properly. The domains I hosted had IPv4 and IPv6 addresses with forward and reverse DNS matching exactly. SPF was set perfectly, according to multiple test sites. DKIM was always used and always validated, again according to multiple test sites. I even signed up for a DMARC endpoint account at report-uri.com. Didn't matter. Messages would be spontaneously rejected, sometimes in mid-conversation (this happened to my wife quite a lot). Other times, the remote end would claim to accept the message and then it would disappear into the great bit bucket in the sky. It would be like this for a day or two then spontaneously go back to working. I finally gave up and switched entirely over to Fastmail awhile back. No more delivery problems, but no more self-hosting my own e-mail, something I'd done for twenty years prior (my domain is older than Mozilla and Google).

hardwaresofton 5y ago
> I finally gave up and switched entirely over to Fastmail awhile back. No more delivery problems, but no more self-hosting my own e-mail, something I'd done for twenty years prior (my domain is older than Mozilla and Google). Can anyone speak to what a provider like Fastmail does behind the scenes that guarantees their delivery? Is it the threat to sue/kick up dirt/raise issues with the appropriate regulatory body if perfectly good emails don't go through? Merely having a seat at some sort of regulatory body or committee?
- tallanvor 5y ago
  From what I can tell, there are two main reasons companies like Fastmail don't have these problems. The first is that good email providers spend a lot of time maintaining the reputation of the IP addresses they use and shut down bad actors as quickly as possible. The second is that the more people that use the service, the higher percentage of good quality emails being sent, reducing the effect of the occasional bad actor.
- jraph 5y ago
  I'm self-hosting my mails. Microsoft expects you to send enough mails to consider your mails not as spam. One thing Fastmail does that people who self-host can't is: sending enough mails. I don't know what other measure they may take but this alone probably goes a long way. And yes, this is fucking frustrating. I'm not going to send thousands of mails per months just for the sake of it and don't know how I should do that without spamming. This is so fucked up.

hyldmo 5y ago

Meanwhile, I get so much spam on my hotmail account (from obvious spam addresses too) that I’ve had to switch to gmail. It seems both the false positive and false negative rate is sky-high.

Clewza313 5y ago

> SmartScreen® Filter technology is always adapting and learning more about what is and isn’t unwanted mail, it is not possible for us to offer specific advice about improving your mail content. Translation: "The filtering is based on machine learning. If there are false positives, too bad, even we don't know what's causing them. Try to look less like spam or something?"

donmcronald 5y ago
They should be liable for their shitty ML algorithms. It’s extra detrimental to small businesses who get their email dropped for no good reason. Silently dropping email is malicious IMO.
swiley 5y ago
ML is the software form of cheap plastic crap that quickly breaks.

adevx 5y ago

This sounds similar to my experience with Microsoft based email (Outlook, Hotmail, Live, custom 365 domains) I eventually decided to route Microsoft hosted emails over Amazon SES instead of a VPS hosted Postfix setup. This did help a bit. The fact that all other email providers work perfectly fine and Microsoft is the problematic one I think signals an issue with their spam filtering.

cyborgx7 5y ago

Oh hey, Microsoft is breaking another open decentralized standard again as they are pushing their own proprietary alternative. But let's keep pretending they changed.

pteraspidomorph 5y ago
Speaking as someone who has been running MTAs for more than 15 years - Microsoft has been breaking e-mail for years. They are an order of magnitude more awful than anyone else, and no one should have their e-mail with them for any reason. See also (recent): https://answers.microsoft.com/en-us/outlook_com/forum/all/hotmailoutlook-block-list-s3140-blocks-all-new/699f3a56-406e-4804-97e2-cbe23b9bb01c https://answers.microsoft.com/en-us/outlook_com/forum/all/ho...
- mnw21cam 5y ago
  It all started with top-posting, and went downhill from there.
- jiggawatts 5y ago
  This is why IT should unionise, or form a guild. Imagine if this was turned around, and simultaneously a huge chunk of the world instantly black-holed Office 365 outbound email. Then in response to the roaring noise from Redmond, simply send back their canned response of "Not qualified for mitigation. Our investigation has determined that the above IP(s) do not qualify for mitigation." Do that for 24 hours, then 48 hours, and so on until they smarten up. I guarantee you they'll have their CEO breathing down the necks of every moron in the spam filter team until they fix it. Until then? Nothing will happen. Nothing at all. We'll complain on YC News, we'll complain on /r/sysadmin, and a bunch of small businesses will go out of business. Microsoft 365 will continue to grow to consume the world. Email will be rebranded "Teams Mail", and as far as everyone is concerned that will make perfect sense. Either we act, or we live with the consequences of inaction.
  - pas 5y ago
    Collectivist action is great, when it's great. But with it comes all the usual ossification problems. (For a collective to have power others have to give it to them. Either the collective manages to secure a monopoly, like the various professional licensing/accreditation bodies, legal bar association, medical residency programs with fixed number of slots. Or stakeholders - companies, professionals, regulators - have to join the collective and give up at least some of their independence during the process.) Yes, email is kind of important. But it's also pretty shoddy. It always has been. (Confidentiality, integrity, authentication, signed receipt of delivery. All are important for regular business correspondence and by default all were [and still are] hit and miss with email.) This practice of MS of not accepting email might be abuse of market power. But they can easily say their clients signed up for Outlook to have exactly this protection. What would the courts think? Who knows.

pulse7 5y ago

Governments don't like self-hosting, because they need to ask for data every time they need it. For big hosting providers like Google, Microsoft, Fastmail and others they have mails already. So there are incentives to make it harder and harder to self-host...

nonamesleft 5y ago

I started getting this on our transactional mail relay some years ago, hotmail responded with "Not qualified for mitigation", therefore instead of spending pointless effort dealing with these miserable jollems i used o365 to counter it (my organization was already using o365, which also never did this S3150 thing to me) by: Adding a relay user to the o365 then configuring all the domains i needed to send from on the o365 tenant (without changing the MX records naturally). (Using a normal o365 user account to relay is possible for me as our typical customer base is enterprise and education, not random end users) Adding distribution lists as the from-addresses that i needed to send from and gave send-as rights to the relay user, compiled a list of hotmail/outlook domains (which i've had to add to over the years but it is relatively stable for me by now), then configured the outgoing relay server that does all the dkim-stamping to route all outgoing mail to outlook/hotmail domains through o365. When i see a S3150 in the logs i just add another domain to the list, i should probably make this pre-emptive by looking at the target mx records before sending, as its not trivial to make exim resend something that ended in a 5xx. All other mail providers have removed blocks by simply asking, not hotmail. Also all our newsletter-like mail goes through separate services, these are all transactional mails (meeting invites, user account creation, password resets and such).

agent327 5y ago

Despite all the outrage, there is also this: "As far as I know, emails from my business custmers are branded, formatted following best practices, have unsubscribe links and a valid contact footer." In other words, his customers are sending out the type of emails that actually require unsubscribe links. You know, _spam_. So maybe it isn't Microsoft who is the bad guy here?

anfogoat 5y ago
Microsoft is telling this guy they received the email for delivery and then silently dropped it. If you're not going to deliver an email you either inform the sender or shutdown your mail servers and remove your MX. > Despite all the outrage Hah! Please, there's hardly any. Certainly nowhere close the outrage this deserves.
- agent327 5y ago
  Oh please. It was the commercial spammers that destroyed email as a useful communication medium. Not sending all sorts of useless notifications is just another defence mechanism against those a*holes. Once in a while I still get an undeliverable notification for Chinese spam; they just configured my personal email as their return address, and some stupid mail server decided to tell me it couldn't accept the email. Great job guys, now you're spamming innocent bystanders! So yes, telling people that their spam-load was accepted, and then just not delivering it, seems perfectly fine to me. It's a tough world out there, and it was made that way by precisely the kind of people that need "unsubscribe" links in their emails to begin with. I feel no sympathy for him. These days communication uses web forms, Teams, Skype, Facebook, Twitter, or any other electronic mechanism that isn't email. They are all regulated by their respective owners, so they have a slightly better chance of surviving the onslaught of the advertisers. Email works fine for contact with friends and family, but not for spam, and that's how it should be.
  - account42 5y ago
    Backscatter spam only happens with a misconfigured email service. If you are not going to deliver the mail, reply with an error during submission, don't send a automatic notification email to the return address.

markonen 5y ago

These details about the proprietary "SmartScreen" were really useful. We have been sending login code emails via AWS SES and have had a lot of issues with Hotmail/Outlook.com not delivering them. My takeaways: 1) There's a risk that a shared IP system like AWS SES will get blocked by SmartScreen based on emails someone else is sending. 2) We really should look at the contents of our (trivial) transactional emails, too.

KingMachiavelli 5y ago

Even the user side of Microsoft's email is confusing and prone to loosing emails. O365 defaults or at least the recommended settings will just quarantine emails without notifying anyone. I guess Microsoft doesn't trust users to not open emails in the spam folder? I think I have it configured now to alert the recipient and me on quarantined emails but there are at least two relevant dashboard (Exchange and umm Security Center? who knows what the current names are today) that probably have like 35 submenus and 1000+ settings. Running my own email server would be easier. Another thing, a few months ago I noticed a couple incoming emails were not quarantined/blocked but also not delivered. I don't think the issue has reoccurred since but it's just crazy that emails are just lost sometimes.

fogihujy 5y ago

It's common knowledge that Microsoft considers everyone to be spammers until proven innocent. Getting to a point where your mails end up in the recipients' inboxes is a long path -- Microsoft doesn't care if you set everything up perfectly, as spammers can do the same -- and one has to provide them with enough data to learn to trust one's IP's/ranges/domains. Contacting Microsoft means you have to go through a difficult dance through multiple canned replies, multiple escalation requests, and being lucky enough to get someone to actually escalate. Silently dropping emails isn't Microsoft-specific, though. It's quite common to have a Postfix/Amavis setup set to discard spam over a certain spam score threshold.

NazakiAid 5y ago

Had the same problem as well when sending an email to a client of mine who used Hotmail. Had had successful communications with them in the past 1.5 years then suddenly, bam. Was put on the "S3140 block list". Had to use my personal Gmail to send emails to them. Never emailed another person who used Microsoft email services. Was told my email server was sending spam by them (as people had reported emails from the IP as unwanted), so I did a full security check (using logs, trying to find holes, etc), and upgraded software. No problems that I could find. After lots of back and forth, they said my IP was blocked as it was "suspicious" and they unblocked it (how kind of them). The process took a long time, which I could imagine could be devastating to a small business (luckily my client understood as I made sure to tell them how bad Microsoft is).

fleddr 5y ago

I can only confirm that out of all the email providers, Microsoft is the most tedious, non-standard and brutal when it comes to dropping email. I'm coming from the perspective of a community site owner that pushes out email notifications to its members. Nothing spammy, all emails are opted-in and essential for the basic functioning of the community. They may be as simple as "person X liked your post". It's purely functional email. Plain text, no links, images, nothing. The entire site is non-commercial. Further, the domain from which it is sent is well established (14 years old) and never used for sending out spam. It also has implemented all the best practices, like DMARC, SPF, the like. It's not in the gray zone by any stretch of the imagination. It's as clean as it gets. Yet still, as random as the weather, it's always hotmail.com and live.com users complaining about email not arriving. It's not in their spam folder, it's just not there at all. I never face this issue with any other email provider, only Microsoft. There's no help at all regarding what triggers it, other than the standard document listing best practices I'm already following. They do have some tools to analyze issues, but guess what, only available for high volume email pushers. There's also a public tool to check blocklists, some of which are shared between email providers, yet even when not blocked anywhere, you're still blocked at Microsoft. So after all this self-analysis, I've learned to raise the ticket. Admittedly, occasionally they admit it was a false positive, and then lift the ban. But they never fix anything structurally, it's an issue that keeps coming back. It's maddening. Since I'm in the mood of self-pity, I'll add to this Microsoft-specific problem by mentioning that it's hell to push out email in general for small websites. For example, besides the functional email notifications, there's also an opt-in weekly newsletter. It's found deeply within user's personal settings, so those finding this setting and enabling it, surely want it. Within the range of a few hundred to a few thousand subscribers, now you have a signal problem. A handful of users may no longer want the newsletter and do not unsubscribe (which is easily done from the bottom of each email). Instead, they may delete it, report it as spam, block the sender. These are convenient to do from an email client, but the problem is that I never see their desire to unsubscribe. I'd gladly honor it. What happens instead is that in the case of low volume, just a handful of these negative signals may push all of your email into the spam folder. Technically this is incorrect. It's not spam. The user opted in, the contents of the emails are not spammy, and the user never indicated to not want them anymore. But email providers don't care, it's all spam now. To resolve this, I compare last activity on the site with the user's opt-in status, and auto unsubscribe everybody not recently active, regardless of whether they want this. This significantly reduces the chance of users flagging the email as unwanted in their email client. At the same time, now I have users complaining their newsletters aren't coming. Bottom line: you can't win. With the best of intentions, fully wanting to comply with every technical and legal guidance in the book, it still does not work.

aliswe 5y ago

When these long-winded issues arise, you need to call people up. Email clearly isn't working. You'd be surprised (or not) by the difference verbal communication makes, not only do your verbal expressions translate better, but the tone of voice may (or not) instill trust in the person on the other end.

account42 5y ago
> Email clearly isn't working. It's working just fine for most people. Email sometimes isn't working for Microsoft customers - but that is entirely Microsoft's doing.

nwellnhof 5y ago

On the opposite side, I found Microsoft Azure to be one of the biggest sources of spam on the internet. I have blocked them completely on my private mail server.

jsilence 5y ago

Hashtag MeeToo

Geee 5y ago

Yeah, these problems are consistent with Microsoft email. I've been using Sendgrid to send emails for our SaaS and some customers who use Microsoft email don't receive transactional messages at all. There's nothing you can do about it. Also, seen this happen with other apps too. Transactional messages don't arrive on Microsoft email addresses.

kseistrup 5y ago

Does setting up MTA-STS have any effect on deliverability? I can see in my webserver logs that both Microsoft and Gmail/Google are checking the MTA-STS settings at regular intervals.

account42 5y ago

Microsoft is also the only server operator that will randomly block me. Since I don't host any customers I have decided to simply not care about them and their customers - if someone using microsoft's email services isn't able to get email from me, it's their problem.

dade_ 5y ago

I had to stop using Office365 for business because it kept doing this same thing. I disabled every spam, and protection I could find, and enlisted the help of support. Some legitimate email would simply never arrive and they couldn’t explain why. It seems there are layers of protection, some with no logging (available to the tenant admin) to troubleshoot, it became a huge waste of time, negating the purpose of using a cloud service. In the end I moved to a different service provider and never had the problem again.

QuadrupleA 5y ago

Had this same issue many times sending via AWS (SES). Spent dozens of hours on it with no help from Microsoft, ultimately Amazon had to sort it out with them. Silently dropping mail (not even to the spam folder) is a maddeningly cryptic action on MS's part, and has squandered massive amounts of developer and system administrator time. If you're in a position to sway anybody from using Outlook.com, Hotmail.com, or Msn.com or Live.com I highly encourage it - MS has made a lot of lives difficult with their email policies, including NerdAdmin's here.

Firehawke 5y ago

I've never hit this with GMail, but I've hit this repeatedly with outlook.com/hotmail.com accounts. There's a persistent 20% chance of any given email to my accounts being dropped silently. It's been enough of a headache that I haven't been able to migrate off GMail and that's frustrating as hell. Especially with important medical emails..

ludditetech 5y ago

Kudos Nerd Admin epic post and work through