The Hotmail complaint saga continues

Hi,
Last week I wrote this list about a situation where I'd received an Email from staff@hotmail.com with the subject, "complaint about message from MYI.PAD.DRE.SS." Then later I received a second such message, identified both complainants as the same person, let her know she'd be put on No Mail if she did it again, and received a response from her saying she's never marked one of my messages as spam or junk.
The other night I received a third such complaint, duly put her on No Mail, and sent her an Email about it. At that point, I was pretty sure these complaints were being generated by some automated process, since they always came in within two to four minutes of the original messages going out. However, this theory was somewhat squashed when she supposedly complained about the very message telling her that due to complaints she was on No Mail…then responded, indicating she has COVID-19 and is putting off everything not critical until later. I sent that message yesterday morning, and the complaint came in this evening, with her response coming about twenty minutes later. This makes me think she's doing something to cause a complaint to be generated, and doesn't realize she's doing it. My questions are as follows:
- Is Linode, my VPS provider, also receiving these complaints? If so,
I'm surprised they haven't at least sent me a notice telling me about them.
- Does anyone know if having received these complaints might cause
Microsoft to be more likely to add my IP to their infamous block list? If they do, I'm going to be in a bad position, because they'd be well within their rights to say, "You've received four complaints within the last three weeks, so no, we won't mitigate anything for you. Get your Email sending practices in order, then maybe someday we'll talk."
- I haven't ever received such complaints before this situation started
on March 24. Is Microsoft noted for somehow generating spurious complaints like this? If so, is that the reason I'm not getting hounded about it from Linode, the "Little Boy who Cried Wolf" situation?
Thanks for any thoughts,
Jayson

Jayson Smith writes:
- Is Linode, my VPS provider, also receiving these complaints? If so,
I'm surprised they haven't at least sent me a notice telling me about them.
Seems unlikely, both on general principles and since you haven't heard from them.
Have you confirmed that these notifications are really from Hotmail staff (or an automated process there)? Although other things equal it's unlikely, the most likely possibility (the subscriber complained) is denied by the subscriber so it could theoretically be some third party trying to mess with you or the subscriber.
Also, have you confirmed that it's actually the specific messages from you or your list that were cited? Is it possible that some spammer is spoofing your return address, and the subscriber is legitimately complaining about mail that to the email provider appear to be from you but to the subscriber are from somebody else? Is it possible your Linode VPS has been hacked, or the MTA is an open relay, and is being used to send spam? If you've confirmed that the complaints are citing mail you know you sent, these possibilities don't apply, and they're fairly unlikely anyway given that it's only one subscriber that's having the issue.
- Does anyone know if having received these complaints might cause
Microsoft to be more likely to add my IP to their infamous block list?
More likely, yes, but how much more likely, you'd have to get an answer from Microsoft. I don't know anybody who has gotten anything useful out of them, though. Mistaken additions to block lists anywhere seem to quite random for good actors, and the blockers are rarely willing to explain what the problem was, or how to avoid it.
You could try explaining the situation to staff@hotmail, and get the subscriber to do so too. But I wouldn't expect too much.
You could also look up what their mitigation strategies, if any, are. Some providers have services you can sign up to which provide more information about complaints, and guidelines on how to keep your list(s) in good standing with the providers. I don't know about Microsoft/Hotmail.
There are also some general rules:
- Check that your server is not in any of the reputable RBLs. I don't have a list offhand. (A couple of RBLs are known to shake down sites by putting them in bad actor lists and then asking for money for a "service" to help clean your reputation. The big providers like Hotmail know who they are and ignore them, you probably can ignore them too.)
- Make sure that your DNS has correct configurations for SPF and DKIM. Make sure that your signing keys are correct. It may halp a little to do DMARC, too, even if you just set a policy of p=none. If your lists accept posts from off-host, you likely would benefit from configuring ARC as well.
- Everything that goes *in* to your MTA *except from Mailman* should be spam- and virus-filtered. That should include mail generated on the Mailman host. Then you can safely forward all mail from Mailman. (Filtering mail *from* Mailman on the way out is very expensive unless you have very few subscribing domains.)
- If your lists are open subscription and of moderate size, and you don't require moderator approval of subscriptions, we recommend setting all new subscribers to "hold for moderation". If the first post is acceptable, then set them to default processing or accept. For many lists that nearly eliminates "drive-by" spams and other unwanted posts. YMMV of course.
- I haven't ever received such complaints before this situation started
on March 24. Is Microsoft noted for somehow generating spurious complaints like this?
Not that I've heard of. Maybe somebody else has. The only case I know of like that was AOL, which put the "Report Spam" button next to the "Delete Message" button. Perhaps Hotmail has a similar issue, but I haven't heard of it. You could ask the subscriber if it's possible she missed and hit the wrong button, but since she's already denied doing that, you'll have to be careful about it.
I'm sorry not to be of more help, but given that big providers like Microsoft are never willing to engage in situations like this, there's little information in the public domain. I'm afraid you're going to have to work it out with the subscriber.

Hi,
I can confirm that the complaints do cite messages I am sending, and know I'm sending. Does anyone know if Microsoft has made any changes to their Email user interface recently that would make marking something as spam or junk by mistake easier than it was before? This problem started out of the blue on March 24. If it makes any difference, the specific subscriber involved has an Email address at msn.com, and she's been subscribed to the list for close to two years with no problem.
Jayson
On 4/15/2022 1:25 AM, Stephen J. Turnbull wrote:
Jayson Smith writes:
- Is Linode, my VPS provider, also receiving these complaints? If so,
I'm surprised they haven't at least sent me a notice telling me about them.
Seems unlikely, both on general principles and since you haven't heard from them.
Have you confirmed that these notifications are really from Hotmail staff (or an automated process there)? Although other things equal it's unlikely, the most likely possibility (the subscriber complained) is denied by the subscriber so it could theoretically be some third party trying to mess with you or the subscriber.
Also, have you confirmed that it's actually the specific messages from you or your list that were cited? Is it possible that some spammer is spoofing your return address, and the subscriber is legitimately complaining about mail that to the email provider appear to be from you but to the subscriber are from somebody else? Is it possible your Linode VPS has been hacked, or the MTA is an open relay, and is being used to send spam? If you've confirmed that the complaints are citing mail you know you sent, these possibilities don't apply, and they're fairly unlikely anyway given that it's only one subscriber that's having the issue.
- Does anyone know if having received these complaints might cause
Microsoft to be more likely to add my IP to their infamous block list?
More likely, yes, but how much more likely, you'd have to get an answer from Microsoft. I don't know anybody who has gotten anything useful out of them, though. Mistaken additions to block lists anywhere seem to quite random for good actors, and the blockers are rarely willing to explain what the problem was, or how to avoid it.
You could try explaining the situation to staff@hotmail, and get the subscriber to do so too. But I wouldn't expect too much.
You could also look up what their mitigation strategies, if any, are. Some providers have services you can sign up to which provide more information about complaints, and guidelines on how to keep your list(s) in good standing with the providers. I don't know about Microsoft/Hotmail.
There are also some general rules:
- Check that your server is not in any of the reputable RBLs. I don't have a list offhand. (A couple of RBLs are known to shake down sites by putting them in bad actor lists and then asking for money for a "service" to help clean your reputation. The big providers like Hotmail know who they are and ignore them, you probably can ignore them too.)
- Make sure that your DNS has correct configurations for SPF and DKIM. Make sure that your signing keys are correct. It may halp a little to do DMARC, too, even if you just set a policy of p=none. If your lists accept posts from off-host, you likely would benefit from configuring ARC as well.
- Everything that goes *in* to your MTA *except from Mailman* should be spam- and virus-filtered. That should include mail generated on the Mailman host. Then you can safely forward all mail from Mailman. (Filtering mail *from* Mailman on the way out is very expensive unless you have very few subscribing domains.)
- If your lists are open subscription and of moderate size, and you don't require moderator approval of subscriptions, we recommend setting all new subscribers to "hold for moderation". If the first post is acceptable, then set them to default processing or accept. For many lists that nearly eliminates "drive-by" spams and other unwanted posts. YMMV of course.
- I haven't ever received such complaints before this situation started
on March 24. Is Microsoft noted for somehow generating spurious complaints like this?
Not that I've heard of. Maybe somebody else has. The only case I know of like that was AOL, which put the "Report Spam" button next to the "Delete Message" button. Perhaps Hotmail has a similar issue, but I haven't heard of it. You could ask the subscriber if it's possible she missed and hit the wrong button, but since she's already denied doing that, you'll have to be careful about it.
I'm sorry not to be of more help, but given that big providers like Microsoft are never willing to engage in situations like this, there's little information in the public domain. I'm afraid you're going to have to work it out with the subscriber.

2-3 years ago on Groups.io groups this began happening. It is related to the new privacy laws. When a message is marked as SPAM at any level, groups.io is required to unsubscribe the person. Groups.io handles this by immediately sending a message to the person telling them why they were unsubscribed and including a link to resubscribe.
I happens 2-3 times a month now. No one knows which level the unsubscribe order came from. One explanation for why it happens on some services and not others is that the larger companies (Yahoo and Google) get away with not doing it but smaller ones have to comply.
I have no more information than that. My Groups.io lists have learned to live with it.
I did have to ask one person with an AOL address to please change because she was unsubscribed many times over several days -- 12 times in 24 hours. She had no idea what was doing the SPAM marking. I think she must have been the last AOL user in the area.
I have no more information than that.
Sharon
On Apr 15, 2022, at 9:21 AM, Jayson Smith jaybird@bluegrasspals.com wrote:
Hi,
I can confirm that the complaints do cite messages I am sending, and know I'm sending. Does anyone know if Microsoft has made any changes to their Email user interface recently that would make marking something as spam or junk by mistake easier than it was before? This problem started out of the blue on March 24. If it makes any difference, the specific subscriber involved has an Email address at msn.com, and she's been subscribed to the list for close to two years with no problem.
Jayson
On 4/15/2022 1:25 AM, Stephen J. Turnbull wrote:
Jayson Smith writes:
- Is Linode, my VPS provider, also receiving these complaints? If so,
I'm surprised they haven't at least sent me a notice telling me about them.
Seems unlikely, both on general principles and since you haven't heard from them.
Have you confirmed that these notifications are really from Hotmail staff (or an automated process there)? Although other things equal it's unlikely, the most likely possibility (the subscriber complained) is denied by the subscriber so it could theoretically be some third party trying to mess with you or the subscriber.
Also, have you confirmed that it's actually the specific messages from you or your list that were cited? Is it possible that some spammer is spoofing your return address, and the subscriber is legitimately complaining about mail that to the email provider appear to be from you but to the subscriber are from somebody else? Is it possible your Linode VPS has been hacked, or the MTA is an open relay, and is being used to send spam? If you've confirmed that the complaints are citing mail you know you sent, these possibilities don't apply, and they're fairly unlikely anyway given that it's only one subscriber that's having the issue.
- Does anyone know if having received these complaints might cause
Microsoft to be more likely to add my IP to their infamous block list?
More likely, yes, but how much more likely, you'd have to get an answer from Microsoft. I don't know anybody who has gotten anything useful out of them, though. Mistaken additions to block lists anywhere seem to quite random for good actors, and the blockers are rarely willing to explain what the problem was, or how to avoid it.
You could try explaining the situation to staff@hotmail, and get the subscriber to do so too. But I wouldn't expect too much.
You could also look up what their mitigation strategies, if any, are. Some providers have services you can sign up to which provide more information about complaints, and guidelines on how to keep your list(s) in good standing with the providers. I don't know about Microsoft/Hotmail.
There are also some general rules:
- Check that your server is not in any of the reputable RBLs. I don't have a list offhand. (A couple of RBLs are known to shake down sites by putting them in bad actor lists and then asking for money for a "service" to help clean your reputation. The big providers like Hotmail know who they are and ignore them, you probably can ignore them too.)
- Make sure that your DNS has correct configurations for SPF and DKIM. Make sure that your signing keys are correct. It may halp a little to do DMARC, too, even if you just set a policy of p=none. If your lists accept posts from off-host, you likely would benefit from configuring ARC as well.
- Everything that goes *in* to your MTA *except from Mailman* should be spam- and virus-filtered. That should include mail generated on the Mailman host. Then you can safely forward all mail from Mailman. (Filtering mail *from* Mailman on the way out is very expensive unless you have very few subscribing domains.)
- If your lists are open subscription and of moderate size, and you don't require moderator approval of subscriptions, we recommend setting all new subscribers to "hold for moderation". If the first post is acceptable, then set them to default processing or accept. For many lists that nearly eliminates "drive-by" spams and other unwanted posts. YMMV of course.
- I haven't ever received such complaints before this situation started
on March 24. Is Microsoft noted for somehow generating spurious complaints like this?
Not that I've heard of. Maybe somebody else has. The only case I know of like that was AOL, which put the "Report Spam" button next to the "Delete Message" button. Perhaps Hotmail has a similar issue, but I haven't heard of it. You could ask the subscriber if it's possible she missed and hit the wrong button, but since she's already denied doing that, you'll have to be careful about it.
I'm sorry not to be of more help, but given that big providers like Microsoft are never willing to engage in situations like this, there's little information in the public domain. I'm afraid you're going to have to work it out with the subscriber.
Mailman-Users mailing list -- mailman-users@python.org To unsubscribe send an email to mailman-users-leave@python.org https://mail.python.org/mailman3/lists/mailman-users.python.org/ Mailman FAQ: http://wiki.list.org/x/AgA3 Security Policy: http://wiki.list.org/x/QIA9 Searchable Archives: https://www.mail-archive.com/mailman-users@python.org/ https://mail.python.org/archives/list/mailman-users@python.org/

We (https://sjdm.org) had a different problem with Hotmail, but it might be related. We are a nonprofit society with a couple of mailing lists, one of which has over 4000 members from around the world. When we moved to Linode (from my office desktop), we had many problems of the sort that Stephen Turnbull described, particularly with our ipv6 address, but I won't discuss those because Microsoft uses ipv4.
Occasionally, every couple of months, we would be unable to send mail to any Microsoft address. These included @hotmail (sometimes hotmail.de or other countries), @outlook, @live and @msn, mostly the first two. There is a complaint procedure here: https://support.microsoft.com/supportrequestform/8ad563e3-288e-2a61-8122-3ba... We went through it, but it didn't do much good. Usually the problem would go away after a few days, but I now think that our complaints had nothing to do with the problem going away. See below.
We also signed up for Sender Support. https://sendersupport.olc.protection.outlook.com/pm/junkemail.aspx and SNDS, e.g. https://sendersupport.olc.protection.outlook.com/snds/FAQ.aspx and https://sendersupport.olc.protection.outlook.com/snds/data.aspx The last thing did list "complaints", but this did not seem to be the problem. There were very few.
The typical message we got when our mail did not get through was this:
"Unfortunately, messages from [45.79.135.144] weren't sent. Please contact your Internet service provider since part of their network is on our block list (S3150)."
The problem is that we do not control "their network" except for the single ipv4 address we use [45.79.135.144]. Microsoft may be looking at other people who use Linode. Once I asked the Linode staff to help, and they complained to Microsoft, explaining the situation, and it got better for a while. I now think that their complaint had nothing to do with the problem getting better. There was nothing else Linode can do except try to monitor every one of their users for spam, and they do not do that. I think that Microsoft may have a (much more expensive) cloud service that works that way, but I am pretty sure that Amazon Web Services does not. The Hotmail/Outlook problem comes and goes.
Occasionally, we would complain and get responses from what appeared to be a person. I now think it was not a person, since the message was always the same. Below is an example. That one came in the middle of a block that lasted for a few weeks.
In the end, we decided to prevent users with Microsoft addresses from signing up for anything, including membership in the Society. So far we have received no complaints about that. All these addresses were automatically removed from our mailing list by Mailman, in the last outage, which was very long, and I did not put them back.
Our main mailing list has over 4000 members with almost 1000 different domains. The only domains that ever block our mail are those controlled by Microsoft, about 90 people (many who already signed up with a different address and never unsubscribed their Microsoft address). Usually every single post to our mailing list goes through, except for occasional "user not found" and "over quota".
My opinion, FWIW, is that Microsoft should not be running an email service of any sort. Verizon is shutting its service down (or already did), and Microsoft should do the same.
#######################
Subject: RE: SRX1530278720ID - [EXTERNAL] Re: Reported deliverability problem to Outlook.com SRX1530278720ID X-Mailer: Microsoft Avondale Mailer
Hello,
My name is Sai and I work with the Outlook.com Deliverability Support Team.
We continue to look into this issue along with the Escalations Team. We understand the urgency of this issue and will provide an update as soon as this is available. Rest assured that this ticket is being tracked and we will get back to you as soon as we have more information to offer.
Thank you for your patience.
Sincerely,
Sai Outlook.com Deliverability Support

Hi Jayson,
... This makes me think she's doing something to cause a complaint to be generated, and doesn't realize she's doing it. ...
We get a fairly steady stream of these "complaint" messages from "staff[AT]hotmail". They don't seem to amount to much and I'm guessing they're simply a result of people leaving messages in their junk folder (where they've been delivered automatically).
- Is Linode, my VPS provider, also receiving these complaints? If so, I'm surprised they haven't at least sent me a notice telling me about them.
The "complaint" messages that we receive are addressed to "postmater[AT]the.sending.servers.domain". They don't appear to be BCCed to the hosting company.
- Does anyone know if having received these complaints might cause Microsoft to be more likely to add my IP to their infamous block list? ...
Quite possibly it does. Once or twice a year Microsoft will block our list messages. The log files will show that our server is on their network block. The process is then:
A. Check that ALL your DNS records are in order (double check your DMARC, DKIM, SOA) and that your IP isn't blacklisted anywhere: https://mxtoolbox.com
B. Check that your server's IP reputation is okay at: https://talosintelligence.com
C. If you're all good with A and B, complete Microsoft's de-list form - https://sender.office.com
D. Your request will generally be refused initially so you need to reply (sometimes more than once) and explain that all your records are in order, the nature of your list, subscribers are double-opt in, and the measures you have put in place to prevent spam being sent.
E. I've found them to be responsive and generally there is a positive result within a day or two.
/Mark
participants (5)
-
Jayson Smith
-
Jon Baron
-
Mark Dale
-
Sharon Villines
-
Stephen J. Turnbull