1 Topic by djones9960 (edited by djones9960 2023-01-24 09:26:33)

  • djones9960
  • Member
  • Offline
  • Registered: 2023-01-24
  • Posts: 9

Topic: Mail sent to Outlook.com mail addresses sent to spam

==== REQUIRED BASIC INFO OF YOUR IREDMAIL SERVER ====
- iRedMail version (check /etc/iredmail-release): 2021091301 (mariadb backend, dockerized eidtion:
- Deployed with iRedMail Easy or the downloadable installer? docker
- Linux/BSD distribution name and version: Debian 11
- Store mail accounts in which backend (LDAP/MySQL/PGSQL): MySQL
- Web server (Apache or Nginx): Nginx
- Manage mail accounts with iRedAdmin-Pro? No.
- [IMPORTANT] Related original log or error message is required if you're experiencing an issue.
====

Hi

I have a ticket in for this with MS but I'm not having much luck with it, so I'm posting here (hopefully someone else has come across this). Mail from my server to gmail, yahoo etc is fine but when I send to MS-affiliated mail addresses (hotmail, outlook & people who pay for Office 365 mail) my mail is going to Junk with an SCL of 5.

I've checked and mxtoolbox reckons my mail is fine, mail-tester dot com gives me 10/10 and checktls dot com gives me OKs across the board (with the exception being DANE which I haven't selected for it to check anyway and shouldn't affect deliverability). Microsoft counts the IP as 'normal' (as in, no complaints received).

This mail was working yesterday, then I updated the SSL keys (all the tests above I re-ran when I did this and they are fine). Now all the mails are 'junk'.

I'm tearing my hair out. It's infuriating.

Anyone come across this? I'd be eternally grateful for any help.

EDIT: I put the old keys back (they aren't expired yet) and the same thing happens. So I'm thinking it's not the keys at all, it's something else. Goodness only knows what, though.

----

Spider Email Archiver: On-Premises, lightweight email archiving software developed by iRedMail team. Supports Amazon S3 compatible storage and custom branding.

2 Reply by jackb (edited by jackb 2023-01-24 16:24:33)

  • jackb
  • Member
  • Offline
  • From: Ireland
  • Registered: 2019-05-06
  • Posts: 118

Re: Mail sent to Outlook.com mail addresses sent to spam

This is a common problem, most likely the Public IP and CIDR has not been added to Microsofts ACL, if your IP and CIDR is not added to Microsofts ACL emails will go into spam or rejected meaning a bounce back email.

Something else to look at, make sure that SPF, DKIM and DMARC is properly implemented if not then this will cause problems. On a lot of Mail Deployment I have done I have always added the Public IP and CIDR to Microsofts ACL which will fix the mail going into SPAM.

Take a look at https://sender.office.com/

3 Reply by djones9960 (edited by djones9960 2023-01-24 18:10:38)

  • djones9960
  • Member
  • Offline
  • Registered: 2023-01-24
  • Posts: 9

Re: Mail sent to Outlook.com mail addresses sent to spam

Thanks for replying; I really wish it were that simple.

First of all, mxtoolbox, mail-tester and checktls check things like DKIM and SPF and they are fine.

Second, the IP is already down as a sender; I'm on SNDS and the IP status is down as 'Normal'.

Still, I tried what you said; it said 'denied' (presumably because the IP address isn't blacklisted) but I clicked to raise it to support anyway (it can't hurt; their deliverability support people have been back to me already and they were of no use).

This is a nightmare.

Thanks anyway though!

4 Reply by jackb

  • jackb
  • Member
  • Offline
  • From: Ireland
  • Registered: 2019-05-06
  • Posts: 118

Re: Mail sent to Outlook.com mail addresses sent to spam

djones9960 wrote:

Thanks for replying; I really wish it were that simple.

First of all, mxtoolbox, mail-tester and checktls check things like DKIM and SPF and they are fine.

Second, the IP is already down as a sender; I'm on SNDS and the IP status is down as 'Normal'.

Still, I tried what you said; it said 'denied' (presumably because the IP address isn't blacklisted) but I clicked to raise it to support anyway (it can't hurt; their deliverability support people have been back to me already and they were of no use).

This is a nightmare.

Thanks anyway though!

Sometimes Microsoft denies but you can appeal it, something to ask is this on Prem or Cloud based Server? because if it's Cloud based then there's the reason why Microsoft is blocking it, a lot of spammers use Cloud based VPS's to send SPAM, so the IP Address of the provider is automatically on blacklists.

5 Reply by djones9960

  • djones9960
  • Member
  • Offline
  • Registered: 2023-01-24
  • Posts: 9

Re: Mail sent to Outlook.com mail addresses sent to spam

Hi

No, it's on a docker container running in a VM on a desktop server I have upstairs smile

I have a VM business account and the IP is static and has PTR set correctly. Although it is relatively new - I only got the static IPs at around the end of 2022 (just before Christmas I think).

Like I say, the IP isn't blacklisted anywhere. It has no reputation whatsoever in fact - maybe that's actually Microsoft's problem. Smaller servers get sent to spam, whereas larger servers (which actually are sending out spam) get through due to volume.

If the Outlook facebook group is to believed a lot gets through, anyway. There's no end of people on there moaning about torrents of spam!

6 Reply by ZhangHuangbin

  • ZhangHuangbin
  • ZhangHuangbin
  • iRedMail Developers
  • Offline
  • Registered: 2009-05-06
  • Posts: 31,131

Re: Mail sent to Outlook.com mail addresses sent to spam

We don't control how Outlook servers judge the received emails, so it's hard for us to help.
You have to contact Outlook instead.

7 Reply by djones9960

  • djones9960
  • Member
  • Offline
  • Registered: 2023-01-24
  • Posts: 9

Re: Mail sent to Outlook.com mail addresses sent to spam

I know; I was just wondering whether (hoping, actually) I'd just missed something!

I have been in touch with Microsoft but I get canned messages from them (talking about adding 'do not send me any more email' headers and whatnot when I'm not operating mailing lists and have already told them that etc).

It's like talking to a brick wall with a recorded message on loop playing behind it.

I will open another ticket with them but I'm not expecting much. It's infuriating, as far as I can see there's nothing wrong with my setup and everyone (apart from Microsoft) seems to agree with that.

Thanks for replying!

8 Reply by chris.23lo

  • chris.23lo
  • Member
  • Offline
  • Registered: 2022-06-30
  • Posts: 54

Re: Mail sent to Outlook.com mail addresses sent to spam

greetings.

check your ip with https://check.spamhaus.org/ and manually unlist your external smtp ip address.

it should work for quite a while, but spamhaus may re-enlist it some time later. if you can talk to the ip owner, talk to them, but it probably longer than you expect.

cheers.

9 Reply by djones9960

  • djones9960
  • Member
  • Offline
  • Registered: 2023-01-24
  • Posts: 9

Re: Mail sent to Outlook.com mail addresses sent to spam

Hi

Thanks for replying, but, and I believe I've said this before, my IP isn't listed on any spam lists. Anywhere. Chiefly, probably, because I *don't* send spam from it and it has no history of being a spam address either (that's the first thing I did when I got the static IP - check it was clean).

I did what you said and it said my IP had 'no issues', with a happy-looking picture of a bot. Not only that, but my IP isn't listed *anywhere* as having any issues of that type.

Microsoft have no reason to give me an SCL of 5 as far as I can see other than I'm small-fry.

Post's attachments

mxtoolbox_spam_listings.jpg
mxtoolbox_spam_listings.jpg 39.02 kb, file has never been downloaded. 

You don't have the permssions to download the attachments of this post.

10 Reply by jackb (edited by jackb 2023-01-30 18:11:13)

  • jackb
  • Member
  • Offline
  • From: Ireland
  • Registered: 2019-05-06
  • Posts: 118

Re: Mail sent to Outlook.com mail addresses sent to spam

djones9960 wrote:

Hi

Thanks for replying, but, and I believe I've said this before, my IP isn't listed on any spam lists. Anywhere. Chiefly, probably, because I *don't* send spam from it and it has no history of being a spam address either (that's the first thing I did when I got the static IP - check it was clean).

I did what you said and it said my IP had 'no issues', with a happy-looking picture of a bot. Not only that, but my IP isn't listed *anywhere* as having any issues of that type.

Microsoft have no reason to give me an SCL of 5 as far as I can see other than I'm small-fry.

Out of ideas i'm afraid. I'm hosting about 23 Domains on mx1 and mx2 and don't have problems. If your emails are going straight into SPAM then this could be a issue with SPF, DMARC, DKIM and IP Address / CIDR is not on Microsofts ACL.

Something to ask, what is your TXT Record for SPF ? (Senders Policy Framework)

11 Reply by djones9960

  • djones9960
  • Member
  • Offline
  • Registered: 2023-01-24
  • Posts: 9

Re: Mail sent to Outlook.com mail addresses sent to spam

Hi

Microsoft's own checkers pass those things. This is from the headers of one of the 'Junk' emails:

Authentication-Results: spf=pass (sender IP is xx.xx.xx.xx) smtp.mailfrom=<URL>; dkim=pass (signature was verified) header.d=<URL>;dmarc=pass action=none header.from=<URL>;compauth=pass reason=100 Received-SPF: Pass (protection.outlook.com: domain of <URL> designates <IP> as permitted sender) receiver=protection.outlook.com; client-ip=<IP>; helo=<mail_URL>; pr=C

I'm down as monitor for the IP (I'm in MSDS) and the IP is down as 'normal'.

The SPF is:
v=spf1 ip4:<IP> include:<second_URL> -all

(Note the email was already going to spam before I added the second URL, and this URL, incidentally, passes all those checks too)

One thing is that the IP of the server and the client IP are the same (as I am using the same connection as the server). That couldn't be it, could it?

12 Reply by jackb (edited by jackb 2023-01-30 19:04:25)

  • jackb
  • Member
  • Offline
  • From: Ireland
  • Registered: 2019-05-06
  • Posts: 118

Re: Mail sent to Outlook.com mail addresses sent to spam

djones9960 wrote:

Hi

Microsoft's own checkers pass those things. This is from the headers of one of the 'Junk' emails:

Authentication-Results: spf=pass (sender IP is xx.xx.xx.xx) smtp.mailfrom=<URL>; dkim=pass (signature was verified) header.d=<URL>;dmarc=pass action=none header.from=<URL>;compauth=pass reason=100 Received-SPF: Pass (protection.outlook.com: domain of <URL> designates <IP> as permitted sender) receiver=protection.outlook.com; client-ip=<IP>; helo=<mail_URL>; pr=C

I'm down as monitor for the IP (I'm in MSDS) and the IP is down as 'normal'.

The SPF is:
v=spf1 ip4:<IP> include:<second_URL> -all

(Note the email was already going to spam before I added the second URL, and this URL, incidentally, passes all those checks too)

One thing is that the IP of the server and the client IP are the same (as I am using the same connection as the server). That couldn't be it, could it?

That is wrong, you are not using outlook/exchange, you are using Postfix and Dovecot so using protection.outlook.com for SPF will go against the Server. in theory you need "v=spf1 ip4:/19 -all" this is what I use. change the IP to your WANs IP also if you have WAN2 and sending mail then you will need to add the second IP.

13 Reply by djones9960 (edited by djones9960 2023-01-30 20:53:01)

  • djones9960
  • Member
  • Offline
  • Registered: 2023-01-24
  • Posts: 9

Re: Mail sent to Outlook.com mail addresses sent to spam

Please read my comment again.

The excerpt headers were from a resultant (sent to spam) email sent to an outlook.com/hotmail.com address, and as I said they passed the SPF. I've been told (by them) that the mails are being caught by their 'smartscreen' filter.

Because of its 'proprietary' nature, they say they can't discuss how it works. They implied that my mails must just look like spam to it.

I replied that I copied and pasted the contents of one of their own emails to me and sent that from that address and it was still sent to spam. They have yet to reply to that email.

14 Reply by g40

  • g40
  • Member
  • Offline
  • Registered: 2017-01-05
  • Posts: 17

Re: Mail sent to Outlook.com mail addresses sent to spam

djones9960 wrote:

==== REQUIRED BASIC INFO OF YOUR IREDMAIL SERVER ====
- iRedMail version (check /etc/iredmail-release): 2021091301 (mariadb backend, dockerized eidtion:
- Deployed with iRedMail Easy or the downloadable installer? docker
- Linux/BSD distribution name and version: Debian 11
- Store mail accounts in which backend (LDAP/MySQL/PGSQL): MySQL
- Web server (Apache or Nginx): Nginx
- Manage mail accounts with iRedAdmin-Pro? No.
- [IMPORTANT] Related original log or error message is required if you're experiencing an issue.
====

Hi

I've checked and mxtoolbox reckons my mail is fine ...

Just a thought. Have you subscribed to MXToolbox blacklist monitor? You might find you are on some obscure blacklist that you never knew existed. One of the more obscure regularly blacklists the entire range of IPV4 addresses assigned to Linode. And they do not give a f**k about doing so.

15 Reply by djones9960 (edited by djones9960 2023-01-31 02:58:49)

  • djones9960
  • Member
  • Offline
  • Registered: 2023-01-24
  • Posts: 9

Re: Mail sent to Outlook.com mail addresses sent to spam

Hi

Thanks for replying; the image I posted above was of an mxtoolbox blacklist check, does their blacklist monitor (which I just signed up for) scan for more than that?