Outlook email being a bit dodgy...

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kiwifidget

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#305876 10-Jun-2023 17:38

I got this pop up a few days ago and again today, but as far as I know there is nothing wrong with my email, I keep getting emails.

I selected "start sending me emails again" but I didn't get any from MA, and now they are complaining again.

Weirdly, MyHeritage was also complaining about my email address and I've stopped receiving from them as well.

Why would I still be receiving emails from everybody else except for these 2 companies who seem to have lost the ability to send email to me?

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MickeyD

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#3088255 10-Jun-2023 19:34

It's not possible to be sure without seeing the mail server logs, which only Might Ape / MyHeritage and Microsoft will have, but:

The issue is with Outlook.com - the mail service, not Outlook the email client. You get what you pay for in terms of email delivery.

I run a small business with apps that send notification email messages. I have nothing but trouble with @outlook.com and @hotmail.com (they use the same filtering). This filtering is different to that used by Microsoft 365 hosted email.

Outlook.com will reject messages from a mail server based solely on the server IP address, even if that sender has valid SPF, DKIM, and DMARC settings and without being on any black lists, simply because they're received spam from an unrelated mail server with an IP address in the same block.

Mighty Ape (and MyHeritage) can apply to have their sending address unblocked. That will work for a while, until another IP address in the same block triggers their filter again and they get blocked.

So, what can you do? Either ask Mighty Ape to look into it, or get an email address with a provider who doesn't have ridiculous reject policies.

kiwifidget

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#3088271 10-Jun-2023 21:51

MickeyD:

So, what can you do? Either ask Mighty Ape to look into it, or get an email address with a provider who doesn't have ridiculous reject policies.

Any recommendations?

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MickeyD

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#3088275 10-Jun-2023 23:26

kiwifidget:

MickeyD:

So, what can you do? Either ask Mighty Ape to look into it, or get an email address with a provider who doesn't have ridiculous reject policies.

Any recommendations?

I use Microsoft 365 Business Basics. The benefit of doing that with your own domain means you're free to move wherever you want without having to change your address. There are many other providers out there, I just don't have any experience with any others.

I'm sure we'll get some good replies on here from what others are doing that may be cheaper.

cddt

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#3088282 11-Jun-2023 06:21

MickeyD:

I run a small business with apps that send notification email messages. I have nothing but trouble with @outlook.com and @hotmail.com (they use the same filtering). This filtering is different to that used by Microsoft 365 hosted email.

As an outlook.com user (for legacy reasons) I can attest to this. The most frustrating thing (as a user) is that outlook often decides a message is junk several hours after it has been received. So from time to time I will receive an email, read the email, and then when I go back to check it a few hours or days later it is no longer there and has been moved to junk! Thought I was going mad before I worked out what was going on.

kiwifidget

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#3106862 22-Jul-2023 10:44

I've managed to change MA to a gmail address, but its a bit trickier for MyHeritage.

Is there any way I can get Outlook to not reject these emails?

I tried whitelisting the addresses but that did not work.

Who do you even talk to?

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networkn

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#3106869 22-Jul-2023 11:44

MS are becoming increasingly strict on who can send them emails. Technical things like SPF Records, DMARC and DKIM are becoming increasingly important records for a sender to have, otherwise stuff like this happens. Sender reputation etc..

I haven't looked into what records exist for those providers, but @mickeyd have your IT people make sure you have those 3 records, and then see if the issues go away.

You aren't going to get MS to change what they do, nor disclose in any particular detail why messages are being caught, after all it's a free service, with limited support, and for security reasons (as frustrating as that is) they wouldn't likely disclose them anyway, otherwise the spammers could get around it too (potentially).

Email Hygenie is becoming so strict now.

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kiwifidget

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#3106941 22-Jul-2023 13:56

😭

This little tiny emoji totally under represents how I feel right now.

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Lias

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#3106992 22-Jul-2023 14:46

If you don't like the limitations of free email, Exchange Online Plan 1 is a whopping $6 a month.

I'm a geek, a gamer, a dad, a Quic user, and an IT Professional. I have a full rack home lab, size 15 feet, an epic beard and Asperger's. I'm a bit of a Cypherpunk, who believes information wants to be free and the Net interprets censorship as damage and routes around it. If you use my Quic signup you can also use the code R570394EKGIZ8 for free setup. Opinions are my own and not the views of my employer.

mattwnz

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#3106993 22-Jul-2023 14:59

I was getting this same issue with an xtra.co.nz email address.

linw

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#3106996 22-Jul-2023 15:33

Been many years on gmail and never seen an issue as described.

Gmail has a darn good spam filter as well.

kiwifidget

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#3106998 22-Jul-2023 15:36

Lias:

If you don't like the limitations of free email, Exchange Online Plan 1 is a whopping $6 a month.

My yearly subscription to Office365 Family doesn't count?

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MickeyD

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#3106999 22-Jul-2023 16:07

networkn:

I haven't looked into what records exist for those providers, but @mickeyd have your IT people make sure you have those 3 records, and then see if the issues go away.

You aren't going to get MS to change what they do, nor disclose in any particular detail why messages are being caught, after all it's a free service, with limited support, and for security reasons (as frustrating as that is) they wouldn't likely disclose them anyway, otherwise the spammers could get around it too (potentially).

I might not have explained myself well @networkn.

I maintain my own mail server for my web apps; and maintain my DNS records. This carries quite a lot of work to maintain security and protect my sender reputation. For non-web app company emails I'm using Microsoft 365.

The domain I send mail from for the web app has valid SPF, DKIM, rDNS, and DMARC records. The IP of this mail server is not on any blacklists. I do not have any issues delivering mail from this mail server to domains other than @hotmail.com and @outlook.com.

Contrary to your message, the hotmail server does provide reasons why the messages are being rejected. Their policy is frustrating if you don't have control of the whole /24 address space, as they'll block delivery if you're in the same /24 space as someone they've added to their own internal block list:

Remote host said: 550 5.7.1 Unfortunately, messages from [XXX.XXX.XXX.XXX] weren't sent. Please contact your Internet service provider since part of their network is on our block list (S3150).

As a user, @kiwifidget has no control over any of that process, other than to choose a different email address. The website maintainer (e.g. in this case MightyApe) has to apply at http://go.microsoft.com/fwlink/?LinkID=614866 to remove themselves from the block list.

MickeyD

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#3107000 22-Jul-2023 16:18

kiwifidget:

My yearly subscription to Office365 Family doesn't count?

If you host your domain with godaddy, and sign up before Nov 30th, you can have that email hosted as part of your Microsoft 365 family setup.

See https://support.office.com/en-gb/article/Get-a-personalized-email-address-in-Office-365-75416a58-b225-4c02-8c07-8979403b427b

kiwifidget

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#3107002 22-Jul-2023 17:00

MickeyD:

kiwifidget:

My yearly subscription to Office365 Family doesn't count?

If you host your domain with godaddy, and sign up before Nov 30th, you can have that email hosted as part of your Microsoft 365 family setup.

See http://go.microsoft.com/fwlink/?LinkID=614866

Thanks, but is that the right link?

It's the same as the one in your earlier post that you said Mighty Ape should use.

(OLC Support Form)

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MickeyD

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#3107007 22-Jul-2023 17:17

kiwifidget:

Thanks, but is that the right link?

It's the same as the one in your earlier post that you said Mighty Ape should use.

(OLC Support Form)

Whoops. It should be this one. I've updated the link in my earlier message now.

For full disclosure, I haven't used this feature myself yet.