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Mail Accounts Remaining Open After Program Closed

Hello,


I'm having an odd problem with mail accounts.


I'm using several Microsoft and Gmail accounts through the Apple Mail app on an M1 iMac that is always running the latest OS. About once a week, I need to use a VPN to connect outside my region (Northeastern US). I learned early on that if the mail app was open, the Microsoft accounts would identify an unusual connection and cause a variety of issues. I made it a habit of always shutting down the mail app before connecting the VPN and it was resolved.


In the past several months, that's no longer a solution. When I connect my VPN, even with mail closed, it triggers Microsoft to detect an unusual connection. Is there a change about how online account connection runs in the background or something else that may explain this?


This seems minor, but it results in about 15 alert texts and emails, having to reset my Microsoft passwords, then update those passwords in many device's mail apps, xbox, Windows Store, etc... EVERY single week and is driving me crazy.

iMac 24″, macOS 12.5

Posted on Aug 26, 2022 6:18 AM

Reply
Question marked as Top-ranking reply

Posted on Aug 27, 2022 8:14 AM

danh62103 wrote:

Hello,

I'm having an odd problem with mail accounts.

I'm using several Microsoft and Gmail accounts through the Apple Mail app on an M1 iMac that is always running the latest OS. About once a week, I need to use a VPN to connect outside my region (Northeastern US). I learned early on that if the mail app was open, the Microsoft accounts would identify an unusual connection and cause a variety of issues. I made it a habit of always shutting down the mail app before connecting the VPN and it was resolved.

In the past several months, that's no longer a solution. When I connect my VPN, even with mail closed, it triggers Microsoft to detect an unusual connection. Is there a change about how online account connection runs in the background or something else that may explain this?

This seems minor, but it results in about 15 alert texts and emails, having to reset my Microsoft passwords, then update those passwords in many device's mail apps, xbox, Windows Store, etc... EVERY single week and is driving me crazy.



Try disabling the VPN and compare your results...



A true VPN tunnel, for example between you and your job, or a Bank server would be of value, otherwise might be time to re-think the usage.


see: Public VPN's are anything but private

https://gist.github.com/joepie91/5a9909939e6ce7d09e29


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7 replies
Question marked as Top-ranking reply

Aug 27, 2022 8:14 AM in response to danh62103

danh62103 wrote:

Hello,

I'm having an odd problem with mail accounts.

I'm using several Microsoft and Gmail accounts through the Apple Mail app on an M1 iMac that is always running the latest OS. About once a week, I need to use a VPN to connect outside my region (Northeastern US). I learned early on that if the mail app was open, the Microsoft accounts would identify an unusual connection and cause a variety of issues. I made it a habit of always shutting down the mail app before connecting the VPN and it was resolved.

In the past several months, that's no longer a solution. When I connect my VPN, even with mail closed, it triggers Microsoft to detect an unusual connection. Is there a change about how online account connection runs in the background or something else that may explain this?

This seems minor, but it results in about 15 alert texts and emails, having to reset my Microsoft passwords, then update those passwords in many device's mail apps, xbox, Windows Store, etc... EVERY single week and is driving me crazy.



Try disabling the VPN and compare your results...



A true VPN tunnel, for example between you and your job, or a Bank server would be of value, otherwise might be time to re-think the usage.


see: Public VPN's are anything but private

https://gist.github.com/joepie91/5a9909939e6ce7d09e29


Aug 28, 2022 12:40 PM in response to danh62103

Your Microsoft account includes Mail but it also includes other services and they are all linked. Just quitting Mail does not quit all the other Microsoft services.


You can get some insight into this by opening System Preferences => Internet Accounts and select Microsoft Exchange or 365 -- whichever version of Microsoft you are using. You will see other services there. See image below. The example I show still has Contacts active and it will stay active even if Mail is completely closed. Even after you quit Mail, those other services may be executing in the background, causing your conflict. There may also be other linked Microsoft account services that aren't shown in the Internet Accounts pane but are still active, for instance Microsoft One Drive, etc. The VPN may be flagging internet traffic from one or more of those other services, even after Mail is closed. Look carefully at everything you are using Microsoft for. In fact, MS-Office (or Office 365) will check for updates in the background often and this activity could be flagged by a VPN.



The issue is not Microsoft, the issue is that your VPN is restricting your normal use of the computer. You should be able to configure the VPN to avoid this issue. Keep in mind that most commercial VPNs do not provide the privacy some people think they provide. In fact there have been many scandals where VPN sellers were found to be misusing (and selling) personal information of their customers. The only VPN you should use is one provided and configured by your employer or financial institution. My employer requires use of one and it is configured so none of those issues you describe are occurring.

Aug 27, 2022 8:53 AM in response to leroydouglas

This isn't quite helpful. The whole point is that there is constant comparison with the VPN on and off on a weekly basis. VPNs are used regularly for a variety of purpose in the personal and professional world and are quite necessary. The VPN is working as it should. The mail accounts are connecting in the background once the Mail program is closed with no explanation that I can see.

Aug 27, 2022 11:39 AM in response to markwmsn

Yes.


The basic workflow would look like: Have Apple Mail app open and in use, Completely quit Apple Mail app, Open VPN program (after a few minutes to a few hours have passed), Connect VPN, Get notification that Microsoft accounts have unusual login activity. This never used to happen before a few months ago and now is repeatable every time.


It would seem like the mail account connection is still open in the background even though the program is closed, but all documentation and research that I read says that shouldn't happen.

Aug 28, 2022 1:33 PM in response to steve626

This is the answer. After I read it, seems really obvious now. I was just honed in on the account being for mail. I didn’t even realize I had those other account services active. That makes total sense thank you.


And I respect your take on it. I have communicated with Microsoft without this same explanation and do feel it’s something they could address. G-mail accounts are running side by side and don’t have the same reaction. In Microsoft’s case, they see my login going from the US to EU and flag it for an unusual login. However, that is usual for me. I can appreciate the attempt at security measures, but it seems like they could have a method where I could identify that it’s my typical, legitimate use and not get flagged. I see it like a credit card company that may flag you if you go to use your card abroad, but then if you tell them it’s you and you’re on a trip, they can add it as an expected exception. That would seem like something reasonable in this case. VPN aside, If I physically traveled to a European country and connected to one of my MS account services, it seems like the same thing would happen. But I shouldn’t have to reset all of my logins if it’s a legitimate non-issue.


The issue actually seems to be brought up a lot by users in posts like this https://answers.microsoft.com/en-us/outlook_com/forum/all/unusual-sign-in-activity-alert-because-of-using/f5923da7-b86f-46d8-ac93-846e59dcf467


Unfortunately, their suggestions were not solving it for me and I was doubly confused since it was happening when mail was closed. But you cleared it up and I’m adjusting those settings as a solution.


Thanks!

Mail Accounts Remaining Open After Program Closed

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