Unable to change members of AD security groups who have access to shared mailboxes

I have an exchange 2013 running for over a year now and never had any problems with it. Until recently.
A request came in to make a new shared mailbox. So I did just that and gave rights to a security (not mail enabled) AD group. Just like I Always do. Everything worked fine. A few hours later I did exactly the same for another request and then the people
could not access the shared mailbox. So I added my regular user to the AD group and I also couldn't (I tested it with OWA and Outlook). I tried to remove myself of one of my own shared mailboxes and the permissions wouldn't stick. When I removed the entire
group then the permissions were gone(and I could not access the shared mailbox). When I added it back I had my permissions back but still wasn't in the group. Then I tried adding a distribution group with the same result.
It seems when I add normal users directly to the permissions everything works.
When I had to restart the server a few days later. All changes were applied but I could not change it again.
i'm a bit stumped on this one. i'm out of options.

Hi Jelle,
"I did exactly the same for another request and then the people could not access the shared mailbox.", I would like to verify if you give the same Security Group rights to multiple shared mailboxes.
If the security group members can't have access to all the shared mailboxes they have rights, you can recreate a security group and grant permissions to shared mailboxes one by one to check the result.
Hope this can be helpful to you.
Best regards,
Amy Wang
TechNet Community Support

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