
36r3m (36r3m) asked a question.
When team members add their Office 365 Mail account to Apple Mail, iOS Mail, Airmail or any other mail client, the connection fails after a couple hours. As a user, you then need to re-login. How can our users set up their mail client so the connection doesn't expire after several hours / a day?

Hello Warre,
I hope you are fine!
If when logging into an Outlook mail client on a Mac, IPhone or any other Apple device, an user is being prompted to authenticate via Okta and is successfully authenticated. Shortly after, the Outlook credential prompt window continues to reappear even though the user has already authenticated; you can follow these steps:
Delete any cached Microsoft passwords and reboot.
Open the Keychain Access program.
In the Keychain search, enter "adal".
Delete any Microsoft-related items that are returned in this search.
In the Keychain search, enter "office".
Delete any Microsoft-related items that are returned in this search.
Reboot the machine.
Open Outlook and re-authenticate as the end user
Above steps applies To:
Office 365
Outlook Thick Client
Mac workstations
IPhone
And the cause of this issue is the stale credentials or token corruption in the local Keychain Access application where the user's credentials are cached.
If you follow above steps and still face issues, I will recommend you to please open a case directly with support so it can be further analyzed.
Thanks,