backend entitlement synchronization bug caused by moving from: Microsoft 365 Personal (Apple-billed) to Microsoft 365 Family (Microsoft-billed)

Question

backend entitlement synchronization bug caused by moving from: Microsoft 365 Personal (Apple-billed) to Microsoft 365 Family (Microsoft-billed)

StealthViper-4040 0

Copilot iPhone App Subscription Recognition Issuel am experiencing an issue with the Copilot app on iPhone.The problem started after I deleted my Copilot chat history. Around the same time, the app began asking me to start a Microsoft 365 trial, even though | already had an active Microsoft 365 Personal subscription purchased through the Apple App Store.! later cancelled the Microsoft 365 Personal subscription purchased via Apple and subscribed to Microsoft 365 Family directly through my Microsoft account. I am now the owner of an active Microsoft 365 Family subscription. Copilot works correctly in a web browser when I sign in with this account. However, the iPhone Copilot app intermittently shows a screen asking me to start a trial. The account remains signed in when this occurs. The app still shows my email as the active account.If I sign out and sign back in, Copilot starts working again. However, the issue returns later, especially after closing and reopening the app.I have already:Verified that my Microsoft 365 Family subscription is active.Confirmed that I am the subscription owner.Reinstalled the Copilot app. Verified that Copilot works correctly in the browserIt appears that the iPhone app may be incorrectly handling or caching subscription information following the change from a Microsoft 365 Personal subscription purchased through Apple to a Microsoft 365 Family subscription purchased directly from Microsoft.Please investigate and advise.

StealthViper-4040 0 Reputation points

2026-09-07T21:08:13.1633333+00:00
The issue occurs consistently after closing and reopening the Copilot app. The account remains signed in, but the app shows a trial/subscription screen until I sign out and back in."
StealthViper-4040 0 Reputation points

2026-09-08T04:04:50.5866667+00:00

Hi Ian, thanks for your comment. Additional information I was signed out of all Hotmail and Outlook email accounts as well as all Microsoft applications, requiring me to manually sign back in to each individual account and app.
Ian-T 10,695 Reputation points Microsoft External Staff Moderator

2026-09-08T04:11:47.0333333+00:00

Thank you, please feel free to contact support following my steps under my answer, include the additional information that you just provided
StealthViper-4040 0 Reputation points

2026-09-10T11:16:26.34+00:00

Hello,

I don’t know what kind of Microsoft support has?!

I find it unacceptable that my ticket has been marked as resolved without addressing the issue or contacting me. I demand that this case be immediately reopened and escalated to a senior supervisor.

I have waited for two days for a promised phone call from the level 3 team support this never happened!

The copilot problem still exists!

1 answer

Your answer

StealthViper-4040 0 Reputation points

2026-09-07T21:08:13.1633333+00:00

The issue occurs consistently after closing and reopening the Copilot app. The account remains signed in, but the app shows a trial/subscription screen until I sign out and back in."
StealthViper-4040 0 Reputation points

2026-09-08T04:04:50.5866667+00:00

Hi Ian, thanks for your comment. Additional information I was signed out of all Hotmail and Outlook email accounts as well as all Microsoft applications, requiring me to manually sign back in to each individual account and app.
Ian-T 10,695 Reputation points Microsoft External Staff Moderator

2026-09-08T04:11:47.0333333+00:00

Thank you, please feel free to contact support following my steps under my answer, include the additional information that you just provided
StealthViper-4040 0 Reputation points

2026-09-10T11:16:26.34+00:00

Hello,

I don’t know what kind of Microsoft support has?!

I find it unacceptable that my ticket has been marked as resolved without addressing the issue or contacting me. I demand that this case be immediately reopened and escalated to a senior supervisor.

I have waited for two days for a promised phone call from the level 3 team support this never happened!

The copilot problem still exists!

Answer 1

HI @StealthViper-4040

Thank you for explaining the sequence clearly. Since Copilot works in the browser, your Microsoft 365 Family subscription is active, and signing back into the iPhone app temporarily restores access, this does not look like a problem with the subscription itself. It more likely involves the app retaining outdated account or subscription information after the billing change.

Deleting your chat history should not normally change your subscription entitlement, so that may simply have happened around the same time.

You have already completed the main troubleshooting steps, including reinstalling the app. Also, because your current Family subscription was purchased directly from Microsoft, I would not try to restore the cancelled Apple purchase.

At this point, please contact Microsoft Support and ask them to check the entitlement associated with your Microsoft account and the Copilot iOS app. Include these details:

The previous plan was Microsoft 365 Personal billed through Apple.
The current plan is Microsoft 365 Family billed directly by Microsoft.
You are the subscription owner.
Copilot works in a browser.
The iPhone app shows the trial screen after being closed and reopened.
Signing out and back in fixes it only temporarily.

This is a user-to-user forum, so forum moderators cannot inspect or refresh the account’s subscription status from the back end.

Thank you for your understanding and time