Hi @David Jadwin,
Thank you for taking the time to explain what you are seeing and for confirming the web experience is still available.
From your description, you are receiving a “subscription expired” message in the new Outlook for Windows even though your Microsoft 365 subscription is paid and Outlook on the web continues to work.
This typically occurs when the Windows app is not successfully refreshing the sign-in and licensing information that is stored locally on the device. As a result, the browser can still open the mailbox because it completes a fresh validation during sign-in, while the desktop app may continue to rely on an older licensing token or a previous subscription state. In addition, when the sign-in option inside the expiration prompt stops responding, it usually indicates the local authentication cache needs to be refreshed so Outlook can validate the active subscription again.
Please try the following advanced options in order, as they are the most suitable for the behavior you described.
1/ Confirm the subscription status and payment state on the exact account used in Outlook
- Close the new Outlook and any Microsoft 365 apps that are open.
- Sign in to the Microsoft account “Services & subscriptions” page and verify the subscription shows as active for the same email address you use to sign in to Outlook.
- If you see any notice such as past due, suspended, or an action required prompt, complete the step shown on that page, and then restart the computer before testing Outlook again.
- Reference: A subscription notice appears when I open a Microsoft 365 application - Microsoft Support
2/ Refresh the local sign-in information on the Windows device and reconnect the account in the new Outlook
- Remove the affected account from the new Outlook, fully close Outlook, and then restart the computer to ensure the session is cleared.
- Open Windows Credential Manager and remove saved entries related to Outlook or Microsoft Office for the affected account, then open the new Outlook and add the account again.
- After re-adding the account, keep Outlook open for a few minutes so it can rebuild the local session and sync the mailbox.
3/ Run Microsoft’s activation repair tool, then reinstall Microsoft 365 if the notice continues
- Run the Microsoft Support and Recovery Assistant for Microsoft 365 activation and follow the prompts on the same Windows PC where the issue occurs. Office error "Account Notice: We've run into a problem with your Microsoft 365 subscription" - Micr…
- Once the tool completes, reopen the new Outlook and confirm whether the subscription message is cleared.
- If the message still appears, uninstall and reinstall Microsoft 365 from the account that shows the active subscription, and then sign in again using the same licensed account.
- Reference: Microsoft 365 Apps activation Subscription expired error - Microsoft 365 Apps | Microsoft Learn
I hope this response has helped address your question and clarify the behavior you're experiencing. Please feel free to reply if you have any further questions, I would be happy to assist further.
Thank you for your patience and your understanding. I look forward to continuing the conversation.
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