Calendar sharing issues starting suddenly across multiple devices and accounts strongly suggest a backend change in the Outlook.com / classic Outlook calendar sharing platform rather than a local configuration problem.
From the available information:
- Classic Outlook / legacy sharing model is known to have issues and has been undergoing changes and improvements over time. Microsoft has a newer sharing model that works best when invitations are accepted from Outlook on the web, iOS, Android, or Windows 10 Calendar, and when calendars are on the “new model.” Older/legacy shares can stop syncing correctly across clients.
- For Outlook.com and personal accounts, mobile clients (iOS/Android) only reliably show shared calendars that were accepted recently from supported clients (web, iOS, Android, Windows 10 Calendar). Older shares can effectively “age out” or break and stop appearing or syncing on mobile.
- When a shared calendar stops appearing on mobile, Microsoft’s documented remediation is:
- Have the owner re-share the calendar.
- Accept the new sharing invitation from Outlook on the web, iOS, Android, or Windows 10 Calendar (not from classic desktop Outlook).
- Alternatively, search for and add the shared calendar directly in the Outlook mobile app using the + button in Calendar view.
Given that re-sharing already failed in this case, the most likely explanation is a backend change that affected legacy/"classic" shares for Outlook.com calendars around that date. The workaround another user found (creating a new Outlook.com account and sharing from there) effectively forces creation of a brand-new calendar and share on the new model, which aligns with Microsoft’s direction for calendar sharing.
Actionable steps that align with documented behavior:
- Ensure the calendar is shared using the current model
- From the owner’s Outlook.com (web): share the calendar again to the partner’s Outlook.com address.
- Make sure the permission level is at least “Can view all details” or similar, not restricted to free/busy only.
- Accept the share from a supported client
- On the recipient side, open the new sharing invitation in:
- Outlook on the web, or
- Outlook for iOS, or
- Outlook for Android.
- Accept the invitation there (not in classic Outlook desktop).
- If the calendar still does not appear on mobile
- On iOS/Android, in Outlook:
- Go to Calendar view.
- Use the + button/menu to search for the owner’s calendar and add it directly.
- This is specifically documented as a way to surface shared calendars that should be visible on mobile.
- If none of the above works
- The behavior is consistent with a service-side regression affecting legacy shares. In that case, the only currently known effective workaround (based on similar user reports) is:
- Create a new Outlook.com calendar identity (or a new primary account) and set up sharing fresh, ensuring invitations are accepted from web/iOS/Android so they are on the new sharing model.
There is no documented client-side fix (settings, cache clearing, etc.) for a scenario where legacy Outlook.com shared calendars stop syncing across all devices at the same time. The pattern and Microsoft’s own guidance around “recently accepted” shares and the new sharing model indicate this is a service/model issue with classic sharing, not a misconfiguration on the devices.
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