How to fix Trello Planner and Outlook not working correctly

Question

Recently my Trello planner and microsoft calendar stopped syncing correctly. Now when i add a card into my Trello calendar it doesn't appear in my outlook calendar.

As well as the above, Trello planner items that where in the outlook previously have all moved to weird times that dont relate to whats in Trello.

Arkadiusz Wroblewski · Answer

Hello and welcome to the Community @Shawn Marshall

If you are using the native iCalendar feed, try removing the calendar from Outlook and re-adding it with a fresh link from Trello's Calendar view under "Sync to personal calendar". Keep in mind that Outlook updates external feeds slowly, and only due dates will sync over. If you are using a Planner Power-Up instead, try disconnecting and reconnecting your Microsoft account within the Power-Up settings to reset the link.

The "weird times" issue is almost always caused by a timezone mismatch, so double-check that your settings match exactly across Trello, Outlook, and your local device.

Best,

Arkadiusz🤠

Germán Morales · Answer

Hi @Shawn Marshall, welcome to the Community. The good news first: Planner does sync both ways with Outlook (that support landed in late 2025), so nothing here is a missing feature, it's a connection that's drifted, and both of your symptoms point the same way.

The items jumping to odd slots is almost always a timezone mismatch. Check that the timezone set in Trello matches the one in Outlook and on your computer. When they disagree, every synced item shifts by the gap between them, which is exactly what you're seeing on the entries that were already there.

For the new cards not reaching Outlook, the connection has most likely dropped. Open your Planner, go to Settings then Manage accounts, remove the Outlook account and add it back to re-authorise it (the exact steps are in Trello's Planner guide). That usually brings the live sync back and realigns the events at the same time. If it won't reconnect, make sure your Microsoft account has an email set on its profile, since a missing one is a known reason the Outlook link fails.