From what I know, this usually boils down to permissions or to the fact that HubSpot treats inbox and calendar as two separate hookups. Quick way to fix it:
Start fresh: in HubSpot go to Settings → General → Email → Connected Accounts, choose “Disconnect.” Then head to your Microsoft 365 security page and remove the “HubSpot” app consent (this wipes stale tokens). knowledge.hubspot.com
Reconnect the inbox first: still in Settings > Email, hit Connect inbox and pick Office 365. Let the Microsoft consent window finish the loop—no skipped screens.
Immediately connect the calendar: Settings → General → Calendar → Connect your calendar → Outlook Calendar. Make sure you tick the right default calendar (HubSpot can’t read shared or secondary calendars). knowledge.hubspot.com and knowledge.hubspot.com
Check admin consent: if you’re on a corporate tenant, the global admin must allow third-party apps the scopes Calendars.ReadWrite and offline_access. Without that, the calendar handshake drops right after the “success” toast. knowledge.hubspot.com
Token refresh tip: any change of password or MFA on the Microsoft side forces a silent disconnect; HubSpot will keep showing the yellow banner until you redo the two steps above. A quick calendar-disconnect-reconnect is enough; no need to touch the inbox unless it also shows as offline. community.hubspot.com
If after a clean reconnect the calendar still flips to “Disconnected,” I’m guessing the mailbox might be on-premise Exchange (not supported) or a shared mailbox (HubSpot won’t sync those). In that case you’d need to switch to an O365 primary mailbox or route bookings through another user.
Hope this helps.
Did my answer help? Please mark it as a solution to help others find it too.
Ruben Burdin HubSpot Advisor Founder @ Stacksync Real-Time Data Sync between any CRM and Database
From what I know, this usually boils down to permissions or to the fact that HubSpot treats inbox and calendar as two separate hookups. Quick way to fix it:
Start fresh: in HubSpot go to Settings → General → Email → Connected Accounts, choose “Disconnect.” Then head to your Microsoft 365 security page and remove the “HubSpot” app consent (this wipes stale tokens). knowledge.hubspot.com
Reconnect the inbox first: still in Settings > Email, hit Connect inbox and pick Office 365. Let the Microsoft consent window finish the loop—no skipped screens.
Immediately connect the calendar: Settings → General → Calendar → Connect your calendar → Outlook Calendar. Make sure you tick the right default calendar (HubSpot can’t read shared or secondary calendars). knowledge.hubspot.com and knowledge.hubspot.com
Check admin consent: if you’re on a corporate tenant, the global admin must allow third-party apps the scopes Calendars.ReadWrite and offline_access. Without that, the calendar handshake drops right after the “success” toast. knowledge.hubspot.com
Token refresh tip: any change of password or MFA on the Microsoft side forces a silent disconnect; HubSpot will keep showing the yellow banner until you redo the two steps above. A quick calendar-disconnect-reconnect is enough; no need to touch the inbox unless it also shows as offline. community.hubspot.com
If after a clean reconnect the calendar still flips to “Disconnected,” I’m guessing the mailbox might be on-premise Exchange (not supported) or a shared mailbox (HubSpot won’t sync those). In that case you’d need to switch to an O365 primary mailbox or route bookings through another user.
Hope this helps.
Did my answer help? Please mark it as a solution to help others find it too.
Ruben Burdin HubSpot Advisor Founder @ Stacksync Real-Time Data Sync between any CRM and Database