Microsoft 365 (Outlook Mail, Outlook Calendar, OneDrive, To Do)

Sidekick connects to the Microsoft 365 stack: Outlook Mail for sending and triaging email, Outlook Calendar for scheduling and conflict-aware booking, OneDrive for document storage and retrieval, and Microsoft To Do for task tracking. Each is a separate governed connector with its own scope and approval rules.

What's covered#

Connector	What Sidekick can do	Approval default
Outlook Mail	Send, draft, search, summarise email; reply with policy guards	Sends require approval at default trust
Outlook Calendar	Read availability, book meetings, propose times, cancel events	Booking external attendees requires approval
OneDrive	Read, write, share documents and files	Writes use Sidekick's destination defaults
Microsoft To Do	Read tasks, create tasks, update status	Creates auto-approved; bulk changes require approval

Setup#

Each connector authorises separately because they use different Microsoft Graph scopes:

Go to Settings → Connections
Click Add Connection and pick the Microsoft 365 connector you want
Authorise through Microsoft OAuth (uses your Microsoft 365 account)
Confirm scopes — Sidekick asks for the minimum needed for the actions in the table above

Common patterns#

Send the kickoff note to the Marketing distribution list
and put a 30-minute follow-up on Tuesday afternoon when
everyone's free.

Sidekick draws on Outlook Mail to compose, Outlook Calendar to find a time, and pauses for approval before sending if your policy requires it.

File the Q3 contract in OneDrive under /Legal/2026/Q3
and add a follow-up task to Microsoft To Do tagged
"Review by 30 April".

OneDrive handles storage; To Do tracks the follow-up.

Capability boundary#

These are governed connectors with bounded action sets — they're not a full Outlook or OneDrive client. Specialised mailbox rules, complex calendar delegation, or Microsoft Graph APIs not on the connector's surface need a Custom MCP server instead.

Governance#

All four connectors respect autonomy policy and surface in the Approvals inbox when a write requires sign-off. Read actions can be auto-approved; sends, bookings with external attendees, and shares default to approval.

info The Outlook Mail connector handles marketing-grade sends through approval; for bulk transactional email use a dedicated provider via Custom MCP or Webhooks.