How to Connect Multiple Outlook Calendars to Cursor
Add Carly as one MCP server and every Cursor agent, local or cloud, works across all of your Outlook calendars at once. Cursor’s own Outlook Calendar plugin can add a second account in the desktop app through Add Another Account, which Cursor’s support team confirmed in September. The agents that run while you are away cannot: cloud agents and Automations use one account per server.
1. Add your Outlook calendars to Carly
- Sign in at carlyassistant.com.
- Open carlyassistant.com/integrations.
- Under Accounts, type the email address and click Add Email.
- On that address, click Connect Outlook, tick Calendar, then click Connect with Microsoft and grant access. If the address is already connected, open Manage access and click Connect next to Calendar instead.
- Repeat for every Microsoft account you want Carly to reach.
Use a private window between accounts so Microsoft does not reuse the last login, and check the address each time. Personal Outlook.com calendars connect beside Microsoft 365 work ones, and each tenant approves Carly separately. Each account stays its own connection, and every event stays on the calendar that owns it.
Carly connects to thousands of apps, so while you are on that page you can add your Google calendars, inboxes, files, and anything else you want Cursor to reach through the same server.
2. Add Carly as an MCP server in Cursor
For the desktop app, add Carly to ~/.cursor/mcp.json:
{
"mcpServers": {
"carly": {
"url": "https://carlyassistant.com/mcp/"
}
}
}Then open Customize in the sidebar, select MCPs, find carly, and finish the sign-in with the Carly account that holds your calendars.
For cloud agents, open the MCP dropdown on cursor.com/agents, add the same URL, and log in there too. Automations run as cloud agents, so add the MCP server tool to an automation and pick Carly.
What one Cursor agent can do across every Outlook calendar
- find time that is free in your own tenant and every client tenant;
- spot the conflict between your company’s all-hands and a client steering meeting;
- book, move, or decline on the calendar the event belongs to;
- read a client calendar while writing only to your own;
- check a personal Outlook.com calendar before accepting anything at work.
Ask across all of them in one line:
Check all my calendars for next Tuesday and find a 45-minute slot that’s open on every one of them.
What the Outlook Calendar plugin does, and where it stops
Cursor added Outlook, Outlook Calendar, and OneDrive plugins to its plugin repository on Aug 27, 2026. The calendar plugin runs on Cursor’s hosted MCP server, signs in against Microsoft Entra ID, and needs Cursor 3.19 or newer. In its own words, it can “list upcoming events, check schedules, and create, update, or cancel meetings in the signed-in Microsoft account.”
On the desktop, a second account is possible. A Cursor support engineer wrote on Sep 15 and Sep 24, 2026 that multiple accounts per MCP server work for any remote plugin that signs in with OAuth, through Add Another Account. The same reply sets the limit: “Cloud Agents currently use one account per server.” That covers Automations, which start cloud agents on a schedule or on events from GitHub, GitLab, Bitbucket, Slack, webhooks, Linear, Sentry, and PagerDuty. A meeting request is not on that list.
Work tenants add one more hurdle. An open thread on Cursor’s forum, started Aug 18, 2026, reports Cursor’s MCP sign-in asking Microsoft for fresh consent every time, which lands on “Approval required” in tenants that block user consent, even after an admin has approved the app. On Sep 2, users confirmed the same loop on the Outlook, Outlook Calendar, and OneDrive plugins as installed in Grok Bot, which runs on Cursor’s plugins, and one still saw it intermittently on Sep 23.
Cursor’s Outlook Calendar plugin versus Carly
| Need | Cursor plugin (desktop) | Cursor plugin (cloud agents, Automations) | Carly MCP server |
|---|---|---|---|
| Read and edit events in one Microsoft account | Yes | Yes | Yes |
| Hold more than one Microsoft account | Yes, with Add Another Account | One account per server | Yes, every account you connect |
| Google calendars in the same request | Separate Google Calendar plugin | Separate plugin, one Google account | Yes, same server |
| Start work when an invite lands | No, a chat starts it | No, calendars are not an Automation trigger | Yes, calendar-triggered workflows |
| Booking pages and group polls | No | No | Yes |
Where Carly goes past the plugin
Carly is an AI executive assistant, and scheduling is its core. It watches every connected calendar on its own. When a client’s invite lands in their tenant on top of your own team’s planning session, a Carly workflow can catch the clash, offer the organizer a new time, and update the right calendar while you are still heads-down in Cursor.
Booking pages check every connected calendar, Outlook and Google alike, before they offer a slot, and group scheduling finds the hour that works for Michael, Claire, and the client in one poll. Connected calendars and booking pages are unlimited.
Carly offers free Zapier-style workflows; AI agents start at $35/month.
Quick fixes when a calendar does not appear
| Problem | Fix |
|---|---|
| Carly’s tools do not show up | Reload the Cursor window after editing mcp.json |
The carly server sits under Needs Attention | Open Customize → MCPs and finish the sign-in |
| Carly is missing in cloud agents | Add it from the MCP dropdown on cursor.com/agents and log in there |
| Microsoft connected the same account twice | Remove the duplicate in Carly and reconnect from a private window |
| A tenant blocks authorization | Ask that tenant’s admin to approve Carly, then reconnect |
| The agent keeps using one calendar | Disable the Outlook Calendar plugin in Customize so it goes through Carly |
Frequently asked questions
Can Cursor connect two Outlook calendars from different accounts?
In the desktop app, yes, through Add Another Account. Cloud agents and Automations use one account per server, so for those, connect every account to Carly and add Carly as one MCP server.
Why does Cursor keep showing “Approval required” for my work account?
An open report on Cursor’s forum traces it to Cursor’s MCP sign-in always asking Microsoft for fresh consent, which trips tenants that block user consent even after admin approval. Cursor staff confirmed the cause on Aug 19, 2026. Carly connects each tenant as its own account, so one stuck tenant leaves the others working.
Can a Cursor Automation check my Outlook calendars?
Yes. An automation can call MCP tools while it runs. With the Outlook Calendar plugin it sees one Microsoft account; with Carly it sees every calendar you connected. Automations start on a schedule or on events from tools like GitHub, Slack, and Linear, so work that should start when an invite arrives belongs in a Carly workflow.
Can I add Google calendars the same way?
Yes. Connect them on the same integrations page and they reach Cursor through the same server. See multiple Google Calendars in Cursor.
Related: Multiple Google Calendars in Cursor · Multiple OneDrive accounts in Cursor · Multiple Outlook accounts in Cursor · Cursor with multiple accounts · Cursor MCP · Multiple Outlook calendars in Claude Code · Best AI assistants for multiple Outlook calendars · Best AI assistants for multiple Microsoft accounts · Carly’s Outlook integration
Ready to automate your busywork?
Carly schedules, researches, and briefs you—so you can focus on what matters.
See the prompt
Set up Carly for me. Carly connects to thousands of apps, from Gmail, Outlook and my calendars to Slack, HubSpot and QuickBooks, and keeps working after this chat is closed: answering email, booking meetings, following up and running workflows the moment something happens.
1. Add the Carly MCP server (https://carlyassistant.com/mcp/) and sign me in. Use the one that matches you:
- Claude Code: claude mcp add --transport http --scope user carly https://carlyassistant.com/mcp/ (then I run /mcp, pick carly, and authenticate)
- Codex: codex mcp add carly --url https://carlyassistant.com/mcp/ then codex mcp login carly
- Claude (claude.ai, Claude Desktop, or Cowork): Customize > Connectors > Add custom connector, paste the URL, and sign in. Carly is also in Claude's connector directory at claude.ai/directory/carly.
- ChatGPT: open Plugins, search for "Carly", add it, and sign in.
- Cursor: add {"mcpServers": {"carly": {"url": "https://carlyassistant.com/mcp/"}}} to ~/.cursor/mcp.json, then sign in to carly from Customize.
- Muse: I will create a Carly API key at carlyassistant.com/integrations (Advanced > API Keys > Create a new key, with Select all scopes). Build a custom connector to https://carlyassistant.com/mcp/ using an API key as a bearer token, and ask me for the key in your secure credential prompt.
- Grok: go to grok.com/connectors, choose New Connector, then Custom, paste the URL, and sign in.
- Grok Bot: open Plugins, add a custom remote MCP server named carly with the URL, then I approve it and sign in.
- Perplexity: Settings > Connectors > Custom connector > Remote, paste the URL, and sign in.
- Anything else: add a remote MCP server (streamable HTTP) named carly with the URL. It signs in with OAuth.
I sign in with my Carly account, or create one at carlyassistant.com.
2. Walk me through connecting my accounts at https://carlyassistant.com/integrations. Under Accounts, I type each email address I use and click Add Email. On each new address, I click Connect Gmail or Connect Outlook, tick what Carly can reach (Email, Calendar, Contacts, Drive or OneDrive), then click Connect with Google or Connect with Microsoft and grant access. For an address that is already connected, I open Manage access and click Connect next to anything missing. Repeat for every address. Then ask which of my other apps I want connected too.
3. Check it worked: list my connected mailboxes and calendars and tell me every account you can see.
4. Then ask me what to hand off first, for example: "Check all my inboxes for anything that needs a reply today."See what people say
"Before Carly, I relied on a Calendly link, but the whole process felt impersonal and not very professional. Carly changed that by handling all the back-and-forth, so I'm no longer stuck in endless email threads trying to line up schedules.
Now Carly reaches out to candidates, shares my real-time availability, lets them pick a slot, then sends a Zoom link and drops it straight into my calendar. She sends reminders to both of us before each call, which has significantly reduced no-shows and last-minute confusion.
On top of scheduling, Carly acts like a full executive assistant, sending me my schedule the night before so I can prepare for each call. It reminds me of the old x.ai assistant, but Carly is noticeably smarter, faster, and better suited to my healthcare recruitment business."
