Littlebird and Outlook Integration Overview

You're in a Slack thread and someone asks if you're free Thursday afternoon. You open Outlook, scan the calendar, close it. Two minutes later, another question: "What did the client say about the timeline?" You open Outlook again, hunt through folders, find the thread, copy the line, close it. By the time you're back in Slack, the conversation moved on.

Littlebird already saw the client's email on screen and transcribed the meeting where you agreed to the timeline. Connect Outlook and Littlebird works with your Microsoft calendar and inbox even when Outlook is closed.

What Littlebird finds

Calendar

Littlebird can view your schedule and upcoming events, so you answer "are you free Thursday?" in Chat without opening Outlook. It can find available meeting times and check coworker availability. Ask "when is Sarah free this week?" and get the answer without the calendar-hopping.

Email

Littlebird can search by keyword, sender, or date across all folders or a specific folder: find the client's original request from three months ago without scrolling. It can read full message content, so you pull the exact wording from an email that was on screen last week. It can view attachment info: file names, sizes, and types, so you see what was attached to the thread even if you never opened the file.

What Littlebird does

Calendar

Littlebird can create and edit events: draft the calendar invite for the follow-up call you agreed to in a meeting Littlebird transcribed, or update the sync when the project shifts.

Email

Littlebird can draft new emails, replies, and forwards. They land in your Drafts folder: sending stays on your side. It can move messages between folders, so you file the thread into the project folder after you've answered it. It can mark messages read or unread, flag and categorize messages, so you triage the inbox from Chat.

All the content I produce starts with Littlebird. It sits in the background, capturing the conversations that matter, so nothing gets lost in the details of a meeting or the bottom of my inbox.

Michelle Dailey, VP Marketing, Checksum

Requirements

Plan

Littlebird Basic (free)

See pricing →

How it works

Go to Settings > Integrations and sign in with your Microsoft account. The integration activates when Littlebird needs data beyond what's visible on screen. It doesn't proactively index your calendar or inbox, it runs when you ask. Littlebird reads Outlook via Microsoft Graph with delegated permissions. One Outlook account can be connected.

Littlebird also works on its own, without integrations, paying attention to your active window and transcribing meetings without a bot on the call. You control what it does. Pause context collection, exclude apps, or delete your data at any time. Nothing is collected without your permission.

Privacy

The app runs on your computer. The memory it builds is encrypted and stored in the AWS cloud.

Encrypted at rest (AES-256) and in transit (TLS 1.3). AWS KMS manages encryption keys.
SOC 2 certified, independently audited. GDPR and CCPA compliant data handling policies.
Littlebird never sells your data and never trains models on your data.
Delete your data, or your entire account, at any time.

Frequently asked

Can Littlebird send email from Outlook?

No. Littlebird drafts emails, replies, and forwards, and they land in your Drafts folder. Sending stays on your side.

Does Littlebird work with Outlook when the app is closed?

Yes. Once connected, Littlebird can read your calendar and inbox, create events, and draft replies even when Outlook isn't open.

How many Outlook accounts can I connect?

One Outlook account can be connected.