Littlebird and Outlook Integration Overview

You're drafting a reply to a client email about the timeline change discussed in yesterday's call. You open Outlook, stare at the thread, then open your notes app to find what was actually agreed to. Then back to the calendar to check the new date. Then back to the draft.

Littlebird already has it. Because it reads your screen and transcribes your meetings, the context is already indexed before you sit down to write. Connect Outlook and Littlebird works with your calendar and mail even when Outlook is closed -- read your schedule, create and edit events, search your inbox, and draft replies in context.

What Littlebird finds

Calendar

View your schedule and upcoming events. Find available meeting times across your team's calendars. Check coworker availability. The calendar becomes searchable context, not another window to open.

Email

Search your inbox by keyword or sender from Chat -- Littlebird already knows the meeting context, so you can ask "find the email where the client confirmed the new scope" and get the thread. Read full message content. View attachment info (file names, sizes, and types) across all folders or in a specific folder.

The search works by what the email is about, not just exact keywords. Because Littlebird transcribed the meeting where the scope change was discussed, it can surface the confirming email even if you don't remember the exact subject line.

What Littlebird does

Calendar

Littlebird can check your coworkers' availability and propose a time, so you skip the reply-all tennis match. Create and edit events from Chat, even when Outlook is closed. Cancel a meeting and notify attendees without opening the app -- the context from the Slack thread where the conflict came up is already in Chat, so you ask and it's done. Delete an event that's no longer needed.

Email

Draft the reply in Chat with the meeting transcript as context, then review and send from Outlook. Littlebird writes the draft; you stay in control of send. New emails, replies, and forwards land in your Drafts folder, ready for you to review.

Move messages between folders. Mark messages read or unread. Flag and categorize messages. Unlike Gmail (which can send), Outlook drafts only -- sending stays on your side. But Outlook can move, flag, and categorize mail (Gmail cannot). The organizing happens from Chat; the final send is yours.

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

Connect Outlook in Settings > Integrations and sign in with your Microsoft account. The integration activates when Littlebird needs data beyond what is visible on screen. Works even when Outlook is not open. Backed by Microsoft Graph via delegated permissions only. One Outlook account can be connected. On macOS, Outlook actions are also available through Hummingbird Quick Access (not on Windows).

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 new emails, replies, and forwards, and they land in your Drafts folder. Sending stays on your side. (Contrast: Gmail integration can send; Outlook cannot. But Outlook can move, flag, and categorize mail; Gmail cannot.)

Does Littlebird work with Outlook when the app is closed?

Yes. Once connected, Littlebird can read your calendar and mail, create and edit events, search your inbox, and draft replies even when Outlook is not open. The integration activates when Littlebird needs data beyond what is visible on screen.

Can I connect more than one Outlook account?

No. One Outlook account can be connected.