AI-native automation

Connect Microsoft Outlook and Rocket Matter with AI

Pick any two tools and Caddi runs the loop between them end-to-end — no complicated workflow builder, no IT ticket.

  • Doesn't break. Caddi reads intent, so when fields move or UIs change, your loop keeps running.
  • Screenshare to set up, chat to improve. Show Caddi once on a screenshare. Tweak it later by chat — no workflow builder to re-architect.

SOC 2 attested · Human-in-the-loop · Full audit trail · 70+ tools across legal, finance, and operations

Caddi can…
Microsoft OutlookProductivity
Caddi can…
Rocket MatterLegal
Get a demoAverage setup: one screenshare, live the same week.

Practical ways to use Microsoft Outlook and Rocket Matter together

  • 01

    Create matter in Rocket Matter when new email in Microsoft Outlook.

    Caddi watches Microsoft Outlook for new email and create matter in Rocket Matter — no copy-paste, no missed records.

  • 02

    Send email in Microsoft Outlook when new matter in Rocket Matter.

    Caddi watches Rocket Matter for new matter and send email in Microsoft Outlook so the two systems stay in lockstep.

  • 03

    Post time entry in Rocket Matter from Microsoft Outlook events.

    When new event happens in Microsoft Outlook, Caddi post time entry in Rocket Matter with the right context attached.

  • Brighton Jones
  • The Planning Center
  • Beveridge & Diamond
  • Palace
  • Portner & Shure
  • Knight Law Group

One continuous loop.

  1. 01Measure

    Caddi watches how the work gets done today.

  2. 02Create

    You screenshare it once. The loop ships.

  3. 03Improve

    Caddi flags upgrades to existing loops and new automations to deploy.

Actions Caddi can take across Microsoft Outlook and Rocket Matter

  • Microsoft Outlook

    New email

    Triggers when a new email arrives in your inbox.

  • Microsoft Outlook

    New event

    Triggers when a new event is added to your calendar.

  • Microsoft Outlook

    Flag set on email

    Triggers when you flag a message for follow-up.

  • Microsoft Outlook

    Send email

    Send a new email from your Outlook account.

  • Microsoft Outlook

    Reply to email

    Reply to an existing email thread.

  • Microsoft Outlook

    Forward email

    Forward an existing email to one or more recipients.

  • Microsoft Outlook

    Create event

    Add a new calendar event with attendees and reminders.

  • Microsoft Outlook

    Move message

    Move an email between folders.

  • Rocket Matter

    New matter

    Triggers when a new matter is opened in Rocket Matter.

  • Rocket Matter

    Time entry posted

    Triggers when a new time entry is recorded.

  • Rocket Matter

    New invoice

    Triggers when an invoice is generated.

  • Rocket Matter

    Create matter

    Open a new Rocket Matter matter with client and billing details.

  • Rocket Matter

    Post time entry

    Record a time entry against a matter.

  • Rocket Matter

    Add expense

    Record a billable expense against a matter.

  • Rocket Matter

    Add note

    Log a timestamped note against a matter.

Common questions

How does Caddi connect Microsoft Outlook and Rocket Matter?

Microsoft Outlook and Rocket Matter just run together. All it takes is showing us how you use them — one screenshare, no workflow builder to wire up. Caddi turns the demo into a verified loop and runs it against Microsoft Outlook and Rocket Matter end-to-end.

Do I need engineering help?

No. Whoever does the work today shows it once on a call. Caddi builds the loop. No code, no IT ticket.

Is my data safe?

Yes. Caddi is SOC 2 attested. The AI watches and builds the automation, but once the loop ships it runs deterministically — no model in the loop at runtime.

Can Caddi connect Microsoft Outlook and Rocket Matter to other tools too?

Yes. Most Caddi loops span 3–6 tools. Once the first Microsoft Outlook + Rocket Matter loop is live, Caddi suggests other tools and other workflows to fold in.

How fast can it go live?

Typical first loops ship within a week of the screenshare. The Caddi team reviews every loop before it runs in production.

Ready to automate Microsoft Outlook and Rocket Matter?

Drop your work email and we'll show you Caddi running end-to-end against Microsoft Outlook, Rocket Matter, and the rest of your stack.