AI-native automation
Automate work across
Microsoft Outlook and 
Rocket Matterwith Caddi AI Agents.
Automate anything you do across Microsoft Outlook, Rocket Matter, and the rest of your tools. Sign in, show or tell Caddi what you want, and it runs end to end. No workflow builder.
How to connect Microsoft Outlook and Rocket Matter
Connect Microsoft Outlook to Caddi
Allow1Sign in to Microsoft Outlook
One click with your own Microsoft Outlook login. No API keys.
Connect Rocket Matter to Caddi
Allow2Sign in to Rocket Matter
The same click again. Both tools are connected.
Create matter in Rocket Matter when new email in Microsoft Outlook.
ScreenshareType it3Show or tell it
Screenshare the job, or type it in chat. Change it any time.
- Running
14 done1 for review
4Watch it run
Caddi does the work and flags anything unsure for review.
What Caddi is and how it works
An AI teammate that runs your back-office loops.
- Doesn't break. Caddi reads intent, so when fields move or UIs change, your loop keeps running.
- Taught like a new hire. Walk Caddi through the work once. Tweak it later by chat, with no workflow builder to re-architect.
SOC 2 attested · Human-in-the-loop · Full audit trail · 150+ tools across legal, finance, and operations
Practical ways to use Microsoft Outlook and Rocket Matter together
In a law firm the work between Microsoft Outlook and Rocket Matter is organized by matter: the right client, the right matter, the right people on it. Caddi carries that context through every step, so nothing is filed against the wrong case.
- 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.
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. You teach Caddi the way you'd teach a new hire: walk it through how you use them today, with no workflow builder to wire up. Caddi turns that walkthrough 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 walks Caddi through it on a call, the same way they'd train a new hire. 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, and once the loop ships it runs as deterministic code, repeatable and logged, with any model step scoped and reviewable.
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 that first walkthrough. The Caddi team reviews every loop before it runs in production.
Does this work for law firms?
Yes. Caddi runs Microsoft Outlook and Rocket Matter with the matter as the unit of work, so documents, time, and communications land against the right client and matter rather than in a general folder. Firms most often start with intake, document filing, or billing prep.
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.
Or skip the demo: sign up free and build it yourself.