AI-native automation
Automate work across
Clio and 
Microsoft Outlookwith Caddi AI Agents.
Automate anything you do across Clio, Microsoft Outlook, 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 Clio and Microsoft Outlook
Connect Clio to Caddi
Allow1Sign in to Clio
One click with your own Clio login. No API keys.
Connect Microsoft Outlook to Caddi
Allow2Sign in to Microsoft Outlook
The same click again. Both tools are connected.
Send email in Microsoft Outlook when new matter in Clio.
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 Clio and Microsoft Outlook together
In a law firm the work between Clio and Microsoft Outlook 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
Send email in Microsoft Outlook when new matter in Clio.
Caddi watches Clio for new matter and send email in Microsoft Outlook. No copy-paste, no missed records.
- 02
Create matter in Clio when new email in Microsoft Outlook.
Caddi watches Microsoft Outlook for new email and create matter in Clio so the two systems stay in lockstep.
- 03
Reply to email in Microsoft Outlook from Clio events.
When new contact happens in Clio, Caddi reply to email in Microsoft Outlook with the right context attached.
Actions Caddi can take across Clio and Microsoft Outlook
- Clio
New matter
Triggers when a new matter is opened in Clio.
- Clio
New contact
Triggers when a new contact is created.
- Clio
Time entry posted
Triggers when a new time entry is recorded.
- Clio
Communication added
Triggers when a call, email, or meeting is logged.
- Clio
Create matter
Open a new Clio matter with client, billing, and intake fields.
- Clio
Create contact
Add a person or company contact to Clio.
- Clio
Create note
Log a timestamped note against a matter.
- Clio
Create time entry
Record time against a matter with rate and activity code.
- Clio
Upload document
Attach a document to a matter with metadata.
- 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.
Common questions
How does Caddi connect Clio and Microsoft Outlook?
Clio and Microsoft Outlook 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 Clio and Microsoft Outlook 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 Clio and Microsoft Outlook to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Clio + Microsoft Outlook 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 Clio and Microsoft Outlook 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 Clio and Microsoft Outlook?
Drop your work email and we'll show you Caddi running end-to-end against Clio, Microsoft Outlook, and the rest of your stack.
Or skip the demo: sign up free and build it yourself.