AI-native automation
Connect Dropbox Sign and Microsoft 365 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
Practical ways to use Dropbox Sign and Microsoft 365 together
- 01
Send email in Microsoft 365 when signature request completed in Dropbox Sign.
Caddi watches Dropbox Sign for signature request completed and send email in Microsoft 365 — no copy-paste, no missed records.
- 02
Send signature request in Dropbox Sign when new email in outlook in Microsoft 365.
Caddi watches Microsoft 365 for new email in outlook and send signature request in Dropbox Sign so the two systems stay in lockstep.
- 03
Create event in Microsoft 365 from Dropbox Sign events.
When signature request sent happens in Dropbox Sign, Caddi create event in Microsoft 365 with the right context attached.
One continuous loop.
- 01Measure
Caddi watches how the work gets done today.
- 02Create
You screenshare it once. The loop ships.
- 03Improve
Caddi flags upgrades to existing loops and new automations to deploy.
Actions Caddi can take across Dropbox Sign and Microsoft 365
- Dropbox Sign
Signature request completed
Triggers when all signers complete a request.
- Dropbox Sign
Signature request sent
Triggers when a request is sent for signature.
- Dropbox Sign
Signer declined
Triggers when a signer declines a request.
- Dropbox Sign
Send signature request
Send a document or template for e-signature.
- Dropbox Sign
Use template
Send a request built from a reusable template.
- Dropbox Sign
Download signed PDF
Pull the executed PDF and audit trail.
- Dropbox Sign
Send reminder
Nudge signers who haven't completed.
- Microsoft 365
New email in Outlook
Triggers when a new email arrives in Outlook.
- Microsoft 365
New calendar event
Triggers when a new event is added to a calendar.
- Microsoft 365
New file in OneDrive
Triggers when a file is added to OneDrive.
- Microsoft 365
Send email
Send a new email from your Outlook account.
- Microsoft 365
Create event
Add a new event with attendees and reminders.
- Microsoft 365
Upload file to OneDrive
Add a file to a OneDrive folder.
- Microsoft 365
Create document in Word
Create a Word document with starter content.
Common questions
How does Caddi connect Dropbox Sign and Microsoft 365?
Dropbox Sign and Microsoft 365 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 Dropbox Sign and Microsoft 365 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 Dropbox Sign and Microsoft 365 to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Dropbox Sign + Microsoft 365 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 Dropbox Sign and Microsoft 365?
Drop your work email and we'll show you Caddi running end-to-end against Dropbox Sign, Microsoft 365, and the rest of your stack.