AI-native automation
Automate work across
Microsoft Outlook and 
Sentrywith Caddi AI Agents.
Automate anything you do across Microsoft Outlook, Sentry, 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 Sentry
Connect Microsoft Outlook to Caddi
Allow1Sign in to Microsoft Outlook
One click with your own Microsoft Outlook login. No API keys.
Connect Sentry to Caddi
Allow2Sign in to Sentry
The same click again. Both tools are connected.
Resolve issue in Sentry 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 Sentry together
- 01
Resolve issue in Sentry when new email in Microsoft Outlook.
Caddi watches Microsoft Outlook for new email and resolve issue in Sentry. No copy-paste, no missed records.
- 02
Send email in Microsoft Outlook when new issue in Sentry.
Caddi watches Sentry for new issue and send email in Microsoft Outlook so the two systems stay in lockstep.
- 03
Assign issue in Sentry from Microsoft Outlook events.
When new event happens in Microsoft Outlook, Caddi assign issue in Sentry with the right context attached.
Actions Caddi can take across Microsoft Outlook and Sentry
- 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.
- Sentry
New issue
Triggers when Sentry groups a new error into an issue.
- Sentry
Issue regressed
Triggers when a resolved issue starts happening again.
- Sentry
Alert fired
Triggers when a Sentry alert rule's threshold is crossed.
- Sentry
Resolve issue
Mark an issue resolved, optionally in the next release.
- Sentry
Assign issue
Assign an issue to a person or team.
- Sentry
Fetch issue details
Pull the stack trace, tags and event counts for an issue.
Common questions
How does Caddi connect Microsoft Outlook and Sentry?
Microsoft Outlook and Sentry 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 Sentry 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 Sentry to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Microsoft Outlook + Sentry 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.
Ready to automate Microsoft Outlook and Sentry?
Drop your work email and we'll show you Caddi running end-to-end against Microsoft Outlook, Sentry, and the rest of your stack.
Or skip the demo: sign up free and build it yourself.