AI-native automation
Automate work across
Microsoft Outlook and 
PDFwith Caddi AI Agents.
Automate anything you do across Microsoft Outlook, PDF, 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 PDF
Connect Microsoft Outlook to Caddi
Allow1Sign in to Microsoft Outlook
One click with your own Microsoft Outlook login. No API keys.
- Engagement letter.pdf
2Add your PDFs
Upload them, or point Caddi at their folder.
Document extract in PDF 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 PDF together
- 01
Document extract in PDF when new email in Microsoft Outlook.
Caddi watches Microsoft Outlook for new email and document extract in PDF. No copy-paste, no missed records.
- 02
Send email in Microsoft Outlook when classify in PDF.
Caddi watches PDF for classify and send email in Microsoft Outlook so the two systems stay in lockstep.
- 03
Extract in PDF from Microsoft Outlook events.
When new event happens in Microsoft Outlook, Caddi extract in PDF with the right context attached.
Actions Caddi can take across Microsoft Outlook and PDF
- 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.
- PDF
Classify
Classifies text content using AI with customizable classification types (language, tone, sentiment, topic, category), accepting content directly or automatically downloading from S3.
- PDF
Summarize
Summarizes text using AI with customizable style and length parameters, accepting content directly or from S3.
- PDF
Get form fields
Discovers all form fields in a PDF including field types, options, and validation rules.
- PDF
Document extract
Extracts text or structured fields from PDF documents and images stored in S3 Use mode "full_text" to extract all document text, or mode "schema" with a JSON Schema to extract specific named values…
- PDF
Extract
Extracts specified information from text using AI, accepting content directly or automatically downloading from S3.
- PDF
Extract data from PDF
Extracts specific field values from PDF documents using AWS Textract for OCR and LLM for intelligent field mapping, with automatic batching strategy for large schemas.
- PDF
Extract fields with OCR
Extracts specified field values from images (JPEG, PNG) and PDFs using AI-powered OCR with confidence scoring and validation, automatically downloading content from S3 (supports both full S3 keys a…
- PDF
Extract multiple fields
Extracts values for specified fields from text using AI, accepting content directly or from S3.
- PDF
Write
Generates written content using AI with customizable style, format, tone, length, language, purpose, and audience parameters, accepting content directly or automatically downloading from S3.
- PDF
Extract pages
Extracts one or more pages from a PDF stored in S3 and saves the result as a new PDF file in S3 Specify start_page and end_page (1-indexed, inclusive) to select the page range.
- PDF
Extract text
Extracts all text from PDFs with support for page ranges and maintains text structure.
- PDF
Fill form
Fills PDF form fields and automatically saves the completed PDF to S3 with optional flattening.
- PDF
Image to PDF
Downloads images from S3, converts them to a multi-page PDF with configurable page sizing, and uploads the result to S3.
- PDF
Merge documents
Downloads multiple PDFs from S3, merges them with optional page range selection, and uploads the merged PDF to S3 Set flatten_form_fields to true when merging PDFs with filled forms or signatures t…
- PDF
Text to PDF
Creates a PDF from text content with configurable formatting options (page size, margins, font size, bold text), and uploads the result to S3.
Common questions
How does Caddi connect Microsoft Outlook and PDF?
Microsoft Outlook and PDF 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 PDF 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 PDF to other tools too?
Yes. Most Caddi loops span 3–6 tools. Once the first Microsoft Outlook + PDF 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 PDF?
Drop your work email and we'll show you Caddi running end-to-end against Microsoft Outlook, PDF, and the rest of your stack.
Or skip the demo: sign up free and build it yourself.