Paperwork & PDFs | AI for Real Life

The pile that doesn't stop.

Warranties for things you bought three years ago. Service agreements buried somewhere. Contracts that automatically renew if you don't say something. School forms. Health forms. Insurance docs. They arrive as paper, as emailed PDFs, as web downloads. They all need to be findable when you suddenly need them — usually months later, usually right now.

This lesson is the workflow for that. Drop paperwork into Home Operations, ask Cowork to file it, get back a clean filename, a short summary, and a flag on anything time-sensitive. Months later when you need it, ask Cowork — it finds it.

Drop and file.

The basic move: drag the PDF (or photo of the paper) into your Home Operations folder, then tell Cowork to handle it.

One way to ask:

Sample — file this paperwork

I just dropped a PDF in this Project's folder — it's the warranty for the dishwasher we bought last week. Take a look at it: rename the file with the date and what it is (use a clear naming convention I can read later), move it to an appropriate subfolder (create one called "warranties" if it doesn't exist yet), add a one-line entry to a Paperwork-Log.md file in this Project, and tell me anything I need to do something about — registration deadlines, terms I should know, claim procedures, when it expires.

Cowork does all of it. You drop. Cowork files. You walk away with a clean folder, a log entry, and (if there's something time-sensitive) a flag.

Pick a naming convention once.

The first time you file a piece of paperwork, tell Cowork the naming convention you want — and then it sticks for every future file. Examples that work:

2026-05-15-dishwasher-warranty.pdf (date-thing-type)
warranty-dishwasher-2026.pdf (type-thing-year)
dishwasher-warranty.pdf (just thing-type, year goes inside)

Whichever you pick, tell Cowork to use that pattern from here on. You stop having to think about it.

Find it later.

The whole point of filing is finding. Six months from now, the dishwasher dies and you need the warranty. Or you're wondering if the alarm system contract auto-renews. Or you need to find proof of when the HVAC was last serviced before calling for a tune-up.

One way to ask:

Sample — find something later

I need to find something in my paperwork. [Describe what you're looking for — "the warranty for our dishwasher," "anything related to our alarm system contract," "the receipt from when we bought the lawnmower."] Search across the PDFs and files in this Project. Tell me which file it's in, the relevant details (don't read me the whole thing — just what I actually need), and where it lives in the folder so I can grab it.

Cowork searches, reads the relevant PDFs, and gives you exactly what you asked for. Often saves the call to wherever you'd otherwise call.

Or just ask the broader question.

Sometimes you don't know exactly what you're looking for — you have a question, and you suspect the answer is in your paperwork somewhere:

"When does our home insurance renew, and what would I need to switch carriers?"
"Are any of our service contracts set to auto-renew in the next 60 days? If yes, give me a list."
"What's our deductible on the appliance protection plan? I think the dryer might qualify."

Cowork looks across the paperwork and answers.

Make it ongoing.

The drop-and-file workflow handles paperwork one piece at a time. The system gets better when you connect it to the streams that paperwork actually comes in on — your phone and your email.

Paper that comes home — snap and Dispatch.

School form, doctor's office handout, anything that arrives on paper. Snap a photo with your phone, open Dispatch, send it to Home Operations:

Sample — paper via Dispatch

Send this to Home Operations: here's a paper [Aiden] brought home (attached). File it the usual way — read it, rename it, save to the right subfolder, add a Paperwork-Log entry, and flag anything time-sensitive.

"The usual way" works because Cowork remembers the filing conventions you set up in Screen 2. No need to re-explain each time.

PDFs from email — pull them automatically.

If you set up Gmail or your Outlook connector in the Email & Calendar module, Cowork can scan your inbox for paperwork and file it without you forwarding each one:

Sample — sweep paperwork from email

Look through my email from the past month for any attached PDFs that look like household paperwork (warranties, contracts, service agreements, bills, school forms, insurance docs). Save each one to my Home Operations folder using my usual filing convention. Add them all to Paperwork-Log.md. Tell me anything time-sensitive across the batch.

Worth running monthly — or set it up as a scheduled task that runs on its own on the first of each month.

Next: Sunday Household Reset.

Last lesson of the module. The weekly rhythm — Cowork pulls together what's worth handling this Sunday based on everything you've added during the week.

Continue to Sunday Household Reset →