Let Claude sort hundreds of messy PDFs into the right folders

🧰 Before you start

• A paid Claude plan (Pro, Max, Team or Enterprise)
• The Claude desktop app (Mac or Windows) for Cowork features
• A folder of PDFs to sort (make a backup copy first)

🪜 Steps (tick as you go)

1. ☐
   1. Back up first

   Copy the messy folder somewhere safe, e.g. an external drive or cloud folder.

2. ☐
   2. Open Cowork

   Open the Claude desktop app, choose Cowork and give it access to the messy folder only.

3. ☐
   3. Agree the folders

   Paste the 'Sort my PDFs' prompt. Let Claude suggest folders first and approve them before it moves anything.

4. ☐
   4. Let it work

   Claude reads each file, renames and moves it. Large folders take a while; you can do other things.

5. ☐
   5. Check the summary

   Open the index file it makes and spot-check 10 files.

6. ☐
   6. Keep it tidyOptional extra

   Repeat monthly, or ask Claude to schedule it.

💬 Prompts to copy

Look at every PDF in this folder. First, propose a folder structure (e.g. Property / Tenancy, Property / Loan, Tax, Bank, Insurance, Receipts, Other) and wait for my OK.
Then: rename each file 'YYYY-MM-DD – who – what.pdf' (e.g. '2026-03-01 – Landlord – Tenancy agreement Unit 12-3.pdf'), move it to the right folder, and make 'index.csv' listing old name, new name, folder and a one-line summary.
Never delete files. Put anything you're unsure about in 'To check'.

🔗 Links

• Reddit thread (source): https://www.reddit.com/r/claude/comments/1ur3x8a/when_or_what_to_use_cowork_for/
• Claude Cowork use cases tested (Substack): https://aiblewmymind.substack.com/p/claude-cowork-use-cases-guide

From https://usecasy.com/use-case/claude-sort-pdfs/ · Guide checked 15 October 2026 · Prices are rough and shown in USD unless stated (MYR where relevant).