Turn receipt PDFs into a completed cover sheet

Stephen Toback used Claude Cowork to pull receipt data from PDFs and assemble the paperwork he normally fills out manually.

Done with Claude Cowork· Intermediate· Feb 2026

What they did
Stephen Toback asked Cowork to read a purchasing-card receipt PDF, gather the relevant fields, and format them for his report paperwork. The agent ran a Python job inside its local Linux environment, ran into an error, then troubleshot it and produced the files anyway. He also tried the same workflow on a directory of PDFs.
How it went
The receipt-processing run finished and the generated files landed in the outputs folder. Afterward, Cowork stalled when its connection failed, and neither reopening the app nor rebooting the machine fixed it; clearing the app’s saved state was needed to get it working again.
Tips
For batch receipt work, this can save manual copying, but a lost connection can interrupt the run. Keep the output directory separate so completed files survive a crash.

Try it yourself with Claude Cowork

I have purchasing-card receipt PDFs in [folder path]. Read each file, capture the vendor, date, amount, and business purpose, and place the results into [cover sheet template or column list]. Process one PDF at a time and write each completed item to an outputs folder as you go. If a file cannot be read, flag it for me. Before any step that would send, submit, delete, or overwrite data, pause and ask for my approval.

Fill in the [brackets]. Agents can make mistakes, so review anything before it is sent, paid or deleted.

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