It’s end of the year and I have some leftover balance in healthcare FSA. So I collected some amazon receipts to try to reimburse.
Amazon invoices conveniently tell you how much in an order was FSA eligible. I went through my orders in 2025 and exported a bunch of PDFs. Then I figured this might be a good opportunity to try out AI!
1st try: Claude Code + Claude Chrome extension
Prompt:
I have PDF invoices with FSA eligible expenses in “~/Downloads/fsa invoices” directory now, I also have the page https://justworks.optumfinancial.com/portal/CC/cdhportal/cdhclaims/paymyself open in chrome that you should be able to access. I want you to submit each PDF as a “Reimburse myself” type of claim Find the “FSA or HSA eligible” amount and the order date in the PDF
What was nice: Claude easily parsed all PDFs and pointed out there were 2 duplicated invoices so it will skip one of them.
What was difficult: Claude Code had a lot of trouble to work with Claude Chrome extension. It couldn’t take screenshot until I disabled all other Chrome extensions.
What broke: Claude Chrome extension could NOT upload files… it can click the “upload” button, but then politely ask me to select the file. What do I need you for??!
2nd try: ChatGPT Agent Mode
So I turned to ChatGPT. I initially want ChatGPT Mac desktop app to control my browser, but couldn’t even find that option. So I used ChatGPT’s “agent mode”, which runs everything on a remote virtual machine.
What was nice: ChatGPT could not read my local PDFs, but after I uploaded all PDF files, it easily parsed them and identified the duplicated invoices too.
What broke: ChatGPT app asked me to “take over” and log into the FSA site, but there is no “take over” button anywhere…. I spent a good 5 minutes to look up and down and couldn’t find that button. I searched reddit and found people reporting the same bug recently. I think OpenAI are shipping too much slop codes written by AI…
3rd try: Claude Desktop App
After some fiddling, I figured Claude desktop app can work with Claude Chrome extension too. You need to turn on a connector then select that connector in chat.
But it failed at the same issue: Claude Chrome extension cannot upload file… and I don’t want to sit around to select a file each time.
Also Claude Chrome extension was quite slow. It took almost a minute for it to find a button to click.
4th try: Claude Code + Good Old Playwright
This time it worked like a charm!
Playwright MCP can upload files, and it works much faster than Claude Chrome extension.
What’s nice is once Claude Code finished the first submission, it did the remaining much faster! It summarized what it did in the first try and wrote some badass playwright script to do the rest in that classic robot click speed 😂
So once this thing worked, 2 minutes later I had a dozen claims auto submitted. It was satisfying.
Now I’m looking forward to the next annual sexual harassment training….