Find a year of forgotten FSA-eligible purchases across three retailers and file 15 claims with an AI agent in Cursor

Posted

Sep 22, 2026 by Ramesh Raman (LinkedIn)

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Last checked

Oct 19, 2026

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Method:

How we verify

Evidence: Described by posterThe person describes what happened in words, without screenshots or video.

Outcome

Ramesh Raman dislikes filing reimbursements, so they pulled 12 months of receipts from three retailer accounts and had an LLM classify every item as FSA-eligible or not. They checked the ones it got wrong themselves until every eligible item had a PDF receipt, then pointed Cursor at their reimbursement portal to file the claims. From 600 transactions it submitted 15 claims worth $242.87, pausing for approval before every upload; they reviewed everything at the end. The first upload took about 2 minutes and the last under 30 seconds. It took about an hour, for a chore they'd put off for months, and mostly recovered small forgotten buys like Tylenol.

Agent

Cursor

The source didn't share its exact prompt, so we wrote this from what it describes.

Before you start, ask me 1–3 short questions about anything important that's missing below. Keep them quick. Then do the task, checking in with me at the key points.

Goal: Find every FSA- or HSA-eligible purchase I made this year and get them reimbursed.

What I can give you (ask for whatever's missing):
- Order histories or receipts from the stores I use: [DETAILS]
- My benefits portal and plan type (FSA or HSA): [DETAILS]
- The plan year: [DATES]

You're not my accountant or financial adviser. Show your working, label estimates as estimates, and tell me which points a professional or the official source should confirm.

Rules:
- Mark each item eligible, not eligible or unsure, using the plan's or IRS's official eligibility list, and show me the unsure ones.
- Make sure every eligible item has a receipt that shows the item and price.
- Group items into claims the portal will accept, and show me the list and total first.
- Ask before each upload or submission, and keep a log of confirmations.
- If a site asks me to sign in, pause and let me do it myself (including any CAPTCHA or two-step code); never guess or store passwords.
- Check facts that can change (prices, opening hours, dates, availability, rules) against the official source, and tell me anything you couldn't verify.

Output: A list of eligible items with receipts, then a log of claims submitted.

You'll know it worked when: all the small eligible purchases I'd forgotten are reimbursed.

Before you start, ask me 1–3 short questions about anything important that's missing below. Keep them quick. Then do the task, checking in with me at the key points.

Goal: Find every FSA- or HSA-eligible purchase I made this year and get them reimbursed.

What I can give you (ask for whatever's missing):
- Order histories or receipts from the stores I use: [DETAILS]
- My benefits portal and plan type (FSA or HSA): [DETAILS]
- The plan year: [DATES]

You're not my accountant or financial adviser. Show your working, label estimates as estimates, and tell me which points a professional or the official source should confirm.

Rules:
- Mark each item eligible, not eligible or unsure, using the plan's or IRS's official eligibility list, and show me the unsure ones.
- Make sure every eligible item has a receipt that shows the item and price.
- Group items into claims the portal will accept, and show me the list and total first.
- Ask before each upload or submission, and keep a log of confirmations.
- If a site asks me to sign in, pause and let me do it myself (including any CAPTCHA or two-step code); never guess or store passwords.
- Check facts that can change (prices, opening hours, dates, availability, rules) against the official source, and tell me anything you couldn't verify.

Output: A list of eligible items with receipts, then a log of claims submitted.

You'll know it worked when: all the small eligible purchases I'd forgotten are reimbursed.

Before you start, ask me 1–3 short questions about anything important that's missing below. Keep them quick. Then do the task, checking in with me at the key points.

Goal: Find every FSA- or HSA-eligible purchase I made this year and get them reimbursed.

What I can give you (ask for whatever's missing):
- Order histories or receipts from the stores I use: [DETAILS]
- My benefits portal and plan type (FSA or HSA): [DETAILS]
- The plan year: [DATES]

You're not my accountant or financial adviser. Show your working, label estimates as estimates, and tell me which points a professional or the official source should confirm.

Rules:
- Mark each item eligible, not eligible or unsure, using the plan's or IRS's official eligibility list, and show me the unsure ones.
- Make sure every eligible item has a receipt that shows the item and price.
- Group items into claims the portal will accept, and show me the list and total first.
- Ask before each upload or submission, and keep a log of confirmations.
- If a site asks me to sign in, pause and let me do it myself (including any CAPTCHA or two-step code); never guess or store passwords.
- Check facts that can change (prices, opening hours, dates, availability, rules) against the official source, and tell me anything you couldn't verify.
- Set up a simple monthly routine so receipts are collected as I go.

Output: A list of eligible items with receipts, then a log of claims submitted.

You'll know it worked when: all the small eligible purchases I'd forgotten are reimbursed.

Before you finish: re-read my goal and constraints, check your answer against each one, and list anything you assumed or couldn't confirm.

Source

https://www.linkedin.com/posts/rameshdotr_i-dislike-filing-reimbursements-so-i-decided-activity-7507951871009906688-L_P6