I gave Claude my card and bank statements, plus PayPal, Venmo and Apple Pay, and asked it to find every recurring charge. It found subscriptions I'd completely forgotten. Between those and a few tax questions, I found $5,500 in less than an hour. Here are my prompts, and what I do before any statement goes near an AI.
I've uploaded my statements from the last 12 months: [list them, e.g. Visa, checking account, PayPal, Venmo]. Account numbers are blacked out. 1. Find every recurring charge: anything that repeats monthly, yearly or on any other schedule. Put them in a table with the merchant, the amount, how often it charges, which account it's on, the first and most recent charge dates, and the total for the year. 2. Flag anything I may have forgotten: - charges I've paid for more than once, or on two different accounts - prices that went up during the year - free trials that turned into paid plans - small charges that are easy to skim past - merchant names you can't identify 3. Show me where I could save money. For each flagged charge, say whether I could cancel it, downgrade it, or switch to a cheaper yearly plan, and what that would save me per year. 4. Give me my total monthly and yearly spend on subscriptions, and the total I'd save if I made every change you suggest. Only use what's in the statements. If you're not sure a charge is recurring, or what a merchant is, say so and ask me. Don't guess.
I've uploaded tax documents and letters I've received: [list them]. Personal numbers are blacked out. 1. Explain each one in plain English: who sent it, what it's about, any amount it mentions and any deadline. 2. List anything that suggests I may have overpaid, been charged twice, or be owed money. For each one, point me to the exact line or paragraph. 3. Turn that list into questions I can take to my accountant. Don't tell me what to file or claim. My accountant makes those calls. If a document is unclear, say so.
The day you start a free trial, set a reminder to cancel it two days before it ends. If you've connected Google Calendar to Claude, ask it: Add an event to my calendar on [date] called Cancel [service] free trial. The Google Calendar connector can create events for you.
Yes, if you give it your statements. Upload 12 months of card, bank, PayPal and Venmo statements to Claude and ask it to list every charge that repeats, with the merchant, amount, how often it charges and the total for the year. Twelve months catches the yearly renewals. Ask it to flag price rises, duplicate charges and free trials that turned into paid plans.
Redact them and check your privacy setting first. Black out full card and account numbers, routing numbers, your address and anything with your Social Security number, then search the file to make sure they're gone. In Claude, switch off Help improve our AI models under Settings, then Privacy, and delete the chat when you're done.
Use a real redaction tool. In Adobe Acrobat Pro, choose All tools, then Redact a PDF, and the content is removed when you save. For a CSV, delete the account number column. Then search the file for one of the numbers you removed. If the search still finds it, redact again.
When you delete a chat in Claude, it leaves your history straight away and is deleted from Anthropic's back-end storage within 30 days. If the model training setting is on, Anthropic may keep your chats in a de-identified form for up to five years. Switch it off under Settings, then Privacy, before you upload statements.
Open Settings, tap your name, tap Subscriptions, choose the subscription and tap Cancel Subscription. That covers anything billed through Apple. For PayPal automatic payments, go to Settings, then Payments, and cancel with the company too, because stopping a payment in PayPal may not cancel your contract.
The bonus gives you my redaction checklist for financial documents, a short prompt to check each new statement against your subscription list, and where to cancel the charges Claude finds.
Use a real redaction tool. In Adobe Acrobat Pro it's All tools, then Redact a PDF, and the content is removed when you save. For a CSV, delete the account number column. Then search the file for the numbers you removed. If the search finds them, redact again.
Here are this month's statements: [list them]. Account numbers are blacked out. Here is my list of known subscriptions from last time: [paste the table Claude gave you last time] 1. List every recurring charge this month. 2. Flag anything new that isn't on my list. 3. Flag any charge on my list that changed price. 4. Flag any free trial that turned into a paid charge. 5. Give me an updated subscription table I can paste in next month. If you're not sure about a charge, ask me.
Apple subscriptions: on your iPhone, open Settings, tap your name, tap Subscriptions, choose the subscription and tap Cancel Subscription.
PayPal: automatic payments are under Settings, then Payments. Stopping one in PayPal stops the charges to PayPal, but it may not cancel your contract with the company. Cancel with the company too.
Everything else: cancel with the company directly, and keep the confirmation email.
Prompts, step-by-step guides and checklists you can put to work today.