← Back to all free guides
A free guide by Mariah Brunner ↗ INSTAGRAM ↗ TIKTOK

5 Ways Claude Should Be
Saving You Money

Point Claude at the boring money stuff and it finds cash you’re leaving on the table. Five ways, each with the prompt, a skill you can download, and how to do it safely.

Claude is great at the money jobs you keep meaning to do and never get to. It can dig through your inbox, compare prices, and write the awkward email or phone script for you.

Each way below has a prompt you can paste into any chat, plus a free skill download if you want Claude to remember it. Claude finds options and spots problems. You still double-check the numbers, and for medical, legal or tax calls, talk to a professional.

1. Bill Watchdog

Connect Gmail and Claude searches your inbox for renewals, price hikes and free trials that are about to charge you. In Claude, open Customize (called Plugins once your app updates), go to Connectors, and connect Gmail. (Gmail connector help) No connector? Paste or attach your last few statements instead.

Prompt: Catch Sneaky Charges Before They Hit
You are my personal subscription and bill auditor. Your job is to find every recurring charge hitting my accounts and tell me exactly which ones to kill. Search my connected Gmail if you have it, or use the receipts, statements, or billing emails I paste or attach. Work only from what you can actually see. Do not invent charges. STEP 1 - FIND EVERYTHING. Search the last 90 days plus anything scheduled ahead: subscription renewals, membership auto-renewals, annual plans about to re-bill, price-increase notices, free trials about to convert, App Store and Google Play subscriptions, and anything charging on a schedule. Good searches: "renewal", "your subscription", "receipt", "trial ends", "price change", "auto-renew". Include the small ones. The 4 to 12 dollar charges are the ones people miss. STEP 2 - BUILD THE TABLE. One table, sorted by next charge date, soonest first. Columns: Service, What it's for, Amount, How often, Next charge date, Keep or cancel. Put any free trial ending in the next 7 days in bold at the very top so I can't miss it. STEP 3 - FLAG THE WASTE. Call out anything I pay for twice (two tools doing the same job), anything that jumped in price, anything I clearly forgot about, and any annual plan where a monthly plan would be cheaper for how I actually use it. STEP 4 - DO THE MATH. Total my recurring spend per month and per year. Then a second number: what I'd save per year if I cancel everything in the cancel column. STEP 5 - MAKE IT EASY. For each cancel, give the steps or the cancellation link from the company's own emails, and whether I lose access immediately or at the end of the period. RULES: Only list charges you can see evidence of. If you're not sure about one, put it in a "double-check these" list instead of guessing. Never cancel, reply, or unsubscribe on my behalf. Ask me a question or two first if it would make the audit sharper.
↓ Download the skill (.zip)

One forgotten subscription at 15 dollars a month is 180 dollars a year, and most people have more than one hiding in there.

2. Best Time To Buy

Tell Claude what you want to buy, like a flight, a mattress, a TV or a car. It tells you when prices usually drop, what a good price looks like, and how to pay even less.

Prompt: Find The Cheapest Time To Buy
You are a sharp deal researcher who knows the pricing cycles for consumer purchases. Help me buy [the item, like a mattress, a flight to a specific city, a 65-inch TV, a used car, a laptop, or an appliance] for the lowest realistic price. My budget is [amount] and I need it by [date, or "no rush"]. STEP 1 - THE TIMING. Tell me the weeks or months this item usually hits its lowest prices, cheapest window first, with one line on why each window works (like new models arriving so last year's model gets cleared out, or holiday sale weekends for this category). If you can search the web, check current prices and any sale happening now. STEP 2 - THE TARGET PRICE. Tell me what a good price looks like for a solid version of this item, a "walk away above this" number, and what a fake deal or a stripped-down model looks like so I don't get fooled. STEP 3 - PAY EVEN LESS. Give me 3 to 5 moves for this exact category: what to ask for, coupons or codes that usually exist, price-match policies, open-box or refurbished options, and a negotiation line that works for this item. STEP 4 - THE WATCH LIST. Tell me which kind of price tracker fits this item (a price-history tool for electronics, fare alerts for flights) and the 2 or 3 signals that mean "buy now, it won't get cheaper." STEP 5 - RED FLAGS. List the traps for this category: fake "was" prices, financing that hides the real cost, restocking fees, and warranty upsells that aren't worth it. RULES: These are patterns, not guarantees, so say so and tell me to confirm the live price before I buy. Don't make up specific prices you haven't checked. If the timing depends on something about me, like travel dates I can move, ask me before you answer.
↓ Download the skill (.zip)

These are patterns, not promises. Prices change constantly, so confirm the live price before you buy.

3. Prescription Savings

Claude finds the generic version of your medication, how to compare pharmacy prices, and a coupon that can beat your copay. This one can save real money every month.

Prompt: Pay Less For Your Prescription
You are a careful prescription-savings researcher. Help me pay the lowest possible price for [medication and dose, for example atorvastatin 20mg, 30-day supply]. My insurance situation: [my plan and copay, or "no insurance"]. My ZIP code: [ZIP]. You are not changing my treatment, only lowering the price of what my doctor already prescribed. STEP 1 - GENERIC CHECK. Tell me the generic name and whether a generic exists, since a generic has the same active ingredient and usually costs far less. If there's no generic yet, say so. STEP 2 - CASH VS INSURANCE. Explain that the cash price with a coupon sometimes beats the insurance copay, and how to check both so I pay whichever is lower. STEP 3 - COUPON WALKTHROUGH. Walk me through a free tool like GoodRx or SingleCare: how to search my exact drug and dose, compare cash prices at pharmacies near me, and what to show the pharmacist before I pay. Note that the coupon replaces insurance at checkout. It does not stack on top, and money paid with a coupon may not count toward my deductible. STEP 4 - COST PLUS DRUGS. Check whether this drug is sold on Mark Cuban's Cost Plus Drugs (costplusdrugs.com), which prices drugs at its cost plus a 15% markup and a small pharmacy fee, plus shipping. If you can search the web, look up the current price. If you can't, tell me how to check it. STEP 5 - OTHER LEVERS. Cover a 90-day supply instead of 30 (often cheaper per pill), pharmacy discount programs, manufacturer copay cards for brand-name drugs, and whether mail-order is cheaper. STEP 6 - MY CHEAPEST PATH. Lay out my single cheapest realistic option in plain terms, and give me 2 questions to ask my pharmacist or doctor to lower it even more. RULES: This is not medical advice and you are not changing my prescription. Never quote a price as fact unless you just checked it, and tell me to confirm the live price. Flag anything I should run past my doctor or pharmacist first.
↓ Download the skill (.zip)

GoodRx and SingleCare are free coupon tools you show the pharmacist before you pay. The coupon replaces your insurance for that fill, so it may not count toward your deductible. Mark Cuban’s Cost Plus Drugs (costplusdrugs.com) sells drugs at its cost plus a 15% markup, a small pharmacy fee and shipping, which can be far cheaper for many generics.

Do This Safely

This isn’t medical advice. Check with your doctor and pharmacist before you switch pharmacies or versions of a drug.

4. Retention Script

Companies save their best discount for when you try to cancel. Claude writes the exact words to get it for your phone, internet, streaming or insurance bill, so you’re not making it up on the spot.

Prompt: Lower A Monthly Bill On The Phone
You are a friendly, sharp negotiation coach who has talked companies down hundreds of times. Write me a word-for-word phone script to lower my [bill, like internet, phone, cable, streaming, or insurance] with [company]. I've been a customer for [number] years, I pay [amount] a month, and a competitor is offering [the competitor and their deal, or say: find a current competing offer I can cite and tell me where you found it]. OPENING. The exact words to open with, calm and friendly. Have me ask early for the retention or cancellations department, since front-line reps usually can't give the real discounts. THE ASK. Word for word: mention how long I've been a customer, that I've been happy but the price keeps creeping up, name the competitor's offer, and ask them to match or beat it. IF THEY SAY NO. A polite escalation line, then the move: say I'm ready to cancel and ask to be transferred to cancellations. Script that transition. AT CANCELLATIONS. The lines that unlock the best save offers, including loyalty credits, current promotions, and dropping a tier instead of paying full price. CLOSE. How to lock in the new rate: get the rep's name, a confirmation number, the exact new monthly price, how long it lasts, and whether it adds a contract. Have me repeat it back. BACKUP. Two backup lines if they still won't budge, including a "let me think about it" exit that keeps my account open so I can call back and get a different rep. FORMAT: Short spoken lines I can read off my phone screen during the call. End with 3 quick do's and don'ts so I stay friendly and firm, never rude. Don't invent competitor prices. If you can't check a real offer, leave a blank for me to fill in.
↓ Download the skill (.zip)

Asking for the retention or cancellations department is the classic move, and it works. In a 2019 Consumer Reports survey of more than 108,000 members, 76% of people who haggled with their cable or internet provider got a discount or another perk.

5. Medical Bill Auditor

Upload a medical bill and your insurance Explanation of Benefits. Claude reads them line by line to find likely errors and overcharges, then writes your dispute letter.

Prompt: Audit A Medical Bill For Errors
You are a meticulous medical-billing advocate. I'm going to upload a medical bill (and my insurance Explanation of Benefits if I have it). Find the likely errors and overcharges, then write my dispute letter. STEP 1 - GET THE RIGHT DOCUMENT. If I only have a summary bill, tell me to request the fully itemized bill first (with billing codes), since the summary hides the line items where errors live. Give me the exact words to ask the provider for it. STEP 2 - LINE-BY-LINE AUDIT. Go through every line and flag: duplicate charges, upcoding (a routine visit billed at a higher complexity level), unbundling (one procedure split into several billed pieces), services or supplies I never received, charges for canceled tests, facility fees that don't match what happened, and any price far above the typical rate. For each, point to the exact line and say in plain English why it looks wrong. STEP 3 - CHECK AGAINST INSURANCE. Compare the bill to my Explanation of Benefits. Flag anything billed to me that insurance should have covered, and any amount above what my plan allowed. If this was emergency care, or an out-of-network provider at an in-network hospital, tell me whether the federal No Surprises Act might protect me. If I'm uninsured and got a Good Faith Estimate, check whether the bill is $400 or more above it. STEP 4 - PRICE REALITY CHECK. For the biggest charges, tell me how to look up a fair price, like the hospital's own public price list (hospitals are required to post one) or a consumer price-lookup tool, so I know which charges to fight hardest. STEP 5 - THE DISPUTE LETTER. Write a short, firm, professional letter to the billing department. List each charge I'm questioning by line and code, ask them to correct it or explain it in writing, request a corrected itemized bill, and ask for a hold on collections while it's reviewed. Leave blanks for my name, account number, and date. STEP 6 - NEXT MOVES. Give me a short checklist: who to call, what to say on the phone, how to escalate to a patient advocate or my state insurance department if they stonewall, and how to ask about financial assistance or a payment plan. RULES: Only flag what the documents actually show, and label each flag "likely error" or "worth asking about." I confirm everything with the provider and my insurer before disputing. This is not legal or medical advice.
↓ Download the skill (.zip)

Billing advocates, including the Medical Billing Advocates of America, estimate that most medical bills they review contain at least one error, with figures as high as 80%. That’s their estimate, not a study, but it means any big bill is worth a careful look. Always ask for the itemized bill first.

Do This Safely

Claude spots likely errors. Confirm each one with the provider and your insurer before you dispute anything. This isn’t legal advice.

Install The Skills

Prompts work in any chat. A skill means you never have to paste it again: Claude picks it up when you ask for that job. Skills work on every Claude plan, including Free.

  1. Turn on code execution. Go to Settings, then Capabilities, and turn on Code execution and file creation (it may say Create and edit files).
  2. Upload the ZIP. Open Customize (or Plugins), then Skills. Click +, then Create skill, then Upload a skill, and pick the ZIP. Don’t unzip it first.
  3. Use it. Start a chat and ask, like "audit my subscriptions" or "help me fight this medical bill."

(Claude’s skills help page)

One Honest Note

Results vary and none of this is a guarantee. Verify every number, price and charge yourself before you act on it. This isn’t financial, medical or legal advice, so for anything big, talk to a professional you trust.