The Subscription Audit

Why subscriptions pile up

Every subscription sends an email when it charges you, and most of us skim right past them. A $29 charge doesn't feel like much on its own, so it renews, and then renews again, long after you stopped opening the tool.

I found that out this fall. I gave Claude access to my Gmail and asked it to list every subscription it could find in my receipts and renewal emails. Then we went through the list one at a time. "HeyGen, do you really need it?" No. I hadn't opened it in months, and it was still charging me $29 a month.

Most of the list went the same way: good tools I'd simply stopped using. A couple needed more care. My accounting software held years of records, so I downloaded everything before canceling it. Another tool was keeping sales tax records for a company I'd already closed, and I'd been paying for it mostly because I was afraid of losing that data. So far the total is $260 a month I don't spend anymore.

Step 1: Find every subscription

There are two ways to do this, depending on whether you're comfortable letting an AI into your email.

If your AI can read your email

Claude and ChatGPT can both connect to Gmail. Before you connect one, check what you're allowing. Claude's help center says its Gmail connection can search and read email and can also draft, send, reply and forward, asking for your approval before each of those by default (checked October 28, 2026). For this job it only needs to read, and the prompt tells it so.

Search my email from the last 12 months for receipts, invoices, renewal notices and anything about a subscription or a plan.

Make one table of every service that charges me again and again, with these columns:
Service | Price | How often it charges | Next renewal date | Email address it was sent to

Rules:
Only list what you actually found in an email. If an email doesn't say the price or the date, leave that cell blank. Don't guess.
Put the most expensive per year at the top.
Don't cancel anything, and don't reply to or send any email. Just read and make the list.

If you'd rather not connect it

Search Gmail yourself, open what it finds and copy the text of each email into the chat. Paste this into Gmail's search box to find the last year of receipts, renewals and invoices:

subscription OR renewal OR receipt OR invoice OR "your plan" newer_than:1y

If your inbox is split into tabs, category:purchases newer_than:1y also finds what Gmail filed under Purchases. Google's page on Gmail search words explains how to change either search. Then give the AI this, with the emails pasted underneath:

Below are emails I copied from my inbox: receipts, invoices and renewal notices.

Make one table of every service that charges me again and again, with these columns:
Service | Price | How often it charges | Next renewal date

Rules:
Only list what is actually in the emails below. If one doesn't say the price or the date, leave that cell blank. Don't guess.
Put the most expensive per year at the top.

[paste the emails here]

Step 2: Read the list it gives you

You should get back one table, most expensive first. Here are three lines from mine, before I started canceling:

Check each price against your bank or card statement. An email shows what you were charged that one time, and prices sometimes change after a trial or a first year ends. A blank in the table is fine. It means the email didn't say, and it's a lot better than a number the AI made up.

Step 3: Ask three questions before you keep each one

Go one at a time. It's tempting to keep everything "just in case," and that's how the list got long in the first place. Copy this once for each subscription:

Service: ____________
Price and how often: ____________

1. When did I last actually use it?
    ____________

2. What would stop working if it ended tomorrow?
    ____________

3. What would I lose by canceling, and can I download it first?
    ____________

Decision: KEEP / CANCEL / DOWNLOAD FIRST, THEN CANCEL / CHEAPER PLAN
Done on: ____________

The third question is the one that kept me paying for that sales tax tool. If the only reason you're keeping something is the data inside it, download the data first, then decide.

Before you click cancel

• Download anything with records in it first: invoices, reports, customer lists, tax records. For accounting software, my post on what to export before canceling lists what I saved.
• Check what else uses the account. A login, a domain or an email address can hang off a service you're about to close. The free Before You Cancel worksheet walks through it.
• Look at the renewal date. On a yearly plan, canceling a few days after it renews can mean paying for a year you won't use, so check the company's own cancellation terms.
• Write down what you canceled and when, so a surprise charge next month is easy to spot.

About Andrew Voskov

Andrew Voskov is the founder of Cherry Pi AI. He spent twenty years running online businesses before AI, and now helps small businesses with marketing, bookkeeping and custom AI tools. There's more about bookkeeping help on the services page.