Quicken Classic for Mac is a good personal finance tool—it simplifies and automates most of my financial tracking. But there are a few tasks I do manually every month:
- Entering transactions for banks that don’t support Quicken Transaction download.
- The dreaded task of categorizing Amazon transactions.
Not anymore. Both of those are now automated.
Anthropic recently released a beta feature for Claude Cowork which allows it to control a Mac.
Image generated using ChatGPT (DALL·E), March 2026
A simple prompt:
“Can you reconcile my [x] account with Quicken?”
And the next thing I know Claude Cowork is on my bank website, finds the transaction history, enters all the missing transactions, and does the reconcile in Quicken.
And for categorizing Amazon transactions:
“For each unreviewed transaction in Quicken in my Amazon Visa account, categorize it (ask me if unsure) using Amazon’s transaction history.”
And it goes to Amazon, finds my orders, and categorizes each one. I didn’t have to teach it what categories I used; it searched for things that made sense until it found the best match.
AI just saved a couple of hours of work each month. And Quicken for Mac doesn’t support MCP; this is interacting with the computer like a human would.
I wouldn’t say it’s fast; it was slower than me, but I sat down and watched a movie with my family while it worked. It kept me updated via messages to my phone so I could have been on a walk or wherever to answer any questions it had. This is like texting Jarvis to do a task for you. I could be out on a hike, have an idea, send Claude a message, and the work would be done on my Mac before I get back home.
It’s not seamless. Claude did ask me to log in to the bank, and I did have to answer a few questions. But I’m confident these rough edges will be worked out over time.
Now, this automation could have been done with some scripting or RPA (Robotic Process Automation)–but I didn’t have to spend hours writing the scripts, and using AI makes the process less likely to break when Quicken releases an update or the websites change. It took 10 seconds to hand that task off to Claude.
This is the first phase of Agentic AI. Automating scutwork with a sentence.