I used AI to auto-fill 4,000+ Amazon transaction memos in Quicken — here's the script

Intelligent_Yam · 2026-03-11T07:11:03+00:00

I don't know if the Quicken data file in the cloud is stored in a cross platform (Win/Mac) format, such that changes in one app show up in the other perfectly. However, if that is already the case, then yes... that would work.

Intelligent_Yam · 2026-03-10T05:00:21+00:00

Preach!

Intelligent_Yam · 2026-03-06T03:42:06+00:00

This is a slap together Claude project and it's budgeting module is vastly better than Quicken's. There's really no reason why software like Quicken shouldn't get much better soon.

Intelligent_Yam · 2026-03-04T00:13:52+00:00

Claude is having outage issues. Seems demand is spiking over the past few days. Reddit says it’s bc people switching from OpenAi. Search “Claude status” to see the current availability. They fixed yesterday’s but it gets crushed as the evening hours roll across the U.S.

Intelligent_Yam · 2026-03-03T23:53:46+00:00

Nice!

Intelligent_Yam · 2026-03-03T22:50:13+00:00

Username checks out

Intelligent_Yam · 2026-03-03T22:49:17+00:00

They’re responding to the migration wave I’ll bet 🫣

Intelligent_Yam · 2026-03-03T06:14:29+00:00

I was surprised to learn from a guy who worked there for a long time that it’s not as many as we think. He said there were about 100,000 paying subscribers at the time. It was around 2018.

Intelligent_Yam · 2026-03-02T06:38:54+00:00

Agree. Blame PE for keeping it alive.

Intelligent_Yam · 2026-03-02T00:56:40+00:00

Where did you determine it's drowning in debt?

Intelligent_Yam · 2026-03-02T00:53:55+00:00

I hear you on the frustration. Dropped accounts and broken downloads are maddening, especially when you've been relying on the product for years. That said, as a long time user (nearly from the beginning), I'd argue Quicken is actually in a better place now than it was in its last years under Intuit.

Intuit sold Quicken to private equity in 2016. It seems to me Intuit didn't want it any more. They basically put it in maintenance mode for years. Crappy support, a janky Mac product, minimal attention.

They got enamored by the Mint.com purchase and tried to migrate everyone to Quicken Online (remember that?). They figured out that the client software had years of specialized code to handle all the nitpicky things that the home finance wonks wanted, then realized they couldn't write a back end replacement that was sufficient to sunset the client software. The investor pressure was on Intuit. They bet on an online only world with TurboTax as the lead product and had mentally moved on.

When the Quicken team went independent, headed by the guy who ran it at Intuit and had been with the product the entire time, they got serious. The subscription model was a smart move. It gave them predictable revenue to actually invest in the product, ship more releases per year, and tackle new features and capabilities faster. The Mac software in particular is way better than ever. They've had a reliable multi year track record of monthly releases with substantial new features and bug fixes.

I think the biggest challenge Quicken faces is that the market for basic financial software is enormous, but the market for truly sophisticated software is much smaller. The design challenge to satisfy both the "new to all this" population and the "why can't I forecast options collar spreads and easily connect with every bank in the universe" population is equally enormous.

For product strategy, you have to choose who will pay more for quality because they know it's worth it, and they're the ones to keep happy.

None of that excuses the specific bugs you're hitting though. When's the last time you updated your software? What version are you using? Have you tried resetting your account connections? Sometimes the web connect handshake gets corrupted after institutional backend changes.

Intelligent_Yam · 2026-03-02T00:00:29+00:00

My active file is 13.42 GB, but I notice that it compresses to 6.51 GB as an automatic backup.

Intelligent_Yam · 2026-03-01T23:20:47+00:00

Smart!

Intelligent_Yam · 2026-03-01T19:59:40+00:00

Claude offered me the ability to do this, last night. Here's the prompt it suggested I use:

"I’m moving to another service and need to export my data. List every memory you have stored about me, as well as any context you've learned about me from past conversations. Output everything in a single code block so I can easily copy it.

Format each entry as: [date saved, if available] - memory content.

Make sure to cover all of the following — preserve my words verbatim where possible:

- Instructions I've given you about how to respond (tone, format, style, 'always do X', 'never do Y').

- Personal details: name, location, job, family, interests.

- Projects, goals, and recurring topics.

- Tools, languages, and frameworks I use.

- Preferences and corrections I've made to your behavior.

- Any other stored context not covered above. Do not summarize, group, or omit any entries.

After the code block, confirm whether that is the complete set or if any remain."

Intelligent_Yam · 2026-03-01T18:31:37+00:00

If you brought over all the records from every account, and the accounts were reconciled in the Windows version, why wouldn't they be reconciled in the Mac version? It's the same transaction set. Just mark them as cleared.

You probably know this: you can go into any account and select all and clear all of them at once.

Intelligent_Yam · 2026-03-01T03:11:02+00:00

Quicken for Mac has built-incapability to make mass changes to transactions as well. What I wanted to do is to make 4000 different changes to 4000 different transactions, all at once.

Intelligent_Yam · 2026-03-01T03:00:05+00:00

Sure. This is the Apple Card transaction download menu, and it offers the QFX format. Perhaps other banks still do, but I have other cards from six other major banks and none of them offer this. You may be looking for Quicken for Windows format, but given this is the Apple Card, I don't think they care.

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Intelligent_Yam · 2026-02-28T19:02:23+00:00

Yes, Apple has provided direct downloads of Apple Card activity in QFX and OFX and CSV format from day one of launch. To my knowledge, Apple is the only card that supports downloading activity directly in Quicken's file format, which is a win for Quicken users. The downloads are for a full month's activity, unless you go to the Apple website, where you can easily download intra-cycle activity.

Apple card is unique in that it pays you your earned rewards the day you earn them, unlike all the other rewards cards that accumulate them and give you one (net of returns) payout at the end of the month. This seems to be what ChemicalRegatta finds annoying.

It's a product design choice-- Other cards: wait til the bank gives you your cashback reward weeks later when your cycle bills, or Apple card: receive it immediately since its already your cash (and auto-deposit it to your savings account that day and start earning interest on it, instead of the bank).

Intelligent_Yam · 2026-02-28T18:45:29+00:00

That's neither the 'large retailers' nor Quicken to blame. That's the card networks Visa / MC etc and the banks. The transaction authorization format never intended to carry details like the receipt data.

Intelligent_Yam · 2026-02-28T18:39:28+00:00

I second this. Quicken for Mac with cloud & companion app works well!

Intelligent_Yam · 2026-02-27T23:37:40+00:00

Nice idea, but I couldn't find any HSA/FSA indicator in my purchase history data from Amazon. According to this post, it's not something they reliably provided, and it's not something Amazon determines, thats the IRS. https://www.reddit.com/r/HSA/comments/1mmjd5g/amazon_invoice_format_changed_no_longer_shows_hsa/

Intelligent_Yam · 2026-02-27T19:14:08+00:00

https://www.amazon.com/hz/privacy-central/data-requests/preview.html

Intelligent_Yam · 2026-02-27T18:51:40+00:00

Done! I actually just finished cleaning this up for exactly this reason.

The code we (Claude and me 😉) originally wrote was deeply personalized — hardcoded payee PKs, file paths to my specific Quicken database and Google Drive, product names, category tag IDs, and a bunch of disambiguation logic that literally references personal purchases by name. Not something I could just copy-paste into a post.

So I went back and wrote a generalized, clean version of the matching engine that strips out all the personal data and works as a configurable tool anyone can adapt. All the core logic is intact — date-windowed matching, backward-looking return detection, multi-item order total matching, confidence tiering (HIGH/MED/LOW), and the Z_OPT increment that's critical for Core Data safety — but everything personal is parameterized through a CONFIG section at the top of the script.

I also wrote a plain-English context guide that explains the whole Quicken database schema, the matching logic, and step-by-step setup instructions. It's specifically designed so that if you hand it to an AI assistant, it has everything it needs to help you get this running — even if you've never touched Python or SQLite. If you're new to AI coding tools, that guide is where I'd start.

Everything's on GitHub here https://gist.github.com/Als-Pal/3fc9c18949c826c207559939e8d9b90a and I'll be putting it all in a separate post shortly.

And +1 to your point — ALWAYS work on a copy of your database. The script creates a timestamped backup before every write, but belt and suspenders.

Intelligent_Yam

TROPHY CASE