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Tax Time Should Be Boring

Published Thu Apr 16 2026

Every year I had the same stupid job: dig through email for rental and share invoices, download the attachments, rename them, and bundle them up for my accountant.

It was not difficult. It was just annoying.

So I handed it to an agent.

To keep it simple, I started with statements and invoices from one supplier. I had already set up a Gmail rule that attached a label to all of those emails, which made the search side trivial.

Even better, each statement email came with the statement itself plus a separate attachment for each invoice. That gave me a clean, repeatable structure to automate.

Now the workflow is simple:

The one-off backfill did the heavy lift. It crawled that labeled batch of old emails and built a clean structure in Google Drive:

Each file gets a deterministic name:

That sounds small, but it kills the real pain: future-me can actually tell what anything is.

The nice part is I did not build some giant custom app for this. I mostly wrote the spec in plain English:

Look for emails under this label. Match subjects that start with “Statement -” or “Year End Statement -”. Download all attachments. File them by financial year. Prefix filenames with the statement date. Then run weekly.

That is the pattern I keep coming back to with agents: be painfully clear about inputs, outputs, and naming. Let the machine do the glue work.

So now the agent checks once a week for anything new and quietly files it away.

No yearly scramble. No inbox archaeology. No “where did that PDF go?” nonsense.

Tax time should be boring.

If you have any recurring workflow that looks like “find email → download attachment → rename → file it”, that is a perfect first automation target.