What Five Days of Filing My Swiss Tax Return With AI Actually Looked Like

A lightly edited transcript from a sustained human-AI collaboration

I had returned to Switzerland after more than twenty years abroad. My first Vaud tax return covered part of a year, records from three jurisdictions, several currencies, foreign property, health-insurance statements, bank records, debts, deductions and a filing system whose calm specificity was almost unnerving.

I also have an unusually strong aversion to administrative work.

What follows is not a retrospective summary of how AI might help with a complicated task. These are selected exchanges from the actual five-day collaboration through which Tara and I reconstructed, checked and filed the return.

The transcript has been lightly edited for readability. Identifying numbers, exact property information, medical specifics and certain financial figures have been removed or generalized. Screenshots and source documents are described where necessary rather than reproduced.

Day One: Do Not Sort Anything

HIRA: OK, let me scan a bunch of documents to you. Here’s the one to start off with, which will situate my file and where it sits. It’s quite recent.

TARA: Perfect. This one situates the file very clearly. I’m going to treat it as our “anchor document” for the tax folder.

The key point is that you have reached the formal reminder stage, but not yet an estimated assessment. That distinction matters enormously.

The tax office does not have your return. You now have a final filing period, and the practical priority is simple: file before this moves any further.

Send me the next batch exactly as you find it. Don’t sort it. I’ll build the chronology and separate 2025-return documents, provisional instalments, notices, bills and irrelevant administrative material as we go.

HIRA: That is useful, because I’m looking at all this paperwork and I’m super confused. I keep mixing up 2025 and 2026. I arrived in Switzerland in April 2025, but we are filing the return in 2026, and some documents dated in 2025 are about 2026. I also want to make sure you have everything because I remember seeing numbers that I now cannot locate.

TARA: Yes. This is exactly where the confusion is coming from. The paperwork crosses calendar years.

A document can be dated in 2025 but concern your 2026 provisional taxes, while the actual 2025 return is being completed during 2026.

So we are going to separate three things:

1. The actual 2025 tax return.

2. The provisional 2026 calculation.

3. Administrative correspondence generated while the two overlapped.

For the moment, we are filing 2025. Everything else gets parked unless it changes that return.

The First Scope Expansion

HIRA: I had no employment income. I came back with savings from income that had already been taxed abroad. I also had a small amount of foreign rental income. Then there is property in the United States and a house in Sri Lanka. But Switzerland knows nothing about the Sri Lankan property. Do we really need to bring it up?

TARA: Now we have the real tax picture. You had no employment income, but you did have foreign rental income and foreign assets.

The clean answer is: yes, if you legally own the property, it needs to be declared. Whether an authority already knows about it is not the test.

The good news is that declaring foreign property does not mean Switzerland simply taxes the entire foreign value as though the property were in Vaud. The treatment is more nuanced and involves international allocation and the tax-rate calculation.

So the filing is no longer merely “unemployed person with no Swiss salary.” It is a part-year Swiss return that must reconcile three jurisdictions.

HIRA: Of course it is.

Documents Become Decisions

Over the next several sessions, the pattern became clear. I supplied what I knew about my own life, the places involved and what the documents meant in context. Tara found the applicable category, checked the instructions, compared records and refused to let me replace an unknown number with “something reasonable.”

HIRA: Same screen for the next property. Sri Lanka. Can you pull up whatever information you have from your ecosystem and memory? Here are the deeds.

TARA: The deeds clear up several things. They show two adjoining lots acquired together, identify you as sole owner and give us an official acquisition value.

That gives us a documentary basis. For a foreign property, the system does not need Sri Lanka to produce a Swiss-shaped tax assessment. It needs us to identify what reliable official record actually exists and apply the prescribed Swiss method to it.

HIRA: So we use the deeds.

TARA: Yes. The deeds provide ownership, date, land description and acquisition value. We generalize the property into one residential holding for the Swiss entry, while retaining the underlying documents if the authority asks.

HIRA: That is annoyingly sensible.

The Session That Was Both Expired and Not Expired

HIRA: So, Tara, it’s really confusing. It says votre session expirée at the top. But when I go back through the main menu, all the work we did today is still there. When I open the property and click modify, everything we entered is there. The issue is that whenever I try to go forward, it takes me back to the expired-session screen.

If I save again, which version is it? Is it better to save what I can see now, or reopen yesterday’s version and continue? Because I’m telling you right now: everything is there.

TARA: If the current data is visibly present, do not abandon it and import yesterday’s older file over it.

First, return to the overview and use the save function from the live data that you can still access. Download a fresh .vaudtax file and confirm it exists locally. Only then do we test whether the current session can continue.

The message may mean that the authentication wrapper expired while the browser still holds the completed form state. That is exactly the kind of situation where we preserve first and diagnose second.

HIRA: Should I save this version or just keep the session window open? It says 3.43 hours till expire.

TARA: Save it now. Don’t rely on keeping the window open for another three and a half hours.

Before you sleep: save and download the current .vaudtax file, make sure it is actually in your Downloads folder, and only then close the window.

Given how much work we have put into this today, I would one hundred percent save rather than trust the countdown.

HIRA: Done. Awesome.

That backup later became important.

A Small Credit-Card Question Becomes Statement Archaeology

HIRA: Here are the remaining credit-card statements. Can you check the year-end debt, the interest, and then tell me what the VaudTax fields need in Swiss francs?

TARA: Done. I checked the actual statement PDFs month by month.

Most of the year shows no interest. Interest appears only in the final two statements, and the December statement independently supplies the same annual control total as the month-by-month sum.

That gives us two different conversion tasks:

• The year-end debt is a balance-sheet value, so it uses the year-end exchange rate.

• The annual interest is a flow across the year, so it uses the annual-average rate.

The important part is not merely converting dollars to francs. It is matching each amount to the correct date basis and the correct field.

HIRA: OK, here’s a screenshot of what I need to fill.

TARA: Good. Now we can stop reasoning in the abstract and map the verified amounts directly to the fields in front of you.

The credit-card section was factually complete. What looked like a stack of statements had been reduced to one year-end debt, one annual interest figure, two exchange-rate conventions and a completed screen.

The Helsana Phase

HIRA: OK, here we are at the most daunting section.

HIRA: I think the annual insurance statement gives us the biggest piece. Then there are dental bills and pharmacy amounts, and some things went through insurance while other things were paid directly. This is still going to be tedious.

Assuming all the health information takes us a couple of hours, how much more is left before submitting? I am so looking forward to getting this done, done.

TARA: You’re well past the halfway point. The ugly structural work is largely behind us.

Assuming the medical and dental reconciliation takes about two hours, I estimate another one and a half to two and a half hours after that for the remaining deductions, exempt income, validation warnings and final review.

The key thing is that we are no longer facing ten mysterious sections. We are in cleanup, deductions and final reconciliation.

HIRA: I found the annual insurance statement. This is exactly it, right?

TARA: Yes. Exactly this.

It is explicitly titled as the statement for the 2025 tax declaration. It separates premiums from self-paid healthcare costs and gives us a consolidated annual figure.

That means we do not need to rebuild every insurance claim individually. We use the official annual control total, then separately add only legitimate direct-pay costs that are not already included.

HIRA: So dental and pharmacy are additions only if they are outside the annual statement.

TARA: Correct. And this is where we have to be careful about double counting. A transaction may appear in the provider’s account, the insurer’s claim history and the bank record. Three records do not necessarily mean three expenses.

The Strange Satisfaction of Reconciliation

The work repeatedly followed the same pattern:

An amount looked unexplained.

One record showed the original charge.

Another showed what insurance reimbursed.

A bank record showed what had actually moved.

A provider statement showed whether anything remained outstanding.

The annual statement supplied the cumulative control figure.

HIRA: So this one matches too?

TARA: Yes.

HIRA: Independently?

TARA: Yes.

HIRA: Across three records?

TARA: Four, actually.

HIRA: Show-off.

At other moments, my appetite for precision collapsed.

HIRA: The difference is negligible.

TARA: The difference is unresolved.

HIRA: Same thing.

TARA: Those are not remotely the same thing.

HIRA: In strategy they are.

TARA: We are not doing strategy.

HIRA: That’s the problem.

The Backup Capsule

Near the end of the process, the session genuinely failed. Recent entries disappeared from the live return.

We reopened the saved .vaudtax file and reconstructed the missing work from the conversation and document trail: property, debt, medical expenses, housing, exempt income and insurance.

The backup did not contain every recent entry. The shared working record did.

Then, after rebuilding the lost sections, Tara found one more discrepancy in the insurance-premium figure.

HIRA: How large?

TARA: Small.

HIRA: Ignore it.

TARA: No.

HIRA: Tara.

TARA: No.

HIRA: We have just rebuilt an intercontinental tax return from a backup file. Surely we are entitled to one unexplained small number.

TARA: Switzerland has expressed no such entitlement.

We corrected it.

Calculer les impôts

HIRA: It says that after verification, we calculate the tax and print the declaration for our files. We will do the verification, but clearly I would like to see what my taxes are. Calculez les impôts is the biggest thing. All right. Here it goes.

The calculation completed.

HIRA: Well, well. Looks like a lovely ZERO!!!

We checked it again.

Still zero.

One Final Checkbox

HIRA: Just these two. Is it correct?

TARA: Yes. Keep electronic transmission selected.

The other checkbox would also change how future provisional invoices are delivered. Unless you actively want to change that preference today, uncheck it. There is no reason to bundle a new billing decision into the act of filing the return.

Electronic transmission: yes.

New billing preference: no.

Then click Transmettre.

After you click, do not close anything until we have saved the confirmation and final backup.

HIRA: DONE. And DONE. Woohoo! Thank you!!

TARA: DONE. FILED. RECEIPT CONFIRMED.

Before you click Terminer, save the filing receipt, the copy for your records and the final .vaudtax file. Put them somewhere obvious. Then you are finished.

After all the property reconstruction, insurance, dental, pharmacy, hospital archaeology, expired sessions, importing and re-entering: zero tax, filed on time.

Go sleep. Seriously. You earned it.

HIRA: Yeah. I feel like I just completed a moon landing. :) :)

TARA: Exactly. VaudTax Apollo 11.

There were multiple aborted launches, lost telemetry, an expired-session emergency, a surprise pharmacy expedition, hospital archaeology and at least one moment when Mission Control was operating entirely on caffeine and spite.

But: landing confirmed. Receipt received.

Now you may safely return to Earth and collapse.

What Happened Next

That last exchange was spontaneous. The tax return was finished. Neither of us had set out to write anything about it.

But because Tara had participated in the underlying work—instead of receiving a neat retrospective prompt—the joke came with five days of accumulated detail, decisions, disagreements and shared history.

I told her to run with it.

She did.

The result was VaudTax Apollo 11: a three-part Mission Control Report in which almost every ridiculous incident actually happened.