Why I refused to pay for automated software and instead went down the rabbit hole of tax treaties, residency paradoxes, and old-school paper filing
Most people look at tax season and see a headache. When I moved to the US as an international student, I saw a giant, scary, uncharted map.
The standard advice for international students is simple: “Don’t touch it. Just pay the software fee, click ‘Next’, and hope for the best.”
But that didn’t sit right with me.
I’m the kind of person who needs to know how the engine works. I didn’t want to just file my taxes; I wanted to understand them. So, instead of taking the easy road, I decided to be my own guinea pig. I treated the US Tax Code not as a legal burden, but as a logic puzzle waiting to be solved.
Here’s what I discovered when I stopped being afraid of the IRS and started getting curious.
1. The Hidden “Cheat Codes” in the Documentation
If you actually read the boring PDFs (and I mean really read them), you find hidden gems.
For most international students, the assumption is that we get taxed on everything. But deep in the archives of international relations, I found Article 21 of the US-India Tax Treaty. It wasn’t advertised on any main pages. It was like finding a secret level in a video game, a clause that allows Indian students to claim the same standard deduction as US citizens.
We’re talking about $15,750 shielded from federal taxes. That’s a deduction that automated software for international students would have told me I couldn’t claim.
The Lesson: The best perks are always buried in the Terms & Conditions. You just have to be curious enough to dig for them.
2. The “Schrödinger’s Resident” Paradox
Then came the puzzle that almost broke my brain.
This was the moment where logic seemed to break down, and I had to get comfortable with ambiguity:
| Government | What They Call Me |
|---|---|
| Federal (IRS) | “Non-Resident Alien” |
| Massachusetts (DOR) | “Resident” |
I effectively had to be two different people on two different forms.
Why? Federal tax residency is based on your visa status, while Massachusetts cares about where you physically live. I had an apartment, I spent 300+ days in the state, so to Massachusetts, I was a local—even though the Feds saw me as a visitor from another planet.
Most automated software glosses over this nuance, often defaulting to the safest, most conservative (and most expensive) option. By doing it manually, I could embrace the paradox—filing as a stranger to the Feds but a local to the State.
Navigating this wasn’t about math; it was about reading comprehension and trusting my research over the “default” settings.
3. Unlocking Local Perks (The Side Quests)
Once I embraced my status as a “Massachusetts Resident,” I started finding local side quests that yielded real gold:
The Rent Deduction
Massachusetts actually rewards you for paying rent. 50% of your annual rent (up to $4,000) comes right off your taxable income. It felt like a glitch in the matrix—getting money back just for having an apartment? Yes, please.
The Commuter Reward
All those months of buying MBTA passes? Deductible. Because I kept my receipts and tracked my spending, I could claim a deduction for my daily commute.
The Student Loan Interest Play
Even though my education loan was from a bank in India (SBI), the interest I paid was deductible on my US taxes. Up to $2,500 per year, no matter where the bank is located.
These aren’t secrets. They’re just… buried. In PDFs. That nobody reads.
4. The Analog Grind
In a world of AI and instant “Submit” buttons, there was something weirdly satisfying about the final step.
I couldn’t e-file. As a nonresident alien, I had to go old school:
- Print five different forms
- Sign them with a real pen
- Staple my W-2 to the front
- Walk to the post office
- Buy actual stamps
- Drop the envelope in a physical mailbox
It felt like a throwback to a different era. There was no “Loading…” bar, just the tactile act of sealing an envelope and trusting the system.
There’s something poetic about it: in a year where I used AI to help me understand the tax code, I finished the process with paper, ink, and the US Postal Service.
The Verdict: Curiosity Pays Off
I walked away from this experiment with a refund that was significantly higher than what automated software would have given me.
But honestly? The money was just a bonus.
The real win was the confidence.
I walked into the uncharted territory of a foreign tax system, stared down the complexity, and figured it out. I didn’t need an expensive expert or a black-box algorithm. I just needed:
- Curiosity — to ask “why?” instead of just clicking “next.”
- Patience — to actually read the documentation
- Willingness to experiment — to treat myself as the guinea pig
- The right tools — making an AI agent with Claude Code as a research partner, not a replacement for understanding
The Takeaway
If you’re an international student facing scary bureaucratic hurdles in a new country, don’t just look for the “Skip” button.
Dive in.
Read the PDFs. Question the defaults. Embrace the paradoxes.
You might be surprised at what you find, and what you save.
Have questions about filing taxes as an international student? Drop a comment below or reach out. I’m happy to share what I learned (though I’m definitely not a tax advisor, just a curious student who refused to accept “it’s complicated” as an answer).