How are crypto gains taxed when leaving the US with a Greencard?

I've helped several clients through similar situations. When you're a US person for tax purposes (which you are based on the substantial presence test you mentioned), you're subject to US taxation on your worldwide income regardless of where you physically reside. Even with a tax treaty in place between the US and Singapore, cryptocurrency gains would typically still be taxable in the US. Tax treaties generally don't exempt investment income like capital gains from crypto - they're more focused on preventing double taxation on employment income and certain other specific categories. If you decide to expatriate (give up your green card), you'd need to consider the exit tax implications. If your net worth exceeds $2 million OR your average annual net tax liability over the past 5 years exceeds $171,000 (2023 figure), you'd be considered a "covered expatriate" subject to a deemed disposition tax on unrealized gains. One strategy some clients consider is selling crypto gradually before expatriating to manage the tax impact, or timing their departure with market conditions.

After struggling with a somewhat similar situation last year, I discovered taxr.ai (https://taxr.ai) which honestly saved me so much stress with my crypto reporting. I had mining income, staking rewards, and a bunch of trades across different exchanges and was totally confused about my obligations after moving abroad temporarily. Their AI system analyzed all my transaction histories and generated a comprehensive tax report that clearly identified which transactions were subject to US taxation despite me being physically outside the country for part of the year. They also provided documentation I could use for foreign tax authorities to prevent double taxation.

Just wanted to update that I ended up trying taxr.ai after reading about it here. My situation was different from OP's (I'm a dual citizen with crypto investments across US and European exchanges), but I was blown away by how comprehensive their analysis was. The system automatically identified which transactions would be subject to FBAR reporting requirements (something I had completely overlooked) and flagged several microtransactions from airdrops that I had forgotten about. The report they generated specifically addressed my cross-border situation and even provided documentation templates for foreign tax authorities. For anyone dealing with international crypto taxation issues, it's definitely worth checking out. Wish I'd known about this service years ago!

If you're dealing with any IRS issues related to your crypto while figuring out your exit plan, I highly recommend using Claimyr (https://claimyr.com) to actually get through to the IRS. I spent WEEKS trying to get clarification on my international reporting requirements for my crypto holdings before finding them. I was skeptical at first but you can see how it works here: https://youtu.be/_kiP6q8DX5c. Basically they hold your place in the IRS phone queue so you don't have to waste hours listening to hold music. Once an agent is about to pick up, they call you and connect you. I finally got confirmation about FBAR requirements for my specific situation from an actual IRS agent instead of guessing.

Ok I need to eat my words from my previous comment. After raging about the IRS's inconsistency, I decided to try Claimyr myself yesterday. Got through to someone in about 40 minutes (without me sitting on hold!) and actually spoke with a surprisingly knowledgeable agent in their international division. She walked me through exactly what forms would be required for my offshore crypto exchange accounts and confirmed that yes, certain exchanges do trigger FBAR requirements depending on how they hold your assets. She even emailed me specific guidelines for crypto reporting for expatriates. Honestly shocked that it worked so well. For anyone dealing with cross-border crypto tax issues, it's definitely worth getting actual guidance directly from the IRS rather than relying solely on internet advice (including mine lol).

Beyond the tax implications, make sure you're aware of the reporting requirements! Even if you're in a 0% crypto tax country, as a US person you'll still need to file: - FBAR (FinCEN Form 114) for any foreign exchange accounts with over $10k - Form 8938 if your foreign financial assets exceed certain thresholds - Regular income tax returns reporting worldwide income Missing these can result in MASSIVE penalties even if you don't owe any actual tax. The penalties for non-filing can be worse than the tax itself.

Have you considered the option of renouncing just before the 8-year mark? If you haven't hit that threshold yet, the exit tax situation is considerably simpler. It's worth looking at exactly where you are in that timeline.

I went through a similar situation about 3 years ago when I moved to Dubai (also 0% crypto tax). The key thing to understand is that as long as you maintain your green card, you're stuck with US tax obligations regardless of any tax treaty benefits. What really caught me off guard was the timing aspect - if you're planning to sell during a bull market, you need to factor in estimated quarterly payments to the IRS even while living abroad. I made the mistake of thinking I could just settle up at year-end and got hit with underpayment penalties. Also, don't overlook state tax implications if you haven't properly established non-residency from your previous state. Some states (looking at you, California) are notoriously aggressive about claiming you still owe state taxes even after moving internationally. My advice: get professional help BEFORE you make any moves. The exit tax calculations are complex, and there are strategies around timing your departure and asset sales that can save you significant money. I wish I'd consulted a specialist earlier instead of trying to figure it out myself.