Do you happen to know which states have different deadlines? I'm working on returns for clients in multiple states and now I'm worried...

I don't have a comprehensive list, but I know California strictly enforces their own cutoff time. New York and Illinois have occasionally had different timing requirements too, especially during extension periods. The safest approach is to check each state's department of revenue website directly. Most will have a specific notice about e-filing deadlines on their homepage this time of year. If you can't find clear information, finish those multi-state returns at least 24 hours before the federal deadline to be safe.

YES! This happened to me with Drake last year. The system was crawling and I nearly missed the deadline. This year I'm finishing everything by noon on the final day just to avoid the stress.

How much does Koinly cost? Their website pricing is confusing with all the different tiers.

The price depends on how many transactions you have annually. I'm on the $99 plan which covers up to 1,000 transactions per tax year. They have cheaper options if you have fewer transactions and more expensive if you're a heavy trader. I've found it worth it because it automatically categorizes everything correctly - transfers, trades, income from staking, etc. You can also manually edit any transactions if needed. At tax time, it generates all the forms needed for filing including Schedule D and Form 8949.

Nope, sending to your Ledger is still just a transfer - not taxable. I document these with screenshots showing the transaction, addresses, and confirmation details. Makes tax time way easier.

Thanks for this info! What do you mean by "paper entity" and the nexus issue? Our company is registered in Wyoming, has a registered agent there, and a US bank account, but all actual operations (including me as the owner/operator) are in China. Could this cause problems?

The "nexus" issue refers to where your business has sufficient presence or connection for tax purposes. If all actual business activities (management, operations, inventory) are in China, the IRS could potentially view the business as a foreign entity despite the US registration. This could work both ways. If determined to be a foreign entity, you might only need to report US-sourced income to the IRS, potentially reducing your tax burden. However, it could also trigger complex reporting requirements like Form 5471 for foreign corporations. To strengthen your US nexus, consider: maintaining a US phone number, having some business activities conducted in the US (even if remotely), using US-based services, and clearly documenting the business purpose of your US entity. Having just a registered agent and bank account might be seen as insufficient to establish true US operations.

Actually, this information isn't quite right. The $600 threshold was supposed to take effect for 2023 taxes (filing in 2024), but the IRS delayed it. They've announced another delay for the 2024 tax year too. So the $20,000 AND 200 transactions threshold is still in effect for both years. I just want to make sure nobody's confused when filing!

Thanks for this tip! Do you remember approximately how long it took to process both the tax return and ITIN renewal when you did it this way? I'm wondering if it delays the refund significantly.

When we did it this way, the whole process took about 11 weeks total - definitely longer than a regular tax return. Our refund was held until the ITIN was fully processed. If you're counting on getting your refund quickly, you might want to do the ITIN renewal separately before filing. I'd also add that the IRS sent us a letter about 4 weeks after filing to confirm they received the ITIN renewal application, which gave us some peace of mind during the wait.

You sent the original passport?? Isn't there any way around that? No way I'm sending my husband's original passport through the mail...

Can you explain what a "qualifying or disqualifying disposition" means? The tax document they sent me does mention something about a "disqualifying disposition" but doesn't explain what that means.

A qualifying disposition means you held the ESPP shares for both: 1) at least 1 year after the purchase date, and 2) at least 2 years after the offering date (when the purchase period began). If you meet both holding periods, you get more favorable tax treatment. A disqualifying disposition means you sold before meeting either of those holding periods. In that case, the entire discount gets taxed as ordinary income. It's strange they're mentioning "disqualifying disposition" if you haven't sold yet. That term typically only applies when you actually sell the shares. This reinforces my suspicion that there's a communication problem or misunderstanding with your benefits department. I'd specifically ask them why they're referencing a disqualifying disposition when you still hold the shares.

This is an excellent point. My company does something similar - they provide an optional tax withholding program for equity compensation. They calculate the projected tax impact and let us choose whether to have extra withholding throughout the year. It's actually really helpful for cash flow management.