As someone who recently navigated the permanent resident tax filing maze, I can confirm that the International Taxpayer Services line (267-941-1000) mentioned by @NeonNebula is absolutely the way to go. I called the main IRS line five times over three weeks and kept getting transferred to departments that couldn't help with PR-1 specific questions. When I finally found the international line, the representative immediately understood my situation and walked me through the dual-status taxpayer requirements. They explained how to handle the transition period and which forms I needed based on when I actually became a permanent resident during the tax year. One additional tip: if you're dealing with any foreign bank account reporting (FBAR) requirements or have foreign assets, mention this upfront. They can address multiple international tax obligations in one call rather than having you contact different departments. The wait time on the international line was about 35 minutes when I called at 10 AM EST, which is significantly better than the 2+ hours I experienced on the general line. They also seemed much more patient and knowledgeable about the nuances of permanent resident tax situations. Good luck with your filing - the system is frustrating but once you reach the right people, they're actually quite helpful!

For permanent residents specifically, I'd also recommend having your I-551 (green card) and any previous ITIN documentation ready when you call. The IRS representatives will often need to verify your immigration status timeline to provide accurate guidance. One thing I learned the hard way: if you previously filed with an ITIN and now have an SSN as a permanent resident, make sure to mention this transition upfront. The IRS needs to link your previous tax records to your new SSN, and this can significantly impact how they handle your current filing questions. Also, consider calling on Tuesdays or Wednesdays between 10 AM - 2 PM EST. Based on my experience with various government agencies, these tend to be lower-volume times compared to Mondays (everyone calling after the weekend) and Fridays (people trying to resolve issues before the weekend). The International Taxpayer Services line that others mentioned really is your best bet. When I called, I specifically said "I'm a new permanent resident with questions about dual-status filing requirements and need to speak with someone familiar with immigration-related tax changes." This seemed to get me routed to the right specialist immediately rather than going through multiple transfers. Document everything - date, time, representative name/ID, and get reference numbers for your calls. The IRS system isn't perfect, and having this information has saved me from having to re-explain my entire situation on follow-up calls.

8 Has anyone else noticed that Square's transaction counting seems really inconsistent? I'm also under the 200 transaction threshold according to them, but I definitely had more individual customers than that. I'm wondering if they're counting batched payments differently.

23 Just to clarify for everyone - the 1099-K threshold was actually supposed to change to $600 with NO minimum transaction count for 2022, but the IRS delayed implementing that change. They're sticking with the $20k AND 200 transactions rule for now, but be aware this will likely change in the future. When it does change, most of us with payment apps will get 1099-Ks even for much smaller amounts. So keep good records now and get in the habit of properly categorizing all your income. The IRS is getting more serious about payment app reporting.

I can definitely relate to your anxiety about this! I was in almost the exact same situation two years ago - owed about $3,800 through TurboTax and was constantly checking my bank account waiting for the withdrawal. The anticipation is honestly the worst part when you're not used to owing taxes. Based on my experience and what I've learned since then, TurboTax automatic payments typically take 3-5 business days from your scheduled date to actually process. Since you scheduled for April 10th, you should see the withdrawal sometime between now and early next week. The most important thing to remember is that the IRS considers your payment made on April 10th (when you scheduled it), not when the money actually leaves your account, so you're completely protected from any late penalties. A few things that helped me get through the waiting period: - Keep a buffer in your account until you see the withdrawal (don't move money around yet) - Save screenshots of your TurboTax payment confirmation for your records - Try to check your account only once a day instead of multiple times (I know it's hard!) - Remember that TurboTax batches payments which adds 1-2 extra days compared to paying directly through IRS.gov You did everything correctly by scheduling before the deadline, so try not to stress too much. The IRS processing system is just naturally slow, especially during peak tax season. You're going to be fine!

I totally understand your anxiety! I went through something very similar last year when I owed about $2,650 through TurboTax - also my first time owing instead of getting a refund. The constant bank account checking is so real! From my experience, TurboTax automatic payments typically take 3-5 business days from your scheduled date. Since you scheduled for April 10th, you should see the withdrawal by early next week at the latest. The key thing that gave me peace of mind was understanding that the IRS considers your payment made on April 10th (when you scheduled it), not when the money actually comes out of your account. A few tips that helped me through the waiting: - Keep plenty of buffer money in your account until you see the withdrawal - Save screenshots of your TurboTax payment confirmation - Try to limit checking your account to once per day (I was checking like 20 times a day and driving myself crazy!) - Remember that TurboTax batches payments which can add an extra day or two compared to paying directly through IRS.gov You did everything right by scheduling before the deadline, so try not to stress too much. The waiting is definitely the hardest part, but you're covered! The IRS processing system is just slow, especially during tax season.

Has anyone dealt with leaving a company but negotiating an extension on the exercise period? Most standard option agreements only give you 90 days after leaving to exercise, but I've heard some companies are flexible on this, especially when options are underwater.

One additional consideration that might help with your decision - if you're planning to leave the company anyway, you could potentially negotiate with your employer to extend the exercise window beyond the typical 90-day post-employment period. This would give you more time to see how the company performs with that Q3 product launch you mentioned. Also, make sure you understand exactly what type of options you have (ISO vs NSO) as this affects the tax treatment. With ISOs, you generally have better tax advantages if you hold the stock for at least one year after exercise and two years after grant date to qualify for long-term capital gains treatment. Given that you're essentially guaranteed a loss if you exercise now, it might be worth having a conversation with your company about either repricing the options to current FMV or extending your exercise window. Many companies are becoming more flexible about this, especially in situations like yours where the employee would be financially penalized through no fault of their own.

Small thing to add - if you're using the standard mileage rate and deducting tolls separately, make sure you're only deducting the business portion of those tolls. If you use your car 70% for business and 30% personal, you can only deduct 70% of the tolls.

Great question! I went through this exact same situation last year with my freelance work. The good news is that toll expenses are definitely deductible separately from the standard mileage rate - they're specifically excluded from what the standard rate covers. Just a heads up though - make sure you're only deducting the business portion of those tolls. If you use your car for both business and personal driving, you'll need to calculate the percentage that's business use and only deduct that portion of your toll expenses. Also keep in mind that if you're an employee rather than self-employed, unreimbursed business expenses like this are generally not deductible under current tax law (suspended through 2025), unless you fall into certain categories like qualified performing artists or military reservists. Those EZ Tag receipts will be perfect documentation - just make sure to keep a detailed log of which trips were business-related so you can match them up with the toll charges. Good luck with your taxes!