To all those having trouble reaching a human at IRS. I just ran across this video that gave me a shortcut to reach a human. Hope it helps! https://youtu.be/_kiP6q8DX5c

Tax topic 152 is completely normal and just indicates your return is being processed. I had the same code for about 3 weeks before my refund was approved. The key thing is to be patient - the IRS is still working through a backlog from previous years. If it's been more than 21 days since you filed, definitely check your account transcripts online to see if there are any specific codes that might indicate what's holding things up. Most of the time it's just a matter of waiting your turn in the queue. Keep checking WMR and your transcripts for updates!

Has anyone successfully had penalties waived without hiring a tax pro? I'm in a similar situation with my photography LLC and got hit with $2,600 in penalties even though I filed closure paperwork in 2019. I've been unemployed for 7 months and really can't afford this or a tax professional.

This is exactly the kind of bureaucratic nightmare that makes dealing with the IRS so frustrating. You clearly did everything right - submitted proper closure documentation, followed up multiple times, and kept detailed records. The fact that they're now penalizing you for their own processing delays is completely unfair. I want to echo what others have said about filing Form 843 for penalty abatement. Your situation screams "reasonable cause" - you have documented proof of timely submission, multiple attempts to follow up, and the IRS's own letters acknowledging processing delays. Make sure to emphasize in your abatement request that the penalties resulted from IRS administrative delays, not any failure on your part to comply. Also, don't forget to mention your current unemployment situation when requesting abatement. The IRS has provisions for economic hardship considerations, and being unable to pay without severe financial distress is a valid factor they must consider. Your case has all the elements for a successful abatement - you just need to present them clearly and persistently. Keep fighting this. You shouldn't have to pay penalties for the IRS's own administrative failures.

One thing to consider is whether your company allows a "cashless exercise" option. With the spread between $8 and $200 being so large, you'd need $8,000 cash to exercise all options, plus potentially a large AMT bill. A cashless exercise would let you exercise and immediately sell enough shares to cover your costs, then keep the remaining shares. This is essentially a partial disqualifying disposition but can be a good middle ground if you don't have the cash on hand for a full exercise.

This is a complex situation that really highlights why ISO planning should ideally start early! Given your $90k capital loss carryover, you're right that it won't help with AMT on the ISO exercise, but there are still some strategic considerations. One approach worth exploring: if you're comfortable with some market risk, consider exercising just a portion of your options now (maybe 200-300 shares) and spreading the rest over the next year or two. This could help minimize the AMT hit while still capturing some gains. Also, timing matters for your capital loss usage. If you do a disqualifying disposition, you'll have $192k in ordinary income but can only use $3k of your losses against it this year. However, any capital gains you generate from other investments or future stock sales can be fully offset by your loss carryover. Given the volatility risk Isaac mentioned with newly public companies, I'd lean toward taking at least 50-70% of your gains off the table immediately after lockup expires. You've already won the lottery here - don't risk losing it all for tax optimization. Have you checked if your company offers any tax gross-up benefits or financial planning resources for employees dealing with stock options? Many tech companies provide these services specifically because ISO taxation is so complex.

Does anyone know if distributions from a BDIT count as earned income? Like, will I have to pay self-employment tax on it? I'm in the same boat with a trust my grandparents set up, and I'm wondering if I should be making quarterly estimated tax payments this year.

I'm dealing with a similar trust situation and found this thread super helpful! One thing I want to add is that if you're having trouble getting organized information from your trustee, you might want to request a copy of the trust's accounting records too. The trustee should be keeping detailed records of all income, expenses, and distributions. This can help you understand exactly what happened during the tax year and verify that the information on your K-1 is correct when you finally get it. Also, for anyone else in this situation - make sure you keep copies of all the trust-related documents you receive. I learned the hard way that you'll probably need to reference them again next year, and trustees aren't always the most organized about keeping beneficiaries informed throughout the year. The tax implications of these trusts can be really complex, but don't let that scare you away from understanding the basics. Even if you end up using a professional, having some knowledge of how your trust works will help you ask better questions and catch any potential errors.

One thing to check that nobody has mentioned - sometimes the withholding error can be triggered by inconsistencies with your social security numbers. Check that your SSNs are entered exactly the same way on all forms (no extra spaces, dashes in the right places, etc). I had the exact same error last year and spent forever checking withholding amounts only to discover it was because my SSN was entered with dashes on some forms and without dashes on others. Free Fillable Forms treated them as different people with withholding that didn't match up!

I feel your pain with Free Fillable Forms! I had a similar nightmare last year with multiple W-2s. One thing that worked for me was to completely clear out all the withholding entries and re-enter them one by one, making sure to save after each W-2 entry. Also, double-check that you're not accidentally including any estimated tax payments or prior year overpayments in your withholding calculations. Sometimes those get mixed in and cause validation errors. If you're still stuck, try printing out the PDF of your return and manually calculating the totals yourself to compare against what the system is showing. That's how I caught my error - the system was somehow adding an extra $200 that I couldn't account for until I traced through every single line item. Good luck! These technical glitches are so frustrating when you know your numbers are right.