This has been an incredibly thorough discussion! As someone new to dealing with merger tax implications, I really appreciate all the detailed guidance shared here. One thing I wanted to add that might be helpful for others in similar situations - if you're using tax software like TurboTax or TaxAct, make sure it can handle these types of stock reorganizations properly. I had a similar merger situation a few years ago and my tax software initially didn't have good support for reporting the conversion correctly. I ended up having to manually override several calculations and add specific codes on Form 8949 to properly reflect the tax-free reorganization treatment. It might be worth checking with your tax software provider or considering using a tax professional for the year you have this merger, especially if you have multiple lots with different acquisition dates like many of us seem to have. Also, for those who are still deciding between the all-cash vs 50/50 option, don't forget to factor in your current year tax situation. If you're already in a high tax bracket this year, minimizing the taxable cash portion might make sense even if the 50/50 option looks better from a pure investment return perspective. The merger timeline can sometimes shift too, so keep an eye on any updates from Broadcom or your broker about key dates and deadlines for making your election.

New York generally follows federal tax treatment for qualifying reorganizations, so the stock conversion portion should be tax-free at the state level too. However, NY has some specific rules around equity compensation that might affect your ESPP shares differently. I'd recommend double-checking NY Publication 36 (for residents) or Publication 425 (for non-residents) which cover stock transactions. If you have significant ESPP holdings with discounts, NY sometimes requires additional reporting even when the federal treatment is straightforward. Given the complexity you're describing with multiple equity types and the state tax considerations, this might be a good year to work with a tax professional rather than going the software route. The cost of professional help could easily be worth it to ensure everything is reported correctly and you're not missing any optimization opportunities. Also keep in mind that if you're close to higher tax brackets, you might want to consider timing other capital gains/losses this year to help offset the taxable portion of the merger payout.

Has anyone used the IRS Direct Pay system for their quarterly payments? I've heard horror stories about payments not being properly credited to accounts or applied to the wrong tax year. Trying to decide between that and EFTPS.

Great question! I went through this exact transition two years ago and the safe harbor rule was a lifesaver during that first year of uncertainty. One thing I'd add to the excellent advice already given - don't forget to consider your state estimated tax requirements too if you're in a state with income tax. Some states have their own safe harbor rules that might be different from federal, and you'll want to make sure you're covered on both fronts. Also, since you mentioned your income is likely to increase but uncertain, you might want to reassess after your second quarter payment. If your income ends up being significantly higher than expected, you can always increase your remaining quarterly payments to avoid a large balance due at filing time, even though the safe harbor protects you from penalties. The 110% safe harbor rule is definitely the way to go for your first year of self-employment - it takes so much stress out of the guessing game while you figure out your new income patterns. Once you have a full year of self-employment income under your belt, you'll have a much better sense of what to expect for the following year.

8 Microsoft has a free online version of Office (Word, Excel, PowerPoint) that you can use through a web browser at office.com. It's not as full-featured as the desktop version but might be enough for basic work tasks without having to pay for a subscription.

Another alternative worth considering is LibreOffice, which is completely free and open-source. It's compatible with Microsoft Office file formats and includes Writer (Word equivalent), Calc (Excel equivalent), and Impress (PowerPoint equivalent). While it may have a slightly different interface, it handles most business tasks well and could be a good temporary solution while you work on getting your employer to provide or reimburse the Microsoft Office subscription. I've used it for basic document editing and spreadsheet work and found it quite capable for most standard office tasks.

@Freya Andersen - I completely understand your stress about this! I'm actually new to this community and just went through the exact same panic last month when I used a professional tax preparer for the first time. The Form 8879 had me totally confused too. Here's what I learned: The 8879 is basically your digital signature that authorizes your tax preparer to electronically file your return on your behalf. Once you signed it and returned it to them, you've done your part - the preparer handles everything else from there. The form stays with them as proof they had permission to e-file for you. Most preparers will submit your return within a day or two of getting your signed 8879, and the IRS usually confirms acceptance within 24-48 hours. If you haven't heard back from your preparer yet, definitely call them tomorrow morning to ask for confirmation that your return was accepted by the IRS. You can also double-check yourself using the "Where's My Refund?" tool on the IRS website - just have your SSN, filing status, and exact refund amount ready. This will show you if your return was received and is being processed. Don't panic - by signing that 8879, you've completed everything you need to do! The fact that your preparer gave you this form shows they're following proper e-filing procedures. You should be all set for the deadline. I know the anxiety is real when you're not used to this process, but you're in much better shape than you think!

@Freya Andersen - I totally get your panic! I'm also new to this community and just went through this exact same stress when I used a professional tax preparer for the first time this year. The Form 8879 completely threw me off because I'd never seen it before either. Here's what I learned after doing some research and talking to my preparer: The 8879 is essentially your electronic signature that gives your tax preparer permission to file your return digitally with the IRS. Think of it like signing a paper tax return, except this form serves that purpose for electronic filing. Once you signed it and gave it back to your preparer, you've completed your part of the process! Your preparer should file your return within 1-2 business days of receiving your signed 8879, and the IRS typically sends back an acceptance confirmation within 24-48 hours after that. The form itself doesn't get mailed anywhere - your preparer keeps it in their files as proof they had authorization to e-file for you. I'd definitely recommend calling your preparer tomorrow to ask for confirmation that your return was submitted and accepted by the IRS. You can also independently verify using the "Where's My Refund?" tool on irs.gov - you'll need your SSN, filing status, and exact refund amount. Don't stress - by signing that 8879, you've done everything correctly! The fact that your preparer used this form shows they're following proper e-filing procedures. I was anxious about this for days until I got confirmation, but everything worked out perfectly. You should be all set for the deadline!

I'm in a very similar situation with a 470 code that's been pending for about 6 weeks now! Reading through everyone's experiences here is giving me so much hope. The court ruling you have is absolutely huge - that's solid legal documentation that proves the IRS made an error with the original EIC adjustment. From what I've learned through my own research and calling the IRS multiple times, they typically do apply refunds to outstanding balances, but with hardship status and especially with court documentation like yours, you should definitely see at least a partial refund. Most people I've talked to with 470 codes see resolution within 8-12 weeks, though the waiting feels like forever! Make sure you keep multiple copies of that court ruling and consider faxing it directly to the processing center if you haven't already - sometimes things get lost in their system. Keep calling every 2-3 weeks for updates and document everything. Your case looks really strong with all that legal backing! Hang in there - this will work out in your favor! 💪

I've been through this exact scenario! Had a 470 code with an outstanding EIC balance and it was one of the most stressful tax situations I've ever dealt with. The court ruling in your favor is absolutely MASSIVE - that's ironclad legal proof that their original EIC adjustment was wrong. In my case, the IRS did offset about 40% of my refund against the old balance, but with hardship status and solid documentation (though not as strong as a court ruling), I still got the majority of my refund back. The 470 code took exactly 11 weeks to clear, which felt like an eternity but was pretty typical from what I learned. Here's what helped me: 1) Faxed copies of all documentation directly to the processing center with a cover letter explaining the situation, 2) Called every 2 weeks for updates and kept detailed notes of every conversation, 3) Escalated to Taxpayer Advocate Service after week 8. Your court documentation is going to be the game changer here - the IRS really can't argue with a legal ruling. Stay patient but persistent, and definitely keep pushing on that hardship claim. You're in a much stronger position than most people dealing with these codes! 🙏