You can also pay at your local IRS office in person with a check or money order! Just look up "IRS Taxpayer Assistance Center" near you and make an appointment. I did this last year when I had similar online access issues and it was surprisingly easy. Bring your ID and they'll give you a receipt right there.

Does anyone know if paying late affects your future ability to e-file? I missed my estimated payment last year and had to mail my tax return this year because the e-file system kept rejecting me!

I finance everything for my HVAC business and always take the full deduction in year 1. Just make sure you're actually using the bike primarily for business. If you're audited, the IRS will want to see evidence that it wasn't mainly for personal use. I keep a simple log on my phone with client visits, addresses, and whether I used my truck or my bike to get there. Also - if you're making good money, look into setting up a Solo 401k. That's been WAY more valuable for reducing my tax bill than any equipment deduction.

One thing I haven't seen mentioned yet - make sure you understand the recapture rules if you ever sell the bike or stop using it for business before it's fully depreciated. If you take the full Section 179 deduction now but then sell the bike in a couple years, you might have to "recapture" some of that deduction as ordinary income. Also, since you mentioned your business is booming, consider whether you'll hit the Section 179 phase-out limits. For 2023, the deduction starts phasing out if you purchase more than $2.89 million in qualifying property (which probably doesn't apply to you, but good to know). The financing vs. cash question really doesn't matter - what matters is when you put it in service for your business. Keep detailed records of your business routes and maybe take some photos of the bike loaded with your pet care supplies to help document the business use!

Just to add some clarity here - I went through this exact same thing with Robinhood last month. If you don't check that box, they're required to withhold 24% of your investment income and send it to the IRS. Even if you're entitled to that money back later, it's a huge hassle. If you've been filing taxes properly and have an SSN, definitely check the box saying you're NOT subject to backup withholding.

Just wanted to share my experience since I was in almost the exact same situation as you. I'm also waiting on my Green Card approval but have had an SSN for years and been filing taxes properly. I was really confused about that backup withholding checkbox too. I ended up calling a tax professional who confirmed what others here are saying - your immigration status doesn't matter for this specific question. Since you have an SSN and have been filing taxes without issues, you should definitely check the box saying you're NOT subject to backup withholding. The key thing to understand is that backup withholding is basically a penalty for people who haven't been compliant with tax reporting in the past. If you've been filing your returns and paying taxes properly (which it sounds like you have), then you're exempt from it regardless of whether your Green Card is still pending. Don't overthink it - just check the box and move forward with transferring your investments to Fidelity like you planned. Robinhood's sketchy practices are definitely a good reason to switch!

I actually made the same mistake in 2021 and found out through a tax notice. Here's what I learned: Your W-2s from both employers should show your total contributions in Box 12 with code D (traditional) or AA (Roth). Add those up to confirm you actually exceeded the $20,500 limit for 2022. If you did exceed it, and it's a Roth 401k, the excess plus earnings should be distributed to you. The earnings will be taxable in 2023 (when you receive the distribution), not 2022. But theres a 10% early withdrawal penalty on those earnings if you're under 59½.

Just wanted to add some perspective from someone who dealt with this exact situation last year. The stress is real, but you're not alone in this! A few practical tips that helped me: 1. **Document everything** - Keep records of all your communication attempts with Vanguard and your employer. This creates a paper trail showing you made good faith efforts to resolve it properly. 2. **Check your math twice** - Like Isabella mentioned, make sure you're looking at the right W-2 boxes. I initially panicked thinking I was over when I was actually fine. 3. **Don't panic about the October 15 deadline** - While it's ideal to get the excess distributed before then, you can still file Form 5329 with your return to report the excess and pay the 6% excise tax if needed. It's not the end of the world. 4. **Consider professional help** - Whether it's the services others mentioned or a local CPA, sometimes the cost is worth the peace of mind and avoiding bigger penalties. The key thing to remember is that this is a correctable mistake. The IRS has procedures for this exact situation because it happens more often than you'd think with job changes. You're taking the right steps by addressing it now rather than ignoring it. Hang in there - you'll get through this!

Is no one else bothered by the fact that TT basically gives itself an interest-free loan from your refund and then charges YOU for the privilege?? The more I think about it, the more annoyed I get. They're literally using our money to float their business for a few weeks and then charging us for it.

This is exactly why I switched to doing my own taxes using the IRS Free File Fillable Forms. Yes, it takes a bit more work to understand the forms, but at least I know exactly where every dollar is going and I'm not getting hit with surprise fees. The whole SBTPG situation is a perfect example of how these tax prep companies make their money - not just from the software fees, but from all these ancillary services that most people don't even realize they're signing up for. When you're going through the filing process, they make it seem like paying with your refund is just a convenient option, but they don't clearly explain that convenience costs you an extra $40. For anyone who wants to avoid this next year, either pay the software fee upfront or look into the actual IRS Free File options that others have mentioned. Don't let these companies profit off your own money!