One additional tip that might help others in this situation - if you're still within the 60-day window and haven't redeposited yet, consider doing a direct trustee-to-trustee transfer instead of a personal rollover if possible. What I mean is, if you still have the distributed funds and can work with your IRA custodian, sometimes they can facilitate putting the money back as a direct transfer rather than you personally depositing it. This can sometimes avoid confusion with the 1099-R/5498 reporting altogether. Obviously this doesn't help @Aaliyah Jackson since she already completed her rollover (and did it correctly!), but for anyone else reading this thread who finds themselves in a similar situation, it's worth asking your financial institution about this option. Some custodians are more flexible about this than others. That said, the personal rollover route that Aaliyah took is perfectly valid and very common. The key is just making sure to properly report it as everyone has explained - report the 1099-R but indicate it was rolled over so it doesn't get taxed.

This is such a valuable discussion! I've been lurking here trying to figure out my own IRA rollover situation, and this thread answered literally every question I had. One thing I want to emphasize for anyone else dealing with this - don't panic when you see that 1099-R! I almost had a heart attack when I got mine showing a huge distribution that I thought I'd have to pay taxes on. But as everyone here has confirmed, the key is just making sure you properly indicate the rollover when filing. For what it's worth, I used TaxSlayer (another tax software option) and it handled the rollover situation really well. When I entered my 1099-R information, it specifically asked "Was any portion of this distribution rolled over to another retirement account?" I answered yes, entered the rollover amount, and the software immediately zeroed out the taxable portion. The bottom line is that all the major tax software programs can handle this situation - you just have to make sure you don't skip over the rollover questions when entering your 1099-R. Keep both your 1099-R and 5498 as documentation, and you should be all set. Thanks to everyone who shared their experiences and expertise here. This community is incredibly helpful during tax season!

I just wanted to add another perspective as someone who's been dealing with RSU tax issues for years. One thing that really helped me was reaching out to my company's HR or equity compensation team directly. Many companies have dedicated support for employees dealing with tax questions around RSUs, and they often have resources or even partnerships with tax professionals who specialize in equity compensation. My company actually provides a detailed tax guide every year that explains exactly how to handle the cost basis adjustments in different tax software, including TurboTax. They also have sample calculations showing the difference between sell-to-cover and regular sales. It might be worth checking if your employer has similar resources before spending too much time trying to figure this out on your own. Also, if you're planning to continue receiving RSUs in future years, consider setting up a systematic approach now. I keep a simple spreadsheet that tracks every vesting event with the date, number of shares, FMV, and whether shares were sold to cover taxes. It makes tax season so much easier when you have everything organized from the start rather than trying to reconstruct it months later.

I've been following this thread and wanted to share another approach that might help. If you're still having trouble manually adjusting each transaction, you can also try exporting your transaction history directly from E*Trade and cross-referencing it with your equity portal data before even importing into TurboTax. E*Trade allows you to download a detailed CSV file of all your transactions for the year, which includes more granular information than what appears on the 1099-B. In this export, you can often see transaction types like "Journal" or "Stock Plan Activity" which correspond to the sell-to-cover events. This makes it much easier to identify which transactions need cost basis adjustments. Once you have this mapping, you can either manually enter the transactions in TurboTax with the correct cost basis from the start, or import the 1099-B and then make targeted adjustments only to the transactions you've identified as needing correction. This approach has saved me a lot of time compared to going through every single transaction blindly. The key is getting organized with your data first, then working with the tax software rather than trying to fix everything after the import has already created confusion.

Does anybody know if buying snacks for the team after games counts as a deductible expense? I probably spent like $400 last season on post-game treats for my volleyball team.

Great thread everyone! As someone who's coached youth tennis for 6 years, I want to emphasize the importance of keeping detailed records from day one. I learned this the hard way when the IRS questioned my deductions in year 3. A few additional tips from my experience: - Take photos of equipment you buy for the team (with receipts) showing it stays with the organization - Keep a simple log of volunteer hours even though you can't deduct time - it helps establish the scope of your volunteer commitment - If you travel to away tournaments, overnight travel expenses (hotels, meals) can also be deductible if the trip is primarily for volunteer purposes - Don't forget about uniforms or coaching gear you purchase that has the team/organization logo - these are clearly for volunteer use only The 14 cents per mile adds up fast when you're driving to multiple practices and games per week. Last year I deducted over $600 in mileage alone, plus another $300 in equipment and supplies. Just make sure your youth organization is actually a registered 501(c)(3) - you can verify this on the IRS website or ask them for their determination letter. Keep volunteering and helping these kids - the tax benefits are just a nice bonus for the great work you're already doing!

Mine was supposed to come the 3rd and still nothing. Starting to get worried ngl

Also waiting on my March 10th deposit here in Ann Arbor! Filed Feb 2nd and got the same date. From what I've seen in other MI tax groups, seems like a lot of us are in the same boat. The state website is pretty much useless for real-time updates unfortunately. Fingers crossed it hits soon 🤞

Most people forget you can also get free tax help through VITA (Volunteer Income Tax Assistance) if you make under $60k. They can help with basic investment forms like 1099-DIV. Just google "VITA tax help near me" to find locations. I used them last year and they were great!

Don't stress too much about the 1099-DIV - it's actually pretty straightforward once you understand the basics! The key thing to remember is that TurboTax will walk you through each box step by step. You'll enter the amounts from Box 1a (total ordinary dividends) and Box 1b (qualified dividends), and the software automatically calculates the tax differences for you. One tip: keep your 1099-DIV with your other tax documents for next year. As your dividend income grows, you might want to consider making quarterly estimated tax payments if it becomes substantial, but at $780 you're nowhere near that point yet. Also, since you're using Fidelity, they usually have good tax resources on their website that explain dividend taxation in plain English if you want to learn more about how this all works for future years.