


Ask the community...
11 Make sure you keep ALL your settlement paperwork forever! I had a personal injury settlement 7 years ago, thought everything was fine, then got a surprise letter from the IRS questioning it during a random review. Because I had the original settlement documentation clearly showing it was for physical injuries, I was able to resolve it quickly. But without that paperwork, it would have been a nightmare.
1 How long do you actually need to keep settlement documents? Is 7 years standard or should I be keeping this stuff even longer?
11 You should keep settlement documents indefinitely, honestly. The standard recommendation for most tax documents is 7 years, but for something like a settlement that could be questioned many years later, I wouldn't risk discarding them. The IRS generally has 3 years to audit your return, but this extends to 6 years if they suspect you underreported income by more than 25%. And there's no statute of limitations at all if they suspect fraud. Since a settlement can be a large sum that might look like "missing income" during automated reviews, having your documentation ready even 10-15 years later could save you a massive headache.
2 Did your settlement include any punitive damages? That part is definitely taxable! My cousin didn't realize this and ended up with a huge tax bill the following year.
19 This is super important! I work at an accounting firm and see this mistake constantly. Personal injury settlements are only tax-free for compensatory damages (medical bills, pain/suffering, etc). Punitive damages are 100% taxable, and sometimes they're not clearly separated in settlement paperwork.
One thing nobody's mentioned yet is the potential impact of the SECURE Act 2.0 on your decision. The new law changes RMD requirements for Roth 401(k)s starting in 2024. Under the new rules, Roth 401(k) accounts won't be subject to RMDs anymore, which removes one of the big advantages that Roth IRAs had previously. This might make keeping money in an Individual Roth 401(k) more attractive than rolling to a Roth IRA, especially if you find a provider with good investment options and reasonable fees. The 401(k) still gives you higher contribution limits if you ever decide to contribute to the Roth side again in the future.
That's really interesting and completely changes the equation! I hadn't heard about that change to the RMD rules for Roth 401(k)s. If they're removing RMDs, then it seems like the main advantage of the Roth IRA is gone. Are there any other differences I should consider now that RMDs won't be a factor for either account type?
Even with the RMD changes, there are still some differences to consider. Roth IRAs still offer more flexibility for early withdrawals of contributions without penalties, which can be valuable if you might need access to funds before retirement. Inheritance rules also differ slightly between the two account types. Non-spouse beneficiaries of Roth IRAs have more flexible distribution options in some cases compared to Roth 401(k) beneficiaries. Additionally, Roth IRAs typically offer more diverse investment options than 401(k) plans, though this depends entirely on the specific providers you're considering. If the investment options and fees are comparable between your choices, the withdrawal flexibility of the Roth IRA might still make it slightly more advantageous.
Don't overlook state tax implications in your decision! I rolled my Solo 401(k) to a Roth IRA last year, and there was a state-specific tax wrinkle I hadn't considered. In my state, there are different creditor protections for retirement accounts. My Roth IRA only gets protected up to a certain dollar amount, while the 401(k) had unlimited protection. For someone running their own business where liability is a concern, this could be important.
This is a good point. Which state are you in? I'm in California and heard the protections are different here too, but couldn't find clear info online.
Just want to add my experience with the disappearing bars. Mine vanished on 2/10 after filing on 1/29. No status bars for 3 weeks then suddenly my refund was approved and deposited 2 days later. I claimed the American Opportunity Credit for my son's college expenses. So hang in there - it doesn't mean anything bad necessarily!
Thanks for sharing your timeline! That's encouraging to hear. Did you get any kind of notification when it was approved or did you just have to keep checking the IRS site?
Does anyone know if this happens with state tax returns too? My federal return was processed normally but my state return status disappeared completely from the tracker.
It can happen with state returns too but it varies by state. In my experience, state tax systems are even less transparent than the IRS about status changes. Which state are you dealing with?
For multiple W2 jobs, you should definitely check the "Multiple Jobs" box in Step 2 of your W4, or complete the worksheet to determine additional withholding. Checking "Exempt" means NO federal taxes are withheld! Also, file that 2022 return ASAP! The penalty for not filing (5% of unpaid taxes per month, up to 25% max) is much worse than just not paying (0.5% per month). You can set up a payment plan for what you owe if you can't pay it all at once.
Thank you for the advice! I've already started working on my 2022 return and will file it this week. Is there any way to reduce the penalties since this is my first time making this mistake?
You can request penalty abatement under the IRS First Time Penalty Abatement policy if you haven't had any significant penalties in the past 3 tax years and have filed (or filed extensions for) all required returns. Call the IRS after you file and pay or set up a payment plan. Tell them you want to request "first-time penalty abatement" for reasonable cause. Explain that you misunderstood the withholding requirements with multiple jobs and that you've taken steps to correct it for the future. Many people get approved, especially for first-time mistakes.
I'm in almost the exact same situation! Work as a server nights/weekends and have an office job during weekdays. I owe $9200 this year because both jobs were withholding as if they were my only income. My tax guy said this happens all the time with people working multiple jobs. For the rest of 2025, I'm having an extra $500 taken out of each office paycheck. It hurts now but better than another shock next April.
Zainab Khalil
Have you tried entering your 1095-A info in a different tax program just to see if it works? I ran into similar problems with TurboTax this year and ended up using FreeTaxUSA just to check if my 1095-A info would go through somewhere else. It worked fine there, which confirmed it was a TurboTax glitch and not my form. You could input it in a free program just to verify your data, then go back to TurboTax once you know the issue. Sometimes seeing how another program handles the same form can be enlightening!
0 coins
Amara Adeyemi
ā¢That's actually a really smart idea I hadn't considered. Did you end up sticking with FreeTaxUSA or did you eventually get it working in TurboTax? I'm still hoping to stay with TurboTax since I've used it for years, but at this point I just want to get my taxes filed correctly.
0 coins
Zainab Khalil
ā¢I actually ended up switching completely to FreeTaxUSA. I found their interface for the 1095-A much more straightforward, and it was significantly cheaper too. The transition wasn't as painful as I expected - I just had to re-enter my basic info and import my W-2 again. If you really want to stick with TurboTax, try the month-by-month entry method someone mentioned above. But honestly, I was surprised how easy the switch was, and I saved about $80 compared to what TurboTax was going to charge me for the same filing status.
0 coins
QuantumQuest
Something nobody's mentioned - check if you received an UPDATED 1095-A! The marketplace often sends corrected forms in February or even March. The updated forms usually have a small checkbox marked in the top right corner indicating it's a corrected form. I spent weeks fighting with TurboTax over my 1095-A until I realized I had a corrected form sitting in my mail pile that I hadn't opened. The original form had incorrect premium amounts which is why TurboTax kept giving me errors.
0 coins
Connor Murphy
ā¢This happened to me too! My corrected form wasn't even mailed - it was just sitting in my marketplace account online. I never got a notification about it. Definitely worth checking your healthcare.gov account (or your state marketplace site) to see if there's an updated form.
0 coins