As someone who works as a tax preparer, PLEASE DO NOT try to claim your girlfriend. Her income is too high anyway, but more importantly, attempting to claim someone who's legally married to someone else is a huge red flag. I've seen the IRS come after people for less. Just file Head of Household with your son as your dependent, take the child tax credit if he qualifies, and leave your girlfriend's tax situation separate.

I'm going through a similar situation with my partner who's been separated for years but not legally divorced. After reading through all these responses, it sounds like your girlfriend's income of $11,000 would disqualify her anyway since the limit for qualifying relatives is around $5,000. Even if her income was lower, the marriage complication makes this risky. I'd definitely recommend following the advice about just filing Head of Household with your son - that's already a significant tax advantage compared to filing single, and you'll get the child tax credit too. If you really want a definitive answer about your specific situation, it might be worth using one of those services mentioned to get through to an actual IRS agent. But honestly, it sounds like the safest and most beneficial approach is to keep things simple and just claim your son while filing HOH. The tax savings from that status change alone should be substantial.

Has anyone found a good way to track foreign taxes throughout the year? I always get surprised by how much foreign tax I've paid when tax forms arrive in January. Trying to stay under that $300 threshold.

This is a really helpful thread! I'm dealing with a similar situation where I have about $450 in foreign taxes from my Vanguard Total International Stock Index Fund. I was also confused about why my tax software was showing different results when I experimented with the amounts. What I learned from my tax preparer is that the Form 1116 limitation formula can be especially harsh if you have a lot of domestic income relative to your foreign dividend income. In my case, the foreign dividends were only about 2% of my total income, so the limitation calculation really reduced my available credit. One thing that helped me understand this better was looking at the actual Form 1116 instructions and working through the calculation manually. The limitation is designed to prevent you from using foreign tax credits to offset U.S. taxes on U.S. income, which makes sense conceptually but can be frustrating when you see that full credit amount sitting there unused. For anyone dealing with this, make sure you're also checking if you can carry forward any unused foreign tax credits to future years - that's on Form 1116 as well and could help recover some of that "lost" credit over time.

Quick question - do I face the same issue with multiple brokerage accounts? I have accounts with Fidelity, Robinhood and Webull, and only received 1099s from Fidelity so far.

Hey Romeo, I totally understand your stress about this! I went through something similar last year. Here's what I learned: First, check if your investment platform has a minimum threshold for issuing 1099s. Some smaller platforms only issue them if you have $10+ in dividends or $600+ in other income. With $750 in total trades, you might fall below their threshold. However, you're still legally required to report all investment income and losses regardless of whether you receive a 1099. The good news is that if you lost money overall, those losses can actually help reduce your tax burden! Here's my suggestion: Download your complete transaction history from the platform (this is usually available even if 1099s aren't). You'll need the purchase date, sale date, purchase price, and sale price for each transaction. Then you can either: 1. Use tax software that can import trading data 2. Manually fill out Form 8949 and Schedule D 3. Use one of the specialized tax tools mentioned above Don't panic about the deadline - you can always file an extension if needed. The most important thing is to report accurately, even if it means using your transaction history instead of waiting for a 1099 that might not even be coming. You've got this! The $200 loss you mentioned can actually offset other income, so it's worth documenting properly.

My sister works for the IRS (not speaking officially ofc) and she always says they have bigger fish to fry than chasing people over a few dollars. Their computer matching system might catch it, but most likely it would fall below their internal threshold for sending notices.

I'm an EA and deal with these situations regularly. For $12 in qualified dividends, you're looking at maybe $1-3 in additional tax depending on your bracket. The practical reality is that the IRS automated matching system might flag it, but it would likely fall below their enforcement threshold. That said, if you want to be 100% compliant, you can file Form 1040X. Most tax software charges around $40-60 for amendments, so you'd be paying significantly more than the actual tax owed. My recommendation for clients in similar situations: Keep the 1099-DIV with your tax records and document your decision. If you ever get a notice (highly unlikely for this amount), you can respond showing you received the document after filing and the minimal tax impact. The IRS is much more understanding when they see you have the documentation and there's clearly no intent to evade taxes.

Anyone know if Vanguard generally fixes these 1099-R issues quickly? I have a similar problem but with Fidelity and I'm getting anxious about tax deadlines approaching.

This is a really common misunderstanding with brokerages! You're absolutely correct based on the IRS rules. I work in tax compliance and see this issue frequently - the key is that recharacterizations are tied to the tax year of the original contribution, not when the transfer physically settles. Since both of your recharacterizations were for 2023 contributions and both were completed before your 2023 tax filing deadline, they should both be reported for tax year 2023. The fact that one settled in January 2024 is irrelevant. When you call Vanguard back, specifically ask for their "Retirement Services Tax Team" or "IRA Tax Specialist" rather than general customer service. Have Publication 590-A ready with the exact quotes you mentioned. Most importantly, reference the "timing" rule you cited - it's very clear that the election and transfer must both occur before the filing deadline for the contribution year. If they still push back, ask them to cite which specific IRS publication supports their position. They won't be able to because the rules are clear. Document everything in case you need to escalate to a supervisor.