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I tried to do this last year with Ethereum and totally messed up my taxes. I thought I was just taking out my initial investment of $4300 but my accountant explained that because I had bought in at different price points over time, I couldn't just consider it a withdrawal of my original funds. We had to go back and calculate the average cost basis of all my purchases, and then figure out what percentage of my total ETH I sold. Ended up having to pay taxes on about $1850 of gains I didn't think I had lol. Lesson learned.
This is such a common misconception that trips up so many people! The key thing to understand is that when you sell ANY portion of an investment, you're not withdrawing your "original money" - you're selling a percentage of your total holdings. Think of it this way: if you buy 100 shares of a stock for $25 each ($2500 total) and they double to $50 each, you now have $5000 worth of stock. If you sell 50 shares at $50 each (getting $2500), you're not getting your "original investment" back - you're selling half your position, which has a cost basis of $1250 (50 shares Γ $25 original cost) and realizing $1250 in taxable gains. This applies regardless of whether it's stocks, crypto, or other investments. The IRS doesn't care that the dollar amount you're withdrawing equals your original investment - they care about the cost basis of what you're actually selling. For your tax planning purposes, if you sell $2500 worth in 2025, you'll owe taxes on the gains portion in that tax year. The exact amount depends on your cost basis calculation method (FIFO, LIFO, or specific identification if you have proper documentation).
Last year I had a similar situation with Navy Federal. I set up text alerts for any deposits over $100 and that helped me know the moment it hit. I also found that logging into the mobile app was more reliable than the website for seeing pending deposits. In my experience, they don't usually do the early deposit thing for tax refunds like they do for paychecks, at least not for me over the past three years.
I'm also waiting on a Navy Federal deposit with a 2/24 DDD! Filed jointly for the first time this year too. Haven't received mine yet, but based on what others are saying, I'm planning to check my account first thing tomorrow morning. The text alert suggestion from Edward is really smart - I just set that up now so I don't have to keep obsessively checking my account. It's reassuring to hear that Navy Federal is generally reliable with posting on the actual DDD date. Fingers crossed we both see our deposits hit tomorrow!
Just want to add one practical tip - when you take over as trustee for a revocable trust, it's usually a good idea to get an EIN for the trust even if you're not filing 1041s. Many financial institutions require an EIN for trust accounts, and having one doesn't obligate you to file trust tax returns if it's a grantor trust.
Does getting an EIN mean you have to file a 1041 though? I thought having a tax ID for the trust means you're required to file trust tax returns. That's what my bank told me when I set up accounts for my dad's trust.
No, getting an EIN doesn't automatically require you to file 1041s. The filing requirement depends on the type of trust and circumstances, not just having a tax ID number. For a revocable trust with a living grantor, you can have an EIN for banking purposes without being required to file Form 1041. The confusion often comes from bank representatives who may not fully understand trust taxation rules. They see a trust EIN and assume tax filings are required, but that's not necessarily the case. The EIN is primarily needed because financial institutions need a tax identification number to open accounts and report income - they can't use the grantor's SSN for trust accounts even when it's a grantor trust for tax purposes. So you can safely get an EIN for operational purposes while still reporting all trust income directly on your dad's personal tax return.
Based on everyone's helpful responses, it sounds like the corporate trustee definitely made an error by filing 1041s for your uncle's revocable trust. Since he's still living and the trust is revocable, all income should indeed flow directly to his Form 1040. Regarding those high trustee fees ($38,000 on $75,000 of income seems excessive), you might want to review the trust document to see what fee structure was agreed upon. Even if the fees were legitimate, they shouldn't be generating K-1s in a grantor trust situation. For going forward, I'd recommend: 1) Stop filing 1041s immediately, 2) Consider whether amended returns for recent years make sense (especially if there were tax benefits your uncle missed), and 3) Make sure all future trust income gets reported directly on his personal return. The various tools others mentioned (TaxR.ai, Claimyr) might be worth exploring if you need professional guidance, but definitely consult with a CPA who understands trust taxation to clean this up properly. Six years of incorrect filings is a lot to unwind, but it's definitely fixable.
Former benefits administrator here. Your instincts are right - you absolutely need to stop that last HSA contribution. The problem is that FSA eligibility makes you HSA-ineligible, regardless of whether you actually use the FSA or not. Since that contribution would physically happen on 2/6, when you're already FSA eligible, it creates a compliance issue. Your HR department is confusing two different scenarios. They're thinking about the rule that lets you make prior-year HSA contributions until April 15th, but that only applies if you remained HSA-eligible. Once you have FSA coverage, you can't make any HSA contributions, even for periods when you were previously eligible.
Thanks for the clear explanation! Just to make sure I understand - is this still true even though the contribution would be processed through payroll and specifically coded for the January pay period? Or does the physical date of the money transfer override everything else?
The physical date matters here. The IRS looks at when the contribution actually occurs, not just how it's coded in payroll. Even though the contribution would be allocated to January, the fact that it physically happens on February 6th when you have active FSA coverage is what creates the problem. I've seen this exact situation trigger compliance issues during audits. The safest approach is to make sure your last HSA contribution happens while you're still HSA-eligible without any FSA coverage. The payroll coding unfortunately doesn't protect you here - it's about when the money actually moves.
I work in benefits administration and deal with this every year. Here's a simple rule: NEVER have overlapping HSA and FSA coverage, even for a single day. The safest approach is to: 1) Terminate HSA contributions with your last January paycheck (the one paid on/before Jan 31) 2) Start FSA with your first February paycheck Technically, your HSA contribution limit for 2025 will be prorated for just January, so you're only eligible for 1/12 of the annual limit anyway during this year of transition. If you've already maxed out January's prorated amount with your first two January paychecks, you're already at your limit.
Are you sure about that 1/12 proration? I thought the HSA limit wasn't prorated as long as you're eligible on December 1st and satisfy the testing period. But if you lose eligibility early in the year, do you actually need to prorate?
You're right to question that - the proration rule is more complex. If you're HSA-eligible on December 1st, you can contribute the full annual amount regardless of when during the year you became eligible (this is called the "last month rule"). However, if you lose HSA eligibility before December 1st, then yes, your contribution limit gets prorated based on the number of months you were eligible. In the original poster's case, since they're switching to FSA coverage starting February 1st, they won't be HSA-eligible on December 1st, so their 2025 HSA contribution limit will indeed be prorated to just January (1/12 of the annual limit). If they've already contributed more than that 1/12 amount in their first two January paychecks, they'd actually have excess contributions that need to be corrected.
Sean Murphy
2 Has your client established an LLC or other business entity for their influencer activities? This can help strengthen the argument that these are legitimate business expenses rather than hobby expenses.
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Sean Murphy
β’4 Not OP but this is a really good point. Having a formal business structure adds legitimacy to these types of deductions and creates clearer separation between personal and business activities.
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Jake Sinclair
For golf influencers, I'd recommend establishing clear documentation standards from the start. Create a simple spreadsheet tracking each equipment purchase with columns for: purchase date, item description, cost, content where it was featured, and revenue attribution. The IRS looks favorably on taxpayers who can demonstrate a clear business purpose and profit motive. If your client is genuinely making income from this content and treating it as a business (not just a hobby), equipment purchases are much more defensible. One thing to watch out for: make sure they're not double-dipping by deducting equipment they later sell or give away. If they do equipment reviews and then sell the clubs, that sale price should be reported as income, and the original purchase becomes cost of goods sold rather than a business expense. Also consider depreciation for expensive items like club sets - depending on how long they plan to use them for content creation, it might be better to depreciate over several years rather than expense everything in year one.
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