I'm a trust beneficiary who went through a similar situation two years ago, and I want to share what I learned that might help you prepare for the conversation with your sister. When I requested documentation from my brother (who was trustee), I found it helpful to emphasize that proper records protect both the trustee and beneficiaries. I said something like: "I know you're handling everything correctly, but having clear documentation will protect both of us if there are ever any questions from the IRS or other beneficiaries." One thing that really opened his eyes was when I explained that trustees can be held personally liable for trust losses if they can't demonstrate proper administration. He suddenly became much more cooperative about providing detailed accounting and getting the EIN situation sorted out. Also, consider asking for a meeting (in person or video call) rather than just exchanging texts or phone calls. Being able to go through documents together made the whole process feel less adversarial and more collaborative. We ended up catching a few calculation errors that would have affected everyone's K-1s. The key is framing this as "let's make sure we're both protected" rather than "prove you're doing this right." Good luck with the conversation - I hope she responds positively to your reasonable requests for transparency.

I'm an estate attorney and want to add a perspective that hasn't been fully covered yet - the importance of getting this documentation request in writing. While the collaborative approach others have suggested is excellent, you should also send a formal written request for trust accounting as a beneficiary. This isn't being adversarial - it's protecting your legal rights. Under most state laws, beneficiaries have the right to receive periodic accounting from trustees, including detailed records of all trust assets, income, expenses, and distributions. A written request creates a clear timeline and legal record of your request for transparency. I'd suggest sending an email that says something like: "As a beneficiary of [Trust Name], I'm formally requesting a complete accounting of trust administration for the period since you became trustee. This should include all asset valuations, income received, expenses paid, and distribution calculations. I'd also like confirmation of the tax identification number being used for reporting and copies of any tax returns before they're filed." Keep it professional and factual. If she provides everything promptly, great - you have the documentation you need. If she refuses or delays unreasonably, you have grounds to petition the court for an accounting if necessary. Most trustees comply quickly once they receive a formal written request because they understand the legal implications. Having this documentation isn't just about taxes - it's about ensuring proper trust administration and protecting everyone's interests.

I work as a tax preparer and see this situation fairly often during tax season. The good news is that duplicate payments are usually resolved automatically by the IRS within 6-8 weeks after both checks clear. Their systems are pretty good at catching identical payments with matching SSNs and tax years. Here's what I recommend: First, monitor your bank account to confirm when both checks are cashed. Then give it about 2 months before following up. If you don't receive an automatic refund by then, call the IRS using the number Isabella mentioned (800-829-1040) or consider using one of those callback services others have mentioned to avoid the long hold times. One thing to keep in mind - if you owe taxes for next year, you can also request that the overpayment be applied as an estimated tax payment for 2025 instead of getting a refund. This might actually work out better from a cash flow perspective and saves you from having to make quarterly payments later. Don't stress too much about this - it's an honest mistake that happens more than you'd think, especially during the hectic tax deadline period!

I just wanted to share my recent experience with this exact situation! About 6 weeks ago, I accidentally sent two checks for $2,850 each (same story - panic mode during tax season). I was terrified the IRS would think I was trying to scam them somehow. I ended up calling them after reading advice similar to what Isabella shared, and the representative was actually really understanding. She explained that duplicate payments happen all the time and their systems flag them automatically. She confirmed both checks had been received and that a refund was already being processed. The refund check arrived about 10 weeks after my second payment cleared - so it did take a while, but it came through without any additional hassle. The representative also mentioned that I could have requested to apply it to next year's taxes instead, which I didn't know was an option. One thing I learned is to definitely keep detailed records of everything - dates you sent the checks, when they cleared, confirmation numbers from any calls you make, etc. It really helped when I had to reference the situation later. Don't beat yourself up about it - the stress of tax deadline makes people do all sorts of things!

Does anyone know if you need the more expensive TurboTax versions to handle multiple states? I was using the Free Edition but now I'm worried it won't support my situation with two states.

Great advice from everyone here! I just want to add one more tip that saved me a lot of headache with my multi-state filing - make sure to keep detailed records of which state you were physically working in for each pay period. I moved from Texas to Colorado mid-year and thought I had everything figured out, but it turned out some of my remote work days while technically employed by my Colorado company were done while I was still physically in Texas. This affected how the income was allocated between states. TurboTax will ask you specific questions about work location and dates, so having a calendar or log of where you actually performed the work (not just where your employer is located) can be really helpful. Also, don't forget about any state-specific deductions you might qualify for - each state I filed in had different rules about what could be deducted!

This is a really helpful discussion! I've been following along as someone who's fairly new to S Corp accounting, and I'm wondering about the practical timeline considerations here. When you're planning a treasury stock buyout like this, are there any IRS notification requirements or deadlines you need to be aware of? For example, do you need to update your corporate records or file anything with the IRS within a certain timeframe after the transaction? Also, I'm curious about the mechanics of updating shareholder basis calculations. Since the remaining shareholders will have increased voting percentages (as Haley mentioned), but their actual ownership percentages stay the same until the treasury shares are resold, how do you track basis adjustments for future distributions? Do you calculate distributions based on the original share percentages or the effective percentages after excluding treasury shares? Sorry for all the questions - just trying to understand the full picture before our company potentially goes down this path!

I appreciate all the detailed responses here! As someone who's dealt with similar S Corp treasury stock situations, I want to emphasize the importance of getting your shareholder agreement language right from the start. One thing I learned the hard way is that your buy-sell agreement should clearly specify whether buyouts will be treated as redemptions or treasury stock purchases, and what valuation method you'll use. In your case, paying $67,500 for shares with a $13,500 basis suggests you're using fair market value rather than book value. Also, make sure your agreement addresses what happens to the treasury shares long-term. Will they be retired after a certain period? Reserved for employee incentive plans? Offered first to existing shareholders? Having this clarity upfront can save you from difficult decisions later. One more practical tip - if you're planning to resell those treasury shares soon after the buyout, consider whether the timing might create any appearance of a pre-arranged transaction that could affect how the IRS views the original redemption. The tax treatment should be the same either way, but clear documentation of your business reasons for each transaction never hurts. The journal entries that Tony outlined earlier are spot-on for the accounting treatment. Just remember that good documentation and clear corporate governance are just as important as getting the numbers right!

This happened to me last year. Called my second employer just to check and they confirmed they didn't file anything with IRS since I earned $0. But I screenshot our email convo just in case there was ever an audit question. Better safe than sorry!

Just to reinforce what others have said - you're absolutely fine not including that second job on your return. I had a similar situation a couple years back with a consulting gig that never materialized into actual work. No income = nothing to report. The key thing to remember is that the IRS cares about money you actually received, not jobs you held or were eligible for. Since you didn't get any W-2, 1099, or other tax documents from them, there's no paper trail for the IRS to match against your return anyway. Focus on making sure your main job's W-2 is accurately reported and you'll be all set!