Remember that the holding period for gifted stock transfers with the gift! So if you held the stock for over a year before gifting it, and your daughter sells it immediately, she still gets long-term capital gains treatment. This is different from inherited stock where the basis gets stepped up but the holding period resets.

This is a great question that many people struggle with! Just to add one more important detail - make sure your daughter keeps good records of the gift transaction, including the date of transfer and the fair market value on that date. The IRS may ask for documentation if they audit the return. For the dual basis situation with the first stock, it's worth noting that if she had sold between $23 and $26 per share, she would have reported no gain or loss at all. This "no man's land" between the two basis amounts is unique to gifted depreciated assets. Also, since you mentioned this is for 2025 tax filing, keep in mind that the annual gift tax exclusion amounts may change, so double-check the current limits when you're preparing your own return if the total value exceeded the threshold.

Have you considered the dependency exemption allocation? This might be key to optimizing your tax situation. Can either of you waive the right to claim certain children? Would splitting the dependents across tax years work better? What about the impact on child tax credits and earned income credits? Have you calculated the difference in tax liability under each scenario? Did you account for state tax implications as well?

For military families in your situation, here are some important points to consider: • Military BAH (Basic Allowance for Housing) is not taxable income but does count toward support calculations for HOH status • If you lived in on-base housing, special rules may apply for determining "cost of keeping up a home" • The Service Members Civil Relief Act provides certain protections but doesn't directly impact filing status • If your spouse was deployed to a combat zone, there may be additional tax considerations • State of legal residence vs. physical residence can impact state tax obligations • The stimulus payments from previous years should have gone to whoever claimed the children Documenting your separate living situation is crucial in case of audit. Keep records of separate addresses, utility bills, etc.

I just want to add something that might help speed up your ITIN application process. When I applied for my ITIN last year for a similar situation, I discovered that you can actually submit your W-7 application through an IRS-authorized Certified Acceptance Agent (CAA). The big advantage is that CAAs can review your original documents (like your passport) and then submit certified copies to the IRS, so you don't have to mail your actual passport to the IRS. This eliminates the risk of losing your passport in the mail and can sometimes speed up processing since the IRS trusts the CAA's document verification. You can find a list of CAAs on the IRS website - many are accounting firms or tax preparation services that specialize in helping foreign nationals. Some even offer virtual services where you can video call to show your documents. Also, once you get your ITIN and submit the 8822-B, make sure to keep copies of everything and send it via certified mail. The IRS can take 4-6 weeks just to process the responsible party change, and having tracking helps if you need to follow up.

I went through this exact process about 6 months ago when I bought a Delaware LLC as a non-resident. Here's what I learned that might save you some time: The ITIN route is definitely the correct path, but there are a few things that can trip you up. First, when you file the W-7, make sure to check the box for "Exception 1(a)" which is specifically for non-resident aliens who need an ITIN for tax treaty benefits or to claim refunds. This helps the IRS understand why you need the ITIN. Second, I'd strongly recommend getting a US-based tax attorney or CPA involved from the start. They can handle both the ITIN application and the 8822-B submission as your authorized representative. This was worth every penny for me because they knew exactly what documentation to include and how to present everything properly. One more thing - while you're waiting for the ITIN, make sure the company's business address with the IRS is updated to an address where you can actually receive mail (or have someone receive it for you). I made the mistake of leaving the previous owner's address on file and almost missed some important notices. The whole process took about 10 weeks for me from start to finish, but it was much smoother having professional help. Good luck!

I went through this exact same situation about 8 months ago when setting up multiple LLCs for different trust structures, and I completely understand your frustration with Form SS-4. The instructions really don't make it clear how to handle these non-individual ownership scenarios. Here's what I learned after multiple attempts and conversations with IRS representatives: **For your grantor trust LLC:** You're on the right track. List yourself (the grantor) as the responsible party in Part 3 since you're treated as the owner for tax purposes anyway. Then put the trust name and EIN in Part 7a. The online application can actually work for this scenario - just make sure to select "Other" in the ownership structure dropdown and briefly explain it's a disregarded entity of a grantor trust. **For your non-grantor trust LLC:** Definitely go with the paper form. I wasted weeks trying to force this through the online system before giving up. List one of the trustees as the responsible party, making sure they have full authority to act for the trust. In Part 9, keep your explanation simple: "LLC will be treated as disregarded entity of [Trust Name], EIN [number]. All tax items will be reported on trust's Form 1041." The breakthrough moment for me was realizing that the "responsible party" is purely administrative - it's just who the IRS can contact and hold accountable. It doesn't change how your entity is taxed or who the actual owner is. One thing that really helped was calling the processing center about 2-3 weeks after mailing to confirm receipt and catch any issues early. Use certified mail so you have proof of delivery. The whole process took about 4 weeks total for my paper applications. Don't let the confusing instructions discourage you - once you understand what they're actually asking for versus what it seems like they're asking for, it becomes much more manageable!

I've been dealing with similar EIN applications for complex entity structures in my accounting practice, and I want to add a few practical points that might help streamline your process: **Document preparation tip:** Before filling out Form SS-4, gather all the relevant documents (trust agreements, LLC operating agreements, etc.) and highlight the key sections that define ownership and trustee authorities. This makes it much easier to complete the form accurately and helps if the IRS asks for clarification later. **For the grantor trust LLC:** When using the online application, I've found success by being very concise in the explanation fields. Something like "Disregarded entity of grantor trust - grantor is tax owner" usually works well. The online system seems to handle shorter explanations better than lengthy ones. **Timing considerations:** If you need the EINs urgently for bank account opening, consider applying for the grantor trust LLC online first (since that's typically faster) while simultaneously mailing the paper application for the non-grantor trust LLC. This way you can start some of your banking setup while waiting for the second EIN. **Follow-up strategy:** When calling to check on paper applications, have your complete mailing details ready (date sent, certified mail tracking number, etc.). The IRS representatives can locate applications much faster with this information, and you'll get better service. One last suggestion - keep detailed notes throughout the process. These entity structures tend to come up again for amendments, additional entities, or tax questions, and having a clear record of exactly how you handled the initial EIN applications saves time later.

Relax, this won't impact your chances of becoming an accountant or IRS agent at all. The IRS hires people who understand the tax code and can explain it to others. If anything, this experience gives you a personal story about how complicated tax laws can be! I actually know someone who works at the IRS who had almost the exact same situation happen to them. They now use their experience to help others avoid the same mistake. The key is that you're addressing it voluntarily now rather than hiding it and hoping you never get caught.

I completely understand your panic - this is such a stressful discovery, especially when you're studying to work in tax compliance! But please know that this is an incredibly common mistake that many scholarship recipients make. The distinction between qualified and non-qualified educational expenses isn't intuitive, and the IRS knows this. Here's what I'd recommend based on your situation: First, gather all your scholarship documentation from your school's financial aid office for the past three years. You'll need detailed records showing exactly how much was applied to tuition/fees versus refunded to you. Don't forget that qualified expenses can include more than just tuition - required textbooks, lab fees, and even some technology required for your program may qualify. Since you're dealing with multiple years and potentially significant amounts, I'd suggest getting professional help for at least an initial consultation. Many tax professionals offer free consultations for situations like this, and they can help you determine if you qualify for penalty relief programs. The most important thing is that you're addressing this voluntarily. This demonstrates good faith and will work strongly in your favor. As for your career concerns - this experience will actually make you a better accountant and IRS employee because you'll understand firsthand how complex tax compliance can be for regular people. Your integrity in fixing this mistake is exactly what the IRS looks for in employees.