Is the 1098-T required to claim the credit? My school is weird and doesn't always send them on time.

While the 1098-T is helpful documentation, it's not technically required to claim the Lifetime Learning Credit. If you don't receive one or it's incorrect, you can still claim the credit using your own records of qualified education expenses. Keep documentation like receipts, cancelled checks, credit card statements, and any official statements from your educational institution showing you paid qualified expenses. The burden is on you to prove eligibility if audited, so good record-keeping is important even without the 1098-T.

You can definitely claim both credits in the same tax year, but not for the same student. If you and your wife are both in school, you could potentially claim AOC for one person and LLC for the other, depending on eligibility. That's a great way to maximize education tax benefits on one return!

Tax liens generally remain in place during the OIC process. When you submit your offer, the IRS typically suspends collection activities but doesn't remove existing liens until the offer is accepted and you've fulfilled the terms of the agreement.

Thanks for clarifying. That makes sense - they wouldn't want to remove their security while the negotiation is still happening. Guess I'll have to live with the lien a bit longer!

I hadn't even heard about the currently not collectible option. That might be a good temporary solution while I get everything in order for an OIC. Is the application process similar? Do you use the same financial forms?

Yes, the application process uses similar financial disclosure forms - primarily Form 433-A or 433-F for individuals. You'll need to provide comprehensive financial information showing your income, expenses, assets, and liabilities to demonstrate that paying would create a financial hardship. The standard is generally that paying your tax debt would prevent you from meeting basic living expenses. It's less complicated than an OIC application since you're not proposing a settlement amount, just requesting temporary relief from collection.

What about if the stock value dropped between when I received it and when I sold it? Can I claim a loss in that case? My employer gave us stock at $75/share but by the time I sold it had dropped to $58.

Yes, if the stock value dropped between when you received it and when you sold it, you can absolutely claim a capital loss. In your example, if your stock was valued at $75 per share when granted (and that amount was included in your W-2 income), but you sold at $58 per share, you would have a capital loss of $17 per share. This loss can be used to offset capital gains from other investments, and if your total capital losses exceed your gains, you can deduct up to $3,000 of the excess loss against your ordinary income. Any remaining loss can be carried forward to future tax years.

In TurboTax, when you enter your 1099-B information, there should be a screen that says something like "Review your 1099-B entries" after you input the initial information. On that screen, you can select the specific stock transaction and click "Edit" or "Update." There should be a field labeled "Cost basis" where you can manually enter the correct amount instead of using what's on the form.

Does the FSA administrator ever question therapy expenses or ask for details beyond the superbill? I'm private about my mental health treatment.

In my experience, the FSA administrator has never questioned my therapy expenses or asked for additional details. The superbill usually just lists the service code and amount without any specific details about what was discussed in therapy. It typically shows something generic like "psychotherapy services" or a CPT code. FSA administrators are also bound by privacy rules, so they can't share information about your specific medical treatments with your employer. I've been submitting therapy expenses to my FSA for three years now without any privacy concerns.

Yep! I deducted my Talkspace expenses last year. Online therapy absolutely counts the same as in-person. Just make sure your digital receipts clearly show it was for mental health services. Mine said "psychotherapy session" and had the therapist's license number which was perfect for documentation.

Do you know if the reps had to pay back any of the business deductions they'd claimed? I've been deducting home office, internet, phone, etc., as a 1099 and I'm worried if I get reclassified I'll owe a ton for those past deductions.

From what I understand, the reps didn't have to pay back deductions they had legitimately claimed while operating under the 1099 status. The IRS generally doesn't penalize workers in these situations since you were filing based on the classification given to you by the company. However, going forward after reclassification, they could no longer claim those business deductions as W-2 employees. That's definitely something to consider in your calculations - while you save on the employer portion of FICA taxes as a W-2, you lose those valuable business deductions. In some cases, especially if you have significant legitimate business expenses, remaining a 1099 might actually be more financially beneficial despite the higher self-employment tax.

Yes! I managed to negotiate a 12% increase in my commission rate when my company reclassified me from 1099 to W-2 last year. The key was coming prepared with exact numbers showing: 1) The taxes they'd now be paying (7.65% of your income) 2) The benefits costs they'd incur 3) The exact business deductions I'd be losing 4) Market rates for W-2 sales reps with my performance level I presented it as a business case rather than a demand. They actually appreciated the transparency and realized keeping top performers was worth the adjustment.

That's really helpful, thanks for the specific percentage figure and the breakdown of what to include in the negotiation. I'll definitely put together that kind of detailed analysis before approaching them. I'm curious though - did your overall take-home pay end up being higher, lower, or about the same after the transition? And did you notice any benefits to being W-2 beyond just the tax situation?