How much does this quarterly planning service typically cost? I'm interested but worried about the expense.

It's not as expensive as I expected! My CPA charges $350 for the initial planning session, which includes a detailed analysis and setting up the W-4 withholding calculator, and then $150 for each quarterly review (about 30-45 minutes). So about $800 per year total. The way I look at it, we saved about $3,200 in taxes the first year through strategies she suggested (maxing certain pre-tax accounts we weren't utilizing and timing some deductions better). Plus, no more surprise tax bills has improved our financial stress levels dramatically. Even just the peace of mind knowing we're on track is worth it for us.

Thanks for the suggestion! I actually tried the IRS Withholding Estimator last year but got confused halfway through. Maybe I'll give it another shot. I think part of our issue is that we both got promotions mid-year that bumped our withholding into a weird zone. We've also got some investments that generate dividends that aren't being accounted for in withholding. Is there a good resource you'd recommend for learning about tax planning beyond just the withholding part?

Totally understand the confusion with the IRS tool - it's not the most user-friendly! For your situation with promotions and investment income, try the "Two Earners/Multiple Jobs Worksheet" that comes with the W-4 form. That helps account for higher combined income. For investment income, you can either increase withholding to cover it or make quarterly estimated tax payments. If it's under $5,000 of additional tax, just dividing by your remaining pay periods and adding that amount to Line 4(c) of your W-4 is easiest. For learning resources, I really like the Bogleheads wiki for tax planning. They have great articles on tax-efficient investing, understanding tax brackets, and maximizing deductions. The Personal Finance subreddit wiki also has solid tax planning sections. Both are free and pretty comprehensive for people with W-2 income and basic investments.

Thank you! That's a really important detail I wouldn't have thought about. Do you remember what specific form or code they needed to use for correctly documenting the excess contribution removal? I want to make sure I have all the right terminology when I call Fidelity.

For the 1099-SA form, the distribution should be coded properly. There's a box on the form for "distribution code" - for excess contributions returned by the tax filing deadline, it should be coded as "2 - Excess contributions" rather than "1 - Normal distribution." Make sure you specifically tell them it's for "excess contributions that were made when you weren't eligible for an HSA" and give them the specific tax year. I'd also recommend following up with an email if possible so you have written documentation of your request. Fidelity is generally good about this, but having it in writing saved me when my provider initially processed it incorrectly.

Yes, this is handled through the "last-month rule" or prorating your contribution. If you were eligible on December 1st, you can potentially contribute the full annual amount, but you have to remain eligible through the end of the following year (called the testing period). Otherwise, you can only contribute 3/12 of the annual limit for those three eligible months.

Super curious about this too. The IRS letter says I need to respond within 30 days, but I'm worried about what happens if the amendment takes months to process. Do they put collections on hold the whole time?

Amended returns are currently taking 4-6 months to process, sometimes longer depending on complexity. The key is to respond to the notice within the 30-day deadline, explaining that you're filing an amended return to correct the issue. When you respond, include a clear explanation of why you believe the tax assessment is incorrect (gross vs net income) and state that you're preparing an amended return. This formal response will typically pause immediate collection actions. If you can speak with an IRS representative directly, they can often place a more specific hold on your account while the amendment processes.

Yes, typically you'll need to file amended state returns too. Most states automatically get notified of federal adjustments and will adjust your state tax liability accordingly. Better to be proactive and file the state amendment rather than waiting for them to come after you too.

Thanks for this specific breakdown! Yes to all of those questions - they assigned clients, partners reviewed everything before it went out, I had set office hours (9-6 generally), and they provided everything including legal research software and admin support. Sounds like Form 8919 is definitely the right approach here.

You're welcome! With all those factors, you're clearly describing an employee relationship, not an independent contractor situation. Form 8919 is absolutely the right approach. Just one more tip - in Section 3 of the form where it asks for the reason code, use code G since you received both a 1099 and W-2 from the same firm in the same year. This is a textbook example of when to use that code. And keep copies of any firm policies, emails about work requirements, etc. that demonstrate the control they had over your work, just in case questions come up later.

Yes, TurboTax does support Form 8919! I used it last year for this exact situation. When you enter your 1099-MISC, it will ask a series of questions about your working relationship with the payer. Answer those honestly, and if it determines you were misclassified, it will guide you to Form 8919 instead of Schedule C/SE. One tip though - make sure you're using at least TurboTax Deluxe. The free version doesn't support this form.

Thanks for bringing this up! My qualified expenses should be enough since my tuition and required fees were about $18,000 this year, and I only received a $5,000 scholarship. The bond interest I'm trying to exclude is around $2,400. I wasn't counting room and board - good to know that's excluded for this benefit. Does it matter if some of the qualified expenses were paid from a 529 plan? Or does that create another reduction?

Yes, expenses paid with 529 plan distributions would reduce your qualified education expenses for the savings bond interest exclusion. The IRS doesn't allow "double-dipping" of tax benefits. So if you used $8,000 from a 529 plan to pay for some of that $18,000 in tuition and fees, and received a $5,000 scholarship, your remaining qualified expenses for Form 8815 would be reduced to $5,000 ($18,000 - $5,000 - $8,000). That would limit how much bond interest you could exclude.

There's no time limit between when the bonds were issued and when you use them for education. As long as you cash the bonds and pay the qualified education expenses in the same tax year, you can potentially claim the exclusion (assuming you meet all the other requirements about ownership, income limits, etc.). So 2010 bonds used for 2025 education expenses could qualify. Just remember both actions (redeeming the bonds and paying the expenses) need to happen in the same tax year.