The quarterly tax payments thing is new to me! Will TurboTax tell me if I need to do those for next year based on what I enter now? This was just a summer gig, but I might do more freelance work in the future.

Yes, TurboTax will actually alert you if it thinks you should be making quarterly payments based on your current filing. After you complete your return, look for a section about "estimated taxes" or "quarterly payments" - it should provide vouchers with the amounts and due dates. Even if it was just a summer internship, this is good knowledge to have for future freelance work. The quarterly due dates are typically April 15, June 15, September 15, and January 15 of the following year. Missing these can result in penalties, so it's definitely something to be aware of if you pick up more contract work.

Check that you're selecting "Business" or "Self-employment" when it asks about the type of income. Sometimes if you just enter it in the general income section, TurboTax defaults to "Other Income" which is reported differently. You might need to back up a few screens and start that section over.

4 This is really good advice - my father qualified for free help through VITA (Volunteer Income Tax Assistance) program when he got a similar letter last year. They have special assistance for people over 60. Check with local senior centers or call 800-906-9887 to find the nearest location.

8 The Taxpayer Advocate Service can be incredibly helpful, especially for seniors or anyone with financial hardship. They act as an independent organization within the IRS and can help navigate complex tax situations. For the VITA program mentioned, they typically focus on tax preparation rather than representation in tax disputes, but they can often provide guidance and point you toward appropriate resources. Low Income Taxpayer Clinics (LITCs) are another great option - they provide free or low-cost representation for people who need to resolve tax problems with the IRS.

12 This happened to my grandfather too! The scammers had created a letter that looked really official. The only thing that tipped us off was that it asked for payment by money order to an address that wasn't an official IRS processing center. These scammers are getting really sophisticated.

How strict is the "exclusively" part for home office? My desk is in my guest bedroom that we use maybe twice a year when family visits. Can I still claim it?

The "exclusively" requirement is pretty strict in the eyes of the IRS. If you use your desk area solely for business but it's in a room that occasionally serves as a guest bedroom, you might have an issue claiming the entire room. However, you could potentially claim the specific portion of the room that's used exclusively for business. A safer approach would be to clearly partition the business area from the rest of the room using dividers or bookshelves to create a distinct workspace. Take photos of this setup for your records. Some tax professionals also suggest measuring the square footage of just your dedicated work area rather than the entire room to calculate a more defensible deduction.

Actually, meals provided to employees working overtime or during staff meetings can still be 100% deductible! Also, if you're in certain transportation industries, meals during work travel might qualify for 80% deduction. Check IRS Publication 463 for details.

Is there a specific app you recommend for keeping track of all this? I've been just taking random photos of receipts and it's a mess.

I use a combination of Google Drive for storing digital copies of forms and contracts, and then QuickBooks Self-Employed for tracking expenses, mileage, and income. The QB app lets you snap photos of receipts on the go and automatically categorizes them. For W-9s specifically, I just scan them with my phone and upload to the client's folder in Drive. I tried several expense tracking apps before settling on QuickBooks, and it's worth the monthly fee for the time it saves. Some people also like FreshBooks or Wave which are a bit simpler if you don't need all the features.

Wait so I'm confused. I did some graphic design for a company last year and filled out a W-9, but never got any tax forms from them. Should I be worried?

That's really interesting and might explain part of our situation. My husband was making around $6,000/month, then was unemployed for about 2.5 months, but when he returned to work, his new position paid about $7,200/month. So his income pattern was definitely uneven. Would the software automatically check for this "annualized income installment method" or do I need to specifically tell it to use this calculation?

Most tax software doesn't automatically check the annualized income installment method - you typically need to select it manually. Look for a checkbox or option labeled something like "Use Annualized Income Installment Method" or "Special calculation for uneven income" when you're in the estimated tax/penalty section. If your husband's income pattern was uneven as you described, this method might reduce or eliminate any remaining penalty after you fix the decimal point error. The annualized method essentially tells the IRS "I didn't make this money evenly throughout the year, so don't expect my tax payments to be even either.

I've used both TaxHawk and FreeTaxUSA, and I've found FreeTaxUSA to be more accurate with penalty calculations. When I had a similar issue last year, TaxHawk calculated a $1,200 penalty while FreeTaxUSA showed only $340. I ended up filing with FreeTaxUSA and the IRS never questioned it.