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I'm trying to figure out if I can deduct about $33k in mortgage points that aren't actually listed on my settlement statement. We refinanced our home last fall, and I know we paid points to get a better rate (the loan officer definitely mentioned this during the process), but when I look at my closing documents, I don't see them specifically labeled as "points" anywhere. My lender is being super unhelpful - I've called twice and been transferred around to different departments with no clear answer. I'm using TurboTax and it keeps asking me for the amount of points paid, but I honestly don't know what to put since I can't find them listed anywhere! The loan was for $625k if that matters, and I'm pretty sure we paid around 1.25 points to bring down our rate. That's where I'm getting the $33k figure from, but I'm not confident enough to just claim it without proper documentation. Has anyone dealt with this before? Will the IRS flag me if I claim points that aren't clearly listed on my settlement statement?
So I was working as an independent contractor for about 3 years and received 1099s for all that income. I was young and honestly had no clue what I was supposed to do with them, so I just... didn't file my taxes. I know, completely stupid move on my part. Now I'm looking at enlisting one of those tax forgiveness agencies to help me sort this whole mess out before it gets even worse. I'm thinking about joining the military soon and don't want this hanging over my head during the security clearance process. Has anyone here used one of these tax forgiveness/resolution companies? Were they legit or just a scam? I'm looking at probably owing around $15,000 in back taxes plus whatever penalties have added up. Any recommendations or experiences would be super helpful!
My brother used one of those tax relief places advertised on the radio. They charged him $3,500 upfront and literally just filled out the same installment agreement request form he could have done himself for free on the IRS website. Complete waste of money. If you're dealing with unfiled 1099 income, just find a local CPA or EA (Enrolled Agent) who specializes in tax resolution. They'll charge you a reasonable fee to file your back taxes and request a payment plan. Don't fall for the marketing from these national "tax forgiveness" chains.
This is so true! I made the same mistake. The "tax relief experts" took my money and then just submitted an installment agreement. When I asked about the "pennies on the dollar" settlement they promised in their ads, they said I "didn't qualify" but only after they had my money. Do these companies ever actually get anyone an Offer in Compromise?
Very few of their clients actually qualify for an Offer in Compromise (the "pennies on the dollar" program). The IRS only approves those when you can prove you have no ability to pay and limited assets. Most people with steady income don't qualify. What these companies do is take advantage of people's fear of the IRS. They charge premium prices for standard services like filing back tax returns and setting up payment plans. The worst part is they often don't even look for legitimate deductions that could reduce the total amount owed. They're focused on processing as many clients as possible, not giving personalized service.
Quick question - if I use a regular CPA to file my old 1099 tax returns, how far back do I need to go? I haven't filed in like 4 years because I didn't know how to deal with my contractor income.
I'm freaking out a bit with my 2025 taxes right now. Back in January, I did what I thought was a straightforward direct rollover - moved my 401k into a Rollover IRA and my Roth 401k into a Roth IRA. My previous employer's plan administrator sent me a 1099-R form for this rollover. The problem started when I entered this 1099-R information into TurboTax. My expected refund immediately dropped by almost $1,800! I was under the impression that direct rollovers aren't taxable events, so I shouldn't owe anything on this money. I'm wondering if there's something wrong with my 1099-R form. Box 7 on the form has some code that might be incorrect, but I wanted to check with you folks before I call the plan administrator. They were a nightmare to deal with during the actual rollover process (took almost 3 weeks longer than they initially said), so I'm not looking forward to another frustrating phone call if I don't need to make one. Has anyone else dealt with this? Am I missing something about how direct rollovers are supposed to work with taxes?
Make sure you're also checking box 2a on your 1099-R. If the "Taxable amount" field shows your entire distribution as taxable when it shouldn't be, that's another red flag that the form is incorrect. For a direct rollover, box 2a should typically show $0 as the taxable amount, and the "Taxable amount not determined" box might be checked. Another possibility: did you do the rollover within 60 days of receiving the distribution? If there was any delay beyond that window, it could be considered a taxable distribution rather than a rollover.
I just double-checked my 1099-R and box 2a shows the entire amount as taxable! That's definitely wrong since this was a direct rollover (the money went straight from my 401k provider to the new IRA custodian without me touching it). There was no 60-day window concern since I never received the funds. And looking at box 7 again, it has code "1" which I think means early distribution. That's completely incorrect for a direct rollover. This explains why TurboTax is calculating taxes owed. I'm definitely going to have to contact the plan administrator for a corrected form.
Yep, that confirms the problem. Code "1" means early distribution (generally subject to taxes plus a 10% penalty if you're under 59.5 years old), and having the full amount in box 2a as taxable is definitely incorrect for a direct rollover. You need a corrected 1099-R with code "G" in box 7 and ideally "$0" in box 2a. When you contact the administrator, be very specific about these corrections. Sometimes the customer service reps don't understand the tax implications, so you might need to escalate to their tax department.
I had EXACTLY this problem last year! The 401k company messed up the code on my 1099-R and it showed as a regular distribution instead of a rollover. When I called, they tried to tell me it was correct, but I insisted they transfer me to someone in their tax department. The key was having them confirm that they sent the money DIRECTLY to my new IRA custodian. Once they verified that in their records, they had to admit it was coded wrong and issued a corrected 1099-R with code G. Until you get the corrected form, don't file your taxes if possible! It's much easier than having to file an amended return later.
I'm in a weird situation with inherited property and not sure how to handle the taxes. My mom passed away in 2023 without a will, but my sister and I each inherited about 7% of some land she owned (her ownership share was around 15% of the total property). Here's where it gets strange - this property is literally just empty desert land that's been in our family since the 1940s when my great-grandparents homesteaded it. No improvements, no utilities, nothing of value... except apparently its location near a highway exit. The entire property just sold for a shocking $800K! My share comes to about $56K, which is way more than I expected for worthless desert land. For tax purposes, the county's assessed value in 2023 was only $2,450 for the entire parcel. Does this mean I'll pay capital gains tax on my $56K minus my portion of that tiny assessed value (about $172)? The property was never "purchased" since it was homesteaded, so there's no original purchase price to use as a basis. I'm completely confused about how to calculate what I'll owe in taxes. Does anyone understand how this works?
Something nobody's mentioned yet - you should also check if you qualify for the home sale exclusion of up to $250,000 ($500,000 for married filing jointly). This applies if the property was your primary residence for at least 2 of the last 5 years before the sale. Doesn't sound like this applies in your case since it's vacant land, but just throwing it out there in case part of the property included a residence.
Thanks for mentioning this, but no, it was just empty desert land that nobody lived on. No structures at all. It literally sat empty for decades until someone decided it was valuable because of the highway exit nearby.
Good to confirm. One other thing to consider - check if your state has different rules for inherited property taxes. Some states have their own tax treatment that might be more favorable than federal. For example, some states might use their own version of stepped-up basis or have special provisions for long-held family property.
Has anyone considered that the $800K sale might trigger a federal gift tax return requirement? If the property was owned by multiple family members across generations and they're all receiving proceeds, there might be gift tax implications depending on how ownership was structured and transferred over the years.
This wouldn't trigger gift tax because it's a sale at fair market value, not a gift. The inheritance portion already happened when OP's mother passed away, and that would fall under estate tax rules (though with only a 15% interest in land worth $800K, it would be well below the estate tax threshold). The sale itself is just converting an asset to cash at market value - no gifting involved. OP and their sister would just each report their portion of capital gains based on their stepped-up basis.
I'm an independent dog walker in the United States who uses one of those popular pet care apps, and I'm trying to figure out the right way to handle my taxes. The app sends me a 1099 at the end of the year showing all the payments they transferred to me, but I've been keeping my own records of income based on when I actually complete the walks (not when the app decides to pay me, since they batch payments after multiple walks are completed). I'm really confused about a few things: 1. For tax reporting purposes, should I be using the income amount from my own tracking system (based on when I actually performed the services) or should I just go with whatever amount is on the 1099 the platform provides? 2. I drive to different houses for each walk and track my mileage for tax deductions. If I completed walks in December 2024 but the app didn't pay me until January 2025, can I still claim those December mileage deductions on my 2024 taxes? 3. What about the tips clients give me through the app? I've been recording those as income when I complete the walk, but I'm not sure if that's the correct approach according to tax principles or if tips should be handled differently. Any help figuring this out would be greatly appreciated! I want to make sure I'm doing everything correctly before tax season rolls around.
One thing nobody has mentioned yet is that you should be tracking your income and expenses using accounting software designed for small businesses. I use QuickBooks Self-Employed for my house cleaning business, and it has built-in features to handle exactly the issues you're describing. You can record income when earned (accrual) but still reconcile with your 1099s at tax time. It also has excellent mileage tracking that lets you categorize drives by client, so you can easily separate deductible business miles from personal ones. Really worth the money for peace of mind!
Does it handle tips well? My dog walking clients sometimes tip in cash and sometimes in the app, and I'm worried about mixing them up. Also, is there a way to mark certain expenses as "office supplies" vs "pet supplies" so I can track which deductions are for what?
It handles tips perfectly! You can create separate income categories for "service income" and "tips" and then further categorize as "cash tips" vs "app tips" if you want that level of detail. This makes it easy to reconcile against what shows on your 1099 vs. what you received in cash. For expenses, yes, you can create custom categories beyond the standard ones. I have categories for "cleaning supplies" and "office supplies" since they're different types of business expenses. For your situation, "pet supplies" would be a great custom category to track those specific deductions separately.
This might be a dumb question but it's my first year doing pet sitting... do I need to make quarterly tax payments? I started in October and have made about $3,200 so far. The app doesn't withhold any taxes from my payments. I'm worried I'll get hit with a huge tax bill and penalties in April.
You should consider making quarterly estimated tax payments if you expect to owe $1,000 or more in taxes. For self-employment income, you need to pay both income tax and self-employment tax (15.3% for Social Security and Medicare). At $3,200 since October, you're looking at around $490 just in self-employment tax, plus whatever income tax applies based on your total annual income. If you have other income with tax withholding (like a regular job), that withholding might cover your tax obligation from pet sitting.
Arjun Kurti
Something important that nobody has mentioned - if this was a REFINANCE (not a first mortgage), you can't deduct all the points in the year you paid them! You have to spread the deduction over the life of the loan. So if you paid $7,800 in points on a 30-year refinance, you can only deduct about $260 per year. A lot of people miss this and incorrectly deduct the full amount in year one.
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RaΓΊl Mora
Is there any exception to this rule? I thought if you use the refinance money for home improvements, you can deduct points immediately?
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Margot Quinn
Also check your monthly mortgage statements - sometimes they'll list the interest rate reduction you received from paying points. Mine shows "Rate: 4.125% (reduced by 0.75% through discount points)" which helped confirm what I paid for when the settlement statement was unclear.
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Oscar O'Neil
AuthorThat's a really helpful tip - I hadn't thought to check my monthly statements! I'll take a look at mine tonight. Thanks!
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