Did anyone address the OPs question about changing withholdings to "deduct mortgage interest month by month"? My understanding is you can adjust your W-4 to have less tax withheld based on ANTICIPATED deductions, but you're taking a risk if you end up not itemizing.

Great question! I went through this exact same confusion when I bought my first home last year. Here's what I learned after making some mistakes: The key thing everyone's touching on is that you need to compare your TOTAL itemized deductions against the standard deduction ($27,700 for married filing jointly in 2023). With your $425k mortgage, you'll probably pay around $20,000-25,000 in interest the first year (depending on your rate), plus property taxes, but that might still not exceed the standard deduction. Regarding withholding adjustments - yes, you can reduce your withholdings through your W-4 if you anticipate itemizing, but I'd be conservative. Maybe adjust for only 75% of what you think you'll save, because if you end up taking the standard deduction instead, you could owe money at tax time. My advice: Run the numbers with a tax calculator first, then make any withholding adjustments gradually. Better to get a refund than owe penalties!

This thread has been incredibly helpful! I'm in a similar situation with my part-time coffee shop job - been working there since October and just realized they haven't withheld any federal taxes from my $1,400 in earnings so far. What really clicked for me from reading everyone's experiences is understanding that the payroll system at each job operates independently. My coffee shop's system sees my relatively low earnings there and calculates that I won't owe federal income tax on just that amount, even though when combined with my full-time salary, I definitely will. I'm going to use the IRS Tax Withholding Estimator this weekend to figure out exactly how much extra I should have withheld. The idea of just adding a specific dollar amount per paycheck sounds so much simpler than trying to navigate those multiple jobs worksheets on the W-4. Thanks to everyone who shared their stories and solutions - it's really comforting to know this is a common issue with straightforward fixes. Better to handle it now than get surprised at tax time!

I'm going through the exact same thing right now! Started a part-time tutoring job in October and just noticed they haven't withheld any federal taxes from my paychecks either, even though I've made about $1,900 so far. Reading through all these responses has been so enlightening - I had no idea that each employer's payroll system only looks at what you earn at that specific job when calculating withholding. So my tutoring income alone is below the threshold where federal taxes would be withheld, but combined with my main job, I'll definitely owe something at tax time. I'm planning to use the IRS Tax Withholding Estimator this week to figure out how much extra I should have withheld. The suggestion about just requesting additional withholding from my main job rather than trying to coordinate W-4 changes at both places sounds like the way to go. Thanks everyone for sharing your experiences - it's such a relief to know this is normal and fixable! Much better to deal with it now than get hit with a surprise bill in April.

Happy to help clarify this! You're definitely not alone in being confused about TINs - it's one of those things that sounds way more complicated than it actually is. For most people in your situation, your TIN is simply your Social Security Number (SSN). The IRS uses "TIN" as an umbrella term for all taxpayer identification numbers, but for U.S. citizens and permanent residents, that's just your 9-digit SSN in the XXX-XX-XXXX format. You can find your SSN on your Social Security card, any previous tax returns you've filed, W-2 forms from employers, or even bank statements (though some banks only show the last 4 digits for security). If you've ever filled out tax forms before, you've already been using your SSN as your TIN - you just might not have realized that's what it was called! The only time you'd need a different type of TIN is if you were running a business (which would require an EIN) or if you weren't eligible for an SSN but needed to file U.S. taxes (which would require an ITIN). Since you mentioned this is for financial paperwork and you seem to be a regular individual taxpayer, your SSN is definitely what you need. So no need to apply for anything new - you already have your TIN! Just use your SSN wherever the form asks for your taxpayer identification number.

I totally understand the confusion! I went through the exact same thing when I first started dealing with tax paperwork. The good news is that for most people like yourself, your TIN (Taxpayer Identification Number) is simply your Social Security Number (SSN) - they're the same thing! You can find your SSN on: - Your Social Security card (if you still have it) - Any previous tax returns you've filed - W-2 forms from current or past employers - Bank statements or financial documents (though some only show partial numbers for security) The reason this is confusing is that "TIN" is just the IRS's umbrella term for different types of tax identification numbers. For regular U.S. citizens and permanent residents filing individual taxes, that's your 9-digit SSN. You only need different types like an EIN (for businesses) or ITIN (for non-residents) in special circumstances. So for your financial paperwork, just enter your SSN wherever it asks for your TIN. You don't need to apply for anything new - you already have what you need! Don't feel bad about asking - this trips up a lot of people because the government loves using different terminology for the same thing.

Remember that different PARTS of your settlement might be taxed differently. This is something my accountant explained that I hadn't considered: 1. Compensation for physical injuries/sickness: NOT taxable 2. Emotional distress stemming from physical injuries: NOT taxable 3. Emotional distress without physical injury: TAXABLE 4. Punitive damages: Always TAXABLE 5. Lost wages/back pay: TAXABLE 6. Interest on any of the above: Always TAXABLE The paperwork should break this down. If it doesn't clearly state how much falls into each category, you should absolutely ask for clarification from whoever is administering the settlement.

One thing that hasn't been mentioned yet is the timing of when you receive your settlement versus when it's taxable. I learned this the hard way with my own harassment settlement - even if you receive the money in December, you might be able to defer some of the tax impact depending on how the settlement is structured. Some settlements are paid out over multiple years, which can help with the tax bracket issue that Yuki mentioned. Others allow you to choose between a lump sum or structured payments. If you have that option, it's worth running the numbers both ways since spreading the income over several years could significantly reduce your overall tax burden. Also, don't forget about state taxes! Some states don't tax settlement income the same way the federal government does. I was so focused on federal taxes that I completely forgot to research my state's rules until tax time. The key is getting all this figured out BEFORE you receive the money so you can plan accordingly. Once that check is deposited, your options become much more limited.

I went through this exact situation with my dissolved LLC in 2021. The key thing to understand is that the IRS requires a final return even with zero activity - it's how they officially close your business account in their system. Here's what you need to do: 1. File Form 1065 for 2020 with all zeros but check the "Final Return" box at the top 2. Include Schedule K-1s for both members marked as final returns 3. Attach a statement explaining the business was dissolved in 2020 with the dissolution date For penalties, you definitely have grounds for reasonable cause abatement since you genuinely misunderstood the filing requirements. When you file, include a detailed letter explaining that you read the instructions and believed no filing was required due to zero activity. Reference IRC Section 6651(a)(1) and cite "reasonable cause and not due to willful neglect." The IRS agent's suggestion about amending 2019 doesn't make sense - you need the final return for the actual year of dissolution. I successfully got my penalties waived using this approach, so don't panic about the late filing fees.

I had a very similar situation with my dissolved partnership and want to share what worked for me. Like you, I thought no filing was needed for a year with zero activity, but learned the hard way that the IRS still requires that final return. Here's the exact process I followed that got my penalties fully waived: 1. Filed Form 1065 for the dissolution year with all financial lines showing zeros 2. Checked the "Final Return" box prominently at the top of Form 1065 3. Prepared Schedule K-1s for each partner marked as "Final K-1" 4. Included a separate statement with the business name, EIN, and exact dissolution date For the penalty abatement, I wrote a detailed reasonable cause letter explaining that I had carefully read the Form 1065 instructions and genuinely believed no return was required when there was no income, expenses, or business activity. I emphasized that this was an honest misunderstanding of the tax code, not willful neglect. The IRS accepted my explanation and waived all penalties (which would have been over $2,000). The key is being thorough in your documentation and showing you made a good faith effort to comply based on your understanding of the rules. Don't let that IRS rep confuse you about amending 2019 - you definitely need to file the 2020 return as your final return since that's when you actually dissolved. Good luck!