I went through this exact situation with my S-corp last year and completely understand the panic you're feeling right now! That $1,670 penalty for what amounts to a calendar mix-up feels absolutely crushing, especially for a business with zero activity. Here's what worked for me: I wrote a concise but detailed letter explaining the reasonable cause - specifically that I confused the S-corp March 15th deadline with individual tax deadlines since the business had been completely inactive. I made sure to emphasize three key points: 1) the business has had zero income/activity since it went dormant, 2) there was no tax impact to the Treasury, and 3) I have a clean compliance history and was requesting First Time Penalty Abatement. The IRS approved my request in about 6 weeks and removed the entire penalty. What really seemed to matter was being honest about the mistake while showing that this was a genuine error for an inactive business, not tax avoidance. Don't lose hope - the IRS is actually quite reasonable about these situations when you can demonstrate reasonable cause. The fact that your business is truly inactive with zero dollars at stake works strongly in your favor. You've got this!

I went through this exact same situation with my S-corp about 6 months ago - dormant since 2018, filed the zero-activity 1120S in April instead of March, and got hit with that same $1,670 penalty that makes your stomach drop. After reading through all the advice here, I decided to try both approaches: called the business line at 800-829-4933 first, then followed up with a written request. The phone call was surprisingly productive - the representative was knowledgeable and understanding about deadline confusion for inactive businesses. She started the penalty abatement process immediately and explained that cases like mine with zero tax impact are typically approved under reasonable cause relief. I also sent a follow-up letter to the address on my penalty notice, specifically mentioning "First Time Penalty Abatement" and emphasizing that my business had been completely inactive with no income or tax revenue impact to the Treasury. The combination approach seemed to work well - I received full penalty abatement confirmation about 7 weeks later. The key insight from my experience is that the IRS really does understand these are honest mistakes, especially when there's no actual tax avoidance involved. For inactive S-corps, the deadline confusion is incredibly common and they handle these cases routinely. Don't let the penalty amount scare you - with your circumstances (inactive business, zero activity, clean history), you have an excellent chance of success!

Don't forget about property tax reassessment! In some counties, a transfer - even between family members - can trigger a reassessment of the property value for property tax purposes. In my area, property that had been assessed at 1980s values suddenly got updated to current market value after a family transfer, and the annual property taxes increased by 5x! Make sure you check with your local tax assessor about any potential property tax implications before making the transfer.

Great point about property tax reassessment! This happened to a neighbor of mine too. One thing that might help is checking if your state has any family transfer exemptions. Some states like California have Proposition 19 rules that can limit reassessment for certain parent-to-child transfers, though the rules have gotten more restrictive recently. Also, if the land is currently classified as agricultural or forestry land for tax purposes, make sure the transfer won't cause it to lose that classification. Agricultural land often gets significant property tax breaks, and losing that status could mean a huge jump in annual taxes even without a reassessment of value. It's worth calling your county assessor's office before the transfer to ask specifically about their family transfer policies. Some counties are more aggressive about triggering reassessments than others, and knowing what to expect can help you plan for any increased tax burden.

This thread has been incredibly helpful for understanding the tax implications! I'm in a somewhat similar situation and wanted to share something that might benefit others here. I recently discovered that there are some nuances with state tax treatment that can significantly impact your overall tax bill, especially if you're in a high-tax state. While the federal calculations discussed here are spot-on, many states don't give preferential treatment to capital gains - they tax them as ordinary income at your marginal state tax rate. For example, if you're in California, New York, or New Jersey, you could end up paying 6-13% state tax on those capital gains even if you pay 0% federal tax. This can completely change your tax planning strategy. Also, for those dealing with inherited assets like the original poster, don't forget about potential state inheritance or estate taxes that might apply depending on which state the deceased lived in and where you live now. Some states have much lower exemption thresholds than the federal estate tax. One last tip: if you're doing any charitable giving this year, consider donating some of those appreciated stocks directly instead of cash. You can deduct the full fair market value and avoid paying capital gains tax on the appreciation entirely. It's a win-win that can be especially powerful when you're in a year with significant gains like this!

As someone who recently navigated a similar tax situation with inherited assets, I wanted to add a few practical tips that might help with implementation: First, make sure you have proper documentation for the stepped-up basis that others mentioned. You'll need either a formal appraisal from the date of death or brokerage statements showing values on that specific date. The IRS can be particular about this documentation, and having it organized upfront will save you headaches later. Second, if you're using tax software, double-check how it handles the "stacking" calculation. Some of the basic packages don't always correctly calculate the interaction between ordinary income and capital gains brackets. I ended up having to manually verify the calculations because my software initially got it wrong. Also consider the timing of when you actually realize these gains. If you haven't sold the stocks yet, you might want to think about spreading the sales across December and January to potentially optimize your tax situation across two years. Even a few days can make a difference if it helps you stay within the 0% capital gains bracket. Finally, don't forget about estimated tax payments if this creates a significant tax liability. The IRS expects quarterly payments if you'll owe more than $1,000, and there can be penalties for underpayment even if you get a refund when you file. Based on the calculations in this thread, you should be in good shape, but it's worth double-checking the safe harbor rules for your specific situation.

Pro tip for anyone who's cutting it close to deadline: Take a picture of yourself physically handing over your tax documents to the FedEx/UPS employee along with a photo of the receipt showing the date and time. I've had the IRS question my timely filing before, and having those photos saved me from a penalty.

Something that helped me understand the private delivery service rules better was realizing that the IRS treats these services differently than USPS because they don't have "postmarks" in the traditional sense. With USPS, the postmark date is what matters, but with FedEx/UPS, it's the actual date you hand over the package that counts as your filing date. I always make sure to drop off my tax documents during business hours so there's a clear timestamp on my receipt. If you use a drop box after hours, technically that might be considered the next business day, which could be problematic if you're cutting it close to the deadline. Also worth noting - if you're filing an extension (Form 4868), the same rules apply. The private delivery service has to be on the IRS approved list, and you need that receipt as proof of timely filing.

A lot of good info here but nobody mentioned that the timesheet might be misleading you. Your total pay is still $520 ($327 taxable wages + $193 non-taxable reimbursement). You're not losing money - the company is just separating the taxable from non-taxable portions as they should. Check your final paystub - you should see: - Gross earnings: $327 - Mileage reimbursement: $193 - Total: $520 (before tax withholding) Then taxes would only be calculated on the $327 portion.

This is a really helpful thread! I'm also a delivery driver and was confused about the same thing on my paystubs. Just to add one more perspective - make sure you're keeping good records of your actual miles driven vs. what your employer is reimbursing you for. In my case, I noticed my employer was only reimbursing me for "delivery miles" (the distance between stops) but not for the miles I drove to get to my first delivery or back home from my last one. Those "deadhead" miles can add up over time. Since the reimbursement rate is meant to cover all your vehicle costs (gas, wear and tear, depreciation, etc.), you want to make sure you're being reimbursed fairly for all business-related driving. If there's a significant gap, it might be worth discussing with your employer or at least tracking those unreimbursed miles for your own records.