As a healthcare worker myself, I completely understand the childcare challenges with evening shifts! Based on your situation, here are some practical steps you can take: Since the care is provided at her home with multiple children, she's an independent contractor (not your employee), which simplifies things - no employment taxes for you to worry about. For the Child and Dependent Care Credit, you'll need: 1. Her full name, address, and SSN/EIN for Form 2441 2. Documentation of payments (even if it's a log you create showing dates and amounts) Before claiming the credit, I'd strongly recommend having a conversation with your sitter about the tax implications. You could explain that: - She'll need to report this income (likely as self-employment) - She can deduct business expenses (portion of home used for childcare, utilities, supplies, meals for kids, etc.) - These deductions can significantly reduce her tax liability - She'll also earn Social Security credits and potentially qualify for other benefits Given how difficult it is to find reliable evening childcare, preserving your arrangement might be worth more than the tax credit if she's not willing to report the income. The credit could save you around $1,000-1,400, but finding new childcare for hospital shifts could be nearly impossible. Whatever you decide, document everything going forward - it'll make next year's taxes much easier!

I'm a tax professional and see this situation frequently with healthcare workers. You're asking all the right questions, and the advice here has been mostly solid. A few additional considerations from my experience: **Documentation Strategy**: Even without formal receipts, create a detailed log showing dates, amounts, and purpose of payments. Bank withdrawal records that align with your payment schedule serve as supporting evidence. The IRS accepts reasonable documentation as long as it's consistent and credible. **Provider Conversation Tips**: Frame it as a business opportunity rather than a tax burden. Many informal childcare providers don't realize they can deduct: - 35% of home expenses (utilities, mortgage interest, repairs) for space used exclusively for childcare - All supplies, toys, food provided to children - Professional development/training costs - Vehicle expenses for child-related activities These deductions often offset much of the tax liability, especially for someone watching multiple children. **Risk Assessment**: The Child and Dependent Care Credit could save you $1,000-1,400 annually. But stable evening childcare is invaluable for healthcare workers. Consider whether your provider seems business-minded enough to handle the transition to legitimate reporting. **Alternative Approach**: Some families transition gradually - start with proper documentation and SSN exchange this year, then implement 1099 reporting next year. This gives everyone time to adjust. The fact that she's caring for multiple children suggests she might already be thinking of this as a business, which could work in your favor for the conversation.

Has anyone had success getting interest paid on their wrongfully offset amount? The government took $9,000 of my EIDL grant back in March and I'm still waiting for it to be returned. Seems like I should be entitled to interest since they've essentially had an interest-free loan from me for 5+ months!

I'm dealing with a very similar situation right now - had my EIDL Targeted Advance intercepted by TOP for an old state tax debt last month. Like you, I was told by multiple people that these grants were supposed to be protected from offset under the COVID relief legislation. After reading through all these responses, it sounds like the key is getting the SBA to acknowledge the coding error and submit a formal correction to Treasury. I'm going to try calling the SBA customer service line tomorrow and specifically asking to be transferred to someone in their Payment Processing or Disbursement department who can handle miscoded payment corrections. One question for those who've been through this process - when you called the SBA, did you have to provide any specific documentation beyond your original EIDL paperwork? I want to make sure I have everything ready before I call so I don't have to start over if they ask for additional documents. Thanks for sharing your experience and all the helpful details in this thread. It's frustrating that this is happening to so many people, but at least now I know there's a path to get it resolved.

This is really helpful information - I'm dealing with a similar situation where my income jumped significantly due to a new job and some freelance work on the side. One thing I want to add is that if you're making that estimated payment in December, make sure you use the correct payment method and allow enough time for processing. I learned the hard way that some online payment methods can take a few business days to actually post to your account, especially around the holidays when banks have modified schedules. If you're cutting it close to December 31st, consider using EFTPS (Electronic Federal Tax Payment System) or even mailing a check with enough buffer time. Also, keep really good records of when and how you made the payment. The IRS has specific rules about when payments are considered "made" - generally it's when they receive it, not when you send it (except for mailed payments postmarked by the deadline). The safe harbor rules definitely work as others have described, but the timing piece is crucial to actually getting that protection!

Great discussion everyone! I'm in a very similar boat - sold some RSUs this year and my withholding is way behind. One thing I wanted to add is about the timing of when you actually recognize the income vs when you make the estimated payment. I learned from my tax preparer last year that if you're selling stock near year-end, the settlement date matters more than the trade date for tax purposes. So if you sell on December 29th but it settles January 2nd, that income actually goes on next year's return. This could affect whether you even need to make that big estimated payment this year. Also, for anyone considering the various tools mentioned here - definitely cross-check any automated calculations with a human tax professional if you're dealing with complex situations like stock options, RSUs, or significant income changes. The safe harbor rules are straightforward in principle, but the actual calculations can get tricky with multiple income sources and timing considerations. The 110% rule will absolutely protect you from penalties if calculated correctly, but getting that calculation right is crucial!

Friendly reminder to everyone discussing RSUs: there are actually TWO tax events to worry about! 1. When RSUs vest: This is treated as ordinary income (what everyone's discussing in this thread) 2. When you sell the shares: Any gain or loss after vesting is capital gain/loss For example, if RSUs vest at $100/share and you sell later at $150, you'll pay: - Ordinary income tax on the $100 at vesting - Capital gains tax on the $50 appreciation when you sell I see a lot of people getting confused because they only think about one of these tax events. Both need to be reported properly!

Yes, you should definitely consider filing amended returns if you've been using the wrong cost basis! The cost basis for RSUs is always the fair market value on the vesting date (not the grant date), since that's when you already paid ordinary income tax on that amount. Using the grant date price as your cost basis means you've been paying capital gains tax on appreciation that was already taxed as ordinary income at vesting - essentially double taxation. If you've held and sold RSU shares over multiple years, this could add up to significant overpayment. You can file Form 1040X (Amended U.S. Individual Income Tax Return) for up to 3 years from the original filing date. You'll need your brokerage statements showing actual sale prices and your RSU vesting records showing the fair market value on each vesting date. The IRS will refund any overpaid taxes with interest. Given the complexity of equity compensation, this might be worth consulting with a tax professional who specializes in stock compensation to make sure you're calculating everything correctly before filing amendments.

Consider exploring a Section 1202 qualified small business stock (QSBS) analysis as well. If your S Corp qualifies and your father has held his shares for at least 5 years, he might be eligible for significant capital gains exclusion (up to $10 million or 10x basis, whichever is greater). Also worth discussing with your advisors is the timing of any conversion strategies. Some families benefit from converting to a C Corp temporarily before the sale to take advantage of QSBS benefits, then converting back afterward, though this requires careful planning around the built-in gains tax rules. Another angle to explore is whether your father might benefit from charitable remainder trust (CRT) strategies if he has philanthropic goals. This could allow him to defer capital gains while providing income over time and eventual charitable benefits. The key is running the numbers on multiple scenarios before committing to any single approach. Each family's situation is unique based on the business value, personal tax situations, and long-term goals.

One strategy worth exploring that combines several approaches mentioned here is a "sale to grantor trust" structure. Your father could sell his shares to an intentionally defective grantor trust (IDGT) that you and your sister establish as beneficiaries. The benefits: your father receives installment payments (helping with his cash flow), the growth in business value happens outside his estate, and he pays the income taxes on the trust's earnings (which is actually a benefit since it further reduces his estate without using gift tax exemptions). Meanwhile, you and your sister effectively own the business through the trust structure. This works particularly well when combined with a small gift component - your father could gift a portion of shares to the trust and sell the remainder, reducing the total purchase price you'd need to finance. The trust can use business distributions to make the installment payments to your father, and since he's paying the trust's taxes as the grantor, more cash stays in the trust to service the debt. This is definitely complex and requires experienced estate planning counsel, but for family business transitions it can be incredibly tax-efficient compared to direct purchase arrangements.