As a tax professional, I want to emphasize a few critical points that haven't been fully addressed: 1. **S Corp Owner-Employee Status**: As a single-member S Corp owner, you're considered an employee of your corporation. This means HSA contributions made through payroll are treated as employer contributions, which is exactly what you want for maximum tax benefits. 2. **Documentation is Key**: Make sure your S Corp formally adopts an HSA plan document and maintains records showing the contributions are part of your employee benefits package. This protects you if the IRS ever questions the treatment. 3. **Timing Considerations**: If you just formed your S Corp in 2025, verify that your S Corp election was properly filed (Form 2553) and accepted by the IRS. You can only use the employer contribution method for months when you were actually an S Corp employee. 4. **Comparison vs. Sole Proprietorship**: If you were previously a sole proprietor, the FICA savings alone make the S Corp structure worthwhile for HSA contributions. As a sole proprietor, you'd pay 15.3% self-employment tax on the same income that would fund your HSA. The payroll method through ADP is definitely the right approach - just make sure all your corporate formalities are in order first. The tax savings are substantial and completely legitimate when structured properly.

This thread has been incredibly educational! As someone who's been considering converting my sole proprietorship to an S Corp, the HSA angle adds another compelling reason to make the switch. One question I haven't seen addressed: what happens if you have employees in your S Corp besides yourself? Does offering HSA contributions as an employer benefit need to be extended to all employees, or can you limit it to owner-employees? I'm thinking about potentially hiring someone part-time later this year and want to understand the implications before I set up the HSA payroll structure. Also, @Jamal Harris mentioned board resolutions even for single-member S Corps - is this something that needs to be done annually, or is a one-time resolution sufficient to establish the HSA benefit policy? I want to make sure I'm covering all the corporate formality bases from the start. The tax savings really are substantial when you consider both the FICA savings and the income tax deduction. Thanks to everyone who shared their experiences - this has saved me from making some costly mistakes!

One more piece of advice - make sure to keep copies of EVERYTHING you send to the IRS, and send your response via certified mail with return receipt requested so you have proof of when they received it. Also, if the January 18th deadline is too tight, you can call and request a 30-day extension, which they usually grant. That would give you more time to get the proper documentation from the restaurant group.

I've been through a very similar situation with a payment processor issue, and I want to emphasize something that hasn't been mentioned yet - document EVERYTHING about your employment relationship with the restaurant group. In addition to your W-2, gather any emails, text messages, or other communications that show: 1) You were asked to set up the Square account as part of your job duties 2) You never had control over the funds (they went directly to business accounts) 3) You were acting as an employee, not an independent contractor Also, since the restaurant group was sold to a parent company, try to get documentation of that sale/transfer. This can help establish the business relationship timeline and show the IRS that this was clearly a business operation, not your personal income. If the current accountant doesn't follow through, consider reaching out directly to the parent company's finance department. They may be more responsive since this could affect their tax compliance too. One last tip - when you write your response letter, be very specific about dates, amounts, and the business purpose of each transaction. The more detail you can provide about how this was clearly business income that was misreported, the stronger your case will be. Good luck, and don't let this stress you out too much - these payment processor mix-ups are incredibly common and the IRS has seen it all before!

I used to work as a paralegal at a tax firm. One thing to consider - ask if they can give you a cap on research hours or a flat fee package. Most tax attorneys will be willing to set some limits once they've had an initial consultation and understand the scope. Otherwise, those research hours can add up quickly! Maybe something like "After 5 hours of research, we'll reassess and give you an updated estimate before continuing.

As someone who went through a similar situation with international gift tax complications, I'd suggest getting a second opinion before committing to those rates. While $625/hr isn't completely unreasonable for specialized international tax work, the combination of high hourly rates plus $800 per form seems excessive. I ended up working with a US-based tax attorney via video calls who charged $350/hr and included form preparation in their hourly rate. The time zone difference was manageable, and I saved over $3,000 compared to local quotes. Many US practitioners are very experienced with expat gift tax situations and can work efficiently since they handle these cases regularly. Also consider asking for a detailed scope of work upfront. "Substantial research" can mean different things, and you want to know exactly what they're researching before the clock starts ticking at $625/hr.

INFO: Are you and your boyfriend financially supporting yourselves and your children together, or is your dad providing significant financial support to you? Also, how old are you? The rules are different depending on whether you're over 19 (or 24 if you're a student).

Based on everything you've shared, your dad has absolutely no legal basis to claim you as a dependent. The IRS has very clear rules for this: For a "qualifying child" dependent, you must live with the person claiming you for MORE THAN HALF THE YEAR. Since you haven't lived with your dad at all in the past year, this requirement fails completely. For a "qualifying relative" dependent, the person must provide MORE THAN HALF of your total support. Your dad paying $600/year for car insurance and $50/month for your phone ($1,200 total annually) is nowhere near half of what it costs to support you, your boyfriend, and two children. Your registered domestic partnership establishes that you're part of a separate household unit. You're functioning as a family with your boyfriend and children - this is completely different from being financially dependent on a parent. Tell your dad straight up: "The IRS requires dependents to live with the person claiming them for at least 6 months of the year. Since I haven't lived with you at all, you legally cannot claim me. Period." Don't let him argue with tax law - these aren't opinions, they're federal requirements. If he tries to claim you anyway, the IRS will catch it when returns are processed and he'll face penalties for fraudulent claiming. Protect yourself by filing your own return correctly.

Another thing to consider - if your mom owns her home, she might be eligible for property tax relief or homestead credits in many states. These often require filing a state tax return even when federal filing isn't required. Also, has she been paying estimated taxes during these unfiled years? If not, and she does end up owing, you might want to look into the IRS Fresh Start program which can help with penalties.

I'm going through something very similar with my grandmother right now, so I completely understand the stress and worry you're feeling! One thing that really helped us was getting organized first before diving into the actual filing process. Here's what we did: First, we gathered all her income documents for each year (SSA-1099s, 1099-Rs, 1099-INTs, etc.) and made separate folders for 2021, 2022, and 2023. Then we collected all those IRS notices and sorted them by date to see what they were actually asking for. The biggest relief was discovering that many of the "scary" notices were just automated reminders, not actual threats. Some were even for years she didn't need to file at all! Since your mom's income situation sounds relatively straightforward (Social Security + pension + small interest), this might be manageable to tackle together. But honestly, given that she's been getting IRS correspondence for a while, it might be worth the peace of mind to consult with a tax professional who specializes in unfiled returns. They can quickly determine which years actually require filing and help navigate any correspondence with the IRS. The most important thing is that you're helping her address this now - ignoring it only makes things more complicated. You're being a great child by stepping in to help sort this out!