Great thread! Just want to add that when you're entering the Section 1256 contract information in TaxAct, make sure you double-check that the software is properly splitting your gains/losses using the 60/40 rule. I had an issue last year where TaxAct initially treated all my ES futures gains as short-term capital gains instead of applying the 60/40 split. I had to go back and specifically look for the "Section 1256 Contracts" section rather than just entering it under regular capital gains. Also, if you traded on multiple platforms like you did, make sure you're combining the totals from all your 1099-B forms before entering the aggregate amounts. The IRS wants to see one combined total on Form 6781, not separate entries for each broker.

This is such a helpful thread! I'm in a similar situation with ES futures trading but using FreeTaxUSA instead of TaxAct. Quick question for everyone - when you say "boxes 8-11" on the 1099-B, are you referring to the aggregate profit/loss amounts? My Interactive Brokers 1099-B shows totals in what looks like box 8 (Net Gain or Loss), but I want to make sure I'm looking at the right numbers. Also, has anyone had experience with FreeTaxUSA's Section 1256 contract entry? I'm hoping it's as straightforward as what you all described for TaxAct. The 60/40 rule seems like it should simplify things once I find the right section in the software. Thanks for all the great advice - this thread probably saved me from hours of confusion!

I do this every year for the exact same reason - credit card points! My strategy is a bit different though. Instead of trying to precisely calculate withholding for an $8k balance due, I aim for approximately $15k owed and then make quarterly estimated tax payments to stay within safe harbor limits. This way, I can make my Q4 estimated payment in December using a new credit card that I'm trying to hit a spending bonus on. The math is easier because you're just managing the estimated payments rather than trying to get your employer's withholding exactly right. Just be careful to stay within safe harbor rules - 90% of current year tax or 110% of prior year tax if your AGI exceeds $150k. I actually got hit with a penalty one year when I got too aggressive with this strategy.

I think you guys are way overthinking this. Just use the IRS withholding calculator, but when it asks for your desired refund amount, put in NEGATIVE $8000. That's literally all you need to do. The calculator will then tell you exactly what to put on your W-4 to end up owing $8k. I've been doing this for years for the exact same credit card churning purpose. Just remember to run the calculator again if you get any significant changes to your income during the year (bonus, raise, new job, etc).

Something nobody's mentioned yet - check your state's specific regulations too. AICPA ethics are one thing, but state boards of accountancy often have their own rules about this. In my state, there are additional disclosure requirements and separate engagement letter needs for CPAs who offer multiple service lines. Had to learn this the hard way when I got a letter questioning my compliance 😫

This is such a timely question for me too! I'm in a similar situation where I've been approached about offering financial planning services alongside my tax practice. One thing I've learned from researching this is that documentation is absolutely critical. Beyond just the engagement letters, you need to maintain detailed records showing how you made your tax recommendations independently from any potential sales opportunities. I've started keeping separate files that document my tax analysis process before any discussion of other services even comes up. Also, consider the practical implications - managing two different licensing requirements, continuing education for both areas, and the time investment to stay current in both fields. It's definitely doable but requires serious commitment to maintaining competency in both areas. Have you thought about what your liability insurance situation would look like? That's another area where you might need additional coverage depending on how you structure things.

called the irs about this last month - got transferred 3 times just to get the same answer: no weekend deposits period.

Just to add some context - this is actually due to the Federal Reserve's payment processing system (ACH) which doesn't operate on weekends or federal holidays. It's not just the IRS being old-fashioned, it's the entire banking infrastructure. Your refund gets queued up and processes on the next business day. Most banks will show "pending" deposits over the weekend but won't actually credit your account until Monday.

My accountant told me that Schedule C's with home office deductions get flagged more often. Anyone know if thats true?? I started working from home and want to claim the space but worried it'll trigger something.

As someone who's been freelancing for about 3 years now, I totally get the paranoia! What really helped me was understanding that the IRS is actually looking for patterns that don't make business sense, not just high expenses. For your situation with $7,500 in income, claiming legitimate software subscriptions and equipment is totally normal and expected. The key things that helped me feel more confident: 1. Keep detailed records of HOW you use business expenses (like what percentage of internet is actually for work) 2. Don't claim personal expenses as business ones (even if it's tempting) 3. Be reasonable with your deductions - if you're claiming more in expenses than you made in income, that's when eyebrows get raised I've claimed everything from Adobe subscriptions to a new monitor to client meeting expenses, and never had an issue. The IRS understands that freelancers have legitimate business costs, especially in creative fields where software and equipment are essential. Your income level actually puts you in a lower-risk category for audits. Just keep doing what you're doing - claiming legitimate expenses with proper documentation!