The bonus withholding issue is super common! One thing nobody has mentioned yet is that you can actually ask your employer to withhold at a higher rate specifically for the bonus. Most payroll systems allow your employer to withhold at a different rate for supplemental wages (like bonuses) versus regular wages. You might want to talk to your HR or payroll department about withholding 25% or even 30% on that bonus instead of the standard 22% if you're worried about owing. I had my company do this for my annual bonus last year and it was the first time I didn't get hit with a tax bill in April!

Something else that might be happening - check if your employer is properly withholding for Social Security and Medicare (FICA taxes). I just went through this myself. My employer was withholding correctly for federal income tax but wasn't taking out enough for FICA. I didn't notice until I did my taxes and saw I owed a bunch. Apparently there was some setting in their payroll system that was calculating it wrong for my specific situation. Might be worth double-checking your paystubs to make sure everything looks right across all tax types, not just federal income tax!

One thing to keep in mind about using the Direct Payment method for extensions - make sure you keep the confirmation number they give you! I learned this the hard way last year. The IRS somehow lost track of my extension payment in their system, and when I got a failure-to-file notice with penalties, I had no proof I'd made the payment. Took months to sort out with multiple phone calls. Now I screenshot everything and save confirmations as PDFs.

I'm a bit confused about something... if I file an extension this way, is October 15th the new deadline for BOTH filing my return AND paying any remaining taxes I owe? My tax situation is complicated this year with a new business.

Former tax accountant here - one thing nobody mentioned yet about IRC Sec. 1377 elections is that sometimes neither option is clearly better for everyone. It really depends on: 1) When income was recognized during the year 2) When expenses were recognized 3) If there were any unusual transactions (asset sales, etc.) 4) What your personal tax situation is like In some cases, the remaining shareholders might want the election because the business lost money after you left (so they don't want to share those losses with you). In other cases, they might have had big gains after you left (so they don't want to allocate those to you). I'd demand to see month-by-month P&L statements at minimum before signing anything.

I had an issue with the IRC Sec. 1377 election last year and the remaining owners tried to pull a fast one on me. The key is to ask for the MONTHLY breakdown of: - Gross revenue - Major expenses - Any significant assets purchased/sold - Any debt taken on or paid off In my case, they were pushing hard for me to sign because they had major expenses coming in Q3/Q4 that would offset the income from earlier in the year. Without the election, I would have shared in those expense deductions. With it, they'd get all the deduction benefit.

From my experience with TaxUSA, here's a checklist of what you might be missing: 1. For freelance income: you need the total amount earned, business expenses (keep receipts!), and info about who paid you (name/address) 2. For two-state filing: exact move date, income allocation between states, and any state-specific tax credits 3. Check if you have other income sources: bank interest, investments, rental income, etc. 4. Don't forget deductions like student loan interest, medical expenses, charitable donations The TaxUSA interface does navigate you through most of this, but sometimes it's not clear what specific documents you should have on hand. Their help center has some decent guides if you search "missing information" or "required documents.

Just want to add that TaxUSA has a feature called "Form Finder" that most people don't know about. It's buried in their help menu but super helpful for situations like yours. It asks a series of questions about your life events from the past year (job changes, moves, investments, etc.) and gives you a personalized checklist of forms you should have. Also, for the state issue, speaking from experience - don't try to "guesstimate" your income allocation between states. If you get it wrong, either state might come after you for additional taxes. If you don't have exact numbers, the safest approach is to request a wage and income transcript directly from the IRS which will show the exact amounts reported by state.

Just wanted to add something important - if you owned the land for LESS than a year before selling, the profit would be taxed as ordinary income, not at the lower capital gains rate. This can make a huge difference in your tax bill. Make sure you're clear about your holding period!

Has anyone here used TurboTax to report a land sale? I'm trying to figure out if I need their premier version or if the deluxe can handle this type of transaction.