Thanks for mentioning the state unemployment taxes - I completely forgot about those! Do you know if the QuickBooks payroll service automatically handles those filings or is that something I need to set up separately? And any recommendations on finding a bookkeeper just for year-end stuff? Would I search for someone who specializes in "year-end closing" specifically?

QuickBooks Payroll handles federal and most state payroll taxes, but whether it includes unemployment taxes depends on which tier of service you have. With the higher tiers, they'll calculate and file these automatically, but with basic service you might need to handle filing yourself even if they calculate the amounts. For finding a year-end bookkeeper, I'd recommend searching for someone who specializes in "small business bookkeeping" and specifically mention you need "year-end closing and tax prep assistance." Many bookkeepers offer one-time cleanup services or quarterly/annual packages rather than requiring ongoing monthly work. Check the American Institute of Professional Bookkeepers directory or platforms like Upwork where you can filter for people with QuickBooks and tax prep experience.

Does QuickBooks handle the e-filing of 1099-NEC forms? I've been using QB for years but always had my accountant handle the actual filing part.

I tried it but found it confusing. You have to enter a ton of detailed information and I wasn't sure if I was doing it right. It also doesn't save your information so you have to re-enter everything if you want to try different scenarios.

Thanks for this perspective! I just checked our W-4s online through our employers' portals and yep - neither of us had checked that "two jobs" box. Do you think it's worth trying to get an extension to file since we owe so much? And will we get hit with underpayment penalties?

You can absolutely file for an extension using Form 4868, which gives you until October 15 to file your return. However, it's important to understand that this is only an extension to file the paperwork, not an extension to pay what you owe. You'll still need to estimate and pay your tax by the regular deadline to avoid penalties and interest. Regarding underpayment penalties, you might avoid them if you meet one of the safe harbor provisions: if your withholding and estimated payments cover either 90% of your current year tax or 100% of your prior year tax (110% if your AGI was over $150,000). If you were getting refunds in previous years, you might qualify under the prior year tax safe harbor, but you should check your specific situation.

The online portal is perfectly fine to use for W-4 adjustments. For most people with two relatively similar-paying jobs (like married couples where both work), simply checking the box in Step 2(c) is the easiest approach. This basically tells your employer to withhold at the higher single rate rather than the married rate. If your jobs have very different salaries, or you have more than two jobs, the multiple jobs worksheet or the IRS withholding calculator will give you more accurate results. You'd enter an additional amount to withhold in Step 4(c) based on those calculations.

Do you need to set up EFTPS separately for your business and personal taxes? I have both.

You can use the same EFTPS account for both business and personal taxes. When you make a payment, you select the tax form type and enter your tax ID (SSN for personal, EIN for business). The system keeps track of different payment types separately, so you can pay individual 1040-ES payments and business 941/940 payments through the same account. Really convenient if you have both personal and business tax obligations.

Yes! Same problem. I switched to DirectPay on the IRS website instead (when it works) or EFTPS. Payusatax was always slow to credit the payment even though they took the money from my account right away.

That's a great point about checking the transcript for prior notices! I'll definitely do that. Our business did move offices in early 2023, and I'm now wondering if notices were sent to our old address even though we filed a change of address form. Is there a specific way to mention this when requesting abatement?

If your transcript shows notices were sent but you never received them because of an address issue, definitely mention that when requesting abatement. This falls under "reasonable cause" arguments. Specifically say: "We filed Form 8822-B to change our business address, but it appears notices were sent to our previous location. We never had the opportunity to respond to the original notices before this went to collections." The IRS is generally understanding about address issues, especially if you can show you tried to update your information properly. This would be in addition to requesting First-Time Abatement, giving you multiple angles for relief.

I second this. My first request was denied too, but second time worked. The key was getting actual IRS transcripts that proved we had good filing history. Just saying "we've always filed on time before" isn't enough - they want to see proof in their system.