Just wondering - did you double check the Where's My Refund tool at irs.gov/refunds? Sometimes it will show if your direct deposit was rejected by the bank. If that happens, they automatically convert it to a paper check. Might save you a phone call if it's already been flagged in their system.

I went through this exact same nightmare last year! Here's what finally worked for me: when you call 800-829-1040, immediately press 1 for English, then 2 for personal income tax questions, then 1 for questions about a return already filed, then 3 for all other questions, and finally 2 again. This bypasses most of the automated stuff. The key is calling RIGHT when they open at 7 AM your local time - I got through in about 15 minutes versus the 2+ hour waits later in the day. Have your SSN, exact refund amount from your return, and filing status ready because they'll ask for identity verification before they can help. If your return was just filed last week, there's a good chance they can still intercept the direct deposit before it processes. The rep told me they usually have about 7-10 business days from when they receive an e-filed return before the refund gets sent out. Don't panic - you caught this pretty early!

The most important thing nobody mentioned yet is that if you choose to enter summary information instead of transaction-by-transaction, you MUST check box C (summary) at the top of Form 8949 and attach your broker statements. If you don't check this box but only enter summary info, you could trigger a mismatch notice from the IRS.

I've been dealing with this exact same issue! What worked for me was using TaxAct's "aggregate reporting" feature that I discovered buried in their help section. Instead of entering every single transaction, you can group similar transactions together by category (short-term vs long-term, covered vs non-covered) and enter totals for each group. The key is making sure you select "Statement attached" when prompted, which tells the IRS you're providing summary information and have the detailed backup. This is completely legitimate as long as your totals match your 1099-B exactly. To find this option in TaxAct, when you get to the investment income section, look for "Enter transactions" and then choose "Summary method" instead of "Detail method." It's not super obvious but it's there! This saved me probably 3 hours of data entry last year when I had 40+ stock transactions to report. Just remember to keep all your detailed transaction records in case of an audit - the IRS may want to see the breakdown even though you filed with summary totals.

2 This might be a dumb question but do I need to make quarterly estimated payments on self-employment tax too or just on income tax?

Just to add another perspective - I've been self-employed for about 5 years now and this confusion about SE tax vs income tax trips up almost everyone in their first year. One thing that really helped me was setting up a separate savings account specifically for taxes and automatically transferring about 30% of every payment I receive. This covers both the self-employment tax (around 14% after the deduction for the employer portion) plus income tax. It's better to overestimate and get a refund than to be short come tax time. Also, don't forget that you can deduct half of your self-employment tax when calculating your income tax - it's like getting back the "employer portion" since you're paying both sides as a self-employed person. The tax software handles this automatically but it's good to understand why your taxable income gets reduced.

As someone who just went through setting up health insurance for my small marketing agency, I can confirm everything that's been said here is correct. The full premium amount is deductible as a business expense, even including the employee pretax portions. One thing I'd add is to make sure you're keeping really good records of all this. I set up separate accounting codes for my portion vs. employee contributions just to make it crystal clear during tax time. My bookkeeper recommended tracking the total premium payments to the insurance company in one account, and then showing the employee pretax deductions as a separate line item that offsets payroll expenses. Also, don't forget that if you're using payroll software like QuickBooks or ADP, most of them will automatically handle the pretax calculations and generate the right reports for your tax preparer. Just make sure the pretax deduction is set up correctly in the system from the start - much easier than trying to fix it retroactively! The tax savings really do add up. Between my business deduction and my employees saving on their income and payroll taxes, we're probably saving around $4,000 collectively per year compared to if everyone just bought individual policies. Definitely worth the administrative hassle!

This thread has been incredibly helpful! I'm in a similar situation with my small accounting practice - just added health insurance for my 6 employees with a 60/40 split (I pay 60%, they pay 40% pretax). I was getting conflicting advice from different sources about the deductibility, but reading through all these explanations really clarifies things. The key insight that clicked for me is thinking about it as two separate transactions: my business expense to the insurance company for the full premium, and then the employee salary reduction arrangement that reimburses me for part of that expense. One question I still have - when I'm calculating my quarterly estimated taxes, should I be factoring in the tax savings from the full premium deduction or just my portion? I want to make sure I'm not underpaying throughout the year. My total monthly premiums are about $3,200 and employees contribute $1,280 of that pretax, so the additional deduction beyond my direct contribution is pretty significant for my tax planning. Also really appreciate everyone mentioning the record-keeping best practices and payroll software setup tips. Going to review my QuickBooks configuration this week to make sure everything is categorized correctly!

Your dad's situation is definitely fixable, but time is critical here. I agree with the advice to apply for Social Security immediately - don't wait for the tax situation to be resolved first. The SSA can work with his earnings record that employers have been reporting all these years. For the tax side, start by requesting wage and income transcripts from the IRS for all the unfiled years. You can do this online at irs.gov or by calling them (though as others mentioned, getting through can be challenging). These transcripts will show what income was reported by his employers and any taxes withheld. Since he had taxes withheld from his paychecks, he likely doesn't owe anything and may even be due refunds for some years. The key is getting those last 6 years filed to bring him into compliance. Given the complexity and the urgency with his health situation, I'd strongly recommend working with a tax professional who has experience with unfiled returns - they can streamline the process and help avoid costly mistakes. The most important thing is to take action now rather than letting this drag on any longer. Both his Social Security benefits and potential tax refunds are time-sensitive.

I went through almost the exact same situation with my father-in-law two years ago. He hadn't filed in about 18 years and was panicking about Social Security eligibility. Here's what we learned that might help: First, definitely start the Social Security application ASAP as others have mentioned - the earnings record from employers is what matters most for benefits, not tax filings. We were amazed to discover his full work history was already in their system from employer reporting. For the IRS side, we found out that since taxes were withheld from his paychecks the whole time, he actually qualified for what's called "substitute for return" status for many years where the IRS basically filed simplified returns on his behalf. This meant he wasn't in as much trouble as we feared. The real breakthrough came when we got his wage and income transcripts for all the missing years. It showed that for 4 of the years, he was actually owed refunds totaling over $3,200 (though we could only claim the ones from the last 3 years). We ended up only needing to file the last 6 years to get him current, and the whole process took about 3 months working with a tax professional who specialized in unfiled returns. The key was getting started immediately - don't let fear of the IRS paralyze you into waiting longer. Your dad's health situation makes this urgent, but it's absolutely manageable. The government actually wants people to get caught up and claim their benefits!