If you owe taxes, does it matter when you pay between January 1 and April 15?

What if I file early but can't pay the full amount yet? Would it be better to wait to file until I can pay everything, or file now and pay what I can?

File now regardless of whether you can pay in full. Filing on time (or early) avoids the failure-to-file penalty, which is much steeper than the failure-to-pay penalty (5% versus 0.5% per month). If you can't pay in full, pay as much as possible when you file to reduce interest charges, then look into an IRS payment plan for the remainder. The IRS offers both short-term (120 days) and long-term payment plans with reasonable setup fees. You'll still pay interest on the unpaid balance, but you'll avoid additional penalties as long as you stick to the payment agreement.

Does it actually help with getting the penalties reduced or just tells you that you might qualify? I'm in a similar situation with probably $5k+ in penalties coming.

I'm skeptical about any service claiming to save on tax penalties. Doesn't the IRS have super strict rules? How exactly does this tool interact with the IRS?

It doesn't just tell you that you might qualify - it provides the exact IRS guidelines that apply to your situation and gives you the specific language to use when requesting abatement. In my case, it generated a complete penalty abatement letter with all the right references to IRS policies that I could submit right away. The tool doesn't interact with the IRS directly - you're still responsible for submitting the documentation yourself. But it analyzes your specific scenario against all current IRS regulations and penalty exception criteria, then gives you everything you need to make your case. It's not about finding loopholes but rather identifying legitimate relief options the IRS already offers that most people don't know about.

How does this actually work? The IRS phone system is notoriously horrible... are they just auto-dialing for you or something?

Yeah right. No way this actually works. I've spent literal DAYS trying to reach the IRS. If it was this easy, everyone would know about it. Sounds like a scam.

It's not auto-dialing - it uses a priority callback system that essentially holds your place in line without you having to stay on the phone. The IRS actually has a callback feature, but it's only offered when wait times are below a certain threshold. Claimyr gets you into that queue and then connects you when an agent is available. It's definitely not a scam. I was super skeptical too! But think about it - the IRS does answer phones eventually, just not efficiently. This service simply makes that process work better. I got connected with an actual IRS representative who pulled up my account, discussed my payment options, and helped me set up an installment agreement. The best part was not wasting hours listening to hold music or getting disconnected after waiting forever.

Good point! My state (CA) has a higher interest rate than the IRS, so I definitely paid that one first. Does anyone know if state tax payments are still deductible on federal returns? That might affect the calculation too.

State and local tax payments (SALT) are still deductible but limited to $10,000 total for most filers. This includes property taxes too, not just income taxes. The timing of state tax payments can get tricky for deduction purposes. Generally, you can only deduct state taxes in the year you actually pay them. So if you're trying to maximize deductions, when you pay could matter from that perspective too. But with the $10,000 SALT cap, many people don't benefit from timing strategies anymore unless they have very low property taxes.

TurboTax Premium has an audit risk assessment that highlights potential penalty situations. It also calculates estimated tax payments for the next year to help avoid underpayment. Not cheap but saved me from the same mistake twice.