Will I be charged late fees if I request extension and owe federal taxes in 2025?

I'm trying to figure out a messy situation and hoping someone can help. I think I might need to file for an extension this year because my previous employer is being super slow about sending my 2024 W-2. They keep saying "it's coming" but it's already mid-March! Last year I got hit with a $950 tax bill because I completely messed up the Multiple Jobs worksheet on my 2023 return. Basically no federal taxes were taken from my weekend job in 2023. I've since fixed this by increasing my withholding throughout 2024, but honestly, I'm terrible with numbers and I'm worried I might still end up owing something. My big question is: will the IRS charge me penalty fees if I have to file an extension because I'm waiting on this W-2, especially if I end up owing federal taxes? And if they do charge penalties, can I fight those charges since it's not my fault my employer is dragging their feet on sending my tax document?

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18 comments

Zoe Dimitriou

•8M

Extensions give you more time to file your return, but they don't give you more time to pay what you owe. If you think you'll owe taxes, you should make an estimated payment by the regular April 15 deadline to avoid penalties and interest. You can make an estimated payment even without having your W-2. Look at your final paystub from that employer - it usually shows year-to-date tax info that can help you make a reasonable estimate. The IRS will charge penalties based on any unpaid amount after the filing deadline, regardless of why you couldn't file on time. Also, if your employer hasn't provided your W-2, and it's past January 31, you can contact the IRS at 800-829-1040 for help. They can reach out to the employer and also provide you with a Form 4852 (substitute W-2) that you can use to file your return.

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Zoe Dimitriou

•8M

Your last paystub of the year typically shows the year-to-date totals for all tax withholdings, which are usually very close to what will appear on your W-2. Compare boxes like federal income tax withheld, Social Security, and Medicare. There might be small differences due to taxable benefits, but it's usually close enough to make a reasonable estimate. If your paystubs are significantly different from your W-2s in the past, you can also look at last year's tax return and your current year's income to estimate any potential increase or decrease in tax liability. The goal is to make a good faith payment to minimize penalties, even if it's not exact.

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Jamal Anderson

•8M

I had similar W-2 issues last year and discovered taxr.ai (https://taxr.ai) which was honestly a game changer. I was missing one W-2 and freaking out about penalties, but their system helped me figure out exactly what I needed to pay by the deadline based on my other documents and paystubs. Their document analysis tool scanned my last paystub and gave me the estimates I needed to make my payment on time while waiting for the actual W-2. They also have tax pros who explained exactly how the extension process works (which the IRS website makes super confusing). The peace of mind was worth it because I knew exactly what to pay by April 15 to avoid those nasty penalties.

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Jamal Anderson

•8M

It doesn't connect directly to the IRS - it's more like an analysis tool that helps you understand your tax situation. Their system examines your documents and helps you calculate what you likely owe based on the information you have. I received my analysis within about 24 hours, which gave me plenty of time to make my payment before the deadline. The service doesn't replace filing your taxes - it helps you make that estimated payment to avoid penalties while you wait for missing documents. After I got my missing W-2, I completed my actual return with the correct numbers, but I'd already paid enough to avoid any penalties.

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Liam McGuire

•8M

Just wanted to follow up about my experience with taxr.ai after I was stressing about my missing W-2. The document analysis was super helpful! They looked at my last paystub and previous year's return and gave me a really accurate estimate of what I needed to pay. When I finally got my W-2 two weeks after the deadline, the actual amount I owed was only about $30 different from their estimate. I ended up with zero penalties because I'd already paid enough by April 15th. The step-by-step guidance on how to file the extension properly was exactly what I needed. Wish I'd known about this service years ago when I got hit with those stupid late payment penalties!

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Amara Eze

•8M

If you're having trouble reaching the IRS about your missing W-2 situation, try Claimyr (https://claimyr.com). I wasted HOURS on hold with the IRS trying to get help with a similar issue last year. Claimyr got me through to an actual human at the IRS in under 20 minutes when I'd previously been disconnected after waiting over 2 hours. They have this cool system that navigates the IRS phone tree for you and holds your place in line. You can see a demo at https://youtu.be/_kiP6q8DX5c to get an idea of how it works. The IRS agent I finally spoke with helped me file Form 4852 (the substitute W-2 form) and explained exactly what I needed to do to avoid penalties while waiting for my employer to get their act together.

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Amara Eze

•8M

It's not a scam - it's basically an automated system that dials in and navigates the IRS phone menu for you. When an agent finally picks up, you get a call connecting you directly to them. It saves you from having to sit on hold yourself. The IRS doesn't "allow" or "disallow" it - you're still talking directly to the IRS when connected. It's just handling the waiting part for you. Think of it like having an assistant dial and wait on hold while you do other things. I was skeptical too until I tried it during peak season last year when wait times were over 2 hours according to the IRS's own estimates.

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NeonNomad

•8M

I need to eat my words about Claimyr. After posting that skeptical comment, I was still desperate to talk to someone at the IRS about my extension situation, so I gave it a try. I was absolutely shocked when I got a call back connecting me to an actual IRS representative in about 27 minutes. The agent explained that I needed to file Form 4868 for the extension AND make an estimated payment by the deadline to avoid penalties. She also told me I could file a complaint about my employer for not providing my W-2 on time. The whole conversation took about 15 minutes and solved all my questions. After spending 3+ hours on hold the previous week and getting disconnected, this was actually worth it.

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Fatima Al-Hashemi

•8M

Exactly. The IRS doesn't care why you couldn't pay on time - they only care that you didn't pay by April 15. Your issue with your employer is separate from your obligation to pay taxes on time. That's why you need to make your best estimate and pay that amount by the deadline. Think of it this way: the IRS considers your taxes due as you earn income throughout the year. The April 15 deadline is already a grace period to finalize everything. So waiting on documents doesn't extend your obligation to pay what you already owe.

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