Pretty Soon, It’ll Be Tax Time: Are You Ready?
As tax season approaches, it’s almost time for that annual ritual: gathering your W-2, 1099s, and other financial documents. Your accountant will send their trusty checklist—or maybe you’ll take on the task yourself, cramming like it is finals week to beat the deadline.
Or perhaps you’ll file an extension, hoping for a bit more breathing room. (A reminder: filing an extension doesn’t extend the deadline to pay tax. You must make an estimated payment by April 15 and then true it up when you officially file). Some of us might miss the deadline entirely—something I highly recommend avoiding.
When I was single, I always filed my taxes on time. It felt like a huge weight lifted from my shoulders.
But after I got married, my husband took over tax prep, and suddenly, we were always filing extensions. It drove me crazy! These days, we have an accountant, and yes, they often file extensions too. It turns out there are valid reasons for this:
Reasons for Filing an Extension
- Late K-1s: If you own alternative investments or receive trust income, you’ll need a Schedule K-1. These forms are notorious for being issued late, delaying your entire return.
- Missing Information: Sometimes, clients don’t get all their documents to the accountant in time. (Guilty as charged?)
- Overwhelmed Accountants: Some accountants take on too many clients and use extensions as a way to manage the workload.
If I were an accountant, I’d try to get everything done by April 15 just so I could take a long, well-earned vacation!
Unfortunately, there are consequences for not filing taxes on time…(by the way, filing an extension is a completely legitimate way to get more time to do your taxes, and it will not trigger an audit as many think. It is much better to file an extension than to do nothing and file late!
Not filing your taxes on time or failing to file altogether can lead to significant penalties and headaches. Here’s a quick rundown:
IRS Penalties
- Failure-to-File Penalty: The IRS charges 5% of the unpaid taxes for each month (or part of a month) your return is late, up to 25% of your unpaid taxes.
- Failure-to-Pay Penalty: If you don’t pay your taxes on time, you’ll be charged 0.5% of your unpaid taxes each month, up to 25%.
- Interest Charges: The IRS also charges interest on unpaid taxes, which accrues daily from the original due date of your return.
Example: Suppose you owe $10,000 and don’t file or pay anything for three months. When you finally file, the interest and penalties would add an additional $1,850.00 to your tax bill.
The IRS penalties don’t stop there. Here are a few lesser-known reasons to stay on top of your tax obligations:
Beware of These Red Flags This Tax Season
- Solo 401(k) Filing Requirements: If you’re self-employed and have a Solo 401(k) with more than $250,000, you must file Form 5500 by July 31 or be subject to a $250-per-day penalty until you file. If this seems onerous, it is—the penalties were designed primarily to enforce compliance for large employer-sponsored retirement plans and prevent employers from mismanaging employee retirement funds. Unfortunately, Solo 401(k)s fall under the same penalty structure, even though they don’t pose the same risks.
- State Tax Nexus Issues: Working remotely or in multiple states might mean owing taxes in more than one state. Failing to file the correct state returns can lead to penalties and interest.
- Capital Gains Misreporting: Forgetting to report stock sales or underestimating the basis of your investments can trigger an IRS audit or unexpected tax bills.
- Health Savings Account (HSA) Mistakes: Overcontributing to an HSA or using HSA funds for non-qualified expenses can result in taxes and penalties.
- Gift Tax Filings: If you give someone more than $19,000 in a year (as of 2025), you need to file a gift tax return (Form 709), even if no taxes are due. Missing this step can complicate estate planning down the line.
- Failure to Report Cryptocurrency Transactions: The IRS is cracking down on unreported cryptocurrency gains. If you’ve traded or sold crypto, you must report it on your tax return.
- If you inherited an IRA and don’t take the correct distributions, the IRS imposes a 25% excise tax. They lower the excise tax if you correct the mistake within a correction window.
- IRA Rollovers: If you need cash for a short period of time and tap your IRA for it, there is no problem as long as you redeposit the money back into the IRA within 60 days. However, you can only do this once within a 12-month period. If you do more, the full amount is taxable; if you are under age 59 ½, there is also a 10% penalty.
Make Tax Season Work for You
Instead of scrambling at the last minute or risking penalties, consider these steps to make tax season easier:
- Start Early: Gather your documents as soon as they’re available and set aside time to review them.
- Work with a Professional: A CPA, Enrolled Agent, or financial advisor can help you navigate complex situations and minimize your tax burden.
- Double-Check Everything: Avoid errors by reviewing your return carefully before filing.
Tax season may not be fun, but it’s a lot easier when you stay ahead of the deadlines and know the rules. Filing on time, avoiding penalties, and understanding your options can save you time, money, and stress. And isn’t that worth it?
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