Let’s face it: tax season can be stressful. With tight deadlines and potentially complex paperwork, there’s a lot of pressure to file accurately and on time.

That’s why many taxpayers turn to filing extensions for a little extra time to get over the finish line. In 2024 alone, 19 million Americans asked the IRS for ‌ filing extensions. Unfortunately, an extension doesn’t always simplify things.

Although it gives you more time to submit your tax return, it can delay a refund and doesn’t push back the timeline for payments you still owe. That’s why it often pays off to get organized early and file on time.

To get some pro tips on how to avoid having to ask the IRS for an extension, we sat down for a Q&A session with financial expert Brian Quigley.

Based in Denver, Colorado, Quigley has ‌more than 20 years of experience guiding clients through a range of documentation requirements and tax hurdles to achieve their fiscal goals. In 2020, he founded Beacon Lending — a finance company specializing in mortgage lending and refinancing.

Read on to get Quigley’s take on why people often need a tax extension, steps you can take to avoid asking for one, and find out how solutions like Trustworthy can help you get organized and collaborate with others to stay on top of your filing requirements. 

What Are the Most Common Reasons You Might Need a Tax Extension?

Answer: People often file for a tax extension because they’re missing documents, dealing with unexpected life events, or facing complex financial situations like business income or investments. 

Some just need extra time to ensure accuracy and avoid mistakes that could trigger an audit.

If your financial records are scattered, it can take longer to find income statements, deductions, and receipts. This delays calculations, increases errors, and may force you to file an extension just to sort through the mess.

What Steps Should You Take to Keep Tax Documents Organized Year-Round?

Answer: Create a system to store all tax-related documents, whether digital or physical. 

Regularly update folders for income, expenses, and deductions, automate tracking with finance apps, and review documents monthly instead of waiting until tax season.

Setting up calendar alerts for key tax deadlines helps prevent last-minute panic. Automated reminders for estimated payments, document collection, and filing dates ensure you stay ahead of schedule.

Tracking receipts and deductions as they happen means you won’t have to dig through piles of paperwork when tax season arrives. 

This also reduces the risk of missing deductible expenses that could lower your tax bill.

How Can Technology Be Used to Help You Avoid Getting an Extension?

Answer:  A secure digital storage solution keeps all tax-related documents in one place, making it easy to access everything you need when filing. This eliminates stress, saves time, and prevents lost paperwork from causing unnecessary delays.

Apps that allow you to share documents securely, like Trustworthy’s SecureLinks™, simplify collaboration with your accountant. They prevent lost emails, speed up tax preparation, and offer encrypted file transfers for sensitive information.

Being able to access tax documents from anywhere, whether on a phone, tablet, or computer, makes tax prep far easier. Digital solutions ensure you can upload, review, or share documents no matter where you are.

When Is it Time to Start Working with a Professional to File Your Taxes?

Answer: If your tax situation is complicated, such as handling multiple income sources, large investments, or business expenses, it’s wise to hire a professional. If you’re overwhelmed or worried about errors, an expert can ensure accuracy and help you maximize deductions.

Filing on time avoids late penalties, gives faster access to refunds, and reduces stress. It also lowers the risk of audits and allows more time to plan financial moves for the next tax year.

Boost Your Tax Game And Avoid Late Penalties Using Trustworthy

When it comes to staying on the right side of IRS deadlines, organization is your best friend. That’s why it’s worth partnering with an advanced digital storage solution like Trustworthy.

Trustworthy’s advanced Family Operating System® enables you to upload, organize, and maintain digital versions of your important family documents. Everything lives in one place — whether it’s previous tax returns, old W-2s, insurance policies, contracts, passwords, or your advance directive.

That means you never have to worry about losing important documents and scrambling to find them before tax season. Trustworthy’s AI-powered Autopilot tool streamlines the onboarding process by generating file name suggestions, telling you where to place each upload, and even creating summaries of long documents.

And if you’re working with an accountant to complete your tax return, Trustworthy features like SecureLinks™ let you share granular, timed access with trusted professionals to particular documents in your vault. This makes it easy to collaborate around tax season without compromising your data security.

But don’t just take our word for it. Get started on Trustworthy for free and discover how easy it can be to get organized and avoid asking for tax extensions.