Let’s face it: Tax season can be stressful. With tight deadlines and potentially complex paperwork, there’s 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, 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 it doesn’t push back the deadline for any taxes you may 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.
Quigley, based in Denver, 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, which specializes in mortgage lending and refinancing.
Read on to get Quigley’s take on why taxpayers may need an 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 Common Reasons for Tax Extensions?
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 Can Keep Tax Documents Organized?
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.
Can Technology Help You Avoid 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 Should You Hire 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.
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Avoid Late Penalties With Trustworthy's Help
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 organize, maintain, and share digital versions of your important family documents. Everything is stored in one place — whether it’s previous tax returns, old W-2s, insurance policies, contracts, passwords, or your advance directives.
That means you never have to worry about losing important documents and scrambling to find them before tax season. Trustworthy’s Autopilot tool streamlines the onboarding process by generating file name suggestions, telling you where to place each upload, and even creating summaries of 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.
Get started on Trustworthy for free and discover how easy it can be to get organized and avoid needing tax extensions.
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Trustworthy is an online service providing legal forms and information. We are not a law firm and do not provide legal advice.
