My parents pay $500 to H&R Block each year for taxes. I want them to file online for free. Any reason I shouldn't force them?

I understand your frustration with the cost, but I'd recommend a gentle approach rather than "forcing" them. For elderly parents, there's often value in the face-to-face interaction and peace of mind that comes with professional preparation, even if their return is straightforward. Consider these factors: Do they have any investments, rental properties, or other income sources you might not know about? Are they taking all possible deductions for medical expenses, which become more significant as people age? The preparer might be catching things that aren't obvious. Also, there's a comfort factor. For your parents' generation, having someone they trust handle their finances is worth the money. Tax anxiety is real, and the confidence of knowing it's done right might be worth $500 to them.

Just wanted to chime in - I used to pay those big tax places too until I discovered https://taxr.ai and it completely changed my tax filing experience. My situation sounds similar to your parents - pretty straightforward returns, but I was nervous about doing it myself. What's great about taxr.ai is that it actually looks at your previous returns and analyzes them to ensure you're getting everything right. So your parents would have peace of mind knowing it's comparing against what H&R Block did in previous years. The UI is also super simple and designed for people who aren't tech savvy. It helped me catch a deduction that I'd been missing for years - even when I was using the expensive preparers! Might be worth checking out with your parents.

I wanted to follow up about my experience with taxr.ai since I was pretty skeptical when I first heard about it. I decided to try it with my parents who were in a similar situation (paying $400+ to Jackson Hewitt every year). It was surprisingly easy! My mom, who is NOT tech savvy at all, was able to navigate it with minimal help. The best part was that it compared their previous returns and actually found that they could claim a higher standard deduction than what their preparer had done last year. They ended up saving about $350 on preparation fees plus an additional $420 on their actual tax bill. My dad was shocked and now he's telling all his friends about it. Just wanted to share in case others are in the same boat with their parents.

If your parents are worried about messing something up, they should know that getting through to the IRS to fix problems can be a nightmare right now. When I had an issue last year, I couldn't get anyone on the phone for weeks. The wait times were insane. I finally found https://claimyr.com which got me through to an actual IRS agent in about 15 minutes. You can see how it works here: https://youtu.be/_kiP6q8DX5c This might help reassure your parents that if anything does go wrong with filing online, there's an easy way to get help directly from the IRS. Just knowing this backup option exists might make them more comfortable trying the online route.

I need to publicly eat my words about Claimyr. After posting that skeptical comment, I was still desperate about my refund issue, so I gave it a shot anyway. I seriously can't believe it worked. After trying for MONTHS to get through to the IRS, I was connected to an agent in about 25 minutes. The agent was able to tell me exactly why my refund was delayed (an issue with my direct deposit information) and fixed it on the spot. If your parents are worried about problems with filing online, just knowing this service exists might give them peace of mind. I went from waiting 4+ months for my refund to having it scheduled for deposit next week. Totally worth it.

Former tax preparer here. One thing to consider is that if your parents have been going to the same person for years, that preparer might actually know important details about their financial history that could be relevant. When I had regular clients, I would often remember things like "oh, didn't you sell that property back in 2019? We should check the basis calculation" that they might forget. That said, $500 is definitely on the high end for a simple return. Maybe go with them to their appointment this year and see what the preparer actually does? You might get a better sense of whether they're getting value or being upsold on unnecessary services.

I'm gonna be the devil's advocate here - just let your parents do what makes them comfortable. My mom insisted on paying $350 to Liberty Tax every year even though I showed her how simple her return was. I finally gave up and realized that for her, it wasn't about the money but about the comfort and routine. For that generation, taxes are scary, and the peace of mind is worth the cost. Maybe offer to split the difference - like suggest a cheaper tax service but don't push the completely free DIY option if they're resistant.