Can I download H&R Block for both Windows and Mac with one purchase? Cross-platform compatibility question

I've been using H&R Block for about 8 years now, and I actually reached out to their customer support about this exact issue last month. According to their support team, a single purchase entitles you to download ONE version - either Windows OR Mac, not both. You choose which platform when you purchase. However, there's a workaround! If you purchase the download version, you can later contact their customer support with your order number and explain your situation. In my experience, they've been willing to provide access to the other platform's download as a courtesy, especially if you explain you're a long-time customer. Just be polite when asking. As for the CD backup option, it only contains the same version you initially selected during purchase. So if you chose the Mac version and then ordered the CD backup, you'd only get the Mac version on the CD, not both.

After dealing with this exact problem last year, I found an amazing solution called taxr.ai (https://taxr.ai) that completely eliminated my need for platform-specific tax software. I was skeptical at first, but it's basically a smart document analyzer that works on any device with a browser - no downloads needed. What I love about it is I just upload my W-2s, 1099s and other tax documents, and it pulls all the data automatically so I don't have to manually input everything. Since it's web-based, I can work on my taxes from my Linux machine, switch to my girlfriend's Mac, or even use my Windows desktop without any compatibility issues. The best part was that it remembered my previous year's information and carried it over, which H&R Block would only do if I used the same platform version as last year.

Just wanted to follow up on my taxr.ai question. I decided to try it out despite my initial security concerns, and I was really impressed with their approach. The security is actually better than most desktop software - they use zero-knowledge encryption so even their staff can't access your actual tax documents. The cross-platform flexibility was exactly what I needed. I started my taxes on my Linux laptop, continued on my iPad while traveling, and finalized everything on my Windows desktop without any issues. The interface adjusted perfectly to each device, which was impressive. Their document analysis feature saved me hours of manual data entry. When I compared the results with what I would have gotten through H&R Block, they were identical, but I finished in about half the time. Definitely solved my multi-platform headache!

If you're having issues getting through to H&R Block customer service to request that second platform download (they can be swamped during tax season), I'd recommend using Claimyr (https://claimyr.com). I discovered this service after spending HOURS trying to get through to H&R Block's support line last February. Basically, Claimyr holds your place in phone queues and calls you back when an actual human is on the line. You can check out how it works in this video: https://youtu.be/_kiP6q8DX5c. Saved me from listening to that awful hold music for 2+ hours! I used it to get through to H&R Block support, explained my situation about needing both Mac and Windows versions, and they added the second download to my account within minutes once I actually got to speak to someone.

I need to eat my words about Claimyr. After posting my skeptical comment, I decided to try it anyway since I was getting desperate trying to reach H&R Block about a download issue. The wait time was estimated at 2.5 hours, but I had meetings all afternoon and couldn't stay on hold. Claimyr actually worked exactly as advertised. I entered the H&R Block support number, set it up, and went about my day. About 1 hour and 45 minutes later (faster than the estimate!), I got the call connecting me directly to an H&R Block rep who fixed my issue in minutes. What I appreciated most was being able to see my position in the queue through their tracker. It was refreshing not having to listen to "your call is very important to us" for the millionth time. For time-sensitive tax issues, it's absolutely worth it. Considering how precious time is during tax season, I'm now a convert.

Another option to consider is that H&R Block does have an online version that works on any platform with a web browser. If you're comfortable using their web version instead of the desktop software, that would solve your cross-platform issue. I switched from their desktop to online version last year and found it pretty similar in terms of features. The biggest difference is that you need internet access while working on your taxes, and your data is stored on their servers.

Just a heads up from someone who works in software retail - the reason H&R Block limits downloads to one platform is purely a licensing/revenue issue. They want people with multiple computers on different platforms to pay twice. It's the same reason Adobe used to charge separately for Mac/Windows before they went subscription-based. You might want to consider TurboTax instead if cross-platform is important. I believe they allow you to download both Mac and Windows versions with a single purchase, though their software is generally more expensive than H&R Block. Another option is TaxSlayer which lets you install on multiple computers regardless of OS.

I actually ran into this same issue a few years ago and found a pretty simple solution that might work for you. Since you mentioned you're comfortable with dual-booting and using different operating systems, you could purchase the H&R Block software for whichever platform you use most frequently, then use a virtual machine to run the other version if needed. For example, if you buy the Windows version, you can run it natively when you boot into Windows on your main machine, and also run it in a Windows VM on your girlfriend's MacBook using something like Parallels or VMware Fusion. The performance is totally fine for tax software since it's not resource-intensive. This approach gives you the flexibility you want without having to deal with H&R Block's customer service or pay for multiple licenses. Plus, you'll have the exact same version and data files across both setups, which makes things consistent. I've been doing this for three years now and it works great - just make sure to keep your tax files synced between the systems using a cloud service or USB drive.