Hate taxes? H&R Block’s new AI chatbot aims to reduce your tax frustrations

Like a spoonful of mustard or mayonnaise — or perhaps you prefer sriracha? — it seems no software recipe is complete these days without a dollop of generative AI. The groundbreaking technology plays games better than you, writes songs for you … heck, it can even be your girlfriend (to each their own). And now it can help you with life’s most vexing challenge: taxes.

In mid-December, H&R Block quietly announced AI Tax Assist, a generative AI tool powered by Microsoft’s Azure OpenAI Service. The new offering leverages the tax giant’s decades of experience in tax prep and leans on its stable of more than 60,000 tax pros to answer your thorniest questions about U.S. and state tax laws: Can I deduct this new laptop? Is this a personal expense or a business one? How many roads must a man walk down, before travel is officially part of his job?

We see AI as one of the defining technologies of our time.

Sarah Bird, Responsible AI, Microsoft

In a press preview on Thursday, January 25, in New York City, H&R Block announced another new tool designed to simplify importing last year’s tax returns from the competition. And it offered TechRadar the opportunity to try out the new AI assistant software and talk about the future of tax prep.

“We see AI as one of the defining technologies of our time … but only if we do it responsibility,” explained Sarah Bird, who serves as global lead for responsible AI at Microsoft. (Bird was virtual at the event, a result of possible exposure to Covid.) Microsoft’s Azure OpenAI Service lets developers easily build generative AI experiences, using a set of prebuilt and curated models from OpenAI, Meta and beyond. Her team helps companies like H&R Block ensure that their tools use the highest quality training data, guide you with clever prompts, and so on. “It’s really a best practices implementation in terms of responsible AI,” she said.

H&R Block notes that the tech will not file or even fill out your forms; it merely answers questions. But if you’re hesitant to even ask AI for tax advice, you have good reason. The tech is notorious for hallucinations, where it simply invents the answers to questions if it can’t find the right answer. Some experts worry that problem may never be solved. “This isn’t fixable,” Emily Bender, a linguistics professor at UW's Computational Linguistics Laboratory, told the Associated Press last fall. “It’s inherent in the mismatch between the technology and the proposed use cases.”

One answer to the problem is starting with the right training data. If the AI has reliable, trustworthy sources of data to pore through, it can find the right answer, saving you from hunting through the Kafka-esque bowels of the IRS to find the instruction form for Schedule B or whatever. And off-the-shelf large language models (LLMs) simply don’t have that data, explained Aditya Thadani, VP of Artificial Intelligence Platforms for H&R Block. Ask ChatGPT 4 a question, he noted, and you risk missing out on what’s new: The cut-off date for that LLM's data sources is April of 2023.

“The IRS has released a number of changes since then,” he told attendees at the H&R Block event. “They’re making changes well into December and January, well into the tax season. We’re making sure you get all that information.”

To try out the new system, TechRadar sat down with some sample data and asked a few test prompts: Am I missing any deductions? Can I deduct a car as a business expense? And so on. The chatbot offered reasonable prompts: A few paragraphs of information culled from H&R Block’s deep catalog of data, links to find more information, and so on. The company says it can answer tax theory questions, clarify tax terms, and give guidance on specific tax rules. And crucial to the entire experience: Live, human beings — CPAs even! — are always just a click away.

“When we are not absolutely sure? Don’t guess. Give a response that we are actually confident in,” Thadani said. And if you don’t get the response you are looking for from the AI, you can get it from the tax pro.”

Privacy matters: Who will see your data?

It’s hard to discuss any emerging technology without touching on privacy, and both Microsoft and H&R Block are very aware of the risks. After all, a person’s tax returns are highly personal and confidential – one reason they became such a hot-button in the US presidential elections. Should a company be allowed to train an LLM on your data?

“We’re sitting on a lot of really personal, private information,” Thadani admitted. “As much as we want to use that to answer questions effectively, we have to continue to find the balance.” So the assistant won’t remember you. It won’t ingest your tax forms to answer the questions you pose. And by design, other people won’t benefit from your questions down the road.

The new software also taps into one of the quirks of our modern software assistants. We don’t necessarily talk to them like adults. We’ve been trained to ask Alexa or the Google Assistant halting half-words and phrases. Meanwhile, chatbots can converse in natural language. H&R Block’s tool works fine in either space, Bird explained.

“It’s incredibly enabling because it allows people to speak in words they’re comfortable with,” she said. There’s the real power of technology in a nutshell: “Make a complex thing more accessible to people because the technology meets them where they’re at.”

Now if it could only help us deduct a few holiday pounds from the waistline.

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I’ve had enough of password frustrations – here’s how I’m finally fixing them in 2024

Passwords are a pain, let’s be honest – a necessary evil to keep us secure. None of us wants to have to deal with these cumbersome little beasties, but they’re an inescapable part of online life. In the future, things will change – as a new passwordless reality comes to fruition and passkeys evolve. But for now, traditional typed passwords remain prevalent and in need of taming.

There are simple ways to deal with passwords, some of which are terrible. Like having ridiculously simple passwords that are easy to guess. Or ‘remembering’ them by writing them all down in a notepad, where a nosy person might find them and get access to your online accounts, if they’re a nefarious sort.

I don’t do anything like that, of course – perish the very thought – I use mnemonics to help make passwords complex enough, but still memorable, so they don’t have to be jotted down. However, even that’s not an ideal way of dealing with passwords, and so I have some (admittedly dull) new year’s resolutions to vastly improve my relationship with passwords and my overall online security.

A person using the ExpressVPN Keys password manager on their phone and their laptop.

(Image credit: ExpressVPN)

Taking the plunge with a password manager

This is the main pillar of my reformed relationship with passwords – yes, getting someone else to do them. Or rather, getting something else to do them in the form of an application.

Password manager software automatically generates passwords for all online accounts without me having to lift a finger. These are incredibly secure passwords, too – lengthy strings of garbage that I wouldn’t have a snowball’s chance in hell of remembering.

Taking the plunge with a password manager is something that’s been on my computing to-do list for quite some time, and one of those things I simply haven’t got around to doing. Mainly because it seems easier to carry on as I’ve been doing for a long, long time now (I owned a PC before the worldwide web even existed). So, 2024 is the year it’s going to happen, and I’ll relinquish my old system for a more convenient and secure way of dealing with passwords.

Which password manager am I going to run with? After weighing up the pros and cons of the various options out there, I narrowed it down to either Dashlane or NordPass – but in the end, the latter won out. Why? NordPass scored with its wide-ranging support across multiple platforms, regular updates – and plentiful features – not to mention that it represents a great value proposition.

It’s also the top-ranked product in our roundup of the best password managers, so comes with the TechRadar Pro seal of approval (and a deal to make it even better value, it should be noted). For those after the top freebie option, by the way, check out the best free password managers.

Hand increasing security protection level by turning a knob

(Image credit: Shutterstock)

2FA achievement complete

3 tips for avoiding the worst password pitfalls

1. Never, ever, use stupidly simple passwords
‘Password’ is not a good password, much like a riot shield is a bit pointless if it’s made out of tissue paper. Choose a complex password with a decent mix of characters, and a mnemonic to remember it (or better still, use a password manager).
2. Don’t reuse passwords
Never reuse the same password for multiple online accounts. It may seem tempting to do so for easy recall, but if a hacker or other ne’er-do-well gets hold of that password, obviously they could then access more than one of your services.
3. Don’t keep the same password forever
You don’t have to change any given password much, but it’s worth doing so every now and then. Especially if a company you have an account with has a data breach, it’s a good pre-emptive move just to change your password, even before you’ve been told if you’re affected.

Getting a password manager isn’t necessarily bulletproof, of course. What if that company or their systems are somehow breached in some manner? It’s very unlikely that this will happen with a reputable vendor, but it has happened in the past.

At any rate, a robust approach to security doesn’t rely on a single solution, and 2FA (two-factor authentication) is a seriously valuable addition as a second line of defense to back up passwords. This often takes the form of a code texted to your phone, or emailed, after your initial login to an account.

My problem in this department is that I don’t have 2FA enabled on all my online accounts yet. I do have it running on most important services, mind you, but I need to go through my array of various online accounts, check where it’s supported – in theory, on most big sites and services – and implement it, if 2FA isn’t already active.

Much like migrating over to a password manager, this is something I’ve been meaning to do for some time now – and it’s been nagging away at the back of my mind all that time as a task that really needs attending to. In most cases, it'll simply be a case of going into my account > settings > security (or a variation of that process), and turning on two-factor authentication. So, I shall get it done, and tick another niggle off my list of password blues for 2024.


(Image credit: Shutterstock)

Biometric bonus

While I’m fixing password security issues, my final resolution is to actually use biometrics wherever possible. Until fairly recently, I used a hardware token for logins to my online banking, but have since switched to use the fingerprint sensor on my phone (via the bank’s app). It’s a much more convenient and secure way of logging in, and wherever there’s an option to use a fingerprint login, I’ve resolved to switch to it.

Another point on this subject: while initially I wasn’t convinced about the tech, I now love the Windows Hello login on my Surface Pro tablet – it has got better over time, and works pretty much flawlessly now, even in different lighting conditions. 

I’d advise strongly in favor of using facial recognition, fingerprints, or other biometrics wherever you can turn them on, which is usually a case of exploring an app's settings for security options that can enable hardware like fingerprint sensors. None of this is exactly fun, but you'll go into 2024 feeling all the more secure and smug for it.

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Microsoft OneDrive will soon let you take out your frustrations on those hated files

There may soon be a way to cleanse your Microsoft OneDrive and SharePoint accounts of pesky large folders, freeing up much-needed storage space and decluttering your mind for good.

The company is working on a new update for its cloud storage service that will allow users to delete large folders on Microsoft OneDrive and SharePoint Document Libraries on web.

The move will cover folders holding up to 10,000 items, meaning it could be the solution your overcrowded account needs to make some room for new items.

Microsoft OneDrive purge

The official entry on the Microsoft 365 roadmap notes that the feature is still in development for now, but should have a general release in March 2022. It is listed as being available to all Web users of OneDrive and SharePoint around the world.

With hybrid working now a common experience for most businesses, cloud-based services such as OneDrive have become pivotal to making sure organizations stay connected, wherever they may be located.

Microsoft recently revealed an update for OneDrive that will embed the cloud storage service more deeply into its productivity ecosystem by working more closely with its online collaboration app Microsoft Teams.

The idea is to use this heightened level of interoperability to make it as inconvenient as possible to break away from the Microsoft ecosystem, even if a company or individual has adopted just a small selection of services.

The company also recently made it easier for remote workers to ensure that important tasks don’t slip through the cracks with another OneDrive update that provides a dedicated feed to highlight recent activity associated with their files.

However, concerns were raised in a separate area of Windows recently when Microsoft was forced to admit that its data wiping tool didn't always completely clean everything it needed to.

Although data collected by TechRadar Pro suggests Google Drive is currently the most popular cloud storage service by some margin, Microsoft will hope OneDrive improvements like these will help capture a larger portion of the business market.

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Microsoft Outlook update will address one of the most common office frustrations

Microsoft is readying an update for email service Outlook that will help ensure users don’t get caught without a space ahead of an important meeting.

As per two new entries in the Microsoft 365 product roadmap, users of Outlook for iOS and Android will soon benefit from the ability to browse and reserve meeting rooms on their work phones.

“Need to book a space? Outlook Mobile is here to make your transition to hybrid work easier. Search and book conference rooms when you need to collaborate with colleagues or book a workspace when you need some time to focus,” wrote Microsoft.

The new room finder feature is currently in development across both major mobile platforms, but should roll out to all users by the end of March.

Microsoft Outlook update

As many workers begin to return to the office, at least part-time, there are bound to be a range of issues that businesses will need to iron out.

A number of collaboration software vendors are talking about challenges to do with ensuring meetings remain equitable when participants are split between the home and office. Others are concerned about equipping workers with the tools they need to remain secure and productive, no matter their working environment.

With its latest update for Outlook, Microsoft is honing in on a more practical issue: room bookings. To date, Outlook users have been required to search for available meeting rooms using the desktop app or another alternative system implemented by their company.

Once the latest update takes effect, however, users will be given the freedom to manage room bookings on the go. This could be useful, say, if someone needs to make a last-minute booking while on the way to the office or out at lunch.

In recent months, Microsoft has announced a series of new hybrid working-related features for Outlook, including the ability to specify one’s working location on a day-by-day basis and color-coordinate the calendar to create clearer distinction between meetings.

The idea is that the new room finder feature will combine with these recent updates to improve the overall hybrid working experience for end users.

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