Ask Paul: April 3 ⭐️

Happy Friday! Let’s kick off the weekend a bit early with some great reader questions regarding angst around Apple’s 50th, Windows 11 passkeys, trillion-dollar mistakes, switching online accounts, and more.

Also, semi-randomly, I’ve been sending photos of dangling wires in Mexico City to Stephen Rose for the past few weeks, so I’ve included a few here.

? Getting past Apple’s 50th

christianwilson asks:

Have you read, are reading, or plan to read David Pogue’s Apple: The First 50 Years book? I’m not through it all yet but already found some details I did not know.

No, but I will, begrudgingly, as David Pogue is a horrible human being. Every time I see this guy, I cringe. He’s been on an interview tour in recent months, and he did a bit on CBS This Morning (or whatever, who cares) in which he repeated two lies to Tim Cook’s face that went unchallenged because they were so pro-Apple. Maybe unchallenged is the right word, Cook simply smiled and nodded along. It was like watching a modern day Hitler and Goebbels dancing on the grave of truth.

Long story short, David Pogue isn’t just a liar, he’s a monster. The less said about this individual the better.

“Microsoft is working on a bunch of useful upgrades for Teams”

What the f#$k is “a bunch”?

?️ Not the passkey you’re looking for

Christian Gaeng asks:

Hi Paul, I have a question about passkeys in Windows 11. I’ve noticed a few times that the passkey doesn’t work correctly, for example, when I use my fingerprint on my laptop and my PIN code on another PC. Have you experienced this as well, and is there a solution?

I don’t know what you mean, sorry.

For those unfamiliar with how the built-in passkey support in Windows 11 works, Microsoft now uses what it calls a device-bound passkey to handle the authentication of online accounts (Microsoft account or Entra ID). So when you sign in with that type of account, Windows creates a device-bound passkey–it will be the top passkey in Settings > Accounts > Passkeys–that’s then used for passthrough authentication to Store, OneDrive, Edge, and whatever else. When you use Windows Hello, via PIN, fingerprint, or facial recognition, to prove your identity, it’s using that passkey in the background. I first wrote about this a few years back in The Secret Lives of Passkeys (Premium). The UI has changed a little and there have been some functional additions since then, but the fundamentals are the same.

But the reason I’m not sure what to say here is that the passkey is just the mechanism that Windows uses to store the proof of your identity, so to speak. (The passkey is actually stored in the PC’s TPM encrypted storage, but whatever.) Windows has had this capability for over a decade, pre-passkey. So I feel like the issue here is really Windows Hello, which can fail abruptly, as anyone who uses it can tell you. (“Try another finger” is one of my favorite Windows error messages.) And it’s gotten a bit more tedious to use with the big Windows Hello user experience update we got late last year.

So …

What does it say when it fails? Why do you think this is passkey-related? And have you ever had to reauthenticate your sign-in account in Windows, from the lock/sign-in screen with the underlying service (MSA/Entra)?

“A popular Linux distro now has higher system hardware requirements than Windows 11”

If only you could tell us which one it was

＄Microsoft’s trillion-dollar mistake

ianceicys asks:

Axel Rietschin’s piece on how Microsoft ‘vaporized a trillion dollars’ through Azure mismanagement is a wild read.

Yes. It’s worth reading, though I’m curious about a few details and wonder why he just doesn’t name names in some cases since what he does reveal–job titles and responsibilities, etc.—will help the truly curious find out anyway. But we don’t get this kind of inside look at Microsoft anymore, so this is fascinating on many levels. (Among the tidbits is how Satya Nadella eliminated a role, which laid off many testers, triggering the not-quite-correct rumor about how there were no longer people at the company testing things because it was relying solely on telemetry.)

And to be clear, the premise of this series is that Microsoft has lost a trillion dollars in market capitalization through mistakes it’s made in the AI era. But it also had to earn that value first, so it had a trillion to lose. And with all things market cap related, this is more about marketing and Wall Street speculation than it is about product quality, actual revenues, or any other real-world metrics. Some low-level mistake in Azure didn’t lead to Microsoft “losing” one trillion dollars. If that makes sense.

It got me thinking: if Paul were putting together a short list of other trillion-dollar-class fumbles in Microsoft’s history — moments where they had a category in their hands and let it go — what would make your list? A few candidates I’d throw out:

• Nokia

• MSN

• YouTube (MSN Spaces)

• Zune / PlaysForSure (burned every Entertainment partner on the way out)

• Danger / Sidekick / Windows Phone

Are there are any you think are underrated or forgotten”.”

Given that the notion of a trillion dollars is tied to market value and thus to the impression that this company is somehow killing it, there are two that come to mind.

The first is Nokia/Windows Phone, which I think we can lump into a single overall effort. This comes closest because of the potential size of that market had Microsoft ever somehow established this platform as a third option or, better yet, replaced Android.

The only other fumble of this magnitude, and this one wasn’t as obvious at the time, was getting beat out by Google when it tried to acquire DoubleClick. That went on to be the foundation for Google’s fortunes–today, ads represent about 70 percent of Google’s revenues every quarter–and could have been one of Microsoft’s biggest businesses had it somehow had the same level of success with it. To be fair, that was never going to happen, but allowing a competitor to essentially beat it, revenue- and profit-wise, pretty much every quarter is a loss no matter how you look at it. (That an antitrust case might result in Google losing that business speaks to its size and importance, and to the lost opportunity for Microsoft.)

That Google somehow came away with both halves of that is interesting: It has Android, which divides the mobile market with Apple, and it dominates in online advertising. These are two businesses Microsoft could have had.

But if you want to speak to this more generally, you could make the argument that Microsoft’s evolution over time to focus largely on the biggest businesses only, essentially ceding the consumer market to companies like Apple, Amazon, and Google, might qualify as a trillion-dollar “mistake.” Those companies are worth trillions, and even a relatively small share for Microsoft here would be too.

That said, there are so many caveats. And I don’t see how a company like Microsoft, personal computing’s Oldsmobile, would ever be seen as cool or a leader in that space anyway. There’s really no version of history where Microsoft out-Apples Apple, so to speak. And it’s as easy to argue that staying true to itself has worked out fine for Microsoft. It may be less interesting to us, as individuals, but it’s super-successful financially. (Staying true to itself is basically what Apple has done too, but with consumers, not businesses.)

If you look at how Microsoft (and OpenAI, interestingly) is shifting its focus within AI to be largely based on the biggest businesses–again, staying true to itself, in Microsoft’s case–you can at least say that makes sense. As if anything AI-related in Big Tech makes sense right now.

“People are furious that Microsoft is killing off Publisher”

“People”

1️⃣ April Fools

ianceicys asks:

Did you catch Richard Campbell’s 7-min RunAs Radio episode this week? The gear list is plausible for Richard and genuinely required me a second long. Classic.

Well, we chatted about it, so I knew it was coming, and he had sent me some excerpts. I think he wanted me to have a similar thing for April 1 for Windows Weekly, which was on that day. But I couldn’t really come up with anything. Briefly, I was thinking I would announce that I was switching to the Mac. But that came off more sad and believable than funny. Maybe that was the point. 🙂

“iPhone 18 Pro smaller Dynamic Island claims are from unknown sources”

Notably, that didn’t stop you from writing about them

?️ Switcher

doon asks:

After several years, and some recent concerns about security, I’m considering a move off of Gmail. And I’m looking for the best “secure” (what’s that these days?) solution that I can find. I’m willing to sign up for a paid service but want to avoid having to do this again anytime soon. Everything I’ve read points me to Proton but I’m not certain about the UI or what the pain points will be in switching. I’d appreciate knowing what you use, and what you think.

I can’t speak to this too much yet, but I literally started looking at switching to Proton more fully myself this week after it announced Proton Workspace and Proton Meet. There is a lot to this, and I am almost certainly not clear on all the blockers as I write this. But let me tell you what I’ve done so far, what I plan to do soon, and some of the things I’m looking at.

Background: When I started Thurrott.com with George, the owner of BWW Media, back in late 2016/early 2017, that company was on a Google Workspace infrastructure. I had been using the Thurrott.com domain for the previous couple of decades by then and it had moved between different hosters/providers over time as I tested each, but I was coincidentally also on Google Workspace at that time. So that worked out.

And to be fair to Google, it’s mostly been fine. Gmail, Google Calendar, etc. are all better than anything on the Microsoft side, etc. The one exception, and it was a big one, was the issue I had in early 2025 when YouTube suddenly cut off our access to the Thurrott.com channel. This wasn’t a Workspace issue per se, but it’s part of the whole ecosystem and it triggered a rethink about my online accounts that continues to this day. In fact, it’s top of mind.

Anyway.

Switching this kind of this is difficult, and that’s especially true for an account–whether you’re an individual or a business–that is tied to identity. And this may be complicated by the prevalence of signing into other services using your Google account. When I looked at that in early 2025, I was signing in to about 80 third-party services using the Google infrastructure and it wasn’t clear at first what might happen if that changed. That is, could I move Thurrott.com to another provider and still access those services? What I found was that it should work. But that’s something I would want to look at before switching for real.

In your case, assuming you’re doing this as an individual, you could simply keep the Gmail address, switch to a new service (Proton perhaps), and then just forward your email from Google. You could still sign in to whatever services using Gmail and the “Sign in with Google” infrastructure, or you could go to the trouble of trying to move those services over to the new email address. If you’re using a custom domain with Google, you may want to see what that looks like too (as I’m doing, I mean).

I’ve had a Proton Unlimited subscription for the past year or so. I use Proton Pass (for password and passkey management) and Proton Authenticator (2FA) literally every single day. Here in Mexico, I use Proton VPN every day with my iPad and occasionally on the Apple TV and whatever laptop as needed. But I don’t really use Proton Mail, Proton Calendar, or any of the other services.

Then, two things happened this past week: The Proton announcement and my monthly invoice from Google for Workspace. And these things triggered some new thinking on this potential switch. For Proton, I added the thurrott.org domain so I could really test the service, and I will begin forwarding my email (which all routes through Google Workspace and Thurrott.com now) through that soon. For Google, I need to rethink how many accounts we have in part because of the cost and the fact that much of that could be handled with aliases. And then I need to compare the cost of Google Workspace, now and in some imagined future where maybe there are fewer accounts, with that of Proton Workspace.

I need to see about moving off Sign in with Google. I need to make sure that switching won’t screw things up on some back-end service(s) that we use that I am or possibly am not even aware of. I need to think about other switching “costs” like what happens when I am suddenly using a new service and all these accounts I blocked or spam filters I had in Google Workspace no longer exist. There are many unknowns, I guess. This is why switching can feel daunting enough that many just give up.

But I am going to try. I will definitely be writing about this as it happens, and whether I succeed or not. It’s worth cleaning up the Workspace stuff at the least, and if switching does make sense, I will make it happen. But I feel like I will run into issues here and there … and we’ll see.

I do think this is worth pursuing as an individual, and that Proton is the right choice, even if you just care about the email bit. I would be careful about biting your nose to spite your face, so to speak, in that if this isn’t the center of your life, it may not matter all that much. But there are good reasons to make the switch, just as there are very real questions about the difficulty of doing so and concerns about issues that will only become obvious after the fact. The first step for anyone going this route, I guess, is to just try it for free with a Proton account and see how it goes. If there are real blockers, they will become obvious pretty quickly, and then you’re just where you started. There are worse outcomes.

I will write about this more formally soon, I think.

“Artemis II crew is just like us, needs help with Microsoft Outlook issues”

They wouldn’t have this problem with Google Workspace!