
Happy Friday! We can enjoy a predictably AI-centric installment of Ask Paul before kicking off the weekend a bit early.
ianceicys asks:
Hey Paul – curious to get your take on something I didn’t expect this holiday season.
This year, over a dozen Christmas cards we got from friends and family included handwritten notes like “AI wasn’t used in these photos” or an actual handwritten note saying : “this was NOT written by AI!”
The most surprising thing so far is that you already have over a dozen Christmas cards. 🙂 We tape the Christmas cards we get on a door each year, and for a long time, we got so many that they would overflow to a wall. But in recent years, it’s gone down a lot, and I’ve heard from several friends and family members that they’re not even bothering to send cards anymore.
This isn’t the question, I know, but there is a fine line on these things between reaching out and bragging, sort of like a one-time social media-type experience, that I always worry about. But I made our card last weekend (using Paint with some Affinity) and I don’t see stopping. My usual complaint is that many people just send pictures of their kids (or, God help me, a pet) and it’s always like, guys, you need to be in there, too. The people I actually know, not just the kids I maybe never met or the dog I absolutely do not care about.

Anyway, that’s a natural evolution, of course. We went from handwritten notes to a card with a signature to cards with no writing to no cards. I guess it makes sense. We can keep up with others so much more easily these days.
Sorry for the side track there. :/
The younger Gen Z relatives are the ones handwriting “not from AI” on their cards, almost like a badge of authenticity.
So I see that as a byproduct of a generation thing where these younger people are for whatever reason embracing old technology like record players, faux film or instant cameras, and so, at least to some degree. I jokingly refer to this as being a hipster, with the definition of that term being “one who is nostalgic for a time they did not experience.” This is the plot of the movie Midnight in Paris and probably countless other books and movies, when you think about it.
And to be fair, this is nice in some ways. One of my observations about younger people, to overgeneralize, is that because they grew up in a world in which there are literally a million different ways to get news, consumer TV shows and movies, and so on, they have fewer connective experiences. When I was young, we all had three or four main TV channels on VHF and even fewer on UHF, and so the next day at work or school we would all discuss the same thing. Likewise, growing up as a fan of music, I listened to music from previous eras, back to the 1950s, and not just that from my own era. My kids and other younger people don’t seem to do that, and I feel like they’re missing something.
So in this case, you might argue that in handwriting (or otherwise creating) a Christmas card, they’re harkening back to an earlier era and providing a more personal touch than the single letter, acronym, or slang-based text messages that are more common for that generation. And that I do like. Not everyone will do it, but it shows some humanity.
At church Sunday, our pastor joked about using AI for his sermon and 1,200 people instantly and loudly booed. He laughed it off and his message was about being hopeful, but it was a real moment of collective recoil by a sizeable crowd.
I’m in my 40s, and even in my guy friend groups, my friends keep moving from text threads to weekly FaceTime calls.
Apparently, not having misspellings and “sounding too polished” in chats has proven out multiple AI generated text messages.
So, here’s my question: How are you reading this cultural moment? AI isn’t going away, but people seem intent on signaling “this is human made.”
I’m of two minds on all this.
On the one hand, it’s clear that AI is being pushed so aggressively and so incessantly that there is a real negative vibe around it, a pushback against what is essentially a marketing term that seems to be used to describe almost everything these days. We sort of forget this, but in the calmer (from an AI perspective) years of 10 or 15 years ago, Microsoft would talk up AI to the point where they were retroactively claiming that even the first spell checking features they had were early AI, which they were not, and it felt fake and forced. But that was just in a subset of the tech space. Today, it’s in our faces all the time, and it’s too much.
On the other hand, the fears about AI, especially around job loss, are so out of control and detached from reality that I’m starting to just recoil against all the knee-jerk anti-AI stuff. That’s why I wrote When AI Works the other day, and I think that’s going to turn into an ongoing series with some very specific deep dives. And this has come up on Windows Weekly (and elsewhere) a lot, too. I made the point a week or two ago that if we just described or thought about these AI features as “technology,” there wouldn’t be a visceral, negative reaction.
AI is not about curing cancer. It’s just a wide and broad set of advances to the tools and workflows we use, and, yes, it’s happening very quickly and in real time, but it’s also no different from other technology shifts over the years. When we started laying down cross-continental train tracks, people were worried about jobs and about how the world was getting smaller. And then planes. And then jets. And then on and on we go.
There is maybe an irony to the fact that we are finally becoming broadly aware of the problems of a handful of companies that are now exponentially richer and more powerful than any companies have ever been, all run by evil and selfish billionaires trying to buy elections and push their way around the regulations that should/would otherwise constrain their bad behaviors. But it doesn’t help with the marketing. Every time someone complains about anyone specific (Elon Musk, for example), or a particularly bad company (Meta), I think, yeah, wait until you see all the other villains out there. These are not isolated cases. The saddest thing about what’s happening right now is that the most likely outcome is that the five most powerful Big Tech companies will still be the five most powerful Big Tech companies when the dust on this era finally settles.
Is this just growing pains, or a lasting shift in how we value authenticity? Do you think we will see content with something along the lines of an “Organic” label?
Both are true.
This is definitely just growing pains. But we live in a world in which everything is broadcast instantaneously to the entire planet and so the perceived reaction is perhaps over-amplified compared to the past. There is no doubt that human-made goods of whatever kind will be more “valuable” in the sense that they will be, by nature, more expensive, just like building computer chips in the U.S. is, by nature, more expensive than doing so in China or now Vietnam or wherever the next place is. But the question is whether they will always be “better.” Sometimes yes, sometimes no, but AI-created or enhanced content or goods will catch up, whether it’s music, writing, videos, or whatever else.
We will definitely look back on this and wonder what the fuss was all about. And then some future generation will wonder why anyone would push back against anything that made their lives better, through saving time, saving money, saving both, or just generally taking away some drudgery. It will seem quaint. But we’re living it, and transitions are difficult for some, especially if their livelihood or self-worth is tied up in some expertise that just became obsolete.
I saw a funny meme-thing on some social network that basically said, if you’re wondering why my generation is so angry all the time, it’s because we replaced our album collections with cassette tape collections and the CD collections and then digital music downloads, and now we all pay Spotify $20 a month to stream the same music. So, yes, absolutely. But each of those was also a net improvement in some way over the previous way we did things, and that’s true even when there are very specific cases where that wasn’t true (CDs skipped where cassettes did not), was supposedly not true (albums sound “warmer” than cassettes or CDs), or is at least questionable (we will never stop paying Spotify if we want to keep listening).
This is a big topic. But if you look at When AI Works again, or think about some of the probably many things I left out of that (like photography), there is no way to deny the net benefit occurring right now. There will be steps forward and some steps back. Mistakes. Big problems, even. But we are moving forward. And whether we’re OK with it or not, it’s happening, and really is better overall. Already, even right now.
People fear change. This is may be the most human thing of all.
MRCashins asks:
Have you heard from anyone at Microsoft about your criticism of the enshittification of Windows? Have you heard any plans to correct any of the issues you have identified?
Yes and no. I would split this into three groups. There is the current Windows team, which I have not heard from on this specific topic. There are other current employees at Microsoft, and I have absolutely heard from several of them in the past year. And then there are former Microsoft employees, of whom I know many. And that is a constant ongoing set of discussions that depresses just about everyone involved.
I can’t really name names here, but there are a couple of general points worth considering.
The Windows team today has inherited a mess, and it’s a mess that requires them to conform to some broader strategy that the company’s leadership sees as key to its ongoing success and growth. A lot of the mess that we see today is tied to Windows not fitting in with Satya Nadella’s cloud computing-centric Microsoft, it’s why we have constant upsells on subscription services, bundled crapware, Windows as a Service (WaaS), telemetry, and whatever else. It was/is a tough fit. The good news, and bear with me on this one, is that this new AI push puts Windows back under the spotlight. It’s a much better fit.
Given the discussion in the previous question, and the silliness of the video someone posted to the forums today, there is obvious pushback to AI, but also specifically AI in Windows. But I think it’s important to think clearly here. There is literal enshittification, there are things we might not like, and there is Microsoft strategy that triggers either or both of those. But there are also net wins to be had there, and that’s something I can’t say that we saw during the cloud era.
Off the top of my head: The writing help in Notepad. Several of the new capabilities in Paint. The improvements to the Snipping Tool. Click to Do. And so on. Each of these probably triggers some angst in certain bubbles, but these are all good, and when I look at Microsoft’s plans for making Windows 11 more agentic, I don’t see what all the haters were ranting about (which is the subject yet again of the video linked to in the forums). At all. I just see change-averse fear and small minded personal attacks. We need to be better than that.
In the post In Defense of Requiring a Windows 11 Online Account Sign-In, I made the case that Microsoft will do certain things to Windows that we as power users don’t like, but that’s it’s OK, there’s a sort of silent contract, if you will, as long as we can opt out of that stuff or just disable it. Sometimes that capability is right in the UI. Sometimes you can use a workaround. And sometimes you need a more nuclear option. That’s not ideal, of course. But it’s there.
Consider Notepad as a typical example of people getting their panties in a bunch over nothing.
I use this app all day every day and I love the updates Microsoft made. Unlike File Explorer, it looks great and runs great. And it’s gotten really powerful in useful ways without subverting its simplicity. Do I agree with every design/feature change? No. For example, I configure Notepad to open new files in a new window, not in a tab. And I configure it to start fresh when it starts up and not save the previous document state. But that’s just me. Other than the tab-based UI, you can literally disable every single change that Microsoft has made to Notepad in Windows 11. (And even then, you can use it in a one document per window mode, as I do.) That’s good. It’s right that we have those choices.
But people complain. And then others ride that unjustified anger by sensationalizing it, as Dave Plummer did in his ridiculous video Microsoft “Improved” Notepad. I Un-Improved It. As I pointed out in WinUIpad: Two Steps Forward, Two Steps Sideways, anyone pining for the classic, Win32 version of Notepad for some reason can literally re-enable it in Windows 11 right now, with just a few clicks. But consider the irony (hypocrisy?) in Plummer using AI to “fix” a “problem” with Notepad that most critics would describe as being an AI problem. Hilarious. What are we cheering about exactly?
Regarding the state of Windows 11 and my discussions with former Microsoft employees and executives, one of them pinged me ahead of Ignite because they would be there for the first time in several years and they wanted to get together. I didn’t go to Ignite, but this kicked off a days-long text message thread in which we reminisced a bit and discussed what was wrong there today. He told me that in his era, Windows was viewed as the evil part of Windows and was resented everywhere else in the company. But today, Windows is 100x worse and no one even seems to care about the product or that team within the company. Things have changed so much.
The last time I had the ear of Windows leadership was the Terry Myerson era, and so there are mixed feelings there, given that the issues we associate with Windows today mostly started (or perhaps escalated, in some cases) then. He was a good guy, but he made some mistakes, and he was forced down a path by Nadella that was not good for Windows. Windows was then rudderless for a few years, with no representation in the Senior Leadership Team. And the next guy was a buffoon who didn’t warrant the responsibilities he was given. So I look at Pavan Davuluri today and I like what I see. A good person. A technical person. He seems to want to do the right thing with Windows. And so we will see. But it’s better now, in many ways, than it’s been in a long, long time. Even with all the concerns, whether anyone thinks they’re real or imagined.
Put another way, I felt like I cared more about Windows than its leadership for several years there. And I don’t feel that way anymore. I don’t agree with everything, of course. That’s why I write about all the ways one can fix or workaround the bad behaviors. But there is a better vibe right now than there’s been since the Windows 10 introduction. I wish others could see this.
JHeredia asks:
Hi Paul, given the recent Gartner report about avoiding Agentic AI Browsers at all costs, I was wondering what your browser of choice is these days? I’ve been trying Comet, as I know you were, but I do find I don’t use the agentic capabilities much at all and I am concerned about privacy in general.
I like the look of Edge and the fact it’s the “default” (whether I want it to be or not most of the time). I’ve used Brave extensively, tried Opera, but I’m not landing on anything, so I was wondering if you had.
Brave is always my first choice. It’s safer, more private, and faster than any other web browser, and that’s pretty much true everywhere (desktop/mobile).
That said, I have to test other browsers continuously so I move in and out of various browsers constantly. And thanks to all this AI and agentic stuff happening now, it’s a quickly changing space all of a sudden.
I really like Opera Air. That might be a close second, and this is a curious thing, more subjective than objective. I can’t explain why the look and feel speak to me, but it does.
On the iPhone and iPad (and Mac, though I use that a lot less often), I’ve started using a browser I only recently found out about called Orion. This is made by Kagi, the company that makes the paid Google Search alternative of the same name. And I have to say, I kind of love it. There are plans for Windows and Linux versions, but nothing yet. (And, yes, I’ve been using Kagi a lot lately but I need more time before I have an educated opinion.)
Regarding agentic browsers and the above discussions about AI, I do feel like I should clarify something. This is one of the “not mutually exclusive” things. That is, there’s no doubt that AI capabilities are useful today in browsers, especially things like article, document, and video summaries. But there’s also no doubt that we do not yet understand the risks of integrated agentic capabilities, and I agree with Gartner’s assessment that until (if?) we do and have measures to protect ourselves, they are a security risk today. And so I have to sort of continue testing these things, of course (I just installed Open AI’s ChatGPT Atlas on the Mac, for example). But I won’t give one of these things my credit card numbers or whatever else, not now at least. We’ll see how that develops.
But I do think that Opera Neon and Perplexity Comet are the most interesting and functionally complete agentic browsers if you’re living on that edge, and I suspect that ChatGPT Atlas is right in the mix now too. Microsoft Edge, curiously, is more aggressive with the agentic capabilities right now than, say, Chrome, though that should change in time. But it’s not quite where Neon and Comet are.
The thing about Brave that may be curiously off-putting is that it’s kind of boring. It looks boring, and there’s no real UI innovation going on there. But in a literal “it just works” sense, it’s the best. Not just functionally/compatibility-wise but in the way it protects you from the terribleness online out of the box. You have to do some work to get anywhere close to that with other browsers. And many of them (Edge, for example) are busier looking, which is of course subjective.
helix2301 asks:
You talk about services and shows you watch. I know you have a NAS. Have you ever had interest in hosting your own Plex server on one of those? I know people like Andy Inocko do just wondering your thoughts. Leo talks about the issues of not owning your media all the time. Just curious about your thoughts?
When I got the first Synology NAS this past summer, my primary goal was to figure out whether this would be a file storage/access backup for some cloud service (Google Drive, OneDrive, etc.) or whether it could replace one of those. I was happy to discover that it worked wonderfully well in that second configuration and off we go. But Plex (or Jellyfin) was a secondary question, and I did spend a bit of time trying to make that work, unsuccessfully. It’s surprisingly difficult, at least to me.
I do have a close friend with a Plex server and so I actually watch (his) content on Plex pretty regularly. But for my own content, what I have amounts to a static backup of my music collection, now out of date, my photos, which are in other places as well, and a video collection consisting of DVDs of movies and TV shows I ripped decades ago and some other random videos (purchased MST3K/Rifftrax videos, etc.). And I don’t really want or need to watch that all that often. I ended up putting the Infuse app on my Apple TVs: This is a surprisingly good front end to this video collection (both in PA and in Mexico), and it negated any desire to continue struggling with Plex. Which was a sort of secondary (tertiary?) use case anyway.
So I guess I won’t be doing that.
helix2301 asks:
Will you be on year-end Twit this year?
I guess not, in that no one has asked and I assume they’ve already lined that up by now. But Richard and I recorded a special end of year episode of Windows Weekly with Leo that is kind of fun, and different from past years when Leo would host a clip show. I won’t ruin it per se, but we did a nice holiday set thing and I think/hope it came out nicely.
Any good stories from you and Richard hanging out?
Richard, like Mary Jo, is one of those people you meet and then it becomes obvious over time that they’re bucking the normal trend with people in that they don’t get worse over time, they get better. The year before the pandemic, my wife and I flew to Vancouver ahead of Build and then drove up to Richard’s lake house for a long weekend with him and his wife Stacy. And then Steph flew home and Richard and I drove down to Seattle for the conference. We figured this would become an annual tradition, but … the pandemic did happen and that was that.

Before that, however, Richard stayed with us at the house in Pennsylvania the week heading into the lockdown. Our kids were in Jamaica at the time, part of a church group that was helping out a school for the deaf there, and we did the whole local thing, various restaurants and bars, and so on. And he barely made it home. During that trip, a conference he was helping run/organize was getting scaled back and then canceled because of the looming lockdown, and then he had to leave at 3 am on the final day to get one of the last flights out. Our kids flew home that same day and we weren’t sure they were going to get home, either, but that worked out as well.
And then years went by. Since then, he joined Windows Weekly, of course, which was a wonderful surprise. And we get to talk a lot more often in addition to our normal ongoing text messages. Last year, we flew to see Richard and Stacy in Puerto Vallarta at the start of our four months in Mexico. And this coming January, we will do the same, but in Acapulco, and then they’re coming to our place in Mexico City for a long weekend after. So that annual tradition is finally happening. (We also saw them on the TWiT Alaska cruise in mid-2022.)
This past week, Richard was in Lithuania and him and Carl were asked if they could do a live .NET Rocks recording to commemorate the retirement of Bill Wolff, who had led the philly.NET user group. I had spoken there at least once since I moved here, and had been to the Microsoft Technology Center near Philadelphia where they have their meetings at least a few other times. And so Richard asked me if we’d be home at that time, which we were, so he flew in last Saturday, we hung out through Wednesday, and then that day, we drove down to Philly and recorded Windows Weekly there. And then I watched the .NET Rocks event and we all went out to dinner afterward. It was a late night, but of the good kind.


This past week and those other times we’ve gotten together, along with the sporadic live Build and Ignite events I’ve attended in the past few years were all solid reminders of how important in-person meetings/get-togethers are. I used to travel for work far too much before the pandemic, but that’s eased up since, and it feels more balanced and manageable now. Richard, like Mary Jo, is one of those people I’m always happy to see and spend time with. It was pretty great, and then we’ll see and Stacy again in about three weeks, in Mexico.
Most of what we did while he was in Pennsylvania was about going out and eating and drinking, but he was able to meet some friends and people we know there and I think it was a nice introduction to the community we’ve become part of. It worked out really well.

If you remember the From the Editor’s Desk: One Story post, my one Richard story, so to speak, was an early hint at what I’ve come to know much more clearly since then, which is that he is one of the most thoughtful people I’ve ever met. We were all in Orlando one year for whatever TechEd/Ignite show years ago, and he had emailed me ahead of the show to see whether we could get together at all. I was really busy that week, and I always tried to get out of that place as quickly as possible, and so I recommended that we get together at a meet-up that Mary Jo had (as always) arranged.
But the night of the meet-up, I was surrounded by show attendees and kind of stuck, and of course, I didn’t want to snub anyone. And so Richard would walk by, see that I was surrounded, and then go off and talk to whoever else. Within an hour, I was backed up against a wall and it was clear we were never really going to have time to chat privately. But he walked up with a drink, stuck it in my hand, said, “You look like you need this,” and then walked away so I could continue talking with the group of people around me.
I apologized to him later, but he understood, and I was always impressed that he thought about my needs instead of being upset or whatever. And as he describes it, I was “holding up a wall” and surrounded by other people. He’s just incredibly nice like that. I just love the guy.
train_wreck asks:
What do you think of the ugly Christmas Microsoft sweaters? ?
Honestly, they’re not as bad as usual, and some of them, in particular the brown Zune sweater and the artifact sweater, are actually things I’d consider getting if that were somehow still possible and/or they weren’t so expensive.
It’s amusing to me, in a way, that these are such a hit with people. But it is perhaps sobering to realize that all of these things are essentially nostalgia pieces for things that weren’t all that popular when they were current. There’s probably little that Microsoft does now that will ever trigger that emotion in the future.
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