September 26, 2025
Helpful episodes to listen to first
Do I Need to Upgrade to Windows 11?
Episode summaryIf you’re wondering whether to upgrade to Windows 11, the answer is probably: yes - if your computer can handle it.
If you have an older PC, it might not meet the requirements. You can check by installing Microsoft’s PC Health Check App.
From a security perspective, there’s not a huge difference between Windows 10 and 11. But, if you decide to stick with Windows 10, please make sure you pay for security updates. I explain how and why that’s important in episode 79.
LinksThioJoe talks about Windows 11 upgrade
Leo video about Windows 11 upgrade
Leo article about Windows 11 upgrade
How to use the PC Health Check app
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:00):
Welcome to Super Simple Security Principles, where you learn how to think, not just what to do.
I'm Nick Jackson, here to learn along with you from my good buddy, Makani Mason.
We'll do it that way.
This is episode 82.
(00:23):
So, should I upgrade to Windows 11?
And, okay, Makani, I'm going to be real with you.
Can I be real with you before we dive into this?
Yeah.
So, we've been doing this for a hot minute.
We've been recording for well over a year now.
Yeah, come on.
And, you know, everything that I've kind of learned so far is make sure you're upgrading to stay safe.
(00:49):
Now you bring in this question.
It says, should I upgrade to Windows 11?
Which felt a little counterintuitive for me at first.
You know, because, like, shouldn't we update to the latest, greatest security?
You know, and at least according to Windows claims, didn't they make it sound like, hey, this is going to be so much better?
(01:13):
Yeah, I don't know.
I haven't listed them a lot, but there certainly are those claims that it's going to be better.
Well, and the thing I would just point out, though, too, is, right, like you mentioned there, security.
Yeah.
And that's the critical thing, is we always want to update to the latest and greatest security.
Yeah.
But so much of the time, you can't separate out the new features versus the new security, so to speak.
(01:43):
Oh, okay.
Right?
Okay, yeah.
You know, on an operating system level, they do a lot of times now, like we've talked about, have security updates versus other updates.
But when you're talking about a brand new, you know, Windows 10 to Windows 11, you can't really say, okay, well, I just want the new security feature from Windows 11.
(02:03):
But leave everything else to say about Windows 10, it just doesn't work that way.
Gotcha.
Okay.
Hence the reason for, should I upgrade to Windows 11?
Yeah.
Okay.
Well, and this is a follow-up, so we talked about in episode 79, the Windows 10 end-of-life support.
(02:23):
Yeah.
And I know I probably, I can't remember exactly the tone, but my knee-jerk was, I don't really want to upgrade to Windows 11 myself.
Right.
Right.
But I'm still, like, very much on the fence about it.
I've looked into it more, talked with Cam about it, thought about it, so we're going to dig into that a little bit.
But, so, there, the main focus was just, you know, it's end-of-life, so there's at least a significant question now of if you're going to upgrade or not.
(02:53):
That's really the thing.
But we didn't dig into, should you or not?
Right.
Right.
And so, I will say this at the onset.
Like, if you already have your mind made up, that's fine.
Like, I'm totally happy with whatever decision you make.
I'm not going to try to change your mind.
That's not really what this, I'm not going to be like, yeah, you're wrong.
(03:15):
Either way.
This is just, if you're not sure, I want to help out.
So, sometimes I do want to change your mind, this isn't one of those cases.
This isn't one of those.
Okay.
Yeah, and for the most part, really, we can, you know, I'm going to get into some useful details, but the short answer is yes, just go ahead and upgrade.
(03:36):
I think that's my kind of general recommendation for most people.
Okay.
Despite my own reluctance.
But, yeah, we'll get into that, too.
So, but the main thing, and I'm not sure, I have no idea on the numbers of this, but one of the big questions is if you actually can upgrade.
(03:59):
Right.
Because Windows 11, I don't know how well known this is.
It sounds like you paid a little attention to these things anyway, but there are some hardware requirements.
Right.
And so, you may not be able to update.
So, if you've got an old computer, there's a chance that you're not going to.
(04:19):
Yeah, and I don't know exactly how old.
So, there is an app that you can download for free from the Microsoft Store, and I have a link for it in the show notes, called the PC Health Check App.
Okay.
That, it's a quick and easy download install you can run, and it will tell you if you can upgrade to Windows 11 or not.
(04:40):
Nice.
So, that's the first easy thing.
You don't have to try to figure out, oh, you don't have to look things up.
Just run that app.
It'll tell you.
Yeah.
So, but then my thoughts in terms of, so there's, you know, there's, of course, some differences in how it looks.
And, you know, that's, I don't really have any opinion on that topic.
(05:03):
There's the other major factor that I think of for people is whether or not the apps that they run, especially in a corporate environment, if they need to go to Windows 11 for it, or if they need to stay on Windows 10, it could go either way.
And, of course, the main place, like you alluded to at the beginning, where I have the most to say is relative to security.
(05:28):
Yeah.
So, one of the factors is how old is something.
So, for example, I tend to delay upgrading in general, except for security updates, because typically new features, new products, new releases, when they're shiny new, have a lot of bugs.
(05:50):
Right.
Right.
Right.
So, that's kind of, like, mostly I'm like, yes, upgrade, but only security stuff.
New features, if you can wait, wait, because usually they're more buggy.
So.
Okay.
Now, the good news with Windows 11, it was released in October of 2021.
So, I mean, it's still Windows, still plenty of bugs.
(06:14):
Right.
It doesn't have the extra weight of being new for the bugs, at least.
Okay.
And, for as far as security changes between Windows 10 and 11, as you know, I'm not, like, a heavy, heavy Windows user.
I do use it for gaming regularly.
But, from what I've read, from people, other, you know, experts, Windows experts that I trust and rely on to learn about some of these things, they do have some reasonable improvements.
(06:47):
It's not, like, light years improvements, but they're good, good little upgrades, legitimate ones.
Partly, and that's partly related to the hardware thing, because there's, I won't get into it, but there's a, anyway, that's part of what the security is related to, is there's a new hardware security feature that is dependent on.
(07:09):
So, anyway, but the main thing with security that I want to remind of, and we talked about this in Episode 79, is just, you should either upgrade to Windows 11 or pay for security updates.
Okay.
I remember that.
Either upgrade or pay for the security updates.
One of the two.
Yeah.
And, you know, it doesn't have to be, like, day one, but I personally would recommend not delaying more than a month before you make that decision.
(07:40):
So, make this decision relatively prompt.
Yeah.
And you've got a little wise, I'm not sure what day this will air, but end of life is October 14th.
So, I'd say definitely by Thanksgiving.
Okay.
That's my recommendation, anyway.
All right.
(08:00):
So, the last point I want to cover on this is this thing that we're now seeing called Copilot Plus PCs.
Yeah.
You've seen that label?
I don't know if you've looked at it.
I've seen the label.
I haven't paid much attention to it, to be frank.
Yeah.
So, those, they'll all be, of course, any Windows machine you buy these days is going to be Windows 11, right?
(08:27):
Yeah.
But some of them, and I don't know exactly what percentage yet, and it probably will eventually just be all of them, but some of them will be Copilot Plus enabled or not.
And, I don't know, I at least am very wary of all the AI penetrating our operating systems.
And when Microsoft's running it, it maximizes my paranoia.
(08:51):
I'm not happy about Apple doing it, just to be clear either, but Microsoft, my least trustworthy when it comes to this stuff, to be frank.
Yeah.
Yeah.
So, and I admit a little bit of bias, but that's just my perspective.
So, I don't know, because, like, there's going to be pushback and you disable the things in the Copilot Plus PCs.
(09:15):
But, and the reason I bring all this up is because, so, at some point, you're not going to be able to upgrade.
Maybe you don't want to upgrade.
Maybe you're like, okay, well, maybe this is, you know, that laptop's barely, you know, limping along anyway.
Maybe it's time to get a new machine.
Yeah.
So, just something to keep about, think about when you do buy.
(09:38):
I don't know what the future of AI is going to look like in our operating systems, AI in general, because there's a lot of struggle about it.
A lot of security risks, but we're going to keep an eye on it.
So, and I'm not even saying don't buy a Copilot Plus PC, but it's just something to keep in mind.
You're definitely going to have more AI stuff, potentially.
(10:00):
So, if you're worried about that, that's something to watch out for.
That makes sense, especially knowing that there's additional security risks involved with that AI.
Yeah, that I think is without question.
You know, how well we can mitigate them long-term, but again, they're kind of into that whole shiny new category, right?
(10:23):
Everybody's racing headlong into AI because it's, I mean, it's awesome and it's powerful, right?
Right.
But it's rife with security implications, not to mention the copyright implications and the battle between advertisers.
And I can go on forever about that, but it's, you know, we're racing forward, so.
(10:43):
Okay.
Yeah.
So, that's, those are all the details I have for today.
Time for takeaways.
Well, my takeaway is, yeah, decide what you're going to do.
You know, if you're going to get security updates, get the security updates.
(11:05):
If you're going to bite that bullet and go to Windows 11, well, bite it, go for it.
But if it were me, I'd be super leery of the Copilot.
That's my takeaway from today.
Yeah.
Well, and the thing is, like, none of the security risks are really very specific to Windows 11 because 10 is bringing in Copilot.
(11:25):
I think the Copilot Plus might up it a notch.
Okay.
But I know that's kind of how I portrayed it to you.
And it's just, that's kind of inevitable.
I was trying to kind of have it more balanced because I don't think the AI security risk in Windows 11 is necessarily a reason to avoid upgrading to Windows 11.
(11:46):
Okay.
Yeah, because, I mean, admittedly, with it staying in Windows 10, their ability to push it on you because they're not doing new features and stuff is limited.
So, from a certain perspective, there is a little more, you know, insulation, so to speak, security from AI penetrating your box.
(12:09):
So, I guess it depends on your security level.
I just, I don't know.
I think there's enough people in this space that are going to be fighting against it that, I don't know.
I just, I'm still hopeful that despite the craziness of it all and their pushiness of Microsoft and everybody on AI, that somehow we'll find our way to sanity.
(12:32):
Yeah.
Does that make sense?
That makes total sense.
That makes total sense.
So, I don't want to inspire more paranoia and more headache for people than it was worth it because at the end of the day, I mean, I'm biased.
I don't really want to upgrade, but I might.
I still, I'm really dithering.
You know, I've got, I'm buying my time until October 14th before I make my final decision.
(12:56):
But, I mean, there's a reason why I'm primarily the only game on Windows.
It's like, as a software developer, my needs are different than a lot of people.
Yeah.
And especially my specific kind of software development, Mac, is just much better.
And so, like, I'm biased for a lot of reasons.
So, but my general recommendation for, you know, friends and family, people I talk to, people, because I've had, you know, Wes asked me, my brother, other brother asked me the other day.
(13:22):
And I said, yeah, I'm just upgrading to Windows.
Okay.
So, okay.
There you go.
That was my takeaway.
Okay.
Nice.
That was a good one.
Yeah.
Are you ready to take action and wondering where to start?
Get my Bulletproof My Identity Starter Kit for free.
(13:43):
The seven most vital layers of protection everyone needs.
I'll send you one step at a time and help you if you get stuck.
Just go to bulletproofmyid.com and enter your name and email and I will send you the first step.
Again, that's bulletproofmyid.com.
Welcome to Super Simple Security Principles, where you learn how to think, not just what to do.
I'm Nick Jackson, here to learn along with you from my good buddy, Makani Mason.
We'll do it that way.
This is episode 82.
(00:23):
So, should I upgrade to Windows 11?
And, okay, Makani, I'm going to be real with you.
Can I be real with you before we dive into this?
Yeah.
So, we've been doing this for a hot minute.
We've been recording for well over a year now.
Yeah, come on.
And, you know, everything that I've kind of learned so far is make sure you're upgrading to stay safe.
(00:49):
Now you bring in this question.
It says, should I upgrade to Windows 11?
Which felt a little counterintuitive for me at first.
You know, because, like, shouldn't we update to the latest, greatest security?
You know, and at least according to Windows claims, didn't they make it sound like, hey, this is going to be so much better?
(01:13):
Yeah, I don't know.
I haven't listed them a lot, but there certainly are those claims that it's going to be better.
Well, and the thing I would just point out, though, too, is, right, like you mentioned there, security.
Yeah.
And that's the critical thing, is we always want to update to the latest and greatest security.
Yeah.
But so much of the time, you can't separate out the new features versus the new security, so to speak.
(01:43):
Oh, okay.
Right?
Okay, yeah.
You know, on an operating system level, they do a lot of times now, like we've talked about, have security updates versus other updates.
But when you're talking about a brand new, you know, Windows 10 to Windows 11, you can't really say, okay, well, I just want the new security feature from Windows 11.
(02:03):
But leave everything else to say about Windows 10, it just doesn't work that way.
Gotcha.
Okay.
Hence the reason for, should I upgrade to Windows 11?
Yeah.
Okay.
Well, and this is a follow-up, so we talked about in episode 79, the Windows 10 end-of-life support.
(02:23):
Yeah.
And I know I probably, I can't remember exactly the tone, but my knee-jerk was, I don't really want to upgrade to Windows 11 myself.
Right.
Right.
But I'm still, like, very much on the fence about it.
I've looked into it more, talked with Cam about it, thought about it, so we're going to dig into that a little bit.
But, so, there, the main focus was just, you know, it's end-of-life, so there's at least a significant question now of if you're going to upgrade or not.
(02:53):
That's really the thing.
But we didn't dig into, should you or not?
Right.
Right.
And so, I will say this at the onset.
Like, if you already have your mind made up, that's fine.
Like, I'm totally happy with whatever decision you make.
I'm not going to try to change your mind.
That's not really what this, I'm not going to be like, yeah, you're wrong.
(03:15):
Either way.
This is just, if you're not sure, I want to help out.
So, sometimes I do want to change your mind, this isn't one of those cases.
This isn't one of those.
Okay.
Yeah, and for the most part, really, we can, you know, I'm going to get into some useful details, but the short answer is yes, just go ahead and upgrade.
(03:36):
I think that's my kind of general recommendation for most people.
Okay.
Despite my own reluctance.
But, yeah, we'll get into that, too.
So, but the main thing, and I'm not sure, I have no idea on the numbers of this, but one of the big questions is if you actually can upgrade.
(03:59):
Right.
Because Windows 11, I don't know how well known this is.
It sounds like you paid a little attention to these things anyway, but there are some hardware requirements.
Right.
And so, you may not be able to update.
So, if you've got an old computer, there's a chance that you're not going to.
(04:19):
Yeah, and I don't know exactly how old.
So, there is an app that you can download for free from the Microsoft Store, and I have a link for it in the show notes, called the PC Health Check App.
Okay.
That, it's a quick and easy download install you can run, and it will tell you if you can upgrade to Windows 11 or not.
(04:40):
Nice.
So, that's the first easy thing.
You don't have to try to figure out, oh, you don't have to look things up.
Just run that app.
It'll tell you.
Yeah.
So, but then my thoughts in terms of, so there's, you know, there's, of course, some differences in how it looks.
And, you know, that's, I don't really have any opinion on that topic.
(05:03):
There's the other major factor that I think of for people is whether or not the apps that they run, especially in a corporate environment, if they need to go to Windows 11 for it, or if they need to stay on Windows 10, it could go either way.
And, of course, the main place, like you alluded to at the beginning, where I have the most to say is relative to security.
(05:28):
Yeah.
So, one of the factors is how old is something.
So, for example, I tend to delay upgrading in general, except for security updates, because typically new features, new products, new releases, when they're shiny new, have a lot of bugs.
(05:50):
Right.
Right.
Right.
So, that's kind of, like, mostly I'm like, yes, upgrade, but only security stuff.
New features, if you can wait, wait, because usually they're more buggy.
So.
Okay.
Now, the good news with Windows 11, it was released in October of 2021.
So, I mean, it's still Windows, still plenty of bugs.
(06:14):
Right.
It doesn't have the extra weight of being new for the bugs, at least.
Okay.
And, for as far as security changes between Windows 10 and 11, as you know, I'm not, like, a heavy, heavy Windows user.
I do use it for gaming regularly.
But, from what I've read, from people, other, you know, experts, Windows experts that I trust and rely on to learn about some of these things, they do have some reasonable improvements.
(06:47):
It's not, like, light years improvements, but they're good, good little upgrades, legitimate ones.
Partly, and that's partly related to the hardware thing, because there's, I won't get into it, but there's a, anyway, that's part of what the security is related to, is there's a new hardware security feature that is dependent on.
(07:09):
So, anyway, but the main thing with security that I want to remind of, and we talked about this in Episode 79, is just, you should either upgrade to Windows 11 or pay for security updates.
Okay.
I remember that.
Either upgrade or pay for the security updates.
One of the two.
Yeah.
And, you know, it doesn't have to be, like, day one, but I personally would recommend not delaying more than a month before you make that decision.
(07:40):
So, make this decision relatively prompt.
Yeah.
And you've got a little wise, I'm not sure what day this will air, but end of life is October 14th.
So, I'd say definitely by Thanksgiving.
Okay.
That's my recommendation, anyway.
All right.
(08:00):
So, the last point I want to cover on this is this thing that we're now seeing called Copilot Plus PCs.
Yeah.
You've seen that label?
I don't know if you've looked at it.
I've seen the label.
I haven't paid much attention to it, to be frank.
Yeah.
So, those, they'll all be, of course, any Windows machine you buy these days is going to be Windows 11, right?
(08:27):
Yeah.
But some of them, and I don't know exactly what percentage yet, and it probably will eventually just be all of them, but some of them will be Copilot Plus enabled or not.
And, I don't know, I at least am very wary of all the AI penetrating our operating systems.
And when Microsoft's running it, it maximizes my paranoia.
(08:51):
I'm not happy about Apple doing it, just to be clear either, but Microsoft, my least trustworthy when it comes to this stuff, to be frank.
Yeah.
Yeah.
So, and I admit a little bit of bias, but that's just my perspective.
So, I don't know, because, like, there's going to be pushback and you disable the things in the Copilot Plus PCs.
(09:15):
But, and the reason I bring all this up is because, so, at some point, you're not going to be able to upgrade.
Maybe you don't want to upgrade.
Maybe you're like, okay, well, maybe this is, you know, that laptop's barely, you know, limping along anyway.
Maybe it's time to get a new machine.
Yeah.
So, just something to keep about, think about when you do buy.
(09:38):
I don't know what the future of AI is going to look like in our operating systems, AI in general, because there's a lot of struggle about it.
A lot of security risks, but we're going to keep an eye on it.
So, and I'm not even saying don't buy a Copilot Plus PC, but it's just something to keep in mind.
You're definitely going to have more AI stuff, potentially.
(10:00):
So, if you're worried about that, that's something to watch out for.
That makes sense, especially knowing that there's additional security risks involved with that AI.
Yeah, that I think is without question.
You know, how well we can mitigate them long-term, but again, they're kind of into that whole shiny new category, right?
(10:23):
Everybody's racing headlong into AI because it's, I mean, it's awesome and it's powerful, right?
Right.
But it's rife with security implications, not to mention the copyright implications and the battle between advertisers.
And I can go on forever about that, but it's, you know, we're racing forward, so.
(10:43):
Okay.
Yeah.
So, that's, those are all the details I have for today.
Time for takeaways.
Well, my takeaway is, yeah, decide what you're going to do.
You know, if you're going to get security updates, get the security updates.
(11:05):
If you're going to bite that bullet and go to Windows 11, well, bite it, go for it.
But if it were me, I'd be super leery of the Copilot.
That's my takeaway from today.
Yeah.
Well, and the thing is, like, none of the security risks are really very specific to Windows 11 because 10 is bringing in Copilot.
(11:25):
I think the Copilot Plus might up it a notch.
Okay.
But I know that's kind of how I portrayed it to you.
And it's just, that's kind of inevitable.
I was trying to kind of have it more balanced because I don't think the AI security risk in Windows 11 is necessarily a reason to avoid upgrading to Windows 11.
(11:46):
Okay.
Yeah, because, I mean, admittedly, with it staying in Windows 10, their ability to push it on you because they're not doing new features and stuff is limited.
So, from a certain perspective, there is a little more, you know, insulation, so to speak, security from AI penetrating your box.
(12:09):
So, I guess it depends on your security level.
I just, I don't know.
I think there's enough people in this space that are going to be fighting against it that, I don't know.
I just, I'm still hopeful that despite the craziness of it all and their pushiness of Microsoft and everybody on AI, that somehow we'll find our way to sanity.
(12:32):
Yeah.
Does that make sense?
That makes total sense.
That makes total sense.
So, I don't want to inspire more paranoia and more headache for people than it was worth it because at the end of the day, I mean, I'm biased.
I don't really want to upgrade, but I might.
I still, I'm really dithering.
You know, I've got, I'm buying my time until October 14th before I make my final decision.
(12:56):
But, I mean, there's a reason why I'm primarily the only game on Windows.
It's like, as a software developer, my needs are different than a lot of people.
Yeah.
And especially my specific kind of software development, Mac, is just much better.
And so, like, I'm biased for a lot of reasons.
So, but my general recommendation for, you know, friends and family, people I talk to, people, because I've had, you know, Wes asked me, my brother, other brother asked me the other day.
(13:22):
And I said, yeah, I'm just upgrading to Windows.
Okay.
So, okay.
There you go.
That was my takeaway.
Okay.
Nice.
That was a good one.
Yeah.
Are you ready to take action and wondering where to start?
Get my Bulletproof My Identity Starter Kit for free.
(13:43):
The seven most vital layers of protection everyone needs.
I'll send you one step at a time and help you if you get stuck.
Just go to bulletproofmyid.com and enter your name and email and I will send you the first step.
Again, that's bulletproofmyid.com.
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