Optimal Win10 Upgrade Path

In My Humble Opinion
1

It depends.

In late August Lincoln Spector tried to upgrade to Win10 on his hybrid laptop and came away with a world of hurt. Yeah, yeah he intentionally picked a tricky device. Still while giving proper respect to the multiplicity of posters here with a trouble-free upgrade experience, I say to delay until Jan 2016. Allowing for procrastination, that will allow 7 months to jerk around - currently you have until late July 2016 to upgrade to Win10 free.

Spector: Delay will give a chance for the software and device drivers to be fixed, “Even if you’re sick of Win8.” For Win7 users the advantages of Win10 are minimal unless you have a touchscreen. (Me: And if you do have a touchscreen on your desktop or laptop, why do have a touchscreen on your desktop or laptop? Also, bear in mind that Win7 pumpkins in Jan 2020.)

Also the Threshold update to Win10 has been delayed: it might be out in November. Recall that updates for Win10 Home users occur forcibly and involuntarily.

Next Jan:

Figure out your backup system with Win10. Image your HD and do a final incremental backup before Win10 upgrade. I hope to continue with Syncback and maybe backing up a compressed directory on some sort of cloud service.

Also, I’ll encrypt my hard drive for the first time, and let MS store a copy of the key on their servers, as I’ll have a home installation. Better than a non-encrypted drive, presumably.

Consider a clean install. (Is that even possible?)

Figure out your privacy strategy, so you don’t have to make installation decisions on the fly. Here are four broad categories:

  1. Bend over and share your hard drive with Microsoft. [1]

  2. Turn everything off, and accept a little data trickling over to Microsoft anyway. That means you won’t get Cortana, MS’s version of Siri. Oh well. Will you still get hard drive search?

  3. Something in between.

  4. Shell out $100 for an enterprise license ($200 later). I think.

One of the Win10 privacy guides on the internet.

Overall, Microsoft doesn’t deserve my trust. Google, OTOH, has its missteps but frankly I do think they have a more responsible corporate culture. I’m leaning towards option number 2. Any privacy invading service MS provides is probably better implemented by a third party. Not so incidentally, does anybody have desktop or laptop experience with Cortana?

Past threads: “Rah rah I just upgraded Win10 and it happened without a single BSOD”: Win10 Free Upgrade Thread. That thread is for immediate impressions. This thread is a guide for slower adopters.

[1] “It’s not that bad MfM!” No it isn’t. You try explaining in less than 1000 words what MS looks at and how they look at it. My take from poking on the web is that few have a solid grasp on the Win10 privacy issue.

2

We’re probably never going to know for sure exactly what Microsoft, Apple, Google, etc are capturing during our use of their platforms, so I think it’s inevitable that we have to choose a level of trust, or not.

In reality, what’s it going to be though?
Capture of your browsing behaviour - to a certain extent, you can insulate yourself from this by some sort of sandboxing (in a more extreme case, you could run your browser in a VM). IMO, your ISP is as big a risk as anyone else here, but few people think about that as much as they do about the providers of the OS and software.

Capture of your banking data - possible, but Microsoft would have to be pretty damn idiotic to play fast and loose with the regulations surrounding that. Incompetence is a slight risk, malice, not so much.

Capture of your web searches - give it up. This battle is already lost. There is no privacy here.

Capture of your local file searches - why would they bother? Does anyone care to know what spreadsheets and jpegs you looked for on your own machine?

Capture of your mouse and keyboard behaviours - I wouldn’t be surprised if this is going on - so they can get data that may feed into the next wave of OS design changes, or contribute to system optimisation patches. It’s pretty bland data in terms of personal intrusion, I wouldn’t care about it.

I imagine there are a whole load of other things I’ve left out, but it seems like they fall into two broad categories:

[ol]
[li]Private data that could cause you loss or damage if it was released[/li][li]Everything else[/li][/ol]

You can take steps to protect category 1 on pretty much any platform; if you object to category 2 on principle (and I’m not saying that’s wrong), you have to go to greater extremes - and maybe avoid ***all ***of the mainstream platforms.

3

Nice post and that’s not a bad framework. There’s also the matter of FUD and unknown risks. I agree that the largest risk comes from hackers exploiting the multiple Win10 services that send information over the internet without the user’s knowledge, control or sometimes permission. The hacker risk associated with financial services is actually pretty substantial, but that’s a problem with all MS operating systems. US individuals have some level of regulatory protection, but small businesses are advised to do their banking on a live CD or a dedicated PC if that’s feasible.

Much of this could be mitigated with a sophisticated yet easy to use third party firewall that tracks and IDs all incoming and outgoing traffic as well as triggering flags for suspect traffic. Analogously and hijack, some of the compatibility problems could be addressed by running the equivalent of WinXP in a sandbox. None of these tools are currently within my knowledge or skill set.

Web searches: Duck duck go and Startpage are suppose to be privacy friendly.

Bonus question: What’s Cortana like on a desktop or laptop? It is necessary for local hard drive search?

4

Win 10 will never go off the upgrade path they have now. their mission is to monetize the app store.With pro you can delay updates slow path or quik path.

I will say it again MS want to monetize apps! period

I have been a windows insider for 9 months, just got build cant remember i run it on vmware

Or you can kill updates in services which most users dont know.

if you do that they will kill you on security

s pick yer poison but believe me ms wants money for apps

enterprise wise its the cloud
subscription software

5

Not necessary for a local search (in fact hampers a local search by suggesting all sorts of bullshit chaff from the web etc). Not necessary at all really. Google search is superior to Cortana in nearly every way, because Cortana uses Bing, which is awful.

Cortana might be useful if you want virtual PA stuff such as checking your calendar appointments etc.

6

Thanks Mangetout.

Well if they implement it well, I say rock on. Unfortunately we’re discussing Microsoft. I fully expect that on August 1, 2016 immediately following the upgrade deadline, Clippy will appear on all Home screens and announce the exciting new and entirely unavoidable changes to Windows 10. It’s going to be all Tileworld, all the time - just like Windows 8 but without the boring desktop. But fret not productivity fans! Just hop on down to the MS store and get a free 45 day trial of MS’s new Desktop App. Then pay only $3.99 per month while supplies last.
Win 10 gives their users 2 additional years of support. Specifically:

Win 7 pumpkins in Jan 2020,

Win 8.1 pumpkins in Jan 2023, and

Win 10 pumpkins in Oct 2025.

Now MS might provide a free upgrade to Windows Eleventy-One for Win10 users. But they might not: current intentions may not apply.

Yeah, you can upgrade to Win 10 Pro for $100. It gets you Bitlocker encryption for your hard drive and you can pace the upgrades like Enterprises and Win 7-8 users do. Wiki has a chart on Win10 features for various editions. Those who don’t take this route should schedule frequent image backups in case one of MS’s upgrades decides to brick your machine.

As of now, I plan to upgrade my Win8.1 machine after Jan 1, 2016, turn off all privacy settings including the ones providing exciting features, make a full image and file backup beforehand and furthermore beef up my security procedures. (I.e, I hope to backup a small directory with encryted files to the cloud and learn how to work a sandbox.) Maybe I’ll even splurge for Win 10 Pro after a spell.

I’ll keep a Win7 backup machine going, just in case. The hardware may or may not die by Jan 2020 anyway: if it doesn’t I’ll take my chances. I also don’t plan to upgrade my Win7 laptop yet.

7

The reason I think that won’t happen any time too soon is that there is still a vast array of third-party Win32/64 desktop software out there - especially for business - and in many cases, it’s the only reason why people choose Windows as their OS platform.

If that software all eventually migrates to web-based platforms, then Windows can go all tiley-appy, but then everyone would be free to switch to Mac, Linux, Android, ChromeOS, etc

Same thing if those third party applications switch to being tiley-appy apps. Chances are they will be ported to the other app-supporting platforms and again, everyone is free to switch.

MS would be dumb dumb dumb to kill off the desktop. I’m not saying that means it won’t happen, but if they do, it breaks the shackles, rather than clamping them on.

8

Well I was exaggerating for comic effect. The core truth though is that mandated automatic updates permit Microsoft to install downgrades and services that are not in the user’s interest. At that level, we really can’t trust them, based upon their track record. We can’t even trust their business sense.

So that’s a vulnerability. For PCs with expected lifetimes exceeding four years, perhaps paying $100 to avoid mandated and permanent automatic updates isn’t such a bad deal. Yes, I know many people set their PCs to automatic updates now: that’s fine. That is fine, because it can be turned off if MS tries to pull something.

Ok: Here’s a guide to MS privacy settings. I say turn it all off:

Let me work through a seemingly harmless example. “Let websites provide locally relevant content by accessing my language list.” What’s the big deal? I say turn it off because: a) Google already knows I speak English, b) I don’t know who else MS is sharing it with and c) I don’t know whether MS is fulling disclosing all aspects of this feature or whether a hacker can adapt it to their own ends. In other words, MS has earned my distrust.

So although a feature like that is plausibly useful, that’s the wrong framework: the correct framework assumes an antagonistic relationship with the user and Microsoft (and, I would argue, a business relationship with Google and maybe even Amazon.)