Windows 10 Upgrade for 50+ systems

Hello I have to upgrade over 50 systems to windows 10 all of the systems are running windows 7 Pro, my questions is do I have to allow each system to download and go threw the slow process of doing the upgrade it self or can I download an ISO and jump from system to system. Also there are some systems that are not in the office that I know I will not be able to get to until next month witch is after the July deadline is there any trick or suggestions on getting windows for free but after the cut off date?
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David Johnson, CD, MVPRetiredCommented:
use mdt and setup a replace task sequence.

free upgrade after july 29th.. sorry.. you waited too late
JohnBusiness Consultant (Owner)Commented:
Yes, you have waited too late.

You need to test a few machines.

 Windows 7 machines (especially older ones) have legacy and incompatible software. You need to remove this and test.
 The likelihood you could mass upgrade 50+ old machines and come out fine is nearly zero.

 Read my article on Windows 10 one year later.
Deerek11Author Commented:
I have done a few of them doing the year to test out the systems they are all the same make and model systems, I have a large conference room to set them all up on and upgrade all at the same time
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JohnBusiness Consultant (Owner)Commented:
The older the system and the more dissimilar, the more you need to look individually. I have had much different results on different systems. For the most part, any Windows 7 machine that will run Windows 10 had to have a fresh install of Windows 10 to get rid of legacy apps (vendor apps, vendor driver helpers, old antivirus and so on).
Scott CSenior EngineerCommented:
Here's what I'd do at this point.  Upgrade a couple of your machines using an downloaded ISO burned to DVD using the media creation tool.

Do as best testing as you can for 1 or at most 2 days.

If  everything goes well do the rest.

Now for your remote sites...burn more DVDs and send them to these sites....OVERNIGHT.

I'm assuming at this point you have remote access to these machines and someone there who can be your "boots on the ground".  Your remote person will have to click on the initial options...(the 12 or so slide switches).  

Remote to these machines, have someone insert the disk and begin the upgrade process.   I would only do this on one machine at first to make sure everything goes as smooth as possible.

Honestly, you waited too long for this.  We had a year notice of the free upgrade.  You can get this done in time, but you are going to feel the pain of it.

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The upgrade using the iso and running the setup.exe from there goes pretty fast, usually maybe 2 hours or so per machine if they aren't too old and there aren't any problems.

You can also boot the PC from the USB stick or DVD, then you will be doing a clean install, and you will need to use the Windows 7 product key to get the free upgrade. But that goes even faster, usually less than an hour. But of course after that you will have to reinstall software, look for drivers that aren't automatically found, and setup the desktop the way you need it, so the time saved for the upgrade will be lost again for the rest (but you may be able to push those things via GPO, so in the end it may be less work still.
Gary CaseRetiredCommented:
Go to the media creation site and create an ISO, then burn a BUNCH of DVDs from that ISO.

Note that you can either burn a DVD for the x32 version or the x64 version of Windows 10 => so if your machines aren't all the same "bitness" you may need copies of both version (be sure to mark them).

Now, on each machine you need to upgrade, insert the DVD (don't boot to it);  then run Setup from within Windows; and do the update from those DVDs.    The first screen you'll see asks whether or not you want to do the updates during the install -- say NO  (I think the actual answer is "Not at this time") ==>  then wait for it to check things and once you see the screen that confirms what you want to keep you just click on the button to start the upgrade.   You no longer need to be at that machine until it's finished the upgrade process and wants you to answer a few questions r.e. settings.    [ I generally change a LOT of those rather than just accepting the defaults -- but this only takes a minute or two to do].

You can't remove the DVD during the upgrade process -- that's why you'll need to burn a bunch of them.   [As many as you want to be able to do at once.]

As for machines you can't get to before the 29th => you have two choices:  (a) Tell the users to go ahead and do the upgrade via Windows Update (Note that in my experience this isn't as reliable as using media you've created);  or (b) Pay for the upgrade when you eventually do it.
Gary CaseRetiredCommented:
Note that if you burn 10 DVDs and then do 10 systems at a time, you should be able to do 50 systems fairly quickly -- in 2-3 days assuming they're all available.   But you DO need to get started on this NOW !!
JohnBusiness Consultant (Owner)Commented:
Another approach (one we use) is let any Windows 7 machine 2 years old or older run its course as Windows 7. Replace when ready with new OEM Windows 10 Pro machines preloaded with Windows 10 and good machines nearly guaranteed to work well.

Windows 10 works well, but so also does Windows 7.
Gary CaseRetiredCommented:
Agree with John =>  If your Windows 7 systems are working well, it's unlikely there's any compelling reason to switch;  and it's almost certain you'll be replacing them before the end of extended support for '7 (2020).

Windows 10 works very nicely at this point, but the simple fact the upgrade is free is not by itself a good reason to do it.
You don't necessarily need to burn so many DVD's. You can also extract the iso to a network folder and run the setup.exe from there. Or if you run it from the DVD's, you can remove it the first time the process reboots the PC.
Network admins can do it this way:
Extract the ISO to a share (\\server\share) using 7zip.
Configure a startup script or scheduled task:
for keeping progs, settings and data:
\\server\share\setup.exe /auto upgrade

Open in new window

for keeping only data
\\server\share\setup.exe /auto dataonly

Open in new window

for not keeping anything apart from the partitioning:
\\server\share\setup.exe /auto clean

Open in new window

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