Quickest/Easiest way to upgrade Windows 10 to the latest version

So, I used to do a lot of work with Windows 7 deployments. I'd use a VM to make a vanilla install and then use DISM to capture the updated WIM. The updated WIM would only be updated with whatever the latest security updates were to that point. Years ago, in Server 2000, you'd slipstream Service Packs as needed. Those days are missed because it was easy to get a large sum of updates into an OS and ready for deployment but the tools used for deployments are much better these days. However, while MS seems to have taken several steps to make deployments easier, getting the OS fully updated seems to be much harder than it used to be; there are no more Service Packs... You can't slipstream updates into the OS like you used to. So, my question is this: How does one bring a system up to date quickly? Can a series of cumulative updates be installed - in a certain order - to get the OS up to date? With a system already in place but isolated (no web access or access to WSUS), how does one update the system to take advantage of the later builds and their improvements/features? Again, there are no Service Packs...

I know it seems like a strange question and a strange scenario. After all, who has a system that can't reach the update servers? However, standalone systems do still exist - even against my recommendations - and, they should be not be left out when MS releases updates, fixes & new features.

I've worked with a few new computers that came with the original RTM build of 10240. I Upgraded them first to Version 1511 then to Version 1607 Build 14393.0. Then the latest build version was installed which appeared to include everything since 14393.0 to get it to 14393.693 which apparently included all the updates since 14393.0. Or maybe it all happened so fast I did see the entire process! With Microsoft, Nah, never happens.

Berton said:

I've worked with a few new computers that came with the original RTM build of 10240. I Upgraded them first to Version 1511 then to Version 1607 Build 14393.0. Then the latest build version was installed which appeared to include everything since 14393.0 to get it to 14393.693 which apparently included all the updates since 14393.0. Or maybe it all happened so fast I did see the entire process! With Microsoft, Nah, never happens.

That's kind of my point. One must install all these versions. However, I've yet to find a link for the single download to jump from version to version. Yes, I know Windows Update will do the work but, again, it's an isolated system so we don't have that luxury. And, going from version to version takes a while. The last one I did took a couple hours. It would be nice to have an ISO and/or a script to drop the core updates needed to get you from version to version and then you could deal with a small subset of updates to get it up to date from there.

I'd think the Media Creation Tool should get the latest Version but maybe not the newest/latest Build. There's a Tutorial about using the tool. Also in the Updates window on the Settings is a Learn More link that has links through to downloading the the latest update for using on offline computers, I've used it when having connections issues.

Berton said:

I'd think the Media Creation Tool should get the latest Version but maybe not the newest/latest Build. There's a Tutorial about using the tool. Also in the Updates window on the Settings is a Learn More link that has links through to downloading the the latest update for using on offline computers, I've used it when having connections issues.

From what I've read, the Media Creation Tool is used for fresh installs so that option is off the table if that's true. Furthermore, I don't think you can use it for Enterprise or Education versions of the OS so that wouldn't help those users at all. I've seen/followed various links from Windows Update to their KB pages but, again, when you install a fresh OS, Windows Updates seems to have a mess of updates to install. Now, even if you spent the time going out and grabbing all those files (some may not be available to grab), you'd then need to figure out in what order they should be installed. (My best guess for installation order would be numerically but not all updates have the typical KB01234567 naming convention.) Just for grins, I have half a mind to spin up a VM and attempt to install the OS and log updates in hopes I can at least get a list. I'd still need to figure out the order though....

RKillCrazy said:

From what I've read, the Media Creation Tool is used for fresh installs so that option is off the table if that's true. Furthermore, I don't think you can use it for Enterprise or Education versions of the OS so that wouldn't help those users at all. I've seen/followed various links from Windows Update to their KB pages but, again, when you install a fresh OS, Windows Updates seems to have a mess of updates to install. Now, even if you spent the time going out and grabbing all those files (some may not be available to grab), you'd then need to figure out in what order they should be installed. (My best guess for installation order would be numerically but not all updates have the typical KB01234567 naming convention.) Just for grins, I have half a mind to spin up a VM and attempt to install the OS and log updates in hopes I can at least get a list. I'd still need to figure out the order though....

I thought the Media Creation Tool let you do a repair install or in place upgrade. Else, you can use the Windows 10 ISO file - see Windows 10 ISO Download

Steve C said:

I thought the Media Creation Tool let you do a repair install or in place upgrade. Else, you can use the Windows 10 ISO file - see Windows 10 ISO Download

I'll have to test this in a VM... Again, I'm basing my comments on what I've read in the past several months of looking for answers out here. Furthermore, if it can't be used for the Education and Enterprise versions, that will likely screw with people.

I tested the upgrade from v10240 to v14393.

A while back, I created an updated vanilla install via a VM and DISM. Basically, I loaded the VM with the original bits from our Win10 Enterprise (v10240) ISO, updated it via Windows Updates and then captured the image (WIM) with DISM. I created the 1607 (v14393) ISO and have been deploying it ever since. Based on what I had understood about the Enterprise versions of the OS, I never thought to use it for an in-place upgrade.

Since my VM had a snapshot, I rolled back to the original installation (v10240) and then mounted the 1607 (v14393) ISO. From there, it was START > RUN > D:\SETUP.EXE and away it went! It asked me if I wanted to keep my documents and apps. None were present since it was a fresh installation but I chose to save that data anyway - just to test the process. It rebooted after a while and then showed a black screen with, "Upgrading Windows.....Sit back and relax..." and a percentage on it. At about 25%, it rebooted and finally rolled back and showed me an error (0xC1900101 - 0x30017) about it failing in the FIRST_BOOT phase... I tried the upgrade via booting to the ISO and it gave me another warning and forced me out of that process. The following is that poorly formatted warning...

Code:

The computer started using the Windows installation media.  Remove the installation media and restart your computer so that Windows starts normally.  Then, insert the installation media and restart the upgrade.  (Do not select |Custom (advanced)| to perform an upgrade. |Custom (advanced)| installs a new copy of Windows and deletes your programs and settings.)

This is a VM.... It has no apps, antivirus, etc. that could - according to research - interfere with the upgrade process. So, stopping the AV, or disabling a 3rd party firewall isn't going to help me the same as it has for many others. Not looking good for the home team...

I found something that seems to help! Poking around the interwebs led me to an article walking one through the process of snagging an ESD file when Windows 10 pulls down the Anniversary (1607) update. So, I spun up a VM and pulled down updates as needed. When it pulls down the anniversary update, it creates - what looks to be - a directory structure very similar to that of the installation disk/ISO. It's inside a hidden folder but you can find it in C:\$WINDOWS.~BT. Like I said, it has all the familiar symptoms of an OS install ISO... So, C:\$WINDOWS.~BT\sources\install.esd can be copied from that location. Evidently, you're supposed to grab it before you reboot but I found the files were still in place after the reboot. In any case, I grabbed a copy of the file and used a script that pulls the data that is needed to decrypt the file from your registry. It then allows you to create your own upgrade ISO. I first created the ISO with an ESD in it and tested. It worked great until I took it to another machine and tested it! Evidently, the ESD file is only good for the machine it was initially downloaded on. So, I created an ISO with a WIM instead. While the file was much larger than the ESD, it worked on every machine I tested it on...laptop, VM, desktop, etc. There's a catch though... You need to run the upgrade on an OS of the same licensed edition. For instance, In my testing, I tried it on a Win10 PRO VM and it turned it into a Win10 ENTERPRISE load! (That will surely mess with your EULA!) However, if you have a mess of machines that all have the same volume-licensed Enterprise edition like we have here, it works great! I later made one for my PROFESSIONAL builds as well and it worked great with them! And, since Win10 can mount an ISO natively, I never bothered to burn it to disk or dump the data to a thumb drive. You can't use it via booting from it; you need to install from inside Windows - just like you would via Windows Updates. So, I'd mount the ISO and then run: D:\setup.exe /Auto Upgrade /DynamicUpdate Disable

So, this may be as close as we'll get to a Service Pack for WIndows 10. These upgrade ISOs were able to take me from v10240 to v14393 with ease. If you guys are bored and want to play around with it, maybe you can test it on your builds....