Windows 10 Readiness: A Migration Time Machine from Windows XP to Today

With the Windows 10 Anniversary Update arriving on August 2^nd, and as more and more companies brace themselves for the migration plunge, what better time could there be for 1E to launch our new Windows 10 Readiness dashboard in our free Software Intelligence tool? By downloading it today, you can get a free snapshot of exactly how prepared your enterprise is for the latest Microsoft OS, and insight into areas you might need to work on to ensure you get there as quickly and securely as possible.
The main focus for every enterprise preparing to migrate to Windows 10 should be avoiding a repeat performance of Windows XP to Windows 7, which was a nightmare for many companies. Here we take a look at some of the key pain points of the XP migration, and what lessons we can take from it for this time around.

Automation

Then: When people started migrating from Windows XP to 7, there was an assumption that, with Microsoft System Center Configuration Manager, they had a systems management platform that provided automation, and so they could hope to upgrade without having IT visit all of its machines in order to invoke the rebuild…
It didn’t exactly work out that way for most large companies. The vast majority ended up abandoning this approach it in the end and resorting to plan B: sending IT staff out to visit each desk and effect the migration using a USB drive.
Now: Nowadays, surely, things are different, aren’t they? On the one hand, yes, they should be. In principle, a Windows 10 migration should be orders of magnitude easier than your Windows 7 migration was, and (yes) automated. However, for those machines running Windows 7 with Secure Boot, you need to know that the in-place upgrade will not suffice to get you to a fully-secure Windows 10 (with the full working suite of security products).
No, in this instance, what you will need is a wipe-and-load approach, and this can mean that the time and expense required for migration starts to stack up once again. There are ways around this, but first of all you need to know how many of your enterprise’s machines require wipe-and-load.

Applications

Then: It wasn’t uncommon, during the Windows 7 migration, for businesses to migrate and then only afterwards discover that the applications they needed hadn’t been updated for the new OS.
This was, naturally, a hugely beloved and popular oversight by vendors.
Now: Nowadays, vendors are largely much more on their game, and have produced compatible applications for the new OS.
Yet while you can now be more confident that the application will work in the new OS, if it’s not being used then there’s no point in worrying about it in the first place. Before migrating, therefore, a priority should be getting a real sense of your overall ‘software estate’ – that is, the number of different applications you have installed, and what’s actually being used.

Infrastructure

Then: During the migration to Windows 7, every organization found out a lot about their core infrastructure. Typically, they found out it wasn’t up to much. Certainly it wasn’t up to transferring the requisite amount of content.
Another frequent and unwelcome discovery was that they didn’t understand the network configuration at remote offices. These ad hoc corners of infrastructure were stretched when it came to delivering large amount of content for the new OS.
Now: This is still an area you definitely shouldn’t take for granted. You want to make sure Configuration Manager is up to date – ideally you should be on Configuration Manager Current Branch 1602 (while you can deploy Windows 10 with Configuration Manager 2012 SP2, you won’t have all the features for Windows 10 if you do).
Even with an up-to-date Configuration Manager, the migration process can still take some time. You should know exactly how long before you begin…