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I want to migration a mix of 20+ workgroup Windows OS (7, 8 and 10, home & pro version) machines to Active Directory and would need to find out impact to the user & preparation; example application install by them previously, current user setting, state, outlook, printer setting, file ownership, permission, pst, etc.. How to make it as seamless as possible, easy future management (like renaming all workstation in a standard format) and if possible, little headache.

Is there guides, tips, potholes to avoid and pro vs con of difference methods.. Avoid application failure, example; https://community.spiceworks.com/topic/542103-windows-8-1-apps-immediately-close-when-laptop-joined-to-domain

Currently what I'm thinking is; install new AD (x2), use it as the DNS and DHCP for the workstations. Upgrade Home version to pro (few). Join domain, then either use USMT or copy user profile via System Properties (have not test, no idea the pros and cons). Do it manually, since there isn't that much machines and all users are in one location. Test application, example Outlook able access mail server and old pst archives, printing, backup & restoration software of old file still work, etc.. if there is issue, reinstall and reconfigure. Remove user local account admin right on the workstation. Maybe it would be cleaner to reinstall the OS.

Another option, is to outsource to more experience IT support. But, I still need to ensure they know what they are doing.

Thanks.

added after Yagmoth suggestion. And Thanks! I can't use my client environment for testing or have access to it freely. I hope to be prepared, example the Microsoft Account (which happen if it is the same name as the new domain account) and current Drive sync.. Dropbox, Chrome saved password, ERP software, Skype, etc.. I'm setting up a virtual AD environment, Windows 7, 8 and 10 OS.. and will be asking for a list of desktops configure (what info to gather?). I would likely look for trustworthy vendors and use my testing/reading to gauge them. Maybe you are right, using the live environment to test and plan could be the most practical approach.

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If you want time to see how to make it:

Create your AD and dont activate right now your DHCP to distribute your server configuration to your computer.

Take a test computer and put manually the DNS configuration in it, join the domain and watch what is working or not.

From there make a migration plan and test the join from another machine.

Remember that configuring an AD can be done slowly.

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