Upgrading Office 2010 to O365

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My knowledge is lacking a bit when it comes to upgrading Office. I have a customer moving from Office 2010 to O365 (at my request). They are currently using Outlook. When O365 installs do I have to configure Outlook from scratch, or point it at the .pst I want it to use, or does it take over email duties automatically? I'm surprised I haven't had to cross this bridge before but not many Outlook users in the residential work I do.
 
You can completely uninstall 2010 then install 365 and it will pick up the settings, saved email, contacts etc automatically.

That being said - I never trust this to actually work. Always take a backup of the PST, NK2 and any account settings first. Or go one further with the full image like you are doing.
 
This would be my preferred route (with a full image and FAB copy on reserve).

As is mine but it's not really required. Though removing Office 2010 might break things and make you reinstall M365.

But whatever, the thing you're after is the Outlook Profile, which is part of the User Profile on Windows... it's in %appdata%\local\microsoft\outlook, and %appdata\roaming\microsoft\outlook

The problem is? at least for me... I lost a LOT of Outlook profiles going from 2010 to 2013. I have no faith that a modern version is going to fair any better, in fact I have every reason to believe it will be worse.

So backup things first, have the account details on hand, because you need to be ready to rebuild that profile from scratch. You won't lose a PST over it... but having an exported PST with all their junk in it in advance will save your skin. Because even if it does update and work, you're still going to have to juggle the PST a bit to get it into the new format.

If post upgrade Outlook opens to a splash screen that stares at you for more than 5min... yeah... profile is done.
 
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