Joining Existing AD to Existing O365

Customer used to have an on-prem exchange server 12 months ago. This was migrated to O365, but their network was still on a 2003 server, so AD sync was never configured. We want to get this set up and working now though, for password sync mainly, but maybe for user-creation also.

Online instructions are quite lengthy, so after your recommendations. Is it worth installing the "Essentials Experience" just so that I can use the O365 features within it, or should i be going the hole hog and doing it properly?

The O365 information is more current than the AD config, which has now been upgraded to 2012 r2 standard. They are using a domain "company.local" also, which has not yet be changed. Will this cause issues?

O365 is a 15 user environment, with about 100 distribution groups.
AD only has the users configured, and not their group memberships, telephone numbers or job titles (used for email signature generation)
Exclaimer is used to generate email signatures straight from O365.

Ideas?
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Coriron HazManaging DirectorAsked:
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Jeremy WeisingerSenior Network Consultant / EngineerCommented:
Not sure how much help I will be but this is what I know...

1. I never used the Essentials Experience so I can't speak to that.

2. The process of syncing the users from AD to existing users in O365 will overwrite attributes in O365. This means that before setting up DirSync, you need to get the AD objects up to date. If you're just syncing users then only the users need to be updated.

3. Having company.local is not an issue but you do need to add the UPN suffix of domain.com to the forest and then configure the users with that suffix so it matches O365.

4. You also need to have the proxy addresses match (this should be done when you are bringing the AD objects current)

5. I'm a little unclear on how the group membership works with sync'd users and cloud groups.

That's about the extent of what I know. I'm sure others can chime in with more.

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