Server 2012R2 and O365

[RoadRunner]

Hi,

need to get my head around a few things. Have a client I have to move from SBS2011 to O365 and server 2012. They have 5 domain names they use for emails as they have different parts of the business. Sithere might be johndoe@business1.com, johndoe@business2.com and so on. some might just have some domains others all. They want to be able to treat each email separately and setup on their phones as well.
I was thinking to get O365 business premium licenses for all the Users to cover the workstations (with office software) and just "essential" licenses to cover additional email accounts.
I've never done multi domain in O365 but know you can do it. Would it be better to treat each domain name as a separate O365 setup or combine them all in one Microsoft account ?

Also on server 2012R2 standard is there any way to integrate this setup with O365 ?
Used the integration on Server essentials but was rather disappointed as really all it does is to sync passwords.

Can I use Server 2012 essentials as well if I have 30-40 email accounts because of the multiple emails per user setup how will that work/show up with essentials ?

 

[cyabro]

Don't forgot that there is the Exchange Plan 1 option as well, for just an email account, that is slightly cheaper again than the Office Essentials plan.
The Exchange Plan 1 sub doesn't include OneDrive hence the slightly cheaper price.

I don't think Server 2012 R2 Essentials will let you have a single user with multiple separate email accounts on Office 365, only aliases.
You could add a separate user account for each email address but then it seems you will go over the 25 user licenses allowed in server essentials.

What I think you will need to do is decide on a primary email address for each user and add them to the server with that email address.
In the Office 365 Web admin you will need to create new user accounts with the other email addresses that each user requires.
The users will then be able to add each individual email account to Outlook, or smartphones/tablets etc.
The only problem I can see will be that their single sign-on password won't sync to their other email accounts, only the primary one.

 

[RoadRunner]

On server 2012R2 standard I don't have email accounts at all so I create the users on the server and then a whole bunch of O365 email accounts and they are all treated individually.
So If I have 15 users all having 5 domain names I end up with 15 user accounts on the server and 75 email accounts. If someone leaves or needs a password changed its 6 password changes per user to get it all consistent.

 

[YeOldeStonecat]

You can install the Essentials Role on Server 12 Standard....so that you can manage your O365 accounts. I like the Essentials role..it does more than just sync passwords upstream....and being able to centrally manage the O365 accounts on that dashboard is nice.

Anyways...what you have here is really similar to what you had on SBS11...if you think about it.
O365 can indeed handle additional domain recipient policies. I think up to 999 domain names on a mailbox. BUT, as with Exchange 2010 on SBS11...there can only be 1x default "send as" SMTP address on Exchange. So by default, if Joe has a primary account of joe@smith.com and he has a secondary address of joe@wesson.com when Joe replies or sends an e-mail it always comes from joe@smith.com even though he also receives mail from joe@wesson.com

BUT..you can do some tricks..like setup a distribution group named joe@wesson.com and have that forward to joes main mailbox of joe@smith.com, and give Joe send-as rights on that mailbox. So when Joe wants to send from joe@wesson.com he can do that in Outlook.

This way there is no additional costs for O365 licensing.
BUT...depending on how many users there are, I'm sure it can be a pain to setup and admin.
...and I don't know how to get around this on smart phones.

 

[RoadRunner]

We've done stuff like that on SBS2011as well. Even setup additional mailboxes in separate OUs I think but just a pain. It's the same business with different business sections and they have different domain names for them and websites and so on. It's just such a pain to look after. Now that we can put in a new server and O365 I was hoping to start fresh but can't see how to make things easier as every email/domain has to be treated individually.

 

[YeOldeStonecat]

It may come down to just having that conversation with them.
We have quite a few clients with additional domains on their e-mail. They're typically fine with having 1x default "reply to"...not insisting on having to change it to "company B". But I guess I can see where some clients may really want to separate those identities...so if that's the case, they'll have to deal with the expense of the additional accounts. Since if you have several separate O365/Exchange accounts open in Outlook..you can easily keep them separated, and the reply to is based on which mailbox is active/highlighted.

 

[RoadRunner]

They want it separate. One thing is so they can have the accounts on ipads/phones separate as well.
So is there any way to sync this to Server 2012. I would guess if I setup 10 users with 5 different email accounts in O365 and install the essentials role on 2012R2 it would just sync 50 accounts and I would have each user 5 times on the server. I think that should be ok as the user would only ever logon to the local computer with his main account.
That would just mean I need server 2012R2 + essentials role + RDP licenses for remote computer access. As syncing those accounts to a server 2012R2 essentials would blow the 25 user limit.

 

[YeOldeStonecat]

I wouldn't see a need to sync the additional domains or even have local accounts to tie in with the additional O365 accounts. Factor in the cost of all those additional user CALs...ugh! Just the primary..via Essentials console. The rest, just "save password" in the Outlook profile for those additional accounts.

 

[RoadRunner]

But If I setup all emails for the 5 domains in O365 the essentials sync will just connect to the O365 account and sync all users ?

 

[YeOldeStonecat]

Essentials Role will sync the domain users account with 1x O365 account. I do not believe it has the ability to sync a domain users account with multiple O365 accounts. I don't see how that's possible. If you create multiple domain user accounts for a person with the goals of syncing to multiple O365 accounts...I don't see how that could work, as a domain user can only log onto 1x domain user account at a time.