Hi all !
Long time no see but I’m still around, doing some Exchange 2010, 2013, 2016 and Office 365 (mostly Exchange Online but also a bit of Skype For Business – IM and presence only for now) stuff like migrations, knowledge transfer, etc…
So a couple of months ago I was asked the following questions:
> what are the requirements, server-wise, and/or client-wise, to be able to see the Skype for Business presence light for users we add in Outlook To:, Cc: and Bcc: fields in Outlook ?
> same question as above, what’s needed to be able to schedule a Skype for Business meeting from Outlook ? (so that we get the Skype phone conference local and toll numbers, the conference number, the PIN, etc… in the Outlook meeting)
For the two above specific questions, the important thing to keep in mind is that these two particular features : presence light in Outlook + schedule a Skype for Business meeting, there is no interaction between the Skype for Business client and the Exchange server. Also, there is no interaction between the Outlook client and the Skype for Business (or Lync) server. Everything go through the Skype For Business add-on for Outlook !
Yes you heard me : these two features are a client-to-client only interaction, through the Skype for Business for Outlook add-on !
But you need a few conditions for Outlook to be able to “link” these information with Skype. You must install the Skype for Business for Outlook add-on, and the user with which you’re logged in on Outlook must have the Skype SIP address in his list of E-Mail addresses.
NOTE: the Outlook user’s e-mail addresses are configured on the user’s Active Directory properties, through the Exchange Management Console or the Exchange Management Shell (or the Exchange Admin Center for Exchange 2013, 2016, Exchange Online)
Let’s take a user, randomly named “Sammy Krosoft”. His Exchange e-mail address is sammykrosoft@e2010domain.com. He’s on an On-Prem installation of Exchange 2010 (serving e2010domain.com SMTP domain). Now let’s assume he has a Skype for Business account in Office365, on a domain called “sammyservices.onmicrosoft.com” and his SIP address for Skype is “samdrey@sammyservices.onmicrosoft.com”. We want Outlook to display the presence indicator/light of other Skype users from his Skype organization, and also to be able to get Skype meeting details when organizing a Skype meeting from that messaging application.
So concretely here, we will:
1- if not already done, install the Skype for Business for Outlook add-on,
2- the “sammykrosoft@e2010domain.com” mailbox user must have the “SIP: samdrey@sammyservices.onmicrosoft.com” custom address his list of E-Mail address
NOTE: a “ SIP” address is not an SMTP address, there is no mail routing with this. It just serves as a “link” to enable Outlook to use the Skype for Business information (presence and meeting connection details) of a user logged in his Skype client with that SIP: address on the same workstation.
3- that’s pretty much it !
Let’s open his “E-mail addresses” properties in Exchange, and see what this “sammykrosoft@e2010domain.com” user has:
He just has an SMTP address ! That’s not enough to enable his Outlook account to retrieve the Lync information we want ! We must add that “SIP: samdrey@sammyservices.onmicrosoft.com” entry ! Let’s do it:
Add-> Custom Address, and type the SIP addres on the “E-mail address” field, and “SIP” as the E-mail type on the below graphical input box, or if you use Powershell and the “Set-Mailbox” cmdlet, that would be literally “SIP:samdrey@sammyservices.onmicrosoft.com”. So on the GUI you have to type “SIP” and the sip address separately:
And what will we see in the E-Mail addresses window: different domains for Exchange E-mail services and for Skype for Business … we’ll see soon if it works.
==> I’ll add a couple of screenshot of my Skype and my Outlook clients to show the results in a future update, but all the details you need to make this work are there.
To summarize a little bit what we did above, below is some illustrations with more generic accounts, hope it will help you guys make all the above crystal clear:
Here is an illustration of what we need with some more “generic” accounts
=> Nothing works: we get no presence information on Outlook for other Skype users, and we get an error trying to insert Skype meetings details.
=> We got presence working ! But we still get an error trying to insert Skype meetings details.
(*) Note that Skype presence info on Outlook for other users are also provided if either:
1- the SMTP e-mail we put in the recipients fields matches the SIP address of these users
Or
2- the user we put in the recipients fields has a different SMTP address from the SIP address of that user, but is resolved to a user who has the SIP address in his e-mail addresses, that Skype of “user@skype-org.com” is part of the same Skype’s org.
=> Both presence and Skype meeting insertion work ! Hurray !
(*)Note:
* like explained on the previous case, just using other words here – just to be sure everything is understood: Skype client will provide presence information to Outlook for the local user, as well as for any other users in To/Cc/Bcc for resolved users with a “SIP” address in Outlook’s “E-mail addresses” list (aka “proxyaddresses” parameter in Active Directory for users) which corresponds to a Lync user in the same organization as the local logged on Lync user.
CONCLUSION:
The above is true whether you have Skype on O365 and Exchange On-Prem (from Exchange 2010 to Exchange 2016), or Skype on premise and Exchange On-Prem, or Skype On-Prem and Exchange Online (O365), or Exchange Online and Skype Online…
Remember : these presence and Skype meeting details insertion features are given in Outlook by the Skype client. Outlook does NOT query the Skype server directly for either presence or meeting details. Skype 4 business client does it, and passes it on Outlook provided you have the SIP address of the Skype user on the Outlook mailbox’s user e-mail addresses.
I’ll add some screenshots to prove you guys that these are working on a future update, but the essential details to help you make this work are all there 
Cheers !
Sam