Problem: Unable to configure Office 365 Lync on MacOS

Had a support request from a BYOD Mac client in our business today. Thought I’d document it as a little experiment.

Problem: Unable to configure Office 365 Lync on MacOS

We’re dealing with a MacBook Air, fairly recent, and either 10.8 Mountain Lion or 10.9 Mavericks on it. Didn’t really need to pin that down; the problem is more or less the same, although more prevalent in 10.9 with a change to default behaviour of MacOS.

The client had successfully navigated to the Office 365 downloads panel and begun the process, but the Mac wouldn’t let her install it.
The message was something along these lines:
“Lync installer can’t be opened because it is from an unidentified developer”

Unidentified? Microsoft? WTF?!
Why would Microsoft not digitally sign their installers?
A question for another day.

Gatekeeper
Anyway; this is “Gatekeeper” doing its thing – to protect Mac Users from rogue software. With version 10.8, Apple started “walling in” the MacOS garden; making it look a little more like the App Store for iPhone and iPad. The “walled garden” approach that exists for Apple’s mobile users has been an extraordinary part of its success; apps are vetted in-store with the intent of ensuring users have a virus- and malware-free time. New Mac users can expect something similar; the Mac App Store mirrors this approach, and everything that you install from there is automatically assumed by MacOS to be unthreatening.

You’ll find three options for GateKeeper. It’s not labelled as such, but you can find it here:
Apple menu > System Preferences… > Security & Privacy > General tab
Gatekeeper settings are under the header “Allow applications downloaded from:”

Searching for GateKeeper within the System Preferences panel will also find it.

There are three choices for allowing downloaded applications:
*Mac App Store (only! The iPhone way!)
*Mac App Store and identified developers (there’s a list at Apple I guess, and Microsoft aren’t on it for the purposes of this exercise).
*Anywhere (old school; install whatever you want, whenever you want).

Step 1: Deny the gatekeeper!
The first step in solving this problem is to “Allow applications downloaded from: Anywhere”.
Make that change and close System Preferences.

Step 2: Actually installing Lync

1) Sign into Office 365 at Portal.Microsoftonline.com

2) Navigate to “Downloads” for your account.
a. From the cog shape in the top right of the browser window, select “Office 365 Settings”
b. Select “Software: Install and manage software”
c. Select “Lync”

3) Follow the instructions there. Currently, it goes:

a. Download Lync. Install Lync.

b. Download the Lync update. Install the Lync update

At the conclusion of this, we had two Lync icons in the dock. You can remove one of them.
We can now configure Lync.

And, for bonus points, turn Gatekeeper back on; choose a setting other than “anywhere”

Step 3: Configuring Lync

A couple of Microsoft steps, then a couple for us.

1) In the Lync sign-in window, enter your User ID and password.

2) Click Advanced.
Make sure the “Use Kerberos” checkbox is unchecked

3) Click Connection Settings

The following is for our setup; hopefully yours works without it.

4) Click Manual configuration
5) For the Internal Server Name and the External Server Name, enter
sipdir.online.lync.com:443
Same entry in both boxes.

6) Click OK.

…and we’re ready to roll:

7) We should be back at the Lync for Mac sign-in window; click Sign In.

It’s that easy!

Have some other tips regarding changing the home domain for Lync users in a multi-domain Office 365 tenant, but perhaps another day.

Here endeth this little experiment 😉

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