Using Communicator 2011 on a MacBook Pro to connect to Microsoft Lync 2010

If this saves someone some time, it’ll all be to the good; you wouldn’t believe how much time I wasted this morning on getting it to work. Unless you fall into the small section of the population who fit under that SEO-friendly title I wouldn’t bother continuing to read.

We at DevExpress are trying to find a better way to communicate. With staff all over the world, sometimes it’s hard to keep in touch. Over the past couple of weeks or so, we’ve been evaluating Microsoft Lync 2010 (previously known as Office Communications Server or some such). It’s all fine and good if you have Windows PCs across the company, but we have — shock, horror — a few Macs. Including this 13” MacBook Pro I now use for my day-to-day work.

I haven’t abandoned Windows completely of course: I still need a way to use Visual Studio for a start, and Windows Live Writer is still the best way to publish blog posts. So I have a virtual machine set up and use VMWare Fusion to serve it up. Last week while I was in the offices in Glendale we set up the Lync Communicator program in my VM and very nice it was too. Unfortunately, I don’t as a matter of course start up the VM in the morning and have it running constantly. Indeed the opposite is usually the norm: I only start the VM when I need to use those couple of apps I only have in their Windows versions. So, all in all, a bit of a waste.

This weekend I did a bit of research to see what I could do. It turns out that most of the Google hits out there were for previous versions of Microsoft Messenger for the Mac whereas I use Office 2011. It seems with the new version of Office for the Mac, Microsoft made Messenger “personal” and restricted it to only work with Windows Live. No Lync support. Well, fooey to that.

They did, however, create a “business” version that does work with Lync and called it Microsoft Communicator for Mac 2011 (it’s currently at version 13.1.0). So, I just install that and everything will be groovy, right? Short answer: no. Long answer: <gales of hysterical laughter>.

Here’s how to do it.

1. Download Microsoft Communicator for the Mac 2011. I got mine from my MSDN subscription. I don’t think it’s available as a public download. I also don’t know if it’s part of the Microsoft Lync Server download (I’ve not been involved in the setting up of the Lync server).

2. It’s an iso file, so just mount it and install it in the usual way on your Mac. When it asks you for your login details, ignore it and cancel out.

3. Now the fun step. It seems you have to install a certificate as a root certificate on the Mac in order for Communicator to work securely (briefly: the TLS connection needs an X509 certificate to authenticate the server). Azret gave me the URI on our NAS for ours, so I just double-clicked it from within Finder. A Keychain Access dialog came up asking me if I trusted the certificate. I clicked “Always Trust”, and... nothing happened. The certificate wasn’t added. If I tried to login with Communicator (you need your email address, user id, and password), I got this:

Obviously that’s not the way to do it, so I did more searching.

3 bis. This is where it gets squirrely. A lot of the advice out there is for the earlier Leopard version of Mac OS X or is for earlier versions of Messenger for the Mac and talks about having to add the X509Anchors keychain to the list in the Keychain Access utility (although it’s there by default in Leopard) and then adding your company server certificate to that. Sometimes, this advice forgets to add the word “Leopard” making it seem as if it’s valid for all versions of OS X. Since the keychain by default is restricted to writing, you have to issue chmod commands and such to open it up for modification. (See here for an example of such advice, although it does talk about SnowLeopard. Here’s a TechNet article that also sent me down another rabbit hole.)

The answer for SnowLeopard is actually very simple: open Keychain Access (it’s in /Applications/Utilities, although I tend to just use Spotlight to find apps); drag the root certificate to the login keychain; on the dialog that comes up click Always Trust.

4. Start up Communicator for the Mac, type in your email address, user id, and password (I also click the remember password checkbox) and click Sign In. Communicator starts up.

5. (This one’s a bummer.) It seems that Communicator for the Mac does not use Growl for alerts but instead uses its own system. Yah. Boo. Sucks.

As you can see, I set the dock icon bounce to Continuously (the default is Once Only). That way, if I miss someone pinging me immediately, at least I have a better chance of seeing it fairly quickly. I prefer Adium’s bounce once every 5 seconds option though.

Anyway: if you use a Mac and have to connect to your company’s Lync Server for inter-office communications, I hope this post helps.

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