So a question I get quite often is ‘is there a Communicator client for the Mac’?  The answer is yes, sort of.  Actually, the application is called Microsoft Messenger for the Mac and handles both Windows Live and Office Communications Server accounts.  For the purpose of this post, I will only be focusing on the corporate or Office Communications Server aspect of the Mac Messenger.  I wanted to create a post that answered some of the other common questions I get about this client.  So here they are and in no particular order;

Q) Can I use Mac Messenger for LCS 2005 pools?

A) Only the Mac Messenger 6 client will work against LCS 2005, Mac Messenger 7 is required for OCS 2007 or OCS 2007 R2 pools.

Q) Can I do audio/video calls with Mac Messenger?

A) Mac Messenger 7 now supports AV calls as well as PC to PC calls, however no PSTN calls are supported.

Q) How may I get a network traces from a Mac Messenger client?

A) Wireshark does offer a version for the Mac, available here

However, if you are using OS X then there is a faster, easier way to do this built-in.  Using the terminal application you may enable tcpdump logging directly on the interface and collect a logfile this way.  Once done, this file may be opened (or converted) using Wireshark.

Terminal Find the terminal application (usually under applications/utilities)

TCPDump tracing Enter the following command to start the trace (you may need to provide an admin password)

sudo tcpdump –i en0 –w /users/USERNAME/LOGFILENAME.LOG

The –i switch is interface, en0 is the default adapter and –w is the output location for the log.  See resources below for a link to a full article on the syntax.

TCPdump complete Once the trace is complete, use CTRL-C to stop the tracing.  Collect up the log at the location you specified.

Q) Can I get any logging from the Mac Messenger client?

A) Yes, logging is available via both the GUI and plist for the Mac Messenger client.  Unfortunately this logging is client application only and does NOT log SIP traffic.

Mac msg logging Logging option as seen in the Preferences/General tab.

Mac msg plist logging Logging option as seen in the com.microsoft.Messenger.rtc.plist file.

Mac msg plist Both plist files for the Mac Messenger client (located under /Users/username/Library/Preferences).

Mac msg log file Log file created once logging is enabled (located /Users/username/Documents/Microsoft Messenger.log).

The logging looks a little something like this (names changed for this post)

Microsoft Messenger 7.0.2 (090123)
MacOS version 10.4.9 (build 8S165)
2009/12/30 08:50:29.529  Office Communications Server LOGON STARTED:  USER = {DOMAINNAME\USERNAME}
2009/12/30 08:50:39.327 Trying HTTP connection to FQDNofOCSPOOL (port 443)
2009/12/30 08:50:39.327 Using proxy FQDNofPROXY (port 80)
2009/12/30 08:50:39.501 HTTP connection failed (114)
2009/12/30 08:50:39.501 HTTP transaction connect failed (114/0)
2009/12/30 08:50:58.319  Office Communications Server LOGON ENDED:  USER = {DOMAINNAME\USERNAME}
2009/12/30 08:50:58.641 Trying HTTP connection to images.edge.messenger.live.com (port 443)
2009/12/30 08:50:58.641 Using proxy FQDNofPROXY (port 80)
2009/12/30 08:50:58.686 Trying HTTP connection to components.premiumservices.aol.com (port 443)
2009/12/30 08:50:58.686 Using proxy FQDNofPROXY (port 80)
2009/12/30 08:50:58.922 Trying HTTP connection to sec.yimg.com (port 443)
2009/12/30 08:50:58.923 Using proxy FQDNofPROXY (port 80)
2009/12/30 08:53:49.507 Trying HTTP connection to FQDNofOCSPOOL (port 443)
2009/12/30 08:53:49.508 Using proxy FQDNofPROXY (port 80)
2009/12/30 08:53:49.678 HTTP connection failed (114)
2009/12/30 08:53:49.679 HTTP transaction connect failed (114/0)
2009/12/30 09:04:14.137  Office Communications Server LOGOFF ENDED:  USER = {DOMAINNAME\USERNAME}

Q) Ok, so can I get SIP logging from Mac Messenger?

A) Yes.  The easiest way is to collect logging from a PC client while talking to a Mac client, although this may not contain what you are looking for if the issue doesn’t involve IM features (ie. looking for in-band provisioning to the Mac client, etc.) 

Another method I have used is to create a TCP 5060 binding on the pool (not there by default in OCS 2007 but maybe added easily).  Then configure the Mac Messenger client to login via TCP 5060 using manual configuration.  Start a tcpdump trace and start the Mac Messenger client.  Once done, you should have a network trace over TCP 5060 so the SIP is in clear text and can be read.

Of course you could also enable SIP logging on the OCS pool, and filter specifically on the Mac user’s SIP address to collect SIP logging from the server side.

Q) Can I use Kerberos authentication with Mac Messenger?

A) Mac Messenger will support Kerberos authentication but it is only for the SIP login to the pool.  NTLM authentication will still be used for connections to the web services (i.e. address book downloads)

Q) Does the Mac Messenger client use the OCS Address Book?

A) Yes, the client downloads the ABS files in the same manner as the PC client and creates a GALCONTACTS.DB files located in /Users/username/Documents/Microsoft User Data/Messenger Corporate Data folder.

Q) Does the Mac Messenger client support distribution list expansion?

A) No, the client does not support this at this time.  If you have added DL’s (from a PC client) and then login from a Mac Messenger client, you will see the name but it will not expand.

Lots of other good information can be found in the Mac Messenger Deployment Guide(s), links below.  Items like installing certificates, uninstalling the client, items found in the plist file.  I know there are plenty of other questions that I might have missed, feel free to comment and I will try to address them.

Resources