Microsoft Messenger for Mac 7.0.2 and Microsoft Communicator for Mac 2011 are two instant messaging clients that are designed for use with the Apple operating system in an Office Communications Server or Lync Server 2010 unified communications environment. This combination of technologies requires user knowledge of the preliminary steps that are needed to get Mac IM clients connected to the Windows unified communications environment. This article gives you some handy troubleshooting steps that you can use to test Mac connectivity to the Communications Server or Lync Server 2010 pool servers.

Author: Edwin Joseph

Publication date: December 2010

Product version: Microsoft Messenger for Mac 7.0.2, Microsoft Communicator for Mac 2011 version 13.0.0, Communications Server 2007 R2, and Lync Server 2010

The purpose of this article is to help troubleshoot connectivity issues with Microsoft Messenger for Mac 7.0.2 and Microsoft Communicator for Mac 2011 with Office Communications Server 2007 R2 and Microsoft Lync Server 2010 communications software. It is intended for people who have limited experience with Mac OS. In this article, we will discuss how to troubleshoot network connectivity by using utilities such as Ping, port scan, and proxy setup. We will also look at installing certificates on the MAC and verifying certificate presence.  We will also walk through how to set up logging in Messenger for Mac 7.0.2 and Communicator for Mac 2011 for troubleshooting purposes.

 The versions of the MAC operating system that we are going to discuss in this article are:

  • Mac OS X Tiger (version 10.4)
  • Mac OS X Leopard (version 10.5)
  • Mac OS X Snow Leopard (version 10.6)

The steps used for troubleshooting with Mac OS X Leopard and Mac OS X Snow Leopard are nearly the same. The biggest differences are with Mac OS X Tiger.

Note. Finder is the explorer view of files and folder on Mac OS X.

 

The Command key is also commonly known as the apple key.

 

Common Network Utility

The steps in this section are the same for Mac OS X Tiger and Mac OS X Leopard. In this section, we are going to look at common network utilities such as Ping and port scan that enable us to troubleshoot network connectivity issues.

 To get to the network utility on the Mac:

  • 1. Open Finder, and then click Applications.
  • 2. In Applications, click Utilities.
  • 3. In Utilities, click Network Utility (Figure 1).

OR

  • 1. Open Finder, and then in Finder click Applications.
  • 2. Click Go on the menu, and then click Utilities.
  • 3. In Utilities, click Network Utility (Figure 1).

Figure 1 . Network Utility

Info: The Info tool is used to view information such as the hardware address of the network card, IP address, and link speed (Figure 2).

Figure 2. Info

Ping: This is the primary tool used to determine network presence of an IP address or a DNS name (Figure3). Use the Ping network utility with the IP address or fully qualified domain name (FQDN) of the Communications Server 2007 R2 or Lync Server 2010 pool. The tool validates that the IP address or FQDN is reachable by the client. If this fails, double check the IP address or FQDN, and if correct, troubleshoot a network connection problem.

Figure 3. Ping

Port Scan: This tool is used to scan for an open port on a network to ensure that it is available and listening (Figure 4). To troubleshoot sign-in problems, the typical port in question is 5061. Failing to connect to this port usually indicates a problem with a firewall on the client. If all users are failing to connect, it is most likely a problem with the server firewall, and this would require you to work with the administrators responsible for the topology.

Figure 4. Port Scan

Lookup: This tool is used to perform various DNS lookups, such as the MX Record, Name Server, and Start-of-authority record (Figure 5).

Figure 5. Lookup

Clear DNS Cache

To clear the DNS cache on a Mac the logged in user must have Root User access.

To clear the DNS cache via command, you must use the Mac terminal and do the following:

  1. Open Finder, and then click Applications.
  2. In Applications, click Utilities.
  3. In Utilities, click Terminal (Figure 6).

OR

  1. Open Finder, and then click Applications.
  2. Click Go on the menu, and then click Utilities.
  3. In Utilities, click Terminal (Figure 6)

.

Figure 6: Terminal

In the terminal window for Mac OS X Tiger, do the following:

Type lookupd -flushcache and press enter.

For Mac OS X Leopard and Snow Leopard, do the following:

Type dscacheutil -flushcache and press enter.

Troubleshooting Steps for Messenger for Mac 7.0.2 and Communicator for Mac 2011

This section will discuss troubleshooting steps specific to Messenger for Mac 7.0.2 and Communicator for Mac 2011.

Disable Automatic Login Messenger for Mac and Communicator for Mac 

The reason why we discuss this step in troubleshooting is because there is a known issue with Messenger for Mac 7.0.2. If automatic login is enabled and a user password changes or expires in Active Directory Domain Services, it causes an account lockout in Active Directory for that user.

1. Open System Preferences.

2. Select the Accounts options.

3. Click the lock that is at the bottom of the user's list box (Figure 7). 

Figure 7. Click the lock

4. Enter the user name and password.

5. Click the Login Items tab.

6. Highlight Microsoft Messenger or Microsoft Communicator, and then click the minus sign in the bottom left corner of the window to remove the item from automatic login (Figure 8).

 

Figure 8. Accounts

Disable Automatic Login at the User Level

 Prior to making these changes, ensure that the user remembers their user name and password.

  1. Open System Preferences.
  2. Select the Accounts pane.
  3. At the bottom of the list box, click Login Options.
    Change the following settings (Figure 9):
    1. For Mac OS X Tiger (version 10.4), clear the Automatically login as option.
    2. Mac OS X Leopard (version 10.5), set the Automatic login option to Disabled.
    3. Mac OS X Snow Leopard (version 10.6), set the Automatic login option to Off.

Figure 9. Accounts

Certificates

Certificates are a very important part of SIP-TLS connectivity. This means that it is important to know how to install a certificate on a Mac computer. The steps described in this section are the same for Mac OS X Tiger, Mac OS X Leopard, and Mac OS X Snow Leopard.

Verify installed certificates by doing the following:

  1. Open Finder, and then click Applications.
  2. In Applications, click Utilities.
  3. In Utilities, click Keychain Access (Figure 10).

OR

  1. Open Finder, and then click Applications.
  2. Clicks Go on the menu, and then click Utilities.
  3. In Utilities, click Keychain Access (Figure 10).

Figure 10. Keychain Access

Install the Certificate

To complete the certificate installation, see How to install a trusted root CA certificate and an intermediate CA certificate on a computer that is running Microsoft Entourage 2004 for Mac on a Mac OS X 10.3 or a Mac OS X 10.2 operating system.

To install the certificate, you must use the Keychain Access program. To start the Keychain Access program, double-click the certificate file. The Keychain Access program will automatically load, and it will display the Add Certificates dialog box (Figure 11).

 

Figure 11. Add Certificates

Microsoft Mac Messenger 7.0.2

In this section we will walk through setting up common settings for Microsoft Mac messenger 7.0.2.  To open the Preferences dialog box:

1. Open Messenger for Mac 7.0.2, and then press the Command + the comma keys.

OR

1. Open Messenger for Mac 7.0.2, and then click Messenger in the menu options.

2. On the Messenger menu, click Preferences.

3. Click the Accounts tab to change the e-mail address or network settings (Figure 12).

 

Figure 12. Preferences for Messenger for Mac 7.0.2

 Logging in Messenger for Mac 7.2

To enable logging:

1. Open the Preferences dialog box, and then click the General tab (Figure 13).

2. Ensure that Save a log to help troubleshoot Messenger problems is selected.

The logs are located in /Users/username/Documents/Microsoft Messenger.log.

 

Figure 13. Preferences general tab

Microsoft Communicator for Mac 2011

In this section we will walk through common configuration settings for Communicator for Mac 2011.

Note. Communicator for Mac 2011 supports only Intel processors.

To open the Preferences dialog box:

1. Open Communicator for Mac, and then press the Command + comma keys.

Or

1. Open Communicator for Mac, and then click Messenger on the Options menu.

2. On the Communicator menu, click Preferences (Figure 14).

3. Click the Accounts tab to change the e-mail address or change network settings (Figure 14).

 

Figure 14. Preferences for Communicator for Mac

Logging in Communicator for Mac 2011

1. To enable logging, click the General tab in the Preferences dialog box (Figure 15).

2. Select the Turn on logging for troubleshooting check box.

3. Document the log file location (in help) as /Users/username/Library/Logs Microsoft-Communicator-0.log (the zero will increment as the log file grows in size).

 

Figure 15. Preferences General tab

Summary

In this article we have looked at common, network-related troubleshooting steps and utilities for Mac OS X Tiger, Mac OS X Leopard, and Mac OS X Snow Leopard that are useful for Messenger for Mac 7.0.2 and Communicator for Mac 2011 users. Communicator for Mac 2011 is the latest instant messaging client from Microsoft for Mac users to connect to a Communications Server or Lync Server 2010 unified communications environment. Communicator for Mac 2011 can be installed only with a Mac OS that is running an Intel processor. Communicator for Mac 2011 provides good logging information for advanced troubleshooting.

Additional Information

To learn more, check out the following:

Lync Server Resources

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