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So on my windows laptop, Lync 2013 is set to automatically configure the connection settings, however when I try to automatically configure the connection settings on my mac it doesn't work.

Is there any way to get the automatic connection settings from my windows laptop so that I can set them manually on my mac?

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    I'll take a stab at getting you pointed in the correct direction, but we might need to push this to SuperUser if no one here knows how to reverse engineer a Windows program on the Windows OS. – bmike Nov 8 '13 at 16:42
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I just downloaded Lync from Office 365 and had the exact same problem. After a bit of googling I realised that my Lync version was 14.01 and there was an update to 14.09 available. Updating solved my log in problem. Very simple (And stupid: 1. Why does Microsoft not update the package at Office 365? 2. How can login be broken to start with?).

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I don't know how easy it would be to dump the windows registry or the Lync settings or even sniff the network traffic to deduce which servers are being connected, but there are some nice articles on configuring Lync for Mac:

http://technet.microsoft.com/en-us/library/jj945440(v=office.14).aspx

Specifically, it has the following advice to sign in to Lync for Mac 2011 with your Office 365 account:

  • In the Microsoft Lync for Mac sign-in window, type your Office 365 email address, Microsoft Online Services ID, for example, someone@contoso.onmicrosoft.com, and password.
  • Click Advanced.
  • Under Authentication, clear the Use Kerberos check box.
  • Under Connection Settings, click Manual configuration.
  • In both the Internal Server Name box and the External Server Name box, type sipdir.online.lync.com:443.
  • Click OK.
  • Click Sign In.

If that doesn't help, you might need to go fully into the managed preferences and get the values from your IT group on how they set things up and muck in the registry emulation database that Lync maintains in ether of these files:

/Library/Preferences/MicrosoftLyncRegistrationDB.plist
~/Library/Preferences/ByHost/MicrosoftLyncRegistrationDB.<GUID>.plist

Both of the above links come from the overall guide to Lync on Mac

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