Lync 2011 Mac - 14.0.11 unable to connect

Using VPN connecting to Lync is just spinning and unable to connect.
With Lync 14.0.10 and before, the Lync client would go through a few different servers to connect and failing before being able to connect to the external server. For each "internal" server it would then fail with:
InternalConnect, NLCreateConnection returned: -3264,
With Lync 14.0.11, instead of going down the list of servers it instead keeps on trying to go to the same internal server .

Hi ErikHMac,
To narrow down the issue, I would like to confirm the following questions.
Can you manually configure Lync client to connect to Lync Server ? (Manually enter the Internal/External Server Name or IP address)
Can you auto sign in from Internet ?
“With Lync 14.0.11, instead of going down the list of servers it instead keeps on trying to go to the same internal server .”
I did not find the problem that you mentioned.
Microsoft Lync 14.0.11 (150304)
MacOS version 10.10.2 (build 14C109)
2015/03/16 22:08:09.202 Office Communications Server LOGON STARTED: USER = {MyDomain\LyncDemo2}
2015/03/16 22:08:09.202 SIPService::Logon
2015/03/16 22:08:09.241 SIPService::OnEvent(IApplicationLayerEvent &), type: 1, HasSignedIn(): 0, HasSignedOut: 0
2015/03/16 22:08:09.265 SIPService::OnEvent(IApplicationLayerEvent &), type: 3, HasSignedIn(): 0, HasSignedOut: 0
2015/03/16 22:08:09.265 SIPService::OnEvent(IApplicationLayerEvent &), type: 1, HasSignedIn(): 0, HasSignedOut: 0
2015/03/16 22:08:09.269 SIPService::OnEvent(IApplicationLayerEvent &), type: 3, HasSignedIn(): 0, HasSignedOut: 0
2015/03/16 22:08:09.270 SIPService::OnEvent(IApplicationLayerEvent &), type: 1, HasSignedIn(): 0, HasSignedOut: 0
2015/03/16 22:08:09.271 SIPService::OnEvent(IApplicationLayerEvent &), type: 3, HasSignedIn(): 0, HasSignedOut: 0
2015/03/16 22:08:09.271 SIPService::OnEvent(IApplicationLayerEvent &), type: 1, HasSignedIn(): 0, HasSignedOut: 0
2015/03/16 22:08:09.273 SIPService::OnEvent(NModel::ILogonSessionEvent), hr: 0x0, oldState: 10, newState: 20, direction: 0
2015/03/16 22:08:09.421 InternalConnect, NLResolveAddress returned: 0
2015/03/16 22:08:09.423 IsLocalAddress, 'sipinternal.MyDomain.com' is not a local address
2015/03/16 22:08:09.423 FShouldUseProxy, is returning 1
2015/03/16 22:08:09.424 Connecting to sipinternal.MyDomain.com (port 5061)
2015/03/16 22:08:13.502 InternalConnect, NLCreateConnection returned: 0,
2015/03/16 22:08:13.502 InternalConnect, NLCopyConnectionBinding returned: 0,
2015/03/16 22:08:24.009 InternalConnect, NLCreateConnection returned: -3259,
2015/03/16 22:08:24.009 FUsingHttpsTunnelProxies, returning: 0
2015/03/16 22:08:24.011 Listening thread got exception -3259
2015/03/16 22:08:26.072 InternalConnect, NLResolveAddress returned: 0
2015/03/16 22:08:26.073 IsLocalAddress, 'sip.MyDomain.com' is not a local address
2015/03/16 22:08:26.073 FShouldUseProxy, is returning 1
2015/03/16 22:08:26.074 Connecting to sip.MyDomain.com (port 443)
2015/03/16 22:08:26.364 InternalConnect, NLCreateConnection returned: 0,
2015/03/16 22:08:26.364 InternalConnect, NLCopyConnectionBinding returned: 0,
2015/03/16 22:08:28.438 InternalConnect, NLResolveAddress returned: 0
2015/03/16 22:08:28.439 IsLocalAddress, 'sip.MyDomain.com' is not a local address
2015/03/16 22:08:28.439 FShouldUseProxy, is returning 1
2015/03/16 22:08:28.440 Connecting to sip.MyDomain.com (port 5061)
2015/03/16 22:08:28.768 InternalConnect, NLCreateConnection returned: 0,
2015/03/16 22:08:28.768 InternalConnect, NLCopyConnectionBinding returned: 0,
2015/03/16 22:08:29.194 HRESULT GetLinkSpeed(DWORD, DWORD*, WIN_BOOL*): ip 192.168.100.187, link speed 0
2015/03/16 22:08:29.194 HRESULT GetLinkSpeed(DWORD, DWORD*, WIN_BOOL*): Working around 0 link speed
2015/03/16 22:08:29.196 SIPService::OnEvent(NModel::ILogonSessionEvent), hr: 0x0, oldState: 20, newState: 30, direction: 0
2015/03/16 22:08:29.198 SIPService::OnEvent(IApplicationLayerEvent &), type: 3, HasSignedIn(): 0, HasSignedOut: 0
2015/03/16 22:08:29.199 SIPService::OnEvent(IApplicationLayerEvent &), type: 1, HasSignedIn(): 0, HasSignedOut: 0
2015/03/16 22:08:29.204 SIPService::OnEvent(IApplicationLayerEvent &), type: 3, HasSignedIn(): 0, HasSignedOut: 0
2015/03/16 22:08:29.204 SIPService::OnEvent(IApplicationLayerEvent &), type: 1, HasSignedIn(): 0, HasSignedOut: 0
2015/03/16 22:08:29.204 SIPService::OnEvent(IApplicationLayerEvent &), type: 3, HasSignedIn(): 0, HasSignedOut: 0
2015/03/16 22:08:29.204 SIPService::OnEvent(IApplicationLayerEvent &), type: 1, HasSignedIn(): 0, HasSignedOut: 0
2015/03/16 22:08:29.204 SIPService::OnEvent(IApplicationLayerEvent &), type: 3, HasSignedIn(): 0, HasSignedOut: 0
2015/03/16 22:08:29.204 SIPService::OnEvent(IApplicationLayerEvent &), type: 1, HasSignedIn(): 0, HasSignedOut: 0
2015/03/16 22:08:29.222 SIPService::OnEvent(IApplicationLayerEvent &), type: 3, HasSignedIn(): 0, HasSignedOut: 0
2015/03/16 22:08:29.223 SIPService::OnEvent(IApplicationLayerEvent &), type: 1, HasSignedIn(): 0, HasSignedOut: 0
2015/03/16 22:08:29.256 SIPService::OnEvent(IApplicationLayerEvent &), type: 3, HasSignedIn(): 0, HasSignedOut: 0
2015/03/16 22:08:29.256 SIPService::OnEvent(IApplicationLayerEvent &), type: 1, HasSignedIn(): 0, HasSignedOut: 0
2015/03/16 22:08:29.264 SIPService::OnEvent(IApplicationLayerEvent &), type: 3, HasSignedIn(): 0, HasSignedOut: 0
2015/03/16 22:08:29.264 SIPService::OnEvent(IApplicationLayerEvent &), type: 1, HasSignedIn(): 0, HasSignedOut: 0
2015/03/16 22:08:29.286 SIPService::OnEvent(IApplicationLayerEvent &), type: 3, HasSignedIn(): 0, HasSignedOut: 0
2015/03/16 22:08:29.286 SIPService::OnEvent(IApplicationLayerEvent &), type: 1, HasSignedIn(): 0, HasSignedOut: 0
2015/03/16 22:08:29.293 SIPService::OnEvent(IApplicationLayerEvent &), type: 3, HasSignedIn(): 0, HasSignedOut: 0
2015/03/16 22:08:29.293 SIPService::OnEvent(IApplicationLayerEvent &), type: 1, HasSignedIn(): 0, HasSignedOut: 0
2015/03/16 22:08:29.434 SIPService::OnEvent(IApplicationLayerEvent &), type: 3, HasSignedIn(): 0, HasSignedOut: 0
2015/03/16 22:08:29.434 SIPService::OnEvent(IApplicationLayerEvent &), type: 1, HasSignedIn(): 0, HasSignedOut: 0
2015/03/16 22:08:29.437 SIPService::OnEvent(IApplicationLayerEvent &), type: 3, HasSignedIn(): 1, HasSignedOut: 0
2015/03/16 22:08:29.437 virtual void SIPService::OnIdleHandleLogonSucceeded()
2015/03/16 22:08:29.440 Office Communications Server LOGON ENDED: USER = {MyDomain\LyncDemo2}
2015/03/16 22:08:30.101 IsLocalAddress, 'lyncpool01' is not a local address
2015/03/16 22:08:30.101 FShouldUseProxy, is returning 1
2015/03/16 22:08:30.101 IsLocalAddress, 'lyncpool01' is not a local address
2015/03/16 22:08:30.101 FShouldUseProxy, is returning 1
Best regards,
Eric
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0x94f26000 - 0x94f7bff7 com.apple.QuickLookFramework (5.0 - 622.3) <3C6ADC02-2C67-361B-B042-47DDCC0EDA5F> /System/Library/Frameworks/QuickLook.framework/Versions/A/QuickLook
0x95c83000 - 0x95cf8ffb com.apple.framework.IOKit (2.0.1 - 907.1.13) <86D72735-9DFB-35C8-83F7-CE0DCF17D354> /System/Library/Frameworks/IOKit.framework/Versions/A/IOKit
0x95efa000 - 0x95f08ff7 libz.1.dylib (53) <858B4D9F-D87E-3D81-B07A-DF9632BD185F> /usr/lib/libz.1.dylib
0x9633a000 - 0x9633afff com.apple.Carbon (154 - 157) <C49AD4A1-8DE3-357D-AEF3-D6CD39EA91EF> /System/Library/Frameworks/Carbon.framework/Versions/A/Carbon
0x964cc000 - 0x964ccfff com.apple.Cocoa (6.8 - 20) <407DC9E6-BBCE-3D34-9BBB-00C90584FFDF> /System/Library/Frameworks/Cocoa.framework/Versions/A/Cocoa
0x96bd0000 - 0x96e3dff6 com.apple.security (7.0 - 55471) <5FCF76B2-92C6-3404-87D3-91B3F6E203AA> /System/Library/Frameworks/Security.framework/Versions/A/Security
0x96e68000 - 0x96f54ff7 libxml2.2.dylib (26) <32040145-6FD6-3AD2-B98B-39F73BF9AC47> /usr/lib/libxml2.2.dylib
0x980f9000 - 0x98112fff com.apple.Kerberos (3.0 - 1) <91F17EB2-C70C-359C-B09D-96B52D2A9C9F> /System/Library/Frameworks/Kerberos.framework/Versions/A/Kerberos
0x98116000 - 0x98147ff4 com.apple.securityinterface (9.0 - 55047) <0D5ED2B8-C973-3C91-BA45-22501A043263> /System/Library/Frameworks/SecurityInterface.framework/Versions/A/SecurityInterface
0x9849e000 - 0x98610ffb com.apple.audio.toolbox.AudioToolbox (1.9 - 1.9) <E5FFD35D-18CF-333C-BECE-39F8E47BE707> /System/Library/Frameworks/AudioToolbox.framework/Versions/A/AudioToolbox
0x98613000 - 0x98621ff3 com.apple.opengl (9.0.83 - 9.0.83) <16CFFD50-217E-3E18-88AF-7F2AD980628B> /System/Library/Frameworks/OpenGL.framework/Versions/A/OpenGL
0x9ac69000 - 0x9ac86ffb libresolv.9.dylib (54) <3EC12A7F-6BA1-3976-9F1F-6A4B76303028> /usr/lib/libresolv.9.dylib
0x9b41b000 - 0x9b5c7ff1 com.apple.QuartzCore (1.8 - 332.0) <07F9B77F-35A2-3D21-99FA-CD3FCE5B9C7B> /System/Library/Frameworks/QuartzCore.framework/Versions/A/QuartzCore
0x9b8bf000 - 0x9b8c0fff libSystem.B.dylib (1197.1.1) <C58F0CC9-C1FD-3024-9358-D3359A6BBCAD> /usr/lib/libSystem.B.dylib
0x9bb23000 - 0x9bd9fff7 com.apple.QuickTime (7.7.3 - 2826.0.1) <42542002-DCFF-3675-B919-440EC5057D56> /System/Library/Frameworks/QuickTime.framework/Versions/A/QuickTime
0x9bda0000 - 0x9bdf5ff7 com.apple.audio.CoreAudio (4.2.0 - 4.2.0) <0F1C111F-1E64-33BB-A69F-14643B3037D5> /System/Library/Frameworks/CoreAudio.framework/Versions/A/CoreAudio
Model: iMac11,1, BootROM IM111.0034.B02, 4 processors, Intel Core i7, 2.8 GHz, 8 GB, SMC 1.54f36
Graphics: ATI Radeon HD 4850, ATI Radeon HD 4850, PCIe, 512 MB
Memory Module: BANK 0/DIMM0, 2 GB, DDR3, 1067 MHz, 0x80AD, 0x484D54313235533642465238432D47372020
Memory Module: BANK 1/DIMM0, 2 GB, DDR3, 1067 MHz, 0x80AD, 0x484D54313235533642465238432D47372020
Memory Module: BANK 0/DIMM1, 2 GB, DDR3, 1067 MHz, 0x80AD, 0x484D54313235533642465238432D47372020
Memory Module: BANK 1/DIMM1, 2 GB, DDR3, 1067 MHz, 0x80AD, 0x484D54313235533642465238432D47372020
AirPort: spairport_wireless_card_type_airport_extreme (0x168C, 0x8F), Atheros 9280: 4.0.74.0-P2P
Bluetooth: Version 4.2.0f6 12982, 3 services, 23 devices, 1 incoming serial ports
Network Service: Ethernet, Ethernet, en0
Serial ATA Device: ST31000528ASQ, 1 TB
Serial ATA Device: OPTIARC DVD RW AD-5680H
USB Device: Hub
USB Device: PT-9500PC
USB Device: DG Dashuo USB-V4.0
USB Device: BRCM2046 Hub
USB Device: Bluetooth USB Host Controller
USB Device: Internal Memory Card Reader
USB Device: Hub
USB Device: Keyboard Hub
USB Device: Apple Keyboard
USB Device: IR Receiver
USB Device: Built-in iSight
Thunderbolt Bus:
I've checked out all the forums and walked through some of the steps and I think I figured out my issue: I have NO certificate in my keychain whatsoever; Known or unknown. My account/system administrator here is unsure how to get me a certificate because
we use Office 365 and he says when I install Lync or try to log in it should be giving me a new certificate. Does anyone know how to get me a certificate? Or know how my administrator will get it to install a new certificate?

If your OSX filesystem is formatted as: Mac OS Extended (Case-sensitive, Journaled) then the Lync 14.0.7 upgrade will immediately crash. You need to follow the instructions
in the blog post referenced below:
http://preston4tw.blogspot.com.au/2013/12/microsoft-lync-2011-for-mac-1407-bug.html
This will fix the immediate crash and if your Lync worked before the upgrade to 14.0.7 it should work again. If you have certificate problems then this would not be the only
fix required.

Lync 2011 for MAC and Lync 2013 Server Std

Hello,
We are using a Lync 2013 Std (single-server) as a POC. It works fine for Windows-clients but I cannot connect using Lync 2011 for MAC from any MAC machine.
Using automatic configuration, I cannot connect to the Lync server.
Using manual configuration (I tried putting in just the server name and adding port 5061 to it, both to no avail) I keep getting 'Sign in to Lync failed. Please verify your credentials and try again.'.
Lync server is on the latest CU version with all components, MAC clients are on update 140321.
I noticed that Lync tries to create the OC_keycontainer_username@domain, but it seems not te be created. It flashes by and disappears again when the client fails to login. I have imported the Lync server certificate, issued by our windows 2012
root CA, on the Mac clients and have stored it in the 'Login' container.
Does anybody know if Lync2011 for Mac is supported for use with Lync server 2013 Std?
Cheers

Hi,
To clear cached data and corrupted certificates in Lync, you can do the following steps:
First, delete the following folders:
Users/Home Folder/Library/Caches/com.microsoft.Lync
Users/Home Folder/Documents/Microsoft User Data/Microsoft Lync History
Then, delete any corrupted or cached certificates. To do this, follow these steps:
1. Open the Keychain Access certificate management utility. To do this, in Finder, click Applications, click Utilities, and then click Keychain Access. Or, search for Keychain Access by using Spotlight.
2. In the left pane, click login, and then click Certificates.
3. In the right pane, find a certificate that's named Unknown or Communications Server, select it, and then delete it.
Note: You may have to unlock your keychain by using your password.
4. Close Keychain Access.
5. Restart Lync for Mac.
You can refer to Lync Mac for Lync Server online, but similar for Lync on-premises:
http://support.microsoft.com/kb/2629861
Best Regards,
Eason Huang
Eason Huang
TechNet Community Support

Contact pictures not displaying in Lync 2011 for Mac

Using Lync 2011 for Mac I'm not seeing any contact pictures (including my own), though I can see them when signed into Lync 2013 on a Windows PC (7, 8.1, and 10 Technical Preview for Enterprises).
My company uses O365 hosted Exchange and on premise Lync Server.
I'm using OSX 10.10.1 (on a 2014 Air) and Lync for Mac 2011 14.0.10 (141024). I have AutoUpdate set to automatically check weekly and I manually checked (button at the bottom of Microsoft AutoUpdate) so I believe I'm running the current release.
Logging in with another user account on my same Mac/Lync install has the same issue
Another user account on their own Mac also has the same issue
It's also worth noting that the same issue arises when signing into Lync for Android and iOS as well, but not on Windows (Lync 2013).
Any thoughts? Thank you very much for your time and assistance.
Also, my apologies for putting this question in this subforum, but I didn't see any main forum for Office for Mac or Lync 2011 or Lync for Mac at all. If there is such here on technet, please drop the link here and I'll move the thread.

Hi abacus02,
On mobile, you have no control over how photos are displayed. Lync Mobile can only display photos retrieved from Active Directory or SharePoint, it cannot display a photo from a URL. If a user
is displaying a photo from a URL and there is a photo in AD, it will display the photo from AD. If there is no photo in AD, it will display no photo at all.
About Lync for Mac, as I know Lync 2011 for Mac does not support high resolution images. Only in Lync 2013,
In Lync 2013, when the user’s photo experience has been migrated to Exchange 2013 and they are using Lync 2013, high resolution photos can be used.
So please tell us where the photos are stored, we need more information to troubleshoot the issue.
Best regards,
Eric

AD stored user Photos do not display in Lync for Mac 2011

I'm using Lync for Mac 2011 14.0.9 and the my user photo as well as the photos of other users who are using photos stored in our AD do not display. This behaviour has been occurring at least since 14.0.5. The behaviour occurs regardless of whether
I sign in using Kerberos or name / Password. This behaviour is common for all our Mac lync users. The only photos that display are ones from windows lync users that have chosen to use a photo that is stored on the internet somewhere.
The Lync for Mac 2011 client is running against Lync Server 2010 and Exchange 2010 servers.
I also have the common problem that I cannot search the global address book for lync users. Maybe this is related but none of the reports I've seen about the address book search have mentioned anything about photos not displaying.
Anyone Experience similar issues or know where I could start to find the problem with the contacts display? It used to work correctly way back in 14.0.2 and subsequently an update around 14.0.5 killed the features for me.
Oh and the Mac is running OSX 10.9 but the issues also occurred in OSX 10.8
Thanks!

Hi,
Did you choose “Show a picture from a web address” on Windows Lync 2010 client? If yes, on Windows Lync 2010 client, choose “Default corporate picture” instead of “Show a picture from a web address”. Then open Lync 2011 on Mac computer to test the issue.
The choose will sync to all Lync clients for the same Lync account.
Best Regards,
Eason Huang
Eason Huang
TechNet Community Support

Lync 2011 for MAC not connecting externally to On-Premise Lync 2013

Hello,
Hopefully someone has some idea on this or a better direction for me to follow. So currently I have an issue where Lync 2011 for MAC clients will not connect when external to my On-Premise Lync 2013 servers. Everything to do with my Windows based clients
and even cell phone based client’s works just fine. It is currently only Lync 2011 for MAC which will not correct externally.
I did initially have the logon problem internally as noted by other posts online when using an internal CA certificate with Lync. But with the internal certificate imported onto the MAC when internally connected Lync 2011 will login just fine. Now in my
setup I do have a TMG server that clients are connecting to that forwards the connections onto my Lync servers when connecting externally. When I review live real time logs to see what’s connecting to the external URL for Windows based clients I can see them
connect in on port 443 no problem.
But with the MAC I don’t see any attempt from it to connect to the URL like I see with the Windows clients. Now below is what shows up in the Microsoft-Lync.log generated by the MAC. Now initially looking at the log I thought my problem was the fact when
Lync 2011 tires to connect when external that it was doing so on port 5061 which we don’t have open. So I tired entering external.mydomain.com:443 in for my external server in the setup.
And while rechecking the log after doing so shows like it is now trying to connect on port 443. When reviewing TMG I again see no connection attempt by the MAC to connect to the Lync external url or on port 443. Further research so far into the problem has
come up empty on the subject. And most other cases where people report problems connecting externally they are using some form of online service like Office 365. So at this point I am not even sure if Lync 2011 for MAC is supposed to work externally with On-Premise
Lync 2013 deployments or not. If anyone has an thought’s or idea’s please share them as at this point I am stuck on this issue.
Microsoft Lync 14.0.10 (141024)
MacOS version 10.7.5 (build 11G63)
2015/01/08 08:51:11.807 SIPService::OnEvent(IApplicationLayerEvent &), type: 0, HasSignedIn(): 0, HasSignedOut: 0
2015/01/08 08:51:12.670 SIPService::OnEvent(NModel::ILogonSessionEvent), hr: 0x0, oldState: 0, newState: 10, direction: 0
2015/01/08 08:51:12.682 SIPService::OnEvent(IApplicationLayerEvent &), type: 1, HasSignedIn(): 0, HasSignedOut: 0
2015/01/08 08:51:12.685 SIPService::OnEvent(IApplicationLayerEvent &), type: 3, HasSignedIn(): 0, HasSignedOut: 0
2015/01/08 08:51:20.192 Office Communications Server LOGON STARTED: USER = {nsayewich}
2015/01/08 08:51:20.197 SIPService::Logon
2015/01/08 08:51:20.281 SIPService::OnEvent(IApplicationLayerEvent &), type: 1, HasSignedIn(): 0, HasSignedOut: 0
2015/01/08 08:51:20.543 SIPService::OnEvent(IApplicationLayerEvent &), type: 3, HasSignedIn(): 0, HasSignedOut: 0
2015/01/08 08:51:20.543 SIPService::OnEvent(IApplicationLayerEvent &), type: 1, HasSignedIn(): 0, HasSignedOut: 0
2015/01/08 08:51:20.566 SIPService::OnEvent(IApplicationLayerEvent &), type: 3, HasSignedIn(): 0, HasSignedOut: 0
2015/01/08 08:51:20.566 SIPService::OnEvent(IApplicationLayerEvent &), type: 1, HasSignedIn(): 0, HasSignedOut: 0
2015/01/08 08:51:20.568 SIPService::OnEvent(IApplicationLayerEvent &), type: 3, HasSignedIn(): 0, HasSignedOut: 0
2015/01/08 08:51:20.568 SIPService::OnEvent(IApplicationLayerEvent &), type: 1, HasSignedIn(): 0, HasSignedOut: 0
2015/01/08 08:51:20.600 SIPService::OnEvent(NModel::ILogonSessionEvent), hr: 0x0, oldState: 10, newState: 20, direction: 0
2015/01/08 08:51:21.535 InternalConnect, NLResolveAddress returned: -3176
2015/01/08 08:51:21.537 IsLocalAddress, 'internal.mydomain.com' is not a local address
2015/01/08 08:51:21.537 FShouldUseProxy, is returning 1
2015/01/08 08:51:21.537 Connecting to internal.mydomain.com (port 0)
2015/01/08 08:51:21.537 InternalConnect, NLCreateConnection returned: -3176,
2015/01/08 08:51:21.537 FUsingHttpsTunnelProxies, returning: 0
2015/01/08 08:51:21.537 Listening thread got exception -3176
2015/01/08 08:51:23.632 InternalConnect, NLResolveAddress returned: 0
2015/01/08 08:51:23.633 IsLocalAddress, 'external.mydomain.com' is not a local address
2015/01/08 08:51:23.633 FShouldUseProxy, is returning 1
2015/01/08 08:51:23.633 Connecting to external.mydomain.com (port 5061)
2015/01/08 08:51:38.004 InternalConnect, NLCreateConnection returned: -3259,
2015/01/08 08:51:38.004 FUsingHttpsTunnelProxies, returning: 0
2015/01/08 08:51:38.004 Listening thread got exception -3259
2015/01/08 08:51:38.005 InternalConnect, NLResolveAddress returned: 0
2015/01/08 08:51:38.006 IsLocalAddress, 'external.mydomain.com' is not a local address
2015/01/08 08:51:38.006 FShouldUseProxy, is returning 1
2015/01/08 08:51:38.006 Connecting to external.mydomain.com (port 5061)
2015/01/08 08:51:53.008 InternalConnect, NLCreateConnection returned: -3259,
2015/01/08 08:51:53.008 FUsingHttpsTunnelProxies, returning: 0
2015/01/08 08:51:53.008 Listening thread got exception -3259
2015/01/08 08:51:55.026 SIPService::OnEvent(NModel::ILogonSessionEvent), hr: 0x80072743, oldState: 20, newState: 10, direction: 1
2015/01/08 08:51:55.026 Login (1) failed with error: (0.-2147014845)
2015/01/08 08:51:55.036 SIPService::OnEvent(IApplicationLayerEvent &), type: 8, HasSignedIn(): 0, HasSignedOut: 0
2015/01/08 08:51:55.036 SIPService::OnEvent(IApplicationLayerEvent &), type: 2, HasSignedIn(): 0, HasSignedOut: 0
2015/01/08 08:51:55.036 SIPService::OnEvent(IApplicationLayerEvent &), type: 4, HasSignedIn(): 0, HasSignedOut: 0
2015/01/08 08:51:55.037 SIPService::OnEvent(IApplicationLayerEvent &), type: 6, HasSignedIn(): 0, HasSignedOut: 0
2015/01/08 08:51:55.037 SIPService::OnEvent(IApplicationLayerEvent &), type: 4, HasSignedIn(): 0, HasSignedOut: 0
2015/01/08 08:51:55.038 SIPService::OnEvent(IApplicationLayerEvent &), type: 6, HasSignedIn(): 0, HasSignedOut: 0
2015/01/08 08:51:55.038 SIPService::OnEvent(IApplicationLayerEvent &), type: 4, HasSignedIn(): 0, HasSignedOut: 0
2015/01/08 08:51:55.040 SIPService::OnEvent(IApplicationLayerEvent &), type: 6, HasSignedIn(): 0, HasSignedOut: 0

Hi Nicholas Sayewich,
I tested in my lab and without any problem.
I also use TMG as Reverse Proxy and without configuring SRV records (My ISP don’t support SRV), after importing the root certificate onto MacBook, I can sign into Lync everywhere(internal
and external).
Please make sure that the certificate is set up to
Always Trust .
http://blogs.technet.com/b/nexthop/archive/2008/03/05/how-to-install-a-trusted-root-ca-certificate-on-osx-leopard-for-use-with-messenger-for-macintosh.aspx
And my log for your reference:
Microsoft Lync 14.0.10 (141024)
MacOS version 10.10.1 (build 14B25)
2015/01/09 22:40:15.802 SIPService::OnEvent(IApplicationLayerEvent &), type: 0, HasSignedIn(): 0, HasSignedOut: 0
2015/01/09 22:40:16.486 SIPService::OnEvent(NModel::ILogonSessionEvent), hr: 0x0, oldState: 0, newState: 10, direction: 0
2015/01/09 22:40:16.493 SIPService::OnEvent(IApplicationLayerEvent &), type: 1, HasSignedIn(): 0, HasSignedOut: 0
2015/01/09 22:40:16.496 SIPService::OnEvent(IApplicationLayerEvent &), type: 3, HasSignedIn(): 0, HasSignedOut: 0
2015/01/09 22:40:32.595 Office Communications Server LOGON STARTED: USER = {MyDomain\LyncUser1}
2015/01/09 22:40:32.596 SIPService::Logon
2015/01/09 22:40:32.633 SIPService::OnEvent(IApplicationLayerEvent &), type: 1, HasSignedIn(): 0, HasSignedOut: 0
2015/01/09 22:40:32.737 SIPService::OnEvent(IApplicationLayerEvent &), type: 3, HasSignedIn(): 0, HasSignedOut: 0
2015/01/09 22:40:32.738 SIPService::OnEvent(IApplicationLayerEvent &), type: 1, HasSignedIn(): 0, HasSignedOut: 0
2015/01/09 22:40:32.743 SIPService::OnEvent(IApplicationLayerEvent &), type: 3, HasSignedIn(): 0, HasSignedOut: 0
2015/01/09 22:40:32.743 SIPService::OnEvent(IApplicationLayerEvent &), type: 1, HasSignedIn(): 0, HasSignedOut: 0
2015/01/09 22:40:32.744 SIPService::OnEvent(IApplicationLayerEvent &), type: 3, HasSignedIn(): 0, HasSignedOut: 0
2015/01/09 22:40:32.744 SIPService::OnEvent(IApplicationLayerEvent &), type: 1, HasSignedIn(): 0, HasSignedOut: 0
2015/01/09 22:40:32.754 SIPService::OnEvent(NModel::ILogonSessionEvent), hr: 0x0, oldState: 10, newState: 20, direction: 0
2015/01/09 22:40:33.080 InternalConnect, NLResolveAddress returned: 0
2015/01/09 22:40:33.082 IsLocalAddress, 'sipinternal.MyDomain.com' is not a local address
2015/01/09 22:40:33.082 FShouldUseProxy, is returning 1
2015/01/09 22:40:33.082 Connecting to sipinternal.MyDomain.com (port 5061)
2015/01/09 22:40:48.008 InternalConnect, NLCreateConnection returned: -3259,
2015/01/09 22:40:48.008 FUsingHttpsTunnelProxies, returning: 0
2015/01/09 22:40:48.010 Listening thread got exception -3259
2015/01/09 22:40:50.043 InternalConnect, NLResolveAddress returned: 0
2015/01/09 22:40:50.044 IsLocalAddress, 'sip.MyDomain.com' is not a local address
2015/01/09 22:40:50.044 FShouldUseProxy, is returning 1
2015/01/09 22:40:50.044 Connecting to sip.MyDomain.com (port 443)
2015/01/09 22:40:50.896 InternalConnect, NLCreateConnection returned: 0,
2015/01/09 22:40:50.896 InternalConnect, NLCopyConnectionBinding returned: 0,
2015/01/09 22:40:52.980 InternalConnect, NLResolveAddress returned: 0
2015/01/09 22:40:52.981 IsLocalAddress, 'sip.MyDomain.com' is not a local address
2015/01/09 22:40:52.981 FShouldUseProxy, is returning 1
2015/01/09 22:40:52.981 Connecting to sip.MyDomain.com (port 5061)
2015/01/09 22:40:53.291 InternalConnect, NLCreateConnection returned: 0,
2015/01/09 22:40:53.291 InternalConnect, NLCopyConnectionBinding returned: 0,
2015/01/09 22:40:53.522 HRESULT GetLinkSpeed(DWORD, DWORD*, WIN_BOOL*): ip 192.168.100.187, link speed 0
2015/01/09 22:40:53.522 HRESULT GetLinkSpeed(DWORD, DWORD*, WIN_BOOL*): Working around 0 link speed
2015/01/09 22:40:53.526 SIPService::OnEvent(NModel::ILogonSessionEvent), hr: 0x0, oldState: 20, newState: 30, direction: 0
2015/01/09 22:40:53.528 SIPService::OnEvent(IApplicationLayerEvent &), type: 3, HasSignedIn(): 0, HasSignedOut: 0
2015/01/09 22:40:53.529 SIPService::OnEvent(IApplicationLayerEvent &), type: 1, HasSignedIn(): 0, HasSignedOut: 0
2015/01/09 22:40:53.536 SIPService::OnEvent(IApplicationLayerEvent &), type: 3, HasSignedIn(): 0, HasSignedOut: 0
2015/01/09 22:40:53.536 SIPService::OnEvent(IApplicationLayerEvent &), type: 1, HasSignedIn(): 0, HasSignedOut: 0
2015/01/09 22:40:53.536 SIPService::OnEvent(IApplicationLayerEvent &), type: 3, HasSignedIn(): 0, HasSignedOut: 0
2015/01/09 22:40:53.536 SIPService::OnEvent(IApplicationLayerEvent &), type: 1, HasSignedIn(): 0, HasSignedOut: 0
2015/01/09 22:40:53.536 SIPService::OnEvent(IApplicationLayerEvent &), type: 3, HasSignedIn(): 0, HasSignedOut: 0
2015/01/09 22:40:53.536 SIPService::OnEvent(IApplicationLayerEvent &), type: 1, HasSignedIn(): 0, HasSignedOut: 0
2015/01/09 22:40:53.555 SIPService::OnEvent(IApplicationLayerEvent &), type: 3, HasSignedIn(): 0, HasSignedOut: 0
2015/01/09 22:40:53.555 SIPService::OnEvent(IApplicationLayerEvent &), type: 1, HasSignedIn(): 0, HasSignedOut: 0
2015/01/09 22:40:53.583 SIPService::OnEvent(IApplicationLayerEvent &), type: 3, HasSignedIn(): 0, HasSignedOut: 0
2015/01/09 22:40:53.584 SIPService::OnEvent(IApplicationLayerEvent &), type: 1, HasSignedIn(): 0, HasSignedOut: 0
2015/01/09 22:40:53.592 SIPService::OnEvent(IApplicationLayerEvent &), type: 3, HasSignedIn(): 0, HasSignedOut: 0
2015/01/09 22:40:53.592 SIPService::OnEvent(IApplicationLayerEvent &), type: 1, HasSignedIn(): 0, HasSignedOut: 0
2015/01/09 22:40:53.615 SIPService::OnEvent(IApplicationLayerEvent &), type: 3, HasSignedIn(): 0, HasSignedOut: 0
2015/01/09 22:40:53.615 SIPService::OnEvent(IApplicationLayerEvent &), type: 1, HasSignedIn(): 0, HasSignedOut: 0
2015/01/09 22:40:53.622 SIPService::OnEvent(IApplicationLayerEvent &), type: 3, HasSignedIn(): 0, HasSignedOut: 0
2015/01/09 22:40:53.622 SIPService::OnEvent(IApplicationLayerEvent &), type: 1, HasSignedIn(): 0, HasSignedOut: 0
2015/01/09 22:40:53.784 SIPService::OnEvent(IApplicationLayerEvent &), type: 3, HasSignedIn(): 0, HasSignedOut: 0
2015/01/09 22:40:53.784 SIPService::OnEvent(IApplicationLayerEvent &), type: 1, HasSignedIn(): 0, HasSignedOut: 0
2015/01/09 22:40:53.786 SIPService::OnEvent(IApplicationLayerEvent &), type: 3, HasSignedIn(): 1, HasSignedOut: 0
2015/01/09 22:40:53.787 virtual void SIPService::OnIdleHandleLogonSucceeded()
2015/01/09 22:40:53.792 Office Communications Server LOGON ENDED: USER = { MyDomain\LyncUser1}
2015/01/09 22:40:54.151 IsLocalAddress, 'lyncpool01' is not a local address
2015/01/09 22:40:54.151 FShouldUseProxy, is returning 1
2015/01/09 22:40:54.379 IsLocalAddress, 'lyncpool01' is not a local address
2015/01/09 22:40:54.379 FShouldUseProxy, is returning 1
2015/01/09 22:40:55.082 IsLocalAddress, 'lyncpool01' is not a local address
2015/01/09 22:40:55.082 FShouldUseProxy, is returning 1
2015/01/09 22:40:55.440 IsLocalAddress, 'lyncpool01' is not a local address
2015/01/09 22:40:55.440 FShouldUseProxy, is returning 1
2015/01/09 22:40:55.683 IsLocalAddress, 'lyncpool01' is not a local address
2015/01/09 22:40:55.683 FShouldUseProxy, is returning 1
2015/01/09 22:40:57.238 IsLocalAddress, 'lyncpool01' is not a local address
2015/01/09 22:40:57.238 FShouldUseProxy, is returning 1
2015/01/09 22:40:57.239 IsLocalAddress, 'lyncpool01' is not a local address
2015/01/09 22:40:57.239 FShouldUseProxy, is returning 1
2015/01/09 22:40:57.241 IsLocalAddress, 'lyncpool01' is not a local address
2015/01/09 22:40:57.241 IsLocalAddress, 'lyncpool01' is not a local address
2015/01/09 22:40:57.241 IsLocalAddress, 'lyncpool01' is not a local address
2015/01/09 22:40:57.241 FShouldUseProxy, is returning 1
2015/01/09 22:40:57.241 FShouldUseProxy, is returning 1
2015/01/09 22:40:57.241 FShouldUseProxy, is returning 1
Best regards,
Eric

Lync 2011 Mac - 14.0.11 unable to connect

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