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Configuring Lync for External use

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Hi,

I'm trying to expand our use of Lync, which is currently IM/presence-only for internal staff. I've been asked to set up Lync so we can communicate with 3rd parties.

Lync configuration:
SIP addresses = username@corp.domain.com
FE server = aglync.corp.domain.com
Edge server = dmzlync.corp.domain.com (yes, it's on the domain)

There are few obstacles that I've already encountered/changed:
The IT guy who set up this server used an internal FQDN for the external services (ie. dialin.corp.domain.com)
The SIP addresses don't match the SMTP addresses
I can't break the internal deployment of Lync while I change things and get external Lync working

I'm in the midst of making changes, as best I can without impacting current users, and I'm stuck on the autodiscover. So far, I've:
changed my SIP address in Lync to match my email address (username@domain.com).
added that domain as an additional SIP domain.
Changed some of the public URLs
Generated new certificates/refreshed the topology.

External DNS: lyncdiscover.company.com (CNAME) = lyncweb.company.com
lyncweb.company.com = x.x.x.x (public IP for Edge server)
meet.company.com = x.x.x.y (public IP that's translated to FE server)

Current Configuration

I know there are a host of issues still to work through, but I'm trying to tackle them one at a time. First up is autodiscover.

1) When I run the Remote Connectivity Analyzer, I'm told that autodiscover resolves to the right IP address, but port 443 isn't responding. Is there a URL I can test directly against the internal IP to confirm that this isn't the issue?

2) When I run the Lync Connectivity Analyzer, internal tests resolve okay, but the external tests fail (including the mobile tests). Part of the log reads as follows:

[3/28/2014 1:27:28 PM] [SUBHEADING] Starting automatic discovery for secure (HTTPS) external channel
[3/28/2014 1:27:28 PM] [DEBUG] Sending HTTP request to https://lyncdiscover.company.com/?sipuri=greg@company.com
[3/28/2014 1:27:50 PM] [DEBUG] Exception encountered while sending an HTTP request tohttps://lyncdiscover.company.com/?sipuri=greg@company.com: An error occurred while sending the request.. Complete Exception: \r\nSystem.Net.Http.HttpRequestException: An error occurred while sending the request. ---> System.Net.WebException: Unable to connect to the remote server ---> System.Net.Sockets.SocketException: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond 206.172.55.236:443
   at System.Net.Sockets.Socket.EndConnect(IAsyncResult asyncResult)
   at System.Net.ServicePoint.ConnectSocketInternal(Boolean connectFailure, Socket s4, Socket s6, Socket& socket, IPAddress& address, ConnectSocketState state, IAsyncResult asyncResult, Exception& exception)
   --- End of inner exception stack trace ---
   at System.Net.HttpWebRequest.EndGetResponse(IAsyncResult asyncResult)
   at System.Net.Http.HttpClientHandler.GetResponseCallback(IAsyncResult ar)
   --- End of inner exception stack trace ---
   at System.Runtime.CompilerServices.TaskAwaiter.ThrowForNonSuccess(Task task)
   at System.Runtime.CompilerServices.TaskAwaiter.HandleNonSuccessAndDebuggerNotification(Task task)
   at Microsoft.LyncServer.WebServices.AutoDiscoverManager.<SendHttpRequest>d__9.MoveNext()
[3/28/2014 1:27:50 PM] [ERROR] An error occurred while sending the request.
Unable to connect to the remote server
A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond 206.172.55.236:443
[3/28/2014 1:27:50 PM] [INFO] For troubleshooting, try using a browser to open the server discovery URLhttps://lyncdiscover.company.com/?sipuri=greg@company.com
[3/28/2014 1:27:50 PM] [DEBUG] System.Net.Http.HttpRequestException: An error occurred while sending the request. ---> System.Net.WebException: Unable to connect to the remote server ---> System.Net.Sockets.SocketException: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond 206.172.55.236:443
   at System.Net.Sockets.Socket.EndConnect(IAsyncResult asyncResult)
   at System.Net.ServicePoint.ConnectSocketInternal(Boolean connectFailure, Socket s4, Socket s6, Socket& socket, IPAddress& address, ConnectSocketState state, IAsyncResult asyncResult, Exception& exception)
   --- End of inner exception stack trace ---
   at System.Net.HttpWebRequest.EndGetResponse(IAsyncResult asyncResult)
   at System.Net.Http.HttpClientHandler.GetResponseCallback(IAsyncResult ar)
   --- End of inner exception stack trace ---
   at System.Runtime.CompilerServices.TaskAwaiter.ThrowForNonSuccess(Task task)
   at System.Runtime.CompilerServices.TaskAwaiter.HandleNonSuccessAndDebuggerNotification(Task task)
   at Microsoft.LyncServer.WebServices.AutoDiscoverManager.<SendHttpRequest>d__9.MoveNext()
--- End of stack trace from previous location where exception was thrown ---
   at System.Runtime.CompilerServices.TaskAwaiter.ThrowForNonSuccess(Task task)
   at System.Runtime.CompilerServices.TaskAwaiter.HandleNonSuccessAndDebuggerNotification(Task task)
   at System.Runtime.CompilerServices.TaskAwaiter`1.GetResult()
   at Microsoft.LyncServer.WebServices.AutoDiscoverManager.<SendRequest>d__d.MoveNext()
--- End of stack trace from previous location where exception was thrown ---
   at System.Runtime.CompilerServices.TaskAwaiter.ThrowForNonSuccess(Task task)
   at System.Runtime.CompilerServices.TaskAwaiter.HandleNonSuccessAndDebuggerNotification(Task task)
   at System.Runtime.CompilerServices.TaskAwaiter`1.GetResult()
   at Microsoft.LyncServer.WebServices.AutoDiscoverManager.<TryNextUrl>d__3.MoveNext()
--- End of stack trace from previous location where exception was thrown ---
   at System.Runtime.CompilerServices.TaskAwaiter.ThrowForNonSuccess(Task task)
   at System.Runtime.CompilerServices.TaskAwaiter.HandleNonSuccessAndDebuggerNotification(Task task)
   at Microsoft.LyncServer.WebServices.AutoDiscoverManager.<StartDiscoveryJourney>d__0.MoveNext()
--- End of stack trace from previous location where exception was thrown ---
   at System.Runtime.CompilerServices.TaskAwaiter.ThrowForNonSuccess(Task task)
   at System.Runtime.CompilerServices.TaskAwaiter.HandleNonSuccessAndDebuggerNotification(Task task)
   at LyncConnectivityAnalyzerCore.Utilities.<RetrieveUserLocation>d__3e.MoveNext()
[3/28/2014 1:27:50 PM] [SUMMARY_ERROR] Server discovery failed for secured external channel againsthttps://lyncdiscover.company.com/

I don't know where to begin on this issue - is it a setup issue? Is it because I'm trying to log in with a SIP address that wasn't deployed originally? I'm looking for clues that'll help me track down the issue.

Thanks,
Greg


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