Configuring Lync for External use

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 = [email protected]
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 ([email protected]).
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)
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/[email protected]
[3/28/2014 1:27:50 PM] [DEBUG] Exception encountered while sending an HTTP request to
https://lyncdiscover.company.com/[email protected]: 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 URL
https://lyncdiscover.company.com/[email protected]
[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 against
https://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

meet.company.com can not be your Meeting URL and the FQDN of your Edge Services.
Meet/Lyncdiscover/Dialin/External Web Services (lyncweb.company.com)
will all point to Reverse proxy 443-4443 to the FE server
sip.company.com(or whatever FQDN assigned to the Edge) will point to your Edge Public IP.
Take a look at the following TechNet articles:
http://technet.microsoft.com/en-us/library/gg425891.aspx
http://technet.microsoft.com/en-us/library/jj204781.aspx
http://technet.microsoft.com/en-us/library/gg412787.aspx
Please mark posts as answers/helpful if it answers your question.
Blog
Lync Validator - Used to assist in the validation and documentation of Lync Server 2013.

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