OS X 10.10 SSL Not working

Good afternoon.

I followed directions here(generated the pvk, etc) and I cannot get my system to respond on SSL.

I added the hash, but it never even tries to connect via SSL. The certificate I’m using is working for both stab and cp. Any advice?

What do you mean it doesn’t try to connect via SSL?
Did you restart Sonarr?
What do the log files show during startup (it will log when ports and protocols its listening to)

It shows that it’s listening on the proper port.

14-11-13 15:15:24.2|Info|LifecycleService|Restart requested.
14-11-13 15:15:31.2|Info|Bootstrap|Starting NzbDrone - /Applications/NzbDrone/NzbDrone.exe - Version 2.0.0.2180
14-11-13 15:15:34.9|Debug|ProcessProvider|Found 0 processes with the name: NzbDrone.Console
14-11-13 15:15:35.5|Debug|ProcessProvider|Found 0 processes with the name: NzbDrone
14-11-13 15:15:35.7|Info|MigrationLogger|*** Migrating data source=/Users/shaun/.config/NzbDrone/nzbdrone.db;cache size=-10485760;datetimekind=Utc;journal mode=Wal;pooling=True ***
14-11-13 15:15:35.8|Info|MigrationLogger|*** Migrating data source=/Users/shaun/.config/NzbDrone/logs.db;cache size=-10485760;datetimekind=Utc;journal mode=Wal;pooling=True ***
14-11-13 15:15:35.8|Info|Router|Application mode: Interactive
14-11-13 15:15:35.8|Debug|Router|Console selected
14-11-13 15:15:35.9|Info|OwinHostController|Listening on the following URLs:
14-11-13 15:15:35.9|Info|OwinHostController| http://:8989/
14-11-13 15:15:35.9|Info|OwinHostController| https://
:9898/
14-11-13 15:15:35.9|Debug|OwinAppFactory|Attaching NzbDroneVersionMiddleWare to host
14-11-13 15:15:35.9|Debug|OwinAppFactory|Attaching SignalRMiddleWare to host
14-11-13 15:15:36.0|Debug|OwinAppFactory|Attaching NancyMiddleWare to host
14-11-13 15:15:36.0|Info|NancyBootstrapper|Starting NzbDrone API
14-11-13 15:15:36.2|Trace|EventAggregator|Publishing ApplicationStartedEvent
14-11-13 15:15:36.5|Trace|EventAggregator|ApplicationStartedEvent -> DownloadClientFactory
14-11-13 15:15:36.5|Debug|DownloadClientFactory|Initializing Providers. Count 4
14-11-13 15:15:36.6|Trace|EventAggregator|ApplicationStartedEvent <- DownloadClientFactory
14-11-13 15:15:36.6|Trace|EventAggregator|ApplicationStartedEvent -> IndexerFactory
14-11-13 15:15:36.6|Debug|IndexerFactory|Initializing Providers. Count 5
14-11-13 15:15:36.7|Trace|EventAggregator|ApplicationStartedEvent <- IndexerFactory
14-11-13 15:15:36.7|Trace|EventAggregator|ApplicationStartedEvent -> ReconfigureLogging
14-11-13 15:15:37.7|Info|SceneMappingService|Updating Scene mappings
14-11-13 15:15:38.7|Info|HousekeepingService|Running housecleaning tasks
14-11-13 15:15:38.9|Info|Database|Vacuuming database
14-11-13 15:15:39.0|Info|Database|Database Compressed
14-11-13 15:15:40.7|Warn|GlobalExceptionHandlers|SignalR Heartbeat error.
14-11-13 15:16:07.1|Info|RssSyncService|Starting RSS Sync
14-11-13 15:16:12.3|Info|DownloadDecisionMaker|Processing 366 reports
14-11-13 15:16:13.4|Info|RssSyncService|RSS Sync Completed. Reports found: 366, Reports grabbed: 0
14-11-13 15:17:40.7|Error|Owin|/Applications/NzbDrone/Microsoft.AspNet.SignalR.Core.dll Error : 0 : SignalR exception thrown by Task: System.AggregateException: One or more errors occurred —> System.IO.IOException: Write failure —> System.Net.Sockets.SocketException: The socket has been shut down
at System.Net.Sockets.Socket.Send (System.Byte[] buf, Int32 offset, Int32 size, SocketFlags flags) [0x00000] in :0
at System.Net.Sockets.NetworkStream.Write (System.Byte[] buffer, Int32 offset, Int32 size) [0x00000] in :0
— End of inner exception stack trace —
at System.Net.Sockets.NetworkStream.Write (System.Byte[] buffer, Int32 offset, Int32 size) [0x00000] in :0
at System.Net.ResponseStream.InternalWrite (System.Byte[] buffer, Int32 offset, Int32 count) [0x00000] in :0
at System.Net.ResponseStream.Write (System.Byte[] buffer, Int32 offset, Int32 count) [0x00000] in :0
at Microsoft.Owin.Host.HttpListener.RequestProcessing.ExceptionFilterStream.Write (System.Byte[] buffer, Int32 offset, Int32 count) [0x00000] in :0
— End of inner exception stack trace —
–> (Inner exception 0) System.IO.IOException: Write failure —> System.Net.Sockets.SocketException: The socket has been shut down
at System.Net.Sockets.Socket.Send (System.Byte[] buf, Int32 offset, Int32 size, SocketFlags flags) [0x00000] in :0
at System.Net.Sockets.NetworkStream.Write (System.Byte[] buffer, Int32 offset, Int32 size) [0x00000] in :0
— End of inner exception stack trace —
at System.Net.Sockets.NetworkStream.Write (System.Byte[] buffer, Int32 offset, Int32 size) [0x00000] in :0
at System.Net.ResponseStream.InternalWrite (System.Byte[] buffer, Int32 offset, Int32 count) [0x00000] in :0
at System.Net.ResponseStream.Write (System.Byte[] buffer, Int32 offset, Int32 count) [0x00000] in :0
at Microsoft.Owin.Host.HttpListener.RequestProcessing.ExceptionFilterStream.Write (System.Byte[] buffer, Int32 offset, Int32 count) [0x00000] in :0

14-11-13 15:17:40.7|Error|Owin|/Applications/NzbDrone/Microsoft.AspNet.SignalR.Core.dll Error : 0 : SignalR exception thrown by Task: System.AggregateException: One or more errors occurred —> System.IO.IOException: Write failure —> System.Net.Sockets.SocketException: The socket has been shut down
at System.Net.Sockets.Socket.Send (System.Byte[] buf, Int32 offset, Int32 size, SocketFlags flags) [0x00000] in :0
at System.Net.Sockets.NetworkStream.Write (System.Byte[] buffer, Int32 offset, Int32 size) [0x00000] in :0
— End of inner exception stack trace —
at System.Net.Sockets.NetworkStream.Write (System.Byte[] buffer, Int32 offset, Int32 size) [0x00000] in :0
at System.Net.ResponseStream.InternalWrite (System.Byte[] buffer, Int32 offset, Int32 count) [0x00000] in :0
at System.Net.ResponseStream.Write (System.Byte[] buffer, Int32 offset, Int32 count) [0x00000] in :0
at Microsoft.Owin.Host.HttpListener.RequestProcessing.ExceptionFilterStream.Write (System.Byte[] buffer, Int32 offset, Int32 count) [0x00000] in :0
— End of inner exception stack trace —
–> (Inner exception 0) System.IO.IOException: Write failure —> System.Net.Sockets.SocketException: The socket has been shut down
at System.Net.Sockets.Socket.Send (System.Byte[] buf, Int32 offset, Int32 size, SocketFlags flags) [0x00000] in :0
at System.Net.Sockets.NetworkStream.Write (System.Byte[] buffer, Int32 offset, Int32 size) [0x00000] in :0
— End of inner exception stack trace —
at System.Net.Sockets.NetworkStream.Write (System.Byte[] buffer, Int32 offset, Int32 size) [0x00000] in :0
at System.Net.ResponseStream.InternalWrite (System.Byte[] buffer, Int32 offset, Int32 count) [0x00000] in :0
at System.Net.ResponseStream.Write (System.Byte[] buffer, Int32 offset, Int32 count) [0x00000] in :0
at Microsoft.Owin.Host.HttpListener.RequestProcessing.ExceptionFilterStream.Write (System.Byte[] buffer, Int32 offset, Int32 count) [0x00000] in :0

14-11-13 15:27:10.6|Error|Owin|/Applications/NzbDrone/Microsoft.AspNet.SignalR.Core.dll Error : 0 : SignalR exception thrown by Task: System.AggregateException: One or more errors occurred —> System.IO.IOException: Write failure —> System.Net.Sockets.SocketException: The socket has been shut down
at System.Net.Sockets.Socket.Send (System.Byte[] buf, Int32 offset, Int32 size, SocketFlags flags) [0x00000] in :0
at System.Net.Sockets.NetworkStream.Write (System.Byte[] buffer, Int32 offset, Int32 size) [0x00000] in :0
— End of inner exception stack trace —
at System.Net.Sockets.NetworkStream.Write (System.Byte[] buffer, Int32 offset, Int32 size) [0x00000] in :0
at System.Net.ResponseStream.InternalWrite (System.Byte[] buffer, Int32 offset, Int32 count) [0x00000] in :0
at System.Net.ResponseStream.Write (System.Byte[] buffer, Int32 offset, Int32 count) [0x00000] in :0
at Microsoft.Owin.Host.HttpListener.RequestProcessing.ExceptionFilterStream.Write (System.Byte[] buffer, Int32 offset, Int32 count) [0x00000] in :0
— End of inner exception stack trace —
–> (Inner exception 0) System.IO.IOException: Write failure —> System.Net.Sockets.SocketException: The socket has been shut down
at System.Net.Sockets.Socket.Send (System.Byte[] buf, Int32 offset, Int32 size, SocketFlags flags) [0x00000] in :0
at System.Net.Sockets.NetworkStream.Write (System.Byte[] buffer, Int32 offset, Int32 size) [0x00000] in :0
— End of inner exception stack trace —
at System.Net.Sockets.NetworkStream.Write (System.Byte[] buffer, Int32 offset, Int32 size) [0x00000] in :0
at System.Net.ResponseStream.InternalWrite (System.Byte[] buffer, Int32 offset, Int32 count) [0x00000] in :0
at System.Net.ResponseStream.Write (System.Byte[] buffer, Int32 offset, Int32 count) [0x00000] in :0
at Microsoft.Owin.Host.HttpListener.RequestProcessing.ExceptionFilterStream.Write (System.Byte[] buffer, Int32 offset, Int32 count) [0x00000] in :0

14-11-13 15:31:14.1|Info|RssSyncService|Starting RSS Sync
14-11-13 15:31:24.1|Info|DownloadDecisionMaker|Processing 366 reports
14-11-13 15:31:25.2|Info|RssSyncService|RSS Sync Completed. Reports found: 366, Reports grabbed: 0
14-11-13 15:32:25.8|Info|Database|Vacuuming database
14-11-13 15:32:25.8|Info|Database|Database Compressed
14-11-13 15:34:40.6|Error|Owin|/Applications/NzbDrone/Microsoft.AspNet.SignalR.Core.dll Error : 0 : SignalR exception thrown by Task: System.AggregateException: One or more errors occurred —> System.IO.IOException: Write failure —> System.Net.Sockets.SocketException: The socket has been shut down
at System.Net.Sockets.Socket.Send (System.Byte[] buf, Int32 offset, Int32 size, SocketFlags flags) [0x00000] in :0
at System.Net.Sockets.NetworkStream.Write (System.Byte[] buffer, Int32 offset, Int32 size) [0x00000] in :0
— End of inner exception stack trace —
at System.Net.Sockets.NetworkStream.Write (System.Byte[] buffer, Int32 offset, Int32 size) [0x00000] in :0
at System.Net.ResponseStream.InternalWrite (System.Byte[] buffer, Int32 offset, Int32 count) [0x00000] in :0
at System.Net.ResponseStream.Write (System.Byte[] buffer, Int32 offset, Int32 count) [0x00000] in :0
at Microsoft.Owin.Host.HttpListener.RequestProcessing.ExceptionFilterStream.Write (System.Byte[] buffer, Int32 offset, Int32 count) [0x00000] in :0
— End of inner exception stack trace —
–> (Inner exception 0) System.IO.IOException: Write failure —> System.Net.Sockets.SocketException: The socket has been shut down
at System.Net.Sockets.Socket.Send (System.Byte[] buf, Int32 offset, Int32 size, SocketFlags flags) [0x00000] in :0
at System.Net.Sockets.NetworkStream.Write (System.Byte[] buffer, Int32 offset, Int32 size) [0x00000] in :0
— End of inner exception stack trace —
at System.Net.Sockets.NetworkStream.Write (System.Byte[] buffer, Int32 offset, Int32 size) [0x00000] in :0
at System.Net.ResponseStream.InternalWrite (System.Byte[] buffer, Int32 offset, Int32 count) [0x00000] in :0
at System.Net.ResponseStream.Write (System.Byte[] buffer, Int32 offset, Int32 count) [0x00000] in :0
at Microsoft.Owin.Host.HttpListener.RequestProcessing.ExceptionFilterStream.Write (System.Byte[] buffer, Int32 offset, Int32 count) [0x00000] in :0

14-11-13 15:46:26.5|Info|RssSyncService|Starting RSS Sync
14-11-13 15:46:32.4|Info|DownloadDecisionMaker|Processing 371 reports
14-11-13 15:46:33.1|Info|RssSyncService|RSS Sync Completed. Reports found: 371, Reports grabbed: 0
14-11-13 16:01:33.9|Info|RssSyncService|Starting RSS Sync
14-11-13 16:01:41.5|Info|DownloadDecisionMaker|Processing 371 reports
14-11-13 16:01:42.2|Info|RssSyncService|RSS Sync Completed. Reports found: 371, Reports grabbed: 0
14-11-13 16:16:43.3|Info|RssSyncService|Starting RSS Sync
14-11-13 16:16:47.7|Info|DownloadDecisionMaker|Processing 271 reports
14-11-13 16:16:48.2|Info|RssSyncService|RSS Sync Completed. Reports found: 271, Reports grabbed: 0

I’ve been digging testing on all my machines and is appears to only be an issue trying to connect via HTTPS using Safari on an Apple OS. I’ve confirmed this from two different iOS devices and two different Macs. All Apple OS clients get prompted to select a client certificate, multiple times. After the selection process, it will hang and never load. Firefox works on the Mac as well as IE and Firefox on my Windows machine.

This certificate is being used for the two other services without an issue.

Hope this helps and please let me know what other information I can gather.

Thanks.

Are you using a cert that requires an intermediate certificate (a properly signed one from a CA)?

If so, mono’s httpcfg doesn’t support them and will cause it to prompt for a certificate. Similar conclusion here: Mono didn’t support intermediate SSL certificate chains causing problems between nzbToMedia and NzbDrone/Sonarr [fix]

Are there any recommendations/suggestions for a provider to get one? I see the prices and types are all over the place. Thanks.

StartSSL does free ones, but I’m not sure if they have an intermediate cert. You can make a self signed one, but then you’ll get a cert warning.

My first attempt was with a self signed cert from OS X Server. I’ll need to double check what process Keychain Access uses.

Perhaps there should be a documented process for using openssl that could feed its output to your previously defined process. I’ll see what I can find.