Just Had this happen to me aswell. After a month of happy use, the app would not respond. I had to restart it to get it up.
I have included the tail of my jackett log.
2016-06-21 19:45:37.1285 Error Top level exception System.Reflection.TargetInvocationException: Exception has been thrown by the target of an invocation. ---> System.Net.Sockets.SocketException: Address already in use
at System.Net.Sockets.Socket.Bind (System.Net.EndPoint local_end) <0x4207ae80 + 0x000ef> in <filename unknown>:0
at System.Net.EndPointListener..ctor (System.Net.IPAddress addr, Int32 port, Boolean secure) <0x42078380 + 0x00147> in <filename unknown>:0
at System.Net.EndPointManager.GetEPListener (System.String host, Int32 port, System.Net.HttpListener listener, Boolean secure) <0x42077ee0 + 0x002d3> in <filename unknown>:0
at System.Net.EndPointManager.AddPrefixInternal (System.String p, System.Net.HttpListener listener) <0x42076290 + 0x000c3> in <filename unknown>:0
at System.Net.EndPointManager.AddListener (System.Net.HttpListener listener) <0x42075da0 + 0x00147> in <filename unknown>:0
--- End of inner exception stack trace ---
at System.Reflection.MonoMethod.Invoke (System.Object obj, BindingFlags invokeAttr, System.Reflection.Binder binder, System.Object[] parameters, System.Globalization.CultureInfo culture) <0x2acdbb41b960 + 0x000ef> in <filename unknown>:0
at System.Reflection.MethodBase.Invoke (System.Object obj, System.Object[] parameters) <0x2acdbb253ec0 + 0x0002a> in <filename unknown>:0
at Microsoft.Owin.Hosting.ServerFactory.ServerFactoryAdapter.Create (IAppBuilder builder) <0x42072040 + 0x001f2> in <filename unknown>:0
at Microsoft.Owin.Hosting.Engine.HostingEngine.StartServer (Microsoft.Owin.Hosting.Engine.StartContext context) <0x42072000 + 0x00029> in <filename unknown>:0
at Microsoft.Owin.Hosting.Engine.HostingEngine.Start (Microsoft.Owin.Hosting.Engine.StartContext context) <0x42044310 + 0x0015b> in <filename unknown>:0
at Microsoft.Owin.Hosting.Starter.DirectHostingStarter.Start (Microsoft.Owin.Hosting.StartOptions options) <0x42043660 + 0x0005c> in <filename unknown>:0
at Microsoft.Owin.Hosting.Starter.HostingStarter.Start (Microsoft.Owin.Hosting.StartOptions options) <0x42042180 + 0x0007b> in <filename unknown>:0
at Microsoft.Owin.Hosting.WebApp.StartImplementation (IServiceProvider services, Microsoft.Owin.Hosting.StartOptions options) <0x42041b50 + 0x0005e> in <filename unknown>:0
at Microsoft.Owin.Hosting.WebApp.Start (Microsoft.Owin.Hosting.StartOptions options) <0x42040800 + 0x00027> in <filename unknown>:0
at Microsoft.Owin.Hosting.WebApp.Start[TStartup] (Microsoft.Owin.Hosting.StartOptions options) <0x42040710 + 0x00047> in <filename unknown>:0
at Jackett.Services.ServerService.Start () <0x4203fc50 + 0x0020b> in <filename unknown>:0
at JackettConsole.Program.Main (System.String[] args) <0x41f27d60 + 0x00e16> in <filename unknown>:0
I hope this helps in sorting the issue.
If you need more info please let me know.