Ok that worked! I can now see the log info when I try and connect. Here is what I'm getting when I try and connect using SSL
Debug
[2020-06-03 15:37:52.620][18][debug][conn_handler] [source/server/connection_handler_impl.cc:335] [C6] new connection
[2020-06-03 15:37:52.649][18][debug][connection] [source/extensions/transport_sockets/tls/ssl_socket.cc:191] [C6] handshake expecting read
[2020-06-03 15:37:52.649][18][debug][connection] [source/extensions/transport_sockets/tls/ssl_socket.cc:191] [C6] handshake expecting read
[2020-06-03 15:37:52.669][18][debug][connection] [source/extensions/transport_sockets/tls/ssl_socket.cc:198] [C6] handshake error: 5
[2020-06-03 15:37:52.669][18][debug][connection] [source/extensions/transport_sockets/tls/ssl_socket.cc:226] [C6]
[2020-06-03 15:37:52.669][18][debug][connection] [source/common/network/connection_impl.cc:193] [C6] closing socket: 0
[2020-06-03 15:37:52.669][18][debug][conn_handler] [source/server/connection_handler_impl.cc:88] [C6] adding to cleanup list
[2020-06-03 15:37:53.771][7][debug][upstream] [source/common/upstream/logical_dns_cluster.cc:72] starting async DNS resolution for 172.16.0.109
[2020-06-03 15:37:53.771][7][debug][upstream] [source/common/upstream/logical_dns_cluster.cc:79] async DNS resolution complete for 172.16.0.109
[2020-06-03 15:37:54.144][7][debug][main] [source/server/server.cc:175] flushing stats
Trace
[2020-06-03 15:47:31.470][18][debug][conn_handler] [source/server/connection_handler_impl.cc:335] [C9] new connection
[2020-06-03 15:47:31.470][18][trace][connection] [source/common/network/connection_impl.cc:462] [C9] socket event: 3
[2020-06-03 15:47:31.470][18][trace][connection] [source/common/network/connection_impl.cc:550] [C9] write ready
[2020-06-03 15:47:31.498][18][debug][connection] [source/extensions/transport_sockets/tls/ssl_socket.cc:191] [C9] handshake expecting read
[2020-06-03 15:47:31.498][18][trace][connection] [source/common/network/connection_impl.cc:500] [C9] read ready
[2020-06-03 15:47:31.498][18][debug][connection] [source/extensions/transport_sockets/tls/ssl_socket.cc:191] [C9] handshake expecting read
[2020-06-03 15:47:31.503][18][trace][connection] [source/common/network/connection_impl.cc:462] [C9] socket event: 3
[2020-06-03 15:47:31.503][18][trace][connection] [source/common/network/connection_impl.cc:550] [C9] write ready
[2020-06-03 15:47:31.503][18][debug][connection] [source/extensions/transport_sockets/tls/ssl_socket.cc:198] [C9] handshake error: 5
[2020-06-03 15:47:31.503][18][debug][connection] [source/extensions/transport_sockets/tls/ssl_socket.cc:226] [C9]
[2020-06-03 15:47:31.503][18][debug][connection] [source/common/network/connection_impl.cc:193] [C9] closing socket: 0
[2020-06-03 15:47:31.503][18][debug][conn_handler] [source/server/connection_handler_impl.cc:88] [C9] adding to cleanup list
[2020-06-03 15:47:31.503][18][trace][main] [source/common/event/dispatcher_impl.cc:160] item added to deferred deletion list (size=1)
[2020-06-03 15:47:31.503][18][trace][main] [source/common/event/dispatcher_impl.cc:79] clearing deferred deletion list (size=1)
[2020-06-03 15:47:33.821][7][debug][upstream] [source/common/upstream/logical_dns_cluster.cc:72] starting async DNS resolution for 172.16.0.109
[2020-06-03 15:47:33.821][7][debug][upstream] [source/common/upstream/logical_dns_cluster.cc:79] async DNS resolution complete for 172.16.0.109
[2020-06-03 15:47:34.203][7][debug][main] [source/server/server.cc:175] flushing stats
[2020-06-03 15:47:38.821][7][debug][upstream] [source/common/upstream/logical_dns_cluster.cc:72] starting async DNS resolution for 172.16.0.109
[2020-06-03 15:47:38.821][7][debug][upstream] [source/common/upstream/logical_dns_cluster.cc:79] async DNS resolution complete for 172.16.0.109
[2020-06-03 15:47:39.202][7][debug][main] [source/server/server.cc:175] flushing stats
So the question is, what is handshake error: 5?
I looked at the envoy source and based on the line number this appears to be the default error case