diff --git a/agent/agent_endpoint_test.go b/agent/agent_endpoint_test.go
index 47ac0868f..1347055fd 100644
--- a/agent/agent_endpoint_test.go
+++ b/agent/agent_endpoint_test.go
@@ -196,7 +196,10 @@ func TestAgent_Services_Sidecar(t *testing.T) {
 		Proxy: structs.ConnectProxyConfig{
 			DestinationServiceName: "db",
 			Upstreams:              structs.TestUpstreams(t),
-			TransparentProxy:       true,
+			Mode:                   structs.ProxyModeTransparent,
+			TransparentProxy: structs.TransparentProxyConfig{
+				OutboundListenerPort: 10101,
+			},
 		},
 	}
 	a.State.AddService(srv1, "")
@@ -396,7 +399,7 @@ func TestAgent_Service(t *testing.T) {
 		Service:     "web-sidecar-proxy",
 		Port:        8000,
 		Proxy:       expectProxy.ToAPI(),
-		ContentHash: "fa3af167b81f6721",
+		ContentHash: "eb557bc310d4f8a0",
 		Weights: api.AgentWeights{
 			Passing: 1,
 			Warning: 1,
@@ -410,7 +413,7 @@ func TestAgent_Service(t *testing.T) {
 	// Copy and modify
 	updatedResponse := *expectedResponse
 	updatedResponse.Port = 9999
-	updatedResponse.ContentHash = "c7739b50900c7483"
+	updatedResponse.ContentHash = "d61c11f438c7eb02"
 
 	// Simple response for non-proxy service registered in TestAgent config
 	expectWebResponse := &api.AgentService{
diff --git a/agent/config/builder.go b/agent/config/builder.go
index 7e151e760..1238670ea 100644
--- a/agent/config/builder.go
+++ b/agent/config/builder.go
@@ -1691,7 +1691,8 @@ func (b *builder) serviceProxyVal(v *ServiceProxy) *structs.ConnectProxyConfig {
 		Upstreams:              b.upstreamsVal(v.Upstreams),
 		MeshGateway:            b.meshGatewayConfVal(v.MeshGateway),
 		Expose:                 b.exposeConfVal(v.Expose),
-		TransparentProxy:       boolVal(v.TransparentProxy),
+		Mode:                   b.proxyModeVal(v.Mode),
+		TransparentProxy:       b.transparentProxyConfVal(v.TransparentProxy),
 	}
 }
 
@@ -1743,6 +1744,28 @@ func (b *builder) exposeConfVal(v *ExposeConfig) structs.ExposeConfig {
 	return out
 }
 
+func (b *builder) transparentProxyConfVal(tproxyConf *TransparentProxyConfig) structs.TransparentProxyConfig {
+	var out structs.TransparentProxyConfig
+	if tproxyConf == nil {
+		return out
+	}
+
+	out.OutboundListenerPort = intVal(tproxyConf.OutboundListenerPort)
+	return out
+}
+
+func (b *builder) proxyModeVal(v *string) structs.ProxyMode {
+	if v == nil {
+		return structs.ProxyModeDefault
+	}
+
+	mode, err := structs.ValidateProxyMode(*v)
+	if err != nil {
+		b.err = multierror.Append(b.err, err)
+	}
+	return mode
+}
+
 func (b *builder) pathsVal(v []ExposePath) []structs.ExposePath {
 	paths := make([]structs.ExposePath, len(v))
 	for i, p := range v {
diff --git a/agent/config/config.go b/agent/config/config.go
index 937d54388..b65cb5280 100644
--- a/agent/config/config.go
+++ b/agent/config/config.go
@@ -461,6 +461,12 @@ type ServiceProxy struct {
 	// (DestinationServiceID is set) but otherwise will be ignored.
 	LocalServicePort *int `mapstructure:"local_service_port"`
 
+	// TransparentProxy configuration.
+	TransparentProxy *TransparentProxyConfig `mapstructure:"transparent_proxy"`
+
+	// Mode represents how the proxy's inbound and upstream listeners are dialed.
+	Mode *string `mapstructure:"mode"`
+
 	// Config is the arbitrary configuration data provided with the proxy
 	// registration.
 	Config map[string]interface{} `mapstructure:"config"`
@@ -474,10 +480,6 @@ type ServiceProxy struct {
 
 	// Expose defines whether checks or paths are exposed through the proxy
 	Expose *ExposeConfig `mapstructure:"expose"`
-
-	// TransparentProxy toggles whether inbound and outbound traffic is being
-	// redirected to the proxy.
-	TransparentProxy *bool `mapstructure:"transparent_proxy"`
 }
 
 // Upstream represents a single upstream dependency for a service or proxy. It
@@ -523,6 +525,11 @@ type MeshGatewayConfig struct {
 	Mode *string `mapstructure:"mode"`
 }
 
+type TransparentProxyConfig struct {
+	// Mesh Gateway Mode
+	OutboundListenerPort *int `mapstructure:"outbound_listener_port"`
+}
+
 // ExposeConfig describes HTTP paths to expose through Envoy outside of Connect.
 // Users can expose individual paths and/or all HTTP/GRPC paths for checks.
 type ExposeConfig struct {
diff --git a/agent/config/runtime_test.go b/agent/config/runtime_test.go
index 38ea470fb..f4deb8c55 100644
--- a/agent/config/runtime_test.go
+++ b/agent/config/runtime_test.go
@@ -2582,7 +2582,10 @@ func TestLoad_IntegrationWithFlags(t *testing.T) {
 											}
 										]
 									},
-									"transparent_proxy": true,
+									"mode": "transparent",
+									"transparent_proxy": {
+										"outbound_listener_port": 10101
+									},
 									"upstreams": [
 										{
 											"destination_name": "db",
@@ -2619,7 +2622,10 @@ func TestLoad_IntegrationWithFlags(t *testing.T) {
 										}
 									]
 								}
-								transparent_proxy = true
+								mode = "transparent"
+								transparent_proxy = {
+									outbound_listener_port = 10101
+								}
 								upstreams = [
 									{
 										destination_name = "db"
@@ -2659,7 +2665,10 @@ func TestLoad_IntegrationWithFlags(t *testing.T) {
 										},
 									},
 								},
-								TransparentProxy: true,
+								Mode: structs.ProxyModeTransparent,
+								TransparentProxy: structs.TransparentProxyConfig{
+									OutboundListenerPort: 10101,
+								},
 								Upstreams: structs.Upstreams{
 									structs.Upstream{
 										DestinationType: "service",
@@ -2714,7 +2723,10 @@ func TestLoad_IntegrationWithFlags(t *testing.T) {
 											}
 										]
 									},
-									"transparent_proxy": true,
+									"mode": "transparent",
+									"transparent_proxy": {
+										"outbound_listener_port": 10101
+									},
 									"upstreams": [
 										{
 											"destination_name": "db",
@@ -2751,7 +2763,10 @@ func TestLoad_IntegrationWithFlags(t *testing.T) {
 										}
 									]
 								}
-								transparent_proxy = true,
+								mode = "transparent"
+								transparent_proxy = {
+									outbound_listener_port = 10101
+								}
 								upstreams = [
 									{
 										destination_name = "db"
@@ -2791,7 +2806,10 @@ func TestLoad_IntegrationWithFlags(t *testing.T) {
 										},
 									},
 								},
-								TransparentProxy: true,
+								Mode: structs.ProxyModeTransparent,
+								TransparentProxy: structs.TransparentProxyConfig{
+									OutboundListenerPort: 10101,
+								},
 								Upstreams: structs.Upstreams{
 									structs.Upstream{
 										DestinationType: "service",
@@ -3435,7 +3453,10 @@ func TestLoad_IntegrationWithFlags(t *testing.T) {
 							"mesh_gateway": {
 								"mode": "remote"
 							},
-							"transparent_proxy": true
+							"mode": "transparent",
+							"transparent_proxy": {
+								"outbound_listener_port": 10101
+							}
 						}
 					]
 				}
@@ -3454,7 +3475,10 @@ func TestLoad_IntegrationWithFlags(t *testing.T) {
 						mesh_gateway {
 							mode = "remote"
 						}
-						transparent_proxy = true
+						mode = "transparent"
+						transparent_proxy = {
+							outbound_listener_port = 10101
+						}
 					}
 				}`},
 		expected: func(rt *RuntimeConfig) {
@@ -3473,7 +3497,10 @@ func TestLoad_IntegrationWithFlags(t *testing.T) {
 					MeshGateway: structs.MeshGatewayConfig{
 						Mode: structs.MeshGatewayModeRemote,
 					},
-					TransparentProxy: true,
+					Mode: structs.ProxyModeTransparent,
+					TransparentProxy: structs.TransparentProxyConfig{
+						OutboundListenerPort: 10101,
+					},
 				},
 			}
 		},
@@ -3496,7 +3523,10 @@ func TestLoad_IntegrationWithFlags(t *testing.T) {
 							"MeshGateway": {
 								"Mode": "remote"
 							},
-							"TransparentProxy": true
+							"Mode": "transparent",
+							"TransparentProxy": {
+								"OutboundListenerPort": 10101
+							}
 						}
 					]
 				}
@@ -3515,7 +3545,10 @@ func TestLoad_IntegrationWithFlags(t *testing.T) {
 						MeshGateway {
 							Mode = "remote"
 						}
-						TransparentProxy = true
+						Mode = "transparent"
+						TransparentProxy = {
+							OutboundListenerPort = 10101
+						}
 					}
 				}`},
 		expected: func(rt *RuntimeConfig) {
@@ -3534,7 +3567,10 @@ func TestLoad_IntegrationWithFlags(t *testing.T) {
 					MeshGateway: structs.MeshGatewayConfig{
 						Mode: structs.MeshGatewayModeRemote,
 					},
-					TransparentProxy: true,
+					Mode: structs.ProxyModeTransparent,
+					TransparentProxy: structs.TransparentProxyConfig{
+						OutboundListenerPort: 10101,
+					},
 				},
 			}
 		},
@@ -3557,7 +3593,10 @@ func TestLoad_IntegrationWithFlags(t *testing.T) {
 							"mesh_gateway": {
 								"mode": "remote"
 							},
-							"transparent_proxy": true
+							"mode": "transparent",
+							"transparent_proxy": {
+								"outbound_listener_port": 10101
+							}
 						}
 					]
 				}
@@ -3576,7 +3615,10 @@ func TestLoad_IntegrationWithFlags(t *testing.T) {
 						mesh_gateway {
 							mode = "remote"
 						}
-						transparent_proxy = true
+						mode = "transparent"
+						transparent_proxy = {
+							outbound_listener_port = 10101
+						}
 					}
 				}`},
 		expected: func(rt *RuntimeConfig) {
@@ -3595,7 +3637,10 @@ func TestLoad_IntegrationWithFlags(t *testing.T) {
 					MeshGateway: structs.MeshGatewayConfig{
 						Mode: structs.MeshGatewayModeRemote,
 					},
-					TransparentProxy: true,
+					Mode: structs.ProxyModeTransparent,
+					TransparentProxy: structs.TransparentProxyConfig{
+						OutboundListenerPort: 10101,
+					},
 				},
 			}
 		},
@@ -3618,7 +3663,10 @@ func TestLoad_IntegrationWithFlags(t *testing.T) {
 							"MeshGateway": {
 								"Mode": "remote"
 							},
-							"TransparentProxy": true
+							"Mode": "transparent",
+							"TransparentProxy": {
+								"OutboundListenerPort": 10101
+							}
 						}
 					]
 				}
@@ -3637,7 +3685,10 @@ func TestLoad_IntegrationWithFlags(t *testing.T) {
 						MeshGateway {
 							Mode = "remote"
 						}
-						TransparentProxy = true
+						Mode = "transparent"
+						TransparentProxy = {
+							OutboundListenerPort = 10101
+						}
 					}
 				}`},
 		expected: func(rt *RuntimeConfig) {
@@ -3656,7 +3707,10 @@ func TestLoad_IntegrationWithFlags(t *testing.T) {
 					MeshGateway: structs.MeshGatewayConfig{
 						Mode: structs.MeshGatewayModeRemote,
 					},
-					TransparentProxy: true,
+					Mode: structs.ProxyModeTransparent,
+					TransparentProxy: structs.TransparentProxyConfig{
+						OutboundListenerPort: 10101,
+					},
 				},
 			}
 		},
@@ -5598,7 +5652,10 @@ func TestLoad_FullConfig(t *testing.T) {
 							},
 						},
 					},
-					TransparentProxy: true,
+					Mode: structs.ProxyModeTransparent,
+					TransparentProxy: structs.TransparentProxyConfig{
+						OutboundListenerPort: 10101,
+					},
 				},
 				Weights: &structs.Weights{
 					Passing: 1,
diff --git a/agent/config/testdata/full-config.hcl b/agent/config/testdata/full-config.hcl
index 6b56b1bc7..c1323ef22 100644
--- a/agent/config/testdata/full-config.hcl
+++ b/agent/config/testdata/full-config.hcl
@@ -591,7 +591,10 @@ services = [
                     }
                 ]
             }
-            transparent_proxy = true
+            mode = "transparent"
+            transparent_proxy = {
+                outbound_listener_port = 10101
+            }
         }
     },
     {
diff --git a/agent/config/testdata/full-config.json b/agent/config/testdata/full-config.json
index 4443f2879..2c8b26df2 100644
--- a/agent/config/testdata/full-config.json
+++ b/agent/config/testdata/full-config.json
@@ -572,7 +572,10 @@
             }
           ]
         },
-        "transparent_proxy": true,
+        "mode": "transparent",
+        "transparent_proxy": {
+          "outbound_listener_port": 10101
+        },
         "upstreams": [
           {
             "destination_name": "KPtAj2cb",
diff --git a/agent/consul/config_endpoint.go b/agent/consul/config_endpoint.go
index 2b3e345e5..5bf5a5596 100644
--- a/agent/consul/config_endpoint.go
+++ b/agent/consul/config_endpoint.go
@@ -355,9 +355,10 @@ func (c *ConfigEntry) ResolveServiceConfig(args *structs.ServiceConfigRequest, r
 					return fmt.Errorf("failed to copy global proxy-defaults: %v", err)
 				}
 				reply.ProxyConfig = mapCopy.(map[string]interface{})
+				reply.Mode = proxyConf.Mode
+				reply.TransparentProxy = proxyConf.TransparentProxy
 				reply.MeshGateway = proxyConf.MeshGateway
 				reply.Expose = proxyConf.Expose
-				reply.TransparentProxy = proxyConf.TransparentProxy
 
 				// Extract the global protocol from proxyConf for upstream configs.
 				rawProtocol := proxyConf.Config["protocol"]
@@ -396,8 +397,11 @@ func (c *ConfigEntry) ResolveServiceConfig(args *structs.ServiceConfigRequest, r
 					}
 					reply.ProxyConfig["protocol"] = serviceConf.Protocol
 				}
-				if serviceConf.TransparentProxy {
-					reply.TransparentProxy = serviceConf.TransparentProxy
+				if serviceConf.TransparentProxy.OutboundListenerPort != 0 {
+					reply.TransparentProxy.OutboundListenerPort = serviceConf.TransparentProxy.OutboundListenerPort
+				}
+				if serviceConf.Mode != structs.ProxyModeDefault {
+					reply.Mode = serviceConf.Mode
 				}
 			}
 
@@ -413,13 +417,13 @@ func (c *ConfigEntry) ResolveServiceConfig(args *structs.ServiceConfigRequest, r
 			var (
 				noUpstreamArgs = len(upstreamIDs) == 0 && len(args.Upstreams) == 0
 
-				// Check the args and the resolved value. If it was exclusively set via a config entry, then args.TransparentProxy
-				// will never be true because the service config request does not use the resolved value.
-				tproxy = args.TransparentProxy || reply.TransparentProxy
+				// Check the args and the resolved value. If it was exclusively set via a config entry, then args.Mode
+				// will never be transparent because the service config request does not use the resolved value.
+				tproxy = args.Mode == structs.ProxyModeTransparent || reply.Mode == structs.ProxyModeTransparent
 			)
 
 			// The upstreams passed as arguments to this endpoint are the upstreams explicitly defined in a proxy registration.
-			// If no upstreams were passed, then we should only returned the resolved config if the proxy has TransparentProxy mode enabled.
+			// If no upstreams were passed, then we should only returned the resolved config if the proxy in transparent mode.
 			// Otherwise we would return a resolved upstream config to a proxy with no configured upstreams.
 			if noUpstreamArgs && !tproxy {
 				return nil
diff --git a/agent/consul/config_endpoint_test.go b/agent/consul/config_endpoint_test.go
index ea1704201..abbe95239 100644
--- a/agent/consul/config_endpoint_test.go
+++ b/agent/consul/config_endpoint_test.go
@@ -913,7 +913,8 @@ func TestConfigEntry_ResolveServiceConfig_TransparentProxy(t *testing.T) {
 				&structs.ProxyConfigEntry{
 					Kind:             structs.ProxyDefaults,
 					Name:             structs.ProxyConfigGlobal,
-					TransparentProxy: true,
+					Mode:             structs.ProxyModeTransparent,
+					TransparentProxy: structs.TransparentProxyConfig{OutboundListenerPort: 10101},
 				},
 			},
 			request: structs.ServiceConfigRequest{
@@ -921,7 +922,8 @@ func TestConfigEntry_ResolveServiceConfig_TransparentProxy(t *testing.T) {
 				Datacenter: "dc1",
 			},
 			expect: structs.ServiceConfigResponse{
-				TransparentProxy: true,
+				Mode:             structs.ProxyModeTransparent,
+				TransparentProxy: structs.TransparentProxyConfig{OutboundListenerPort: 10101},
 			},
 		},
 		{
@@ -930,7 +932,8 @@ func TestConfigEntry_ResolveServiceConfig_TransparentProxy(t *testing.T) {
 				&structs.ServiceConfigEntry{
 					Kind:             structs.ServiceDefaults,
 					Name:             "foo",
-					TransparentProxy: true,
+					Mode:             structs.ProxyModeTransparent,
+					TransparentProxy: structs.TransparentProxyConfig{OutboundListenerPort: 808},
 				},
 			},
 			request: structs.ServiceConfigRequest{
@@ -938,7 +941,8 @@ func TestConfigEntry_ResolveServiceConfig_TransparentProxy(t *testing.T) {
 				Datacenter: "dc1",
 			},
 			expect: structs.ServiceConfigResponse{
-				TransparentProxy: true,
+				Mode:             structs.ProxyModeTransparent,
+				TransparentProxy: structs.TransparentProxyConfig{OutboundListenerPort: 808},
 			},
 		},
 		{
@@ -947,12 +951,14 @@ func TestConfigEntry_ResolveServiceConfig_TransparentProxy(t *testing.T) {
 				&structs.ProxyConfigEntry{
 					Kind:             structs.ProxyDefaults,
 					Name:             structs.ProxyConfigGlobal,
-					TransparentProxy: false,
+					Mode:             structs.ProxyModeDirect,
+					TransparentProxy: structs.TransparentProxyConfig{OutboundListenerPort: 10101},
 				},
 				&structs.ServiceConfigEntry{
 					Kind:             structs.ServiceDefaults,
 					Name:             "foo",
-					TransparentProxy: true,
+					Mode:             structs.ProxyModeTransparent,
+					TransparentProxy: structs.TransparentProxyConfig{OutboundListenerPort: 808},
 				},
 			},
 			request: structs.ServiceConfigRequest{
@@ -960,7 +966,8 @@ func TestConfigEntry_ResolveServiceConfig_TransparentProxy(t *testing.T) {
 				Datacenter: "dc1",
 			},
 			expect: structs.ServiceConfigResponse{
-				TransparentProxy: true,
+				Mode:             structs.ProxyModeTransparent,
+				TransparentProxy: structs.TransparentProxyConfig{OutboundListenerPort: 808},
 			},
 		},
 	}
@@ -1245,9 +1252,9 @@ func TestConfigEntry_ResolveServiceConfig_Upstreams(t *testing.T) {
 				},
 			},
 			request: structs.ServiceConfigRequest{
-				Name:             "api",
-				Datacenter:       "dc1",
-				TransparentProxy: true,
+				Name:       "api",
+				Datacenter: "dc1",
+				Mode:       structs.ProxyModeTransparent,
 
 				// Empty Upstreams/UpstreamIDs
 			},
@@ -1291,7 +1298,8 @@ func TestConfigEntry_ResolveServiceConfig_Upstreams(t *testing.T) {
 					},
 
 					// TransparentProxy on the config entry but not the config request
-					TransparentProxy: true,
+					Mode:             structs.ProxyModeTransparent,
+					TransparentProxy: structs.TransparentProxyConfig{OutboundListenerPort: 10101},
 				},
 			},
 			request: structs.ServiceConfigRequest{
@@ -1301,7 +1309,8 @@ func TestConfigEntry_ResolveServiceConfig_Upstreams(t *testing.T) {
 				// Empty Upstreams/UpstreamIDs
 			},
 			expect: structs.ServiceConfigResponse{
-				TransparentProxy: true,
+				Mode:             structs.ProxyModeTransparent,
+				TransparentProxy: structs.TransparentProxyConfig{OutboundListenerPort: 10101},
 				UpstreamIDConfigs: structs.OpaqueUpstreamConfigs{
 					{
 						Upstream: wildcard,
@@ -1342,9 +1351,9 @@ func TestConfigEntry_ResolveServiceConfig_Upstreams(t *testing.T) {
 				},
 			},
 			request: structs.ServiceConfigRequest{
-				Name:             "api",
-				Datacenter:       "dc1",
-				TransparentProxy: false,
+				Name:       "api",
+				Datacenter: "dc1",
+				Mode:       structs.ProxyModeDirect,
 
 				// Empty Upstreams/UpstreamIDs
 			},
diff --git a/agent/dns_test.go b/agent/dns_test.go
index 08583caee..db03243bf 100644
--- a/agent/dns_test.go
+++ b/agent/dns_test.go
@@ -6688,7 +6688,7 @@ func TestDNS_trimUDPResponse_NoTrim(t *testing.T) {
 		},
 	}
 
-	cfg := loadRuntimeConfig(t, `data_dir = "a" bind_addr = "127.0.0.1"`)
+	cfg := loadRuntimeConfig(t, `node_name = "test" data_dir = "a" bind_addr = "127.0.0.1"`)
 	if trimmed := trimUDPResponse(req, resp, cfg.DNSUDPAnswerLimit); trimmed {
 		t.Fatalf("Bad %#v", *resp)
 	}
@@ -6722,7 +6722,7 @@ func TestDNS_trimUDPResponse_NoTrim(t *testing.T) {
 
 func TestDNS_trimUDPResponse_TrimLimit(t *testing.T) {
 	t.Parallel()
-	cfg := loadRuntimeConfig(t, `data_dir = "a" bind_addr = "127.0.0.1"`)
+	cfg := loadRuntimeConfig(t, `node_name = "test" data_dir = "a" bind_addr = "127.0.0.1"`)
 
 	req, resp, expected := &dns.Msg{}, &dns.Msg{}, &dns.Msg{}
 	for i := 0; i < cfg.DNSUDPAnswerLimit+1; i++ {
@@ -6770,7 +6770,7 @@ func loadRuntimeConfig(t *testing.T, hcl string) *config.RuntimeConfig {
 
 func TestDNS_trimUDPResponse_TrimSize(t *testing.T) {
 	t.Parallel()
-	cfg := loadRuntimeConfig(t, `data_dir = "a" bind_addr = "127.0.0.1"`)
+	cfg := loadRuntimeConfig(t, `node_name = "test" data_dir = "a" bind_addr = "127.0.0.1"`)
 
 	req, resp := &dns.Msg{}, &dns.Msg{}
 	for i := 0; i < 100; i++ {
@@ -6823,7 +6823,7 @@ func TestDNS_trimUDPResponse_TrimSize(t *testing.T) {
 
 func TestDNS_trimUDPResponse_TrimSizeEDNS(t *testing.T) {
 	t.Parallel()
-	cfg := loadRuntimeConfig(t, `data_dir = "a" bind_addr = "127.0.0.1"`)
+	cfg := loadRuntimeConfig(t, `node_name = "test" data_dir = "a" bind_addr = "127.0.0.1"`)
 
 	req, resp := &dns.Msg{}, &dns.Msg{}
 
diff --git a/agent/proxycfg/snapshot.go b/agent/proxycfg/snapshot.go
index e79fc1507..d0dab4deb 100644
--- a/agent/proxycfg/snapshot.go
+++ b/agent/proxycfg/snapshot.go
@@ -360,7 +360,7 @@ type ConfigSnapshot struct {
 func (s *ConfigSnapshot) Valid() bool {
 	switch s.Kind {
 	case structs.ServiceKindConnectProxy:
-		if s.Proxy.TransparentProxy && !s.ConnectProxy.ClusterConfigSet {
+		if s.Proxy.Mode == structs.ProxyModeTransparent && !s.ConnectProxy.ClusterConfigSet {
 			return false
 		}
 		return s.Roots != nil &&
diff --git a/agent/proxycfg/state.go b/agent/proxycfg/state.go
index 71e2182e2..5d0b88624 100644
--- a/agent/proxycfg/state.go
+++ b/agent/proxycfg/state.go
@@ -305,7 +305,7 @@ func (s *state) initWatchesConnectProxy(snap *ConfigSnapshot) error {
 	// default the namespace to the namespace of this proxy service
 	currentNamespace := s.proxyID.NamespaceOrDefault()
 
-	if s.proxyCfg.TransparentProxy {
+	if s.proxyCfg.Mode == structs.ProxyModeTransparent {
 		// When in transparent proxy we will infer upstreams from intentions with this source
 		err := s.cache.Notify(s.ctx, cachetype.IntentionUpstreamsName, &structs.ServiceSpecificRequest{
 			Datacenter:     s.source.Datacenter,
@@ -350,8 +350,8 @@ func (s *state) initWatchesConnectProxy(snap *ConfigSnapshot) error {
 		if u.Datacenter != "" {
 			dc = u.Datacenter
 		}
-		if s.proxyCfg.TransparentProxy && (dc == "" || dc == s.source.Datacenter) {
-			// In TransparentProxy mode, watches for upstreams in the local DC are handled by the IntentionUpstreams watch.
+		if s.proxyCfg.Mode == structs.ProxyModeTransparent && (dc == "" || dc == s.source.Datacenter) {
+			// In transparent proxy mode, watches for upstreams in the local DC are handled by the IntentionUpstreams watch.
 			continue
 		}
 
diff --git a/agent/proxycfg/state_test.go b/agent/proxycfg/state_test.go
index 8fad4c600..f4c36d5ed 100644
--- a/agent/proxycfg/state_test.go
+++ b/agent/proxycfg/state_test.go
@@ -1541,7 +1541,7 @@ func TestState_WatchesAndUpdates(t *testing.T) {
 				Address: "10.0.1.1",
 				Proxy: structs.ConnectProxyConfig{
 					DestinationServiceName: "api",
-					TransparentProxy:       true,
+					Mode:                   structs.ProxyModeTransparent,
 				},
 			},
 			sourceDC: "dc1",
@@ -1606,7 +1606,7 @@ func TestState_WatchesAndUpdates(t *testing.T) {
 				Address: "10.0.1.1",
 				Proxy: structs.ConnectProxyConfig{
 					DestinationServiceName: "api",
-					TransparentProxy:       true,
+					Mode:                   structs.ProxyModeTransparent,
 					Upstreams: structs.Upstreams{
 						{
 							CentrallyConfigured:  true,
diff --git a/agent/service_manager.go b/agent/service_manager.go
index d48ba2632..e67f30ce0 100644
--- a/agent/service_manager.go
+++ b/agent/service_manager.go
@@ -335,13 +335,13 @@ func makeConfigRequest(bd BaseDeps, addReq AddServiceRequest) *structs.ServiceCo
 	}
 
 	req := &structs.ServiceConfigRequest{
-		Name:             name,
-		Datacenter:       bd.RuntimeConfig.Datacenter,
-		QueryOptions:     structs.QueryOptions{Token: addReq.token},
-		MeshGateway:      ns.Proxy.MeshGateway,
-		TransparentProxy: ns.Proxy.TransparentProxy,
-		UpstreamIDs:      upstreams,
-		EnterpriseMeta:   ns.EnterpriseMeta,
+		Name:           name,
+		Datacenter:     bd.RuntimeConfig.Datacenter,
+		QueryOptions:   structs.QueryOptions{Token: addReq.token},
+		MeshGateway:    ns.Proxy.MeshGateway,
+		Mode:           ns.Proxy.Mode,
+		UpstreamIDs:    upstreams,
+		EnterpriseMeta: ns.EnterpriseMeta,
 	}
 	if req.QueryOptions.Token == "" {
 		req.QueryOptions.Token = bd.Tokens.AgentToken()
@@ -377,8 +377,11 @@ func mergeServiceConfig(defaults *structs.ServiceConfigResponse, service *struct
 	if ns.Proxy.MeshGateway.Mode == structs.MeshGatewayModeDefault {
 		ns.Proxy.MeshGateway.Mode = defaults.MeshGateway.Mode
 	}
-	if !ns.Proxy.TransparentProxy {
-		ns.Proxy.TransparentProxy = defaults.TransparentProxy
+	if ns.Proxy.Mode == structs.ProxyModeDefault {
+		ns.Proxy.Mode = defaults.Mode
+	}
+	if ns.Proxy.TransparentProxy.OutboundListenerPort == 0 {
+		ns.Proxy.TransparentProxy.OutboundListenerPort = defaults.TransparentProxy.OutboundListenerPort
 	}
 
 	// remoteUpstreams contains synthetic Upstreams generated from central config (service-defaults.UpstreamConfigs).
@@ -406,7 +409,7 @@ func mergeServiceConfig(defaults *structs.ServiceConfigResponse, service *struct
 	}
 
 	// localUpstreams stores the upstreams seen from the local registration so that we can merge in the synthetic entries.
-	// In TransparentProxy mode ns.Proxy.Upstreams will likely be empty because users do not need to define upstreams explicitly.
+	// In transparent proxy mode ns.Proxy.Upstreams will likely be empty because users do not need to define upstreams explicitly.
 	// So to store upstream-specific flags from central config, we add entries to ns.Proxy.Upstream with those values.
 	localUpstreams := make(map[structs.ServiceID]struct{})
 
@@ -437,9 +440,9 @@ func mergeServiceConfig(defaults *structs.ServiceConfigResponse, service *struct
 	}
 
 	// Ensure upstreams present in central config are represented in the local configuration.
-	// This does not apply outside of TransparentProxy mode because in that situation every possible upstream already exists
+	// This does not apply outside of transparent mode because in that situation every possible upstream already exists
 	// inside of ns.Proxy.Upstreams.
-	if ns.Proxy.TransparentProxy {
+	if ns.Proxy.Mode == structs.ProxyModeTransparent {
 		for id, remote := range remoteUpstreams {
 			if _, ok := localUpstreams[id]; ok {
 				// Remote upstream is already present locally
diff --git a/agent/service_manager_test.go b/agent/service_manager_test.go
index 7a4ef3eec..464b7087e 100644
--- a/agent/service_manager_test.go
+++ b/agent/service_manager_test.go
@@ -929,7 +929,7 @@ func Test_mergeServiceConfig_UpstreamOverrides(t *testing.T) {
 			},
 		},
 		{
-			name: "remote upstream config expands local upstream list in tproxy mode",
+			name: "remote upstream config expands local upstream list in transparent mode",
 			args: args{
 				defaults: &structs.ServiceConfigResponse{
 					UpstreamIDConfigs: structs.OpaqueUpstreamConfigs{
@@ -950,7 +950,10 @@ func Test_mergeServiceConfig_UpstreamOverrides(t *testing.T) {
 					Proxy: structs.ConnectProxyConfig{
 						DestinationServiceName: "foo",
 						DestinationServiceID:   "foo",
-						TransparentProxy:       true,
+						Mode:                   structs.ProxyModeTransparent,
+						TransparentProxy: structs.TransparentProxyConfig{
+							OutboundListenerPort: 10101,
+						},
 						Upstreams: structs.Upstreams{
 							structs.Upstream{
 								DestinationNamespace: "default",
@@ -970,7 +973,10 @@ func Test_mergeServiceConfig_UpstreamOverrides(t *testing.T) {
 				Proxy: structs.ConnectProxyConfig{
 					DestinationServiceName: "foo",
 					DestinationServiceID:   "foo",
-					TransparentProxy:       true,
+					Mode:                   structs.ProxyModeTransparent,
+					TransparentProxy: structs.TransparentProxyConfig{
+						OutboundListenerPort: 10101,
+					},
 					Upstreams: structs.Upstreams{
 						structs.Upstream{
 							DestinationNamespace: "default",
@@ -993,7 +999,7 @@ func Test_mergeServiceConfig_UpstreamOverrides(t *testing.T) {
 			},
 		},
 		{
-			name: "remote upstream config not added to local upstream list outside of tproxy mode",
+			name: "remote upstream config not added to local upstream list outside of transparent mode",
 			args: args{
 				defaults: &structs.ServiceConfigResponse{
 					UpstreamIDConfigs: structs.OpaqueUpstreamConfigs{
@@ -1014,7 +1020,7 @@ func Test_mergeServiceConfig_UpstreamOverrides(t *testing.T) {
 					Proxy: structs.ConnectProxyConfig{
 						DestinationServiceName: "foo",
 						DestinationServiceID:   "foo",
-						TransparentProxy:       false,
+						Mode:                   structs.ProxyModeDirect,
 						Upstreams: structs.Upstreams{
 							structs.Upstream{
 								DestinationNamespace: "default",
@@ -1034,6 +1040,7 @@ func Test_mergeServiceConfig_UpstreamOverrides(t *testing.T) {
 				Proxy: structs.ConnectProxyConfig{
 					DestinationServiceName: "foo",
 					DestinationServiceID:   "foo",
+					Mode:                   structs.ProxyModeDirect,
 					Upstreams: structs.Upstreams{
 						structs.Upstream{
 							DestinationNamespace: "default",
@@ -1175,3 +1182,81 @@ func Test_mergeServiceConfig_UpstreamOverrides(t *testing.T) {
 		})
 	}
 }
+
+func Test_mergeServiceConfig_TransparentProxy(t *testing.T) {
+	type args struct {
+		defaults *structs.ServiceConfigResponse
+		service  *structs.NodeService
+	}
+	tests := []struct {
+		name string
+		args args
+		want *structs.NodeService
+	}{
+		{
+			name: "inherit transparent proxy settings",
+			args: args{
+				defaults: &structs.ServiceConfigResponse{
+					Mode:             structs.ProxyModeTransparent,
+					TransparentProxy: structs.TransparentProxyConfig{OutboundListenerPort: 10101},
+				},
+				service: &structs.NodeService{
+					ID:      "foo-proxy",
+					Service: "foo-proxy",
+					Proxy: structs.ConnectProxyConfig{
+						DestinationServiceName: "foo",
+						DestinationServiceID:   "foo",
+						Mode:                   structs.ProxyModeDefault,
+						TransparentProxy:       structs.TransparentProxyConfig{},
+					},
+				},
+			},
+			want: &structs.NodeService{
+				ID:      "foo-proxy",
+				Service: "foo-proxy",
+				Proxy: structs.ConnectProxyConfig{
+					DestinationServiceName: "foo",
+					DestinationServiceID:   "foo",
+					Mode:                   structs.ProxyModeTransparent,
+					TransparentProxy:       structs.TransparentProxyConfig{OutboundListenerPort: 10101},
+				},
+			},
+		},
+		{
+			name: "override transparent proxy settings",
+			args: args{
+				defaults: &structs.ServiceConfigResponse{
+					Mode:             structs.ProxyModeTransparent,
+					TransparentProxy: structs.TransparentProxyConfig{OutboundListenerPort: 10101},
+				},
+				service: &structs.NodeService{
+					ID:      "foo-proxy",
+					Service: "foo-proxy",
+					Proxy: structs.ConnectProxyConfig{
+						DestinationServiceName: "foo",
+						DestinationServiceID:   "foo",
+						Mode:                   structs.ProxyModeDirect,
+						TransparentProxy:       structs.TransparentProxyConfig{OutboundListenerPort: 808},
+					},
+				},
+			},
+			want: &structs.NodeService{
+				ID:      "foo-proxy",
+				Service: "foo-proxy",
+				Proxy: structs.ConnectProxyConfig{
+					DestinationServiceName: "foo",
+					DestinationServiceID:   "foo",
+					Mode:                   structs.ProxyModeDirect,
+					TransparentProxy:       structs.TransparentProxyConfig{OutboundListenerPort: 808},
+				},
+			},
+		},
+	}
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			got, err := mergeServiceConfig(tt.args.defaults, tt.args.service)
+			require.NoError(t, err)
+			assert.Equal(t, tt.want, got)
+		})
+	}
+}
diff --git a/agent/structs/config_entry.go b/agent/structs/config_entry.go
index a12e6a407..1b01daaa1 100644
--- a/agent/structs/config_entry.go
+++ b/agent/structs/config_entry.go
@@ -85,9 +85,10 @@ type ServiceConfigEntry struct {
 	Kind             string
 	Name             string
 	Protocol         string
-	MeshGateway      MeshGatewayConfig `json:",omitempty" alias:"mesh_gateway"`
-	Expose           ExposeConfig      `json:",omitempty"`
-	TransparentProxy bool              `json:",omitempty" alias:"transparent_proxy"`
+	Mode             ProxyMode              `json:",omitempty"`
+	TransparentProxy TransparentProxyConfig `json:",omitempty" alias:"transparent_proxy"`
+	MeshGateway      MeshGatewayConfig      `json:",omitempty" alias:"mesh_gateway"`
+	Expose           ExposeConfig           `json:",omitempty"`
 
 	ExternalSNI string `json:",omitempty" alias:"external_sni"`
 
@@ -223,9 +224,10 @@ type ProxyConfigEntry struct {
 	Kind             string
 	Name             string
 	Config           map[string]interface{}
-	MeshGateway      MeshGatewayConfig `json:",omitempty" alias:"mesh_gateway"`
-	Expose           ExposeConfig      `json:",omitempty"`
-	TransparentProxy bool              `json:",omitempty" alias:"transparent_proxy"`
+	Mode             ProxyMode              `json:",omitempty"`
+	TransparentProxy TransparentProxyConfig `json:",omitempty" alias:"transparent_proxy"`
+	MeshGateway      MeshGatewayConfig      `json:",omitempty" alias:"mesh_gateway"`
+	Expose           ExposeConfig           `json:",omitempty"`
 
 	Meta           map[string]string `json:",omitempty"`
 	EnterpriseMeta `hcl:",squash" mapstructure:",squash"`
@@ -595,8 +597,8 @@ type ServiceConfigRequest struct {
 	// MeshGateway contains the mesh gateway configuration from the requesting proxy's registration
 	MeshGateway MeshGatewayConfig
 
-	// TransparentProxy indicates whether the requesting proxy is in transparent proxy mode
-	TransparentProxy bool
+	// Mode indicates how the requesting proxy's listeners are dialed
+	Mode ProxyMode
 
 	UpstreamIDs []ServiceID
 
@@ -859,9 +861,10 @@ type ServiceConfigResponse struct {
 	ProxyConfig       map[string]interface{}
 	UpstreamConfigs   map[string]map[string]interface{}
 	UpstreamIDConfigs OpaqueUpstreamConfigs
-	MeshGateway       MeshGatewayConfig `json:",omitempty"`
-	Expose            ExposeConfig      `json:",omitempty"`
-	TransparentProxy  bool              `json:",omitempty"`
+	MeshGateway       MeshGatewayConfig      `json:",omitempty"`
+	Expose            ExposeConfig           `json:",omitempty"`
+	TransparentProxy  TransparentProxyConfig `json:",omitempty"`
+	Mode              ProxyMode              `json:",omitempty"`
 	QueryMeta
 }
 
diff --git a/agent/structs/connect_proxy_config.go b/agent/structs/connect_proxy_config.go
index 2cf920a74..225c663d7 100644
--- a/agent/structs/connect_proxy_config.go
+++ b/agent/structs/connect_proxy_config.go
@@ -26,8 +26,8 @@ const (
 	// should be direct and not flow through a mesh gateway.
 	MeshGatewayModeNone MeshGatewayMode = "none"
 
-	// MeshGatewayModeLocal represents that the Upstrea Connect connections
-	// should be made to a mesh gateway in the local datacenter. This is
+	// MeshGatewayModeLocal represents that the Upstream Connect connections
+	// should be made to a mesh gateway in the local datacenter.
 	MeshGatewayModeLocal MeshGatewayMode = "local"
 
 	// MeshGatewayModeRemote represents that the Upstream Connect connections
@@ -75,6 +75,45 @@ func (c *MeshGatewayConfig) ToAPI() api.MeshGatewayConfig {
 	return api.MeshGatewayConfig{Mode: api.MeshGatewayMode(c.Mode)}
 }
 
+type ProxyMode string
+
+const (
+	// ProxyModeDefault represents no specific mode and should
+	// be used to indicate that a different layer of the configuration
+	// chain should take precedence
+	ProxyModeDefault ProxyMode = ""
+
+	// ProxyModeTransparent represents that inbound and outbound application
+	// traffic is being captured and redirected through the proxy.
+	ProxyModeTransparent ProxyMode = "transparent"
+
+	// ProxyModeDirect represents that the proxy's listeners must be dialed directly
+	// by the local application and other proxies.
+	ProxyModeDirect ProxyMode = "direct"
+)
+
+func ValidateProxyMode(mode string) (ProxyMode, error) {
+	switch ProxyMode(mode) {
+	case ProxyModeDefault:
+		return ProxyModeDefault, nil
+	case ProxyModeDirect:
+		return ProxyModeDirect, nil
+	case ProxyModeTransparent:
+		return ProxyModeTransparent, nil
+	default:
+		return ProxyModeDefault, fmt.Errorf("Invalid Proxy Mode: %q", mode)
+	}
+}
+
+type TransparentProxyConfig struct {
+	// The port of the listener where outbound application traffic is being redirected to.
+	OutboundListenerPort int `json:",omitempty" alias:"outbound_listener_port"`
+}
+
+func (c TransparentProxyConfig) ToAPI() api.TransparentProxyConfig {
+	return api.TransparentProxyConfig{OutboundListenerPort: c.OutboundListenerPort}
+}
+
 // ConnectProxyConfig describes the configuration needed for any proxy managed
 // or unmanaged. It describes a single logical service's listener and optionally
 // upstreams and sidecar-related config for a single instance. To describe a
@@ -105,6 +144,9 @@ type ConnectProxyConfig struct {
 	// (DestinationServiceID is set) but otherwise will be ignored.
 	LocalServicePort int `json:",omitempty" alias:"local_service_port"`
 
+	// Mode represents how the proxy's inbound and upstream listeners are dialed.
+	Mode ProxyMode
+
 	// Config is the arbitrary configuration data provided with the proxy
 	// registration.
 	Config map[string]interface{} `json:",omitempty" bexpr:"-"`
@@ -119,20 +161,20 @@ type ConnectProxyConfig struct {
 	// Expose defines whether checks or paths are exposed through the proxy
 	Expose ExposeConfig `json:",omitempty"`
 
-	// TransparentProxy toggles whether inbound and outbound traffic is being
-	// redirected to the proxy.
-	TransparentProxy bool `json:",omitempty" alias:"transparent_proxy"`
+	// TransparentProxy defines configuration for when the proxy is in
+	// transparent mode.
+	TransparentProxy TransparentProxyConfig `json:",omitempty" alias:"transparent_proxy"`
 }
 
 func (t *ConnectProxyConfig) UnmarshalJSON(data []byte) (err error) {
 	type Alias ConnectProxyConfig
 	aux := &struct {
-		DestinationServiceNameSnake string            `json:"destination_service_name"`
-		DestinationServiceIDSnake   string            `json:"destination_service_id"`
-		LocalServiceAddressSnake    string            `json:"local_service_address"`
-		LocalServicePortSnake       int               `json:"local_service_port"`
-		MeshGatewaySnake            MeshGatewayConfig `json:"mesh_gateway"`
-		TransparentProxySnake       bool              `json:"transparent_proxy"`
+		DestinationServiceNameSnake string                 `json:"destination_service_name"`
+		DestinationServiceIDSnake   string                 `json:"destination_service_id"`
+		LocalServiceAddressSnake    string                 `json:"local_service_address"`
+		LocalServicePortSnake       int                    `json:"local_service_port"`
+		MeshGatewaySnake            MeshGatewayConfig      `json:"mesh_gateway"`
+		TransparentProxySnake       TransparentProxyConfig `json:"transparent_proxy"`
 
 		*Alias
 	}{
@@ -156,8 +198,8 @@ func (t *ConnectProxyConfig) UnmarshalJSON(data []byte) (err error) {
 	if t.MeshGateway.Mode == "" {
 		t.MeshGateway.Mode = aux.MeshGatewaySnake.Mode
 	}
-	if !t.TransparentProxy {
-		t.TransparentProxy = aux.TransparentProxySnake
+	if t.TransparentProxy.OutboundListenerPort == 0 {
+		t.TransparentProxy.OutboundListenerPort = aux.TransparentProxySnake.OutboundListenerPort
 	}
 
 	return nil
@@ -187,11 +229,12 @@ func (c *ConnectProxyConfig) ToAPI() *api.AgentServiceConnectProxyConfig {
 		DestinationServiceID:   c.DestinationServiceID,
 		LocalServiceAddress:    c.LocalServiceAddress,
 		LocalServicePort:       c.LocalServicePort,
+		Mode:                   api.ProxyMode(c.Mode),
+		TransparentProxy:       c.TransparentProxy.ToAPI(),
 		Config:                 c.Config,
 		Upstreams:              c.Upstreams.ToAPI(),
 		MeshGateway:            c.MeshGateway.ToAPI(),
 		Expose:                 c.Expose.ToAPI(),
-		TransparentProxy:       c.TransparentProxy,
 	}
 }
 
diff --git a/agent/structs/connect_proxy_config_test.go b/agent/structs/connect_proxy_config_test.go
index 7c2c911f8..df680a069 100644
--- a/agent/structs/connect_proxy_config_test.go
+++ b/agent/structs/connect_proxy_config_test.go
@@ -572,3 +572,37 @@ func TestValidateMeshGatewayMode(t *testing.T) {
 		})
 	}
 }
+
+func TestValidateProxyMode(t *testing.T) {
+	for _, tc := range []struct {
+		modeConstant string
+		modeExplicit string
+		expect       ProxyMode
+		ok           bool
+	}{
+		{string(ProxyModeDefault), "", ProxyModeDefault, true},
+		{string(ProxyModeDirect), "direct", ProxyModeDirect, true},
+		{string(ProxyModeTransparent), "transparent", ProxyModeTransparent, true},
+	} {
+		tc := tc
+
+		t.Run(tc.modeConstant+" (constant)", func(t *testing.T) {
+			got, err := ValidateProxyMode(tc.modeConstant)
+			if tc.ok {
+				require.NoError(t, err)
+				require.Equal(t, tc.expect, got)
+			} else {
+				require.Error(t, err)
+			}
+		})
+		t.Run(tc.modeExplicit+" (explicit)", func(t *testing.T) {
+			got, err := ValidateProxyMode(tc.modeExplicit)
+			if tc.ok {
+				require.NoError(t, err)
+				require.Equal(t, tc.expect, got)
+			} else {
+				require.Error(t, err)
+			}
+		})
+	}
+}
diff --git a/agent/structs/structs_filtering_test.go b/agent/structs/structs_filtering_test.go
index 2fa419eeb..eb61b5bfb 100644
--- a/agent/structs/structs_filtering_test.go
+++ b/agent/structs/structs_filtering_test.go
@@ -95,6 +95,14 @@ var expectedFieldConfigMeshGatewayConfig bexpr.FieldConfigurations = bexpr.Field
 	},
 }
 
+var expectedFieldConfigTransparentProxyConfig bexpr.FieldConfigurations = bexpr.FieldConfigurations{
+	"OutboundListenerPort": &bexpr.FieldConfiguration{
+		StructFieldName:     "OutboundListenerPort",
+		CoerceFn:            bexpr.CoerceInt,
+		SupportedOperations: []bexpr.MatchOperator{bexpr.MatchEqual, bexpr.MatchNotEqual},
+	},
+}
+
 var expectedFieldConfigExposeConfig bexpr.FieldConfigurations = bexpr.FieldConfigurations{
 	"Checks": &bexpr.FieldConfiguration{
 		StructFieldName:     "Checks",
@@ -208,9 +216,13 @@ var expectedFieldConfigConnectProxyConfig bexpr.FieldConfigurations = bexpr.Fiel
 		SubFields:       expectedFieldConfigExposeConfig,
 	},
 	"TransparentProxy": &bexpr.FieldConfiguration{
-		StructFieldName:     "TransparentProxy",
-		CoerceFn:            bexpr.CoerceBool,
-		SupportedOperations: []bexpr.MatchOperator{bexpr.MatchEqual, bexpr.MatchNotEqual},
+		StructFieldName: "TransparentProxy",
+		SubFields:       expectedFieldConfigTransparentProxyConfig,
+	},
+	"Mode": &bexpr.FieldConfiguration{
+		StructFieldName:     "Mode",
+		CoerceFn:            bexpr.CoerceString,
+		SupportedOperations: []bexpr.MatchOperator{bexpr.MatchEqual, bexpr.MatchNotEqual, bexpr.MatchIn, bexpr.MatchNotIn, bexpr.MatchMatches, bexpr.MatchNotMatches},
 	},
 }
 
diff --git a/agent/xds/clusters.go b/agent/xds/clusters.go
index 776b6a324..db9910437 100644
--- a/agent/xds/clusters.go
+++ b/agent/xds/clusters.go
@@ -56,10 +56,11 @@ func (s *Server) clustersFromSnapshotConnectProxy(cfgSnap *proxycfg.ConfigSnapsh
 	}
 	clusters = append(clusters, appCluster)
 
-	// In TransparentProxy mode there needs to be a passthrough cluster for traffic going to destinations
+	// In transparent proxy mode there needs to be a passthrough cluster for traffic going to destinations
 	// that aren't in Consul's catalog.
-	// TODO (freddy): Add cluster-wide setting that can disable this cluster and restrict traffic to catalog destinations.
-	if cfgSnap.Proxy.TransparentProxy {
+	if cfgSnap.Proxy.Mode == structs.ProxyModeTransparent &&
+		!cfgSnap.ConnectProxy.ClusterConfig.TransparentProxy.CatalogDestinationsOnly {
+
 		clusters = append(clusters, &envoy_cluster_v3.Cluster{
 			Name: OriginalDestinationClusterName,
 			ClusterDiscoveryType: &envoy_cluster_v3.Cluster_Type{
diff --git a/agent/xds/clusters_test.go b/agent/xds/clusters_test.go
index e3a7e4230..6e82ca946 100644
--- a/agent/xds/clusters_test.go
+++ b/agent/xds/clusters_test.go
@@ -629,7 +629,14 @@ func TestClustersFromSnapshot(t *testing.T) {
 			name:   "transparent-proxy",
 			create: proxycfg.TestConfigSnapshot,
 			setup: func(snap *proxycfg.ConfigSnapshot) {
-				snap.Proxy.TransparentProxy = true
+				snap.Proxy.Mode = structs.ProxyModeTransparent
+
+				snap.ConnectProxy.ClusterConfigSet = true
+				snap.ConnectProxy.ClusterConfig = &structs.ClusterConfigEntry{
+					TransparentProxy: structs.TransparentProxyClusterConfig{
+						CatalogDestinationsOnly: false,
+					},
+				}
 			},
 		},
 	}
diff --git a/agent/xds/listeners.go b/agent/xds/listeners.go
index a8ea5f5c8..08cc81f84 100644
--- a/agent/xds/listeners.go
+++ b/agent/xds/listeners.go
@@ -65,14 +65,19 @@ func (s *Server) listenersFromSnapshotConnectProxy(cInfo connectionInfo, cfgSnap
 		return nil, err
 	}
 
-	// This outboundListener is exclusively used when TransparentProxy mode is active.
+	// This outboundListener is exclusively used when transparent proxy mode is active.
 	// In that situation there is a single listener where we are redirecting outbound traffic,
 	// and each upstream gets a filter chain attached to that listener.
 	var outboundListener *envoy_listener_v3.Listener
 
-	if cfgSnap.Proxy.TransparentProxy {
+	if cfgSnap.Proxy.Mode == structs.ProxyModeTransparent {
+		port := iptables.DefaultTProxyOutboundPort
+		if cfgSnap.Proxy.TransparentProxy.OutboundListenerPort != 0 {
+			port = cfgSnap.Proxy.TransparentProxy.OutboundListenerPort
+		}
+
 		// TODO (freddy) Make DefaultTProxyOutboundPort configurable
-		outboundListener = makeListener(OutboundListenerName, "127.0.0.1", iptables.DefaultTProxyOutboundPort, envoy_core_v3.TrafficDirection_OUTBOUND)
+		outboundListener = makeListener(OutboundListenerName, "127.0.0.1", port, envoy_core_v3.TrafficDirection_OUTBOUND)
 		outboundListener.FilterChains = make([]*envoy_listener_v3.FilterChain, 0)
 		outboundListener.ListenerFilters = []*envoy_listener_v3.ListenerFilter{
 			{
diff --git a/agent/xds/listeners_test.go b/agent/xds/listeners_test.go
index dc2cd2e9d..1bc307c56 100644
--- a/agent/xds/listeners_test.go
+++ b/agent/xds/listeners_test.go
@@ -481,11 +481,11 @@ func TestListenersFromSnapshot(t *testing.T) {
 			name:   "transparent-proxy",
 			create: proxycfg.TestConfigSnapshot,
 			setup: func(snap *proxycfg.ConfigSnapshot) {
-				snap.Proxy.TransparentProxy = true
+				snap.Proxy.Mode = structs.ProxyModeTransparent
 
 				snap.ConnectProxy.ClusterConfigSet = true
 
-				// DiscoveryChain without an UpstreamConfig should yield a filter chain when in TransparentProxy mode
+				// DiscoveryChain without an UpstreamConfig should yield a filter chain when in transparent proxy mode
 				snap.ConnectProxy.DiscoveryChain["google"] = discoverychain.TestCompileConfigEntries(
 					t, "google", "default", "dc1",
 					connect.TestClusterID+".consul", "dc1", nil)
@@ -514,7 +514,7 @@ func TestListenersFromSnapshot(t *testing.T) {
 			name:   "transparent-proxy-catalog-destinations-only",
 			create: proxycfg.TestConfigSnapshot,
 			setup: func(snap *proxycfg.ConfigSnapshot) {
-				snap.Proxy.TransparentProxy = true
+				snap.Proxy.Mode = structs.ProxyModeTransparent
 
 				snap.ConnectProxy.ClusterConfigSet = true
 				snap.ConnectProxy.ClusterConfig = &structs.ClusterConfigEntry{
@@ -525,7 +525,7 @@ func TestListenersFromSnapshot(t *testing.T) {
 					},
 				}
 
-				// DiscoveryChain without an UpstreamConfig should yield a filter chain when in TransparentProxy mode
+				// DiscoveryChain without an UpstreamConfig should yield a filter chain when in transparent proxy mode
 				snap.ConnectProxy.DiscoveryChain["google"] = discoverychain.TestCompileConfigEntries(
 					t, "google", "default", "dc1",
 					connect.TestClusterID+".consul", "dc1", nil)
diff --git a/agent/xds/server.go b/agent/xds/server.go
index bce5d9df4..9907747d2 100644
--- a/agent/xds/server.go
+++ b/agent/xds/server.go
@@ -52,7 +52,7 @@ const (
 	// PublicListenerName is the name we give the public listener in Envoy config.
 	PublicListenerName = "public_listener"
 
-	// OutboundListenerName is the name we give the outbound Envoy listener when TransparentProxy mode is enabled.
+	// OutboundListenerName is the name we give the outbound Envoy listener when transparent proxy mode is enabled.
 	OutboundListenerName = "outbound_listener"
 
 	// LocalAppClusterName is the name we give the local application "cluster" in
@@ -86,7 +86,7 @@ const (
 	// OriginalDestinationClusterName is the name we give to the passthrough
 	// cluster which redirects transparently-proxied requests to their original
 	// destination. This cluster prevents Consul from blocking connections to
-	// destinations outside of the catalog when in TransparentProxy mode.
+	// destinations outside of the catalog when in transparent proxy mode.
 	OriginalDestinationClusterName = "original-destination"
 
 	// DefaultAuthCheckFrequency is the default value for
diff --git a/api/agent.go b/api/agent.go
index 0ed6fc298..acafa9cc9 100644
--- a/api/agent.go
+++ b/api/agent.go
@@ -118,11 +118,12 @@ type AgentServiceConnectProxyConfig struct {
 	DestinationServiceID   string                 `json:",omitempty"`
 	LocalServiceAddress    string                 `json:",omitempty"`
 	LocalServicePort       int                    `json:",omitempty"`
+	Mode                   ProxyMode              `json:",omitempty"`
+	TransparentProxy       TransparentProxyConfig `json:",omitempty"`
 	Config                 map[string]interface{} `json:",omitempty" bexpr:"-"`
 	Upstreams              []Upstream             `json:",omitempty"`
 	MeshGateway            MeshGatewayConfig      `json:",omitempty"`
 	Expose                 ExposeConfig           `json:",omitempty"`
-	TransparentProxy       bool                   `json:",omitempty"`
 }
 
 const (
diff --git a/api/agent_test.go b/api/agent_test.go
index 12056f236..f0a5db2bb 100644
--- a/api/agent_test.go
+++ b/api/agent_test.go
@@ -438,7 +438,7 @@ func TestAPI_AgentServices_ExternalConnectProxy(t *testing.T) {
 		Port: 8001,
 		Proxy: &AgentServiceConnectProxyConfig{
 			DestinationServiceName: "foo",
-			TransparentProxy:       true,
+			Mode:                   ProxyModeTransparent,
 		},
 	}
 	if err := agent.ServiceRegister(reg); err != nil {
@@ -455,7 +455,7 @@ func TestAPI_AgentServices_ExternalConnectProxy(t *testing.T) {
 	if _, ok := services["foo-proxy"]; !ok {
 		t.Fatalf("missing proxy service: %v", services)
 	}
-	if !services["foo-proxy"].Proxy.TransparentProxy {
+	if services["foo-proxy"].Proxy.Mode != ProxyModeTransparent {
 		t.Fatalf("expected transparent proxy mode to be enabled")
 	}
 
diff --git a/api/config_entry.go b/api/config_entry.go
index bfb853057..7ca8e3d78 100644
--- a/api/config_entry.go
+++ b/api/config_entry.go
@@ -48,8 +48,8 @@ const (
 	// should be direct and not flow through a mesh gateway.
 	MeshGatewayModeNone MeshGatewayMode = "none"
 
-	// MeshGatewayModeLocal represents that the Upstrea Connect connections
-	// should be made to a mesh gateway in the local datacenter. This is
+	// MeshGatewayModeLocal represents that the Upstream Connect connections
+	// should be made to a mesh gateway in the local datacenter.
 	MeshGatewayModeLocal MeshGatewayMode = "local"
 
 	// MeshGatewayModeRemote represents that the Upstream Connect connections
@@ -64,6 +64,28 @@ type MeshGatewayConfig struct {
 	Mode MeshGatewayMode `json:",omitempty"`
 }
 
+type ProxyMode string
+
+const (
+	// ProxyModeDefault represents no specific mode and should
+	// be used to indicate that a different layer of the configuration
+	// chain should take precedence
+	ProxyModeDefault ProxyMode = ""
+
+	// ProxyModeTransparent represents that inbound and outbound application
+	// traffic is being captured and redirected through the proxy.
+	ProxyModeTransparent ProxyMode = "transparent"
+
+	// ProxyModeDirect represents that the proxy's listeners must be dialed directly
+	// by the local application and other proxies.
+	ProxyModeDirect ProxyMode = "direct"
+)
+
+type TransparentProxyConfig struct {
+	// The port of the listener where outbound application traffic is being redirected to.
+	OutboundListenerPort int `json:",omitempty" alias:"outbound_listener_port"`
+}
+
 // ExposeConfig describes HTTP paths to expose through Envoy outside of Connect.
 // Users can expose individual paths and/or all HTTP/GRPC paths for checks.
 type ExposeConfig struct {
@@ -171,14 +193,15 @@ type UpstreamLimits struct {
 type ServiceConfigEntry struct {
 	Kind             string
 	Name             string
-	Namespace        string               `json:",omitempty"`
-	Protocol         string               `json:",omitempty"`
-	MeshGateway      MeshGatewayConfig    `json:",omitempty" alias:"mesh_gateway"`
-	Connect          ConnectConfiguration `json:",omitempty"`
-	Expose           ExposeConfig         `json:",omitempty"`
-	TransparentProxy bool                 `json:",omitempty" alias:"transparent_proxy"`
-	ExternalSNI      string               `json:",omitempty" alias:"external_sni"`
-	Meta             map[string]string    `json:",omitempty"`
+	Namespace        string                 `json:",omitempty"`
+	Protocol         string                 `json:",omitempty"`
+	Mode             ProxyMode              `json:",omitempty"`
+	TransparentProxy TransparentProxyConfig `json:",omitempty" alias:"transparent_proxy"`
+	MeshGateway      MeshGatewayConfig      `json:",omitempty" alias:"mesh_gateway"`
+	Connect          ConnectConfiguration   `json:",omitempty"`
+	Expose           ExposeConfig           `json:",omitempty"`
+	ExternalSNI      string                 `json:",omitempty" alias:"external_sni"`
+	Meta             map[string]string      `json:",omitempty"`
 	CreateIndex      uint64
 	ModifyIndex      uint64
 }
@@ -211,10 +234,11 @@ type ProxyConfigEntry struct {
 	Kind             string
 	Name             string
 	Namespace        string                 `json:",omitempty"`
+	Mode             ProxyMode              `json:",omitempty"`
+	TransparentProxy TransparentProxyConfig `json:",omitempty" alias:"transparent_proxy"`
 	Config           map[string]interface{} `json:",omitempty"`
 	MeshGateway      MeshGatewayConfig      `json:",omitempty" alias:"mesh_gateway"`
 	Expose           ExposeConfig           `json:",omitempty"`
-	TransparentProxy bool                   `json:",omitempty" alias:"transparent_proxy"`
 	Meta             map[string]string      `json:",omitempty"`
 	CreateIndex      uint64
 	ModifyIndex      uint64
diff --git a/api/config_entry_test.go b/api/config_entry_test.go
index da4c248ee..7492bc872 100644
--- a/api/config_entry_test.go
+++ b/api/config_entry_test.go
@@ -297,7 +297,10 @@ func TestDecodeConfigEntry(t *testing.T) {
 				"MeshGateway": {
 					"Mode": "remote"
 				},
-				"TransparentProxy": true
+				"Mode": "transparent",
+				"TransparentProxy": {
+					"OutboundListenerPort": 808
+				}
 			}
 			`,
 			expect: &ProxyConfigEntry{
@@ -317,7 +320,8 @@ func TestDecodeConfigEntry(t *testing.T) {
 				MeshGateway: MeshGatewayConfig{
 					Mode: MeshGatewayModeRemote,
 				},
-				TransparentProxy: true,
+				Mode:             ProxyModeTransparent,
+				TransparentProxy: TransparentProxyConfig{OutboundListenerPort: 808},
 			},
 		},
 		{
@@ -335,7 +339,10 @@ func TestDecodeConfigEntry(t *testing.T) {
 				"MeshGateway": {
 					"Mode": "remote"
 				},
-				"TransparentProxy": true,
+				"Mode": "transparent",
+				"TransparentProxy": {
+					"OutboundListenerPort": 808
+				},
 				"Connect": {
 					"UpstreamConfigs": {
 						"redis": {
@@ -380,7 +387,8 @@ func TestDecodeConfigEntry(t *testing.T) {
 				MeshGateway: MeshGatewayConfig{
 					Mode: MeshGatewayModeRemote,
 				},
-				TransparentProxy: true,
+				Mode:             ProxyModeTransparent,
+				TransparentProxy: TransparentProxyConfig{OutboundListenerPort: 808},
 				Connect: ConnectConfiguration{
 					UpstreamConfigs: map[string]UpstreamConfig{
 						"redis": {
diff --git a/command/config/write/config_write_test.go b/command/config/write/config_write_test.go
index 3beebbe07..707b40375 100644
--- a/command/config/write/config_write_test.go
+++ b/command/config/write/config_write_test.go
@@ -182,7 +182,10 @@ func TestParseConfigEntry(t *testing.T) {
 				mesh_gateway {
 					mode = "remote"
 				}
-				transparent_proxy = true
+				mode = "direct"
+				transparent_proxy = {
+					outbound_listener_port = 10101
+				}
 			`,
 			camel: `
 				Kind = "proxy-defaults"
@@ -201,7 +204,10 @@ func TestParseConfigEntry(t *testing.T) {
 				MeshGateway {
 					Mode = "remote"
 				}
-				TransparentProxy = true
+				Mode = "direct"
+				TransparentProxy = {
+					outbound_listener_port = 10101
+				}
 			`,
 			snakeJSON: `
 			{
@@ -221,7 +227,10 @@ func TestParseConfigEntry(t *testing.T) {
 				"mesh_gateway": {
 					"mode": "remote"
 				},
-				"transparent_proxy": true
+				"mode": "direct",
+				"transparent_proxy": {
+					"outbound_listener_port": 10101
+				}
 			}
 			`,
 			camelJSON: `
@@ -242,7 +251,10 @@ func TestParseConfigEntry(t *testing.T) {
 				"MeshGateway": {
 					"Mode": "remote"
 				},
-				"TransparentProxy": true
+				"Mode": "direct",
+				"TransparentProxy": {
+					"OutboundListenerPort": 10101
+				}
 			}
 			`,
 			expect: &api.ProxyConfigEntry{
@@ -262,7 +274,10 @@ func TestParseConfigEntry(t *testing.T) {
 				MeshGateway: api.MeshGatewayConfig{
 					Mode: api.MeshGatewayModeRemote,
 				},
-				TransparentProxy: true,
+				Mode: api.ProxyModeDirect,
+				TransparentProxy: api.TransparentProxyConfig{
+					OutboundListenerPort: 10101,
+				},
 			},
 			expectJSON: &api.ProxyConfigEntry{
 				Kind: "proxy-defaults",
@@ -281,7 +296,10 @@ func TestParseConfigEntry(t *testing.T) {
 				MeshGateway: api.MeshGatewayConfig{
 					Mode: api.MeshGatewayModeRemote,
 				},
-				TransparentProxy: true,
+				Mode: api.ProxyModeDirect,
+				TransparentProxy: api.TransparentProxyConfig{
+					OutboundListenerPort: 10101,
+				},
 			},
 		},
 		{
@@ -443,7 +461,10 @@ func TestParseConfigEntry(t *testing.T) {
 				mesh_gateway {
 					mode = "remote"
 				}
-				transparent_proxy = true
+				mode = "direct"
+				transparent_proxy = {
+					outbound_listener_port = 10101
+				}
 				connect {
 					upstream_configs {
 						"redis" {
@@ -487,7 +508,10 @@ func TestParseConfigEntry(t *testing.T) {
 				MeshGateway {
 					Mode = "remote"
 				}
-				TransparentProxy = true
+				Mode = "direct"
+				TransparentProxy = {
+					outbound_listener_port = 10101
+				}
 				connect = {
 					upstream_configs = {
 						"redis" = {
@@ -532,7 +556,10 @@ func TestParseConfigEntry(t *testing.T) {
 				"mesh_gateway": {
 					"mode": "remote"
 				},
-				"transparent_proxy": true,
+				"mode": "direct",
+				"transparent_proxy": {
+					"outbound_listener_port": 10101
+				},
 				"connect": {
 					"upstream_configs": {
 						"redis": {
@@ -578,7 +605,10 @@ func TestParseConfigEntry(t *testing.T) {
 				"MeshGateway": {
 					"Mode": "remote"
 				},
-				"TransparentProxy": true,
+				"Mode": "direct",
+				"TransparentProxy": {
+					"OutboundListenerPort": 10101
+				},
 				"Connect": {
 					"UpstreamConfigs": {
 						"redis": {
@@ -623,7 +653,10 @@ func TestParseConfigEntry(t *testing.T) {
 				MeshGateway: api.MeshGatewayConfig{
 					Mode: api.MeshGatewayModeRemote,
 				},
-				TransparentProxy: true,
+				Mode: api.ProxyModeDirect,
+				TransparentProxy: api.TransparentProxyConfig{
+					OutboundListenerPort: 10101,
+				},
 				Connect: api.ConnectConfiguration{
 					UpstreamConfigs: map[string]api.UpstreamConfig{
 						"redis": {
diff --git a/proto/pbservice/service.gen.go b/proto/pbservice/service.gen.go
index 0b0bb3443..eab192a4f 100644
--- a/proto/pbservice/service.gen.go
+++ b/proto/pbservice/service.gen.go
@@ -14,7 +14,8 @@ func ConnectProxyConfigToStructs(s ConnectProxyConfig) structs.ConnectProxyConfi
 	t.Upstreams = UpstreamsToStructs(s.Upstreams)
 	t.MeshGateway = MeshGatewayConfigToStructs(s.MeshGateway)
 	t.Expose = ExposeConfigToStructs(s.Expose)
-	t.TransparentProxy = s.TransparentProxy
+	t.TransparentProxy = TransparentProxyConfigToStructs(s.TransparentProxy)
+	t.Mode = s.Mode
 	return t
 }
 func NewConnectProxyConfigFromStructs(t structs.ConnectProxyConfig) ConnectProxyConfig {
@@ -27,7 +28,8 @@ func NewConnectProxyConfigFromStructs(t structs.ConnectProxyConfig) ConnectProxy
 	s.Upstreams = NewUpstreamsFromStructs(t.Upstreams)
 	s.MeshGateway = NewMeshGatewayConfigFromStructs(t.MeshGateway)
 	s.Expose = NewExposeConfigFromStructs(t.Expose)
-	s.TransparentProxy = t.TransparentProxy
+	s.TransparentProxy = NewTransparentProxyConfigFromStructs(t.TransparentProxy)
+	s.Mode = t.Mode
 	return s
 }
 func ExposeConfigToStructs(s ExposeConfig) structs.ExposeConfig {
@@ -70,6 +72,16 @@ func NewMeshGatewayConfigFromStructs(t structs.MeshGatewayConfig) MeshGatewayCon
 	s.Mode = t.Mode
 	return s
 }
+func TransparentProxyConfigToStructs(s TransparentProxyConfig) structs.TransparentProxyConfig {
+	var t structs.TransparentProxyConfig
+	t.OutboundListenerPort = int(s.OutboundListenerPort)
+	return t
+}
+func NewTransparentProxyConfigFromStructs(t structs.TransparentProxyConfig) TransparentProxyConfig {
+	var s TransparentProxyConfig
+	s.OutboundListenerPort = int32(t.OutboundListenerPort)
+	return s
+}
 func ServiceConnectToStructs(s ServiceConnect) structs.ServiceConnect {
 	var t structs.ServiceConnect
 	t.Native = s.Native
diff --git a/proto/pbservice/service.pb.binary.go b/proto/pbservice/service.pb.binary.go
index 2f012d3f1..aa449f239 100644
--- a/proto/pbservice/service.pb.binary.go
+++ b/proto/pbservice/service.pb.binary.go
@@ -67,6 +67,16 @@ func (msg *MeshGatewayConfig) UnmarshalBinary(b []byte) error {
 	return proto.Unmarshal(b, msg)
 }
 
+// MarshalBinary implements encoding.BinaryMarshaler
+func (msg *TransparentProxyConfig) MarshalBinary() ([]byte, error) {
+	return proto.Marshal(msg)
+}
+
+// UnmarshalBinary implements encoding.BinaryUnmarshaler
+func (msg *TransparentProxyConfig) UnmarshalBinary(b []byte) error {
+	return proto.Unmarshal(b, msg)
+}
+
 // MarshalBinary implements encoding.BinaryMarshaler
 func (msg *ServiceDefinition) MarshalBinary() ([]byte, error) {
 	return proto.Marshal(msg)
diff --git a/proto/pbservice/service.pb.go b/proto/pbservice/service.pb.go
index f42fd42e8..4de0ed625 100644
--- a/proto/pbservice/service.pb.go
+++ b/proto/pbservice/service.pb.go
@@ -67,13 +67,15 @@ type ConnectProxyConfig struct {
 	// setup.
 	// mog: func-to=UpstreamsToStructs func-from=NewUpstreamsFromStructs
 	Upstreams []Upstream `protobuf:"bytes,6,rep,name=Upstreams,proto3" json:"Upstreams"`
-	// MeshGateway defines the mesh gateway configuration for this upstream
+	// MeshGateway defines the mesh gateway configuration for upstreams
 	MeshGateway MeshGatewayConfig `protobuf:"bytes,7,opt,name=MeshGateway,proto3" json:"MeshGateway"`
 	// Expose defines whether checks or paths are exposed through the proxy
 	Expose ExposeConfig `protobuf:"bytes,8,opt,name=Expose,proto3" json:"Expose"`
-	// TransparentProxy enables configuring the service mesh as if all inbound
-	// and outbound traffic is being redirected to this proxy
-	TransparentProxy bool `protobuf:"varint,9,opt,name=TransparentProxy,proto3" json:"TransparentProxy,omitempty"`
+	// Mode represents how the proxy's inbound and upstream listeners are dialed.
+	Mode github_com_hashicorp_consul_agent_structs.ProxyMode `protobuf:"bytes,9,opt,name=Mode,proto3,casttype=github.com/hashicorp/consul/agent/structs.ProxyMode" json:"Mode,omitempty"`
+	// TransparentProxy defines configuration for when the proxy is in
+	// transparent mode.
+	TransparentProxy TransparentProxyConfig `protobuf:"bytes,10,opt,name=TransparentProxy,proto3" json:"TransparentProxy"`
 }
 
 func (m *ConnectProxyConfig) Reset()         { *m = ConnectProxyConfig{} }
@@ -387,6 +389,48 @@ func (m *MeshGatewayConfig) XXX_DiscardUnknown() {
 
 var xxx_messageInfo_MeshGatewayConfig proto.InternalMessageInfo
 
+// mog annotation:
+//
+// target=github.com/hashicorp/consul/agent/structs.TransparentProxyConfig
+// output=service.gen.go
+// name=Structs
+type TransparentProxyConfig struct {
+	OutboundListenerPort int32 `protobuf:"varint,1,opt,name=OutboundListenerPort,proto3" json:"OutboundListenerPort,omitempty"`
+}
+
+func (m *TransparentProxyConfig) Reset()         { *m = TransparentProxyConfig{} }
+func (m *TransparentProxyConfig) String() string { return proto.CompactTextString(m) }
+func (*TransparentProxyConfig) ProtoMessage()    {}
+func (*TransparentProxyConfig) Descriptor() ([]byte, []int) {
+	return fileDescriptor_cbb99233b75fb80b, []int{6}
+}
+func (m *TransparentProxyConfig) XXX_Unmarshal(b []byte) error {
+	return m.Unmarshal(b)
+}
+func (m *TransparentProxyConfig) XXX_Marshal(b []byte, deterministic bool) ([]byte, error) {
+	if deterministic {
+		return xxx_messageInfo_TransparentProxyConfig.Marshal(b, m, deterministic)
+	} else {
+		b = b[:cap(b)]
+		n, err := m.MarshalToSizedBuffer(b)
+		if err != nil {
+			return nil, err
+		}
+		return b[:n], nil
+	}
+}
+func (m *TransparentProxyConfig) XXX_Merge(src proto.Message) {
+	xxx_messageInfo_TransparentProxyConfig.Merge(m, src)
+}
+func (m *TransparentProxyConfig) XXX_Size() int {
+	return m.Size()
+}
+func (m *TransparentProxyConfig) XXX_DiscardUnknown() {
+	xxx_messageInfo_TransparentProxyConfig.DiscardUnknown(m)
+}
+
+var xxx_messageInfo_TransparentProxyConfig proto.InternalMessageInfo
+
 // ServiceDefinition is used to JSON decode the Service definitions. For
 // documentation on specific fields see NodeService which is better documented.
 //
@@ -435,7 +479,7 @@ func (m *ServiceDefinition) Reset()         { *m = ServiceDefinition{} }
 func (m *ServiceDefinition) String() string { return proto.CompactTextString(m) }
 func (*ServiceDefinition) ProtoMessage()    {}
 func (*ServiceDefinition) Descriptor() ([]byte, []int) {
-	return fileDescriptor_cbb99233b75fb80b, []int{6}
+	return fileDescriptor_cbb99233b75fb80b, []int{7}
 }
 func (m *ServiceDefinition) XXX_Unmarshal(b []byte) error {
 	return m.Unmarshal(b)
@@ -475,7 +519,7 @@ func (m *ServiceAddress) Reset()         { *m = ServiceAddress{} }
 func (m *ServiceAddress) String() string { return proto.CompactTextString(m) }
 func (*ServiceAddress) ProtoMessage()    {}
 func (*ServiceAddress) Descriptor() ([]byte, []int) {
-	return fileDescriptor_cbb99233b75fb80b, []int{7}
+	return fileDescriptor_cbb99233b75fb80b, []int{8}
 }
 func (m *ServiceAddress) XXX_Unmarshal(b []byte) error {
 	return m.Unmarshal(b)
@@ -516,7 +560,7 @@ func (m *Weights) Reset()         { *m = Weights{} }
 func (m *Weights) String() string { return proto.CompactTextString(m) }
 func (*Weights) ProtoMessage()    {}
 func (*Weights) Descriptor() ([]byte, []int) {
-	return fileDescriptor_cbb99233b75fb80b, []int{8}
+	return fileDescriptor_cbb99233b75fb80b, []int{9}
 }
 func (m *Weights) XXX_Unmarshal(b []byte) error {
 	return m.Unmarshal(b)
@@ -552,6 +596,7 @@ func init() {
 	proto.RegisterType((*ExposeConfig)(nil), "pbservice.ExposeConfig")
 	proto.RegisterType((*ExposePath)(nil), "pbservice.ExposePath")
 	proto.RegisterType((*MeshGatewayConfig)(nil), "pbservice.MeshGatewayConfig")
+	proto.RegisterType((*TransparentProxyConfig)(nil), "pbservice.TransparentProxyConfig")
 	proto.RegisterType((*ServiceDefinition)(nil), "pbservice.ServiceDefinition")
 	proto.RegisterMapType((map[string]string)(nil), "pbservice.ServiceDefinition.MetaEntry")
 	proto.RegisterMapType((map[string]ServiceAddress)(nil), "pbservice.ServiceDefinition.TaggedAddressesEntry")
@@ -562,75 +607,78 @@ func init() {
 func init() { proto.RegisterFile("proto/pbservice/service.proto", fileDescriptor_cbb99233b75fb80b) }
 
 var fileDescriptor_cbb99233b75fb80b = []byte{
-	// 1083 bytes of a gzipped FileDescriptorProto
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+	0x4c, 0xac, 0xf1, 0x73, 0x19, 0x96, 0x66, 0x3a, 0x4d, 0x0e, 0xa1, 0xf8, 0xc2, 0xe7, 0x7d, 0x93,
+	0xf6, 0x93, 0xeb, 0x8b, 0xd5, 0xc7, 0xef, 0x9e, 0xb6, 0xa1, 0xd3, 0x04, 0x0e, 0xd2, 0x90, 0x05,
+	0xc8, 0xc7, 0xaf, 0x4b, 0xfe, 0x79, 0x5b, 0xb7, 0x2a, 0x31, 0xe8, 0xb8, 0xd6, 0xb6, 0x2e, 0xf5,
+	0xa4, 0x5d, 0x5c, 0x2b, 0x68, 0x9b, 0x5e, 0x13, 0x1b, 0xca, 0xd3, 0x83, 0x1c, 0x6d, 0x09, 0x85,
+	0xbb, 0x5d, 0xea, 0x79, 0x2c, 0x1a, 0x68, 0x26, 0xed, 0x45, 0x14, 0xd7, 0xa3, 0xdb, 0x14, 0xdc,
+	0x4c, 0xc5, 0xec, 0x73, 0x15, 0x9c, 0x19, 0xe1, 0xa5, 0xf9, 0xc8, 0x53, 0x28, 0x1e, 0x32, 0x45,
+	0xcd, 0xb3, 0xf2, 0xc9, 0xad, 0xbc, 0xda, 0x11, 0xc9, 0x1c, 0x8c, 0x41, 0x2d, 0xea, 0xca, 0x97,
+	0xb1, 0xf2, 0xb8, 0x26, 0x9b, 0x50, 0x0a, 0xf5, 0x13, 0xde, 0x07, 0xb5, 0x04, 0x21, 0xda, 0xf5,
+	0x0d, 0x1a, 0x0d, 0x01, 0x1a, 0xc8, 0x46, 0x3c, 0x4f, 0x55, 0xcc, 0x21, 0x33, 0x24, 0x9e, 0xb2,
+	0x0d, 0x28, 0xbf, 0x66, 0xbe, 0x37, 0x50, 0xd2, 0xdc, 0xff, 0x24, 0xe1, 0x6e, 0x10, 0x27, 0x72,
+	0x21, 0x35, 0x28, 0x75, 0xc5, 0x09, 0xe3, 0xf6, 0x3c, 0x16, 0x36, 0xdc, 0x90, 0x0d, 0x58, 0xda,
+	0xe7, 0xb4, 0x37, 0x64, 0x5d, 0xea, 0xbd, 0x3a, 0x65, 0x41, 0xe0, 0xf7, 0x99, 0x7d, 0x07, 0xf5,
+	0x3e, 0x0b, 0x90, 0x6d, 0x28, 0x85, 0xef, 0xcd, 0x02, 0x9e, 0xf7, 0x20, 0x99, 0xde, 0xcc, 0xc7,
+	0x8a, 0x13, 0xfa, 0xea, 0xab, 0x67, 0x5f, 0x5f, 0xd7, 0xe3, 0xc0, 0x97, 0x0c, 0x0b, 0xbc, 0x84,
+	0xd1, 0xcb, 0x4d, 0xf3, 0xa9, 0x34, 0x8d, 0x9a, 0x8a, 0xa4, 0x62, 0xc8, 0x36, 0x94, 0xcd, 0x11,
+	0xf6, 0x5d, 0x0c, 0xff, 0x70, 0xb6, 0x3f, 0xc6, 0xc1, 0x89, 0x3c, 0x57, 0x7e, 0x84, 0x5a, 0x96,
+	0x00, 0xc8, 0x22, 0x14, 0x4e, 0xd8, 0x99, 0x79, 0xd4, 0xf4, 0x92, 0xb4, 0xa0, 0x74, 0x4a, 0x87,
+	0x93, 0xf0, 0xe5, 0xca, 0x24, 0x37, 0x14, 0x4e, 0xe8, 0xf7, 0x34, 0xff, 0x85, 0xb5, 0xb2, 0x03,
+	0xd5, 0x58, 0x07, 0x19, 0x9c, 0xb5, 0x24, 0x67, 0x35, 0x11, 0xd8, 0xf8, 0x32, 0xbe, 0xb7, 0x23,
+	0x79, 0x27, 0x84, 0x6f, 0x4d, 0x0b, 0x3f, 0x52, 0x56, 0xfe, 0x46, 0x59, 0x8d, 0x67, 0x71, 0xe7,
+	0x75, 0x60, 0x87, 0x4a, 0xe9, 0x73, 0xcf, 0x4c, 0x7d, 0xb4, 0xd5, 0xc8, 0x6b, 0x1a, 0x70, 0x8d,
+	0x84, 0xb1, 0xd1, 0x76, 0xf7, 0xf0, 0xfc, 0xaf, 0x7a, 0xee, 0xfc, 0xb2, 0x6e, 0xbd, 0xbd, 0xac,
+	0x5b, 0x7f, 0x5e, 0xd6, 0xad, 0x5f, 0xae, 0xea, 0xb9, 0x5f, 0xaf, 0xea, 0xb9, 0xb7, 0x57, 0xf5,
+	0xdc, 0x1f, 0x57, 0xf5, 0xdc, 0x0f, 0x9f, 0xdd, 0x36, 0xfc, 0xa9, 0x6f, 0xda, 0xde, 0x1c, 0x1a,
+	0xb6, 0xff, 0x09, 0x00, 0x00, 0xff, 0xff, 0x1f, 0xf1, 0x41, 0x33, 0x52, 0x0b, 0x00, 0x00,
 }
 
 func (m *ConnectProxyConfig) Marshal() (dAtA []byte, err error) {
@@ -653,15 +701,22 @@ func (m *ConnectProxyConfig) MarshalToSizedBuffer(dAtA []byte) (int, error) {
 	_ = i
 	var l int
 	_ = l
-	if m.TransparentProxy {
-		i--
-		if m.TransparentProxy {
-			dAtA[i] = 1
-		} else {
-			dAtA[i] = 0
+	{
+		size, err := m.TransparentProxy.MarshalToSizedBuffer(dAtA[:i])
+		if err != nil {
+			return 0, err
 		}
+		i -= size
+		i = encodeVarintService(dAtA, i, uint64(size))
+	}
+	i--
+	dAtA[i] = 0x52
+	if len(m.Mode) > 0 {
+		i -= len(m.Mode)
+		copy(dAtA[i:], m.Mode)
+		i = encodeVarintService(dAtA, i, uint64(len(m.Mode)))
 		i--
-		dAtA[i] = 0x48
+		dAtA[i] = 0x4a
 	}
 	{
 		size, err := m.Expose.MarshalToSizedBuffer(dAtA[:i])
@@ -1012,6 +1067,34 @@ func (m *MeshGatewayConfig) MarshalToSizedBuffer(dAtA []byte) (int, error) {
 	return len(dAtA) - i, nil
 }
 
+func (m *TransparentProxyConfig) Marshal() (dAtA []byte, err error) {
+	size := m.Size()
+	dAtA = make([]byte, size)
+	n, err := m.MarshalToSizedBuffer(dAtA[:size])
+	if err != nil {
+		return nil, err
+	}
+	return dAtA[:n], nil
+}
+
+func (m *TransparentProxyConfig) MarshalTo(dAtA []byte) (int, error) {
+	size := m.Size()
+	return m.MarshalToSizedBuffer(dAtA[:size])
+}
+
+func (m *TransparentProxyConfig) MarshalToSizedBuffer(dAtA []byte) (int, error) {
+	i := len(dAtA)
+	_ = i
+	var l int
+	_ = l
+	if m.OutboundListenerPort != 0 {
+		i = encodeVarintService(dAtA, i, uint64(m.OutboundListenerPort))
+		i--
+		dAtA[i] = 0x8
+	}
+	return len(dAtA) - i, nil
+}
+
 func (m *ServiceDefinition) Marshal() (dAtA []byte, err error) {
 	size := m.Size()
 	dAtA = make([]byte, size)
@@ -1325,9 +1408,12 @@ func (m *ConnectProxyConfig) Size() (n int) {
 	n += 1 + l + sovService(uint64(l))
 	l = m.Expose.Size()
 	n += 1 + l + sovService(uint64(l))
-	if m.TransparentProxy {
-		n += 2
+	l = len(m.Mode)
+	if l > 0 {
+		n += 1 + l + sovService(uint64(l))
 	}
+	l = m.TransparentProxy.Size()
+	n += 1 + l + sovService(uint64(l))
 	return n
 }
 
@@ -1445,6 +1531,18 @@ func (m *MeshGatewayConfig) Size() (n int) {
 	return n
 }
 
+func (m *TransparentProxyConfig) Size() (n int) {
+	if m == nil {
+		return 0
+	}
+	var l int
+	_ = l
+	if m.OutboundListenerPort != 0 {
+		n += 1 + sovService(uint64(m.OutboundListenerPort))
+	}
+	return n
+}
+
 func (m *ServiceDefinition) Size() (n int) {
 	if m == nil {
 		return 0
@@ -1843,10 +1941,10 @@ func (m *ConnectProxyConfig) Unmarshal(dAtA []byte) error {
 			}
 			iNdEx = postIndex
 		case 9:
-			if wireType != 0 {
-				return fmt.Errorf("proto: wrong wireType = %d for field TransparentProxy", wireType)
+			if wireType != 2 {
+				return fmt.Errorf("proto: wrong wireType = %d for field Mode", wireType)
 			}
-			var v int
+			var stringLen uint64
 			for shift := uint(0); ; shift += 7 {
 				if shift >= 64 {
 					return ErrIntOverflowService
@@ -1856,12 +1954,57 @@ func (m *ConnectProxyConfig) Unmarshal(dAtA []byte) error {
 				}
 				b := dAtA[iNdEx]
 				iNdEx++
-				v |= int(b&0x7F) << shift
+				stringLen |= uint64(b&0x7F) << shift
 				if b < 0x80 {
 					break
 				}
 			}
-			m.TransparentProxy = bool(v != 0)
+			intStringLen := int(stringLen)
+			if intStringLen < 0 {
+				return ErrInvalidLengthService
+			}
+			postIndex := iNdEx + intStringLen
+			if postIndex < 0 {
+				return ErrInvalidLengthService
+			}
+			if postIndex > l {
+				return io.ErrUnexpectedEOF
+			}
+			m.Mode = github_com_hashicorp_consul_agent_structs.ProxyMode(dAtA[iNdEx:postIndex])
+			iNdEx = postIndex
+		case 10:
+			if wireType != 2 {
+				return fmt.Errorf("proto: wrong wireType = %d for field TransparentProxy", wireType)
+			}
+			var msglen int
+			for shift := uint(0); ; shift += 7 {
+				if shift >= 64 {
+					return ErrIntOverflowService
+				}
+				if iNdEx >= l {
+					return io.ErrUnexpectedEOF
+				}
+				b := dAtA[iNdEx]
+				iNdEx++
+				msglen |= int(b&0x7F) << shift
+				if b < 0x80 {
+					break
+				}
+			}
+			if msglen < 0 {
+				return ErrInvalidLengthService
+			}
+			postIndex := iNdEx + msglen
+			if postIndex < 0 {
+				return ErrInvalidLengthService
+			}
+			if postIndex > l {
+				return io.ErrUnexpectedEOF
+			}
+			if err := m.TransparentProxy.Unmarshal(dAtA[iNdEx:postIndex]); err != nil {
+				return err
+			}
+			iNdEx = postIndex
 		default:
 			iNdEx = preIndex
 			skippy, err := skipService(dAtA[iNdEx:])
@@ -2683,6 +2826,78 @@ func (m *MeshGatewayConfig) Unmarshal(dAtA []byte) error {
 	}
 	return nil
 }
+func (m *TransparentProxyConfig) Unmarshal(dAtA []byte) error {
+	l := len(dAtA)
+	iNdEx := 0
+	for iNdEx < l {
+		preIndex := iNdEx
+		var wire uint64
+		for shift := uint(0); ; shift += 7 {
+			if shift >= 64 {
+				return ErrIntOverflowService
+			}
+			if iNdEx >= l {
+				return io.ErrUnexpectedEOF
+			}
+			b := dAtA[iNdEx]
+			iNdEx++
+			wire |= uint64(b&0x7F) << shift
+			if b < 0x80 {
+				break
+			}
+		}
+		fieldNum := int32(wire >> 3)
+		wireType := int(wire & 0x7)
+		if wireType == 4 {
+			return fmt.Errorf("proto: TransparentProxyConfig: wiretype end group for non-group")
+		}
+		if fieldNum <= 0 {
+			return fmt.Errorf("proto: TransparentProxyConfig: illegal tag %d (wire type %d)", fieldNum, wire)
+		}
+		switch fieldNum {
+		case 1:
+			if wireType != 0 {
+				return fmt.Errorf("proto: wrong wireType = %d for field OutboundListenerPort", wireType)
+			}
+			m.OutboundListenerPort = 0
+			for shift := uint(0); ; shift += 7 {
+				if shift >= 64 {
+					return ErrIntOverflowService
+				}
+				if iNdEx >= l {
+					return io.ErrUnexpectedEOF
+				}
+				b := dAtA[iNdEx]
+				iNdEx++
+				m.OutboundListenerPort |= int32(b&0x7F) << shift
+				if b < 0x80 {
+					break
+				}
+			}
+		default:
+			iNdEx = preIndex
+			skippy, err := skipService(dAtA[iNdEx:])
+			if err != nil {
+				return err
+			}
+			if skippy < 0 {
+				return ErrInvalidLengthService
+			}
+			if (iNdEx + skippy) < 0 {
+				return ErrInvalidLengthService
+			}
+			if (iNdEx + skippy) > l {
+				return io.ErrUnexpectedEOF
+			}
+			iNdEx += skippy
+		}
+	}
+
+	if iNdEx > l {
+		return io.ErrUnexpectedEOF
+	}
+	return nil
+}
 func (m *ServiceDefinition) Unmarshal(dAtA []byte) error {
 	l := len(dAtA)
 	iNdEx := 0
diff --git a/proto/pbservice/service.proto b/proto/pbservice/service.proto
index 89e781d0d..74398597a 100644
--- a/proto/pbservice/service.proto
+++ b/proto/pbservice/service.proto
@@ -64,15 +64,18 @@ message ConnectProxyConfig {
     // mog: func-to=UpstreamsToStructs func-from=NewUpstreamsFromStructs
     repeated Upstream Upstreams = 6 [(gogoproto.nullable) = false];
 
-    // MeshGateway defines the mesh gateway configuration for this upstream
+    // MeshGateway defines the mesh gateway configuration for upstreams
     MeshGatewayConfig MeshGateway = 7 [(gogoproto.nullable) = false];
 
     // Expose defines whether checks or paths are exposed through the proxy
     ExposeConfig Expose = 8 [(gogoproto.nullable) = false];
 
-    // TransparentProxy enables configuring the service mesh as if all inbound
-    // and outbound traffic is being redirected to this proxy
-    bool TransparentProxy = 9;
+    // Mode represents how the proxy's inbound and upstream listeners are dialed.
+    string Mode = 9 [(gogoproto.casttype) = "github.com/hashicorp/consul/agent/structs.ProxyMode"];
+
+    // TransparentProxy defines configuration for when the proxy is in
+    // transparent mode.
+    TransparentProxyConfig TransparentProxy = 10 [(gogoproto.nullable) = false];
 }
 
 // Upstream represents a single upstream dependency for a service or proxy. It
@@ -200,6 +203,15 @@ message MeshGatewayConfig {
     string Mode = 1 [(gogoproto.casttype) = "github.com/hashicorp/consul/agent/structs.MeshGatewayMode"];
 }
 
+// mog annotation:
+//
+// target=github.com/hashicorp/consul/agent/structs.TransparentProxyConfig
+// output=service.gen.go
+// name=Structs
+message TransparentProxyConfig {
+    int32 OutboundListenerPort = 1;
+}
+
 // ServiceDefinition is used to JSON decode the Service definitions. For
 // documentation on specific fields see NodeService which is better documented.
 //