diff --git a/changelog/v1.10.0-beta2/add-tls-timeout.yaml b/changelog/v1.10.0-beta2/add-tls-timeout.yaml
new file mode 100644
index 000000000000..5da43554c9bf
--- /dev/null
+++ b/changelog/v1.10.0-beta2/add-tls-timeout.yaml
@@ -0,0 +1,5 @@
+changelog:
+  - type: NEW_FEATURE
+    issueLink: https://github.com/solo-io/gloo/issues/5438
+    resolvesIssue: true
+    description: TLS handshake timeout is now configurable.
\ No newline at end of file
diff --git a/docs/content/reference/api/github.com/solo-io/gloo/projects/gloo/api/v1/ssl.proto.sk.md b/docs/content/reference/api/github.com/solo-io/gloo/projects/gloo/api/v1/ssl.proto.sk.md
index a37c5f647c4f..a896e90d6e71 100644
--- a/docs/content/reference/api/github.com/solo-io/gloo/projects/gloo/api/v1/ssl.proto.sk.md
+++ b/docs/content/reference/api/github.com/solo-io/gloo/projects/gloo/api/v1/ssl.proto.sk.md
@@ -45,6 +45,7 @@ SslConfig contains the options necessary to configure a virtual host or listener
 "alpnProtocols": []string
 "oneWayTls": .google.protobuf.BoolValue
 "disableTlsSessionResumption": .google.protobuf.BoolValue
+"transportSocketConnectTimeout": .google.protobuf.Duration
 
 ```
 
@@ -59,6 +60,7 @@ SslConfig contains the options necessary to configure a virtual host or listener
 | `alpnProtocols` | `[]string` | Set Application Level Protocol Negotiation If empty, defaults to ["h2", "http/1.1"]. |
 | `oneWayTls` | [.google.protobuf.BoolValue](https://developers.google.com/protocol-buffers/docs/reference/csharp/class/google/protobuf/well-known-types/bool-value) | If the SSL config has the ca.crt (root CA) provided, Gloo uses it to perform mTLS by default. Set oneWayTls to true to disable mTLS in favor of server-only TLS (one-way TLS), even if Gloo has the root CA. If unset, defaults to false. |
 | `disableTlsSessionResumption` | [.google.protobuf.BoolValue](https://developers.google.com/protocol-buffers/docs/reference/csharp/class/google/protobuf/well-known-types/bool-value) | If set to true, the TLS session resumption will be deactivated, note that it deactivates only the tickets based tls session resumption (not the cache). |
+| `transportSocketConnectTimeout` | [.google.protobuf.Duration](https://developers.google.com/protocol-buffers/docs/reference/csharp/class/google/protobuf/well-known-types/duration) | If present and nonzero, the amount of time to allow incoming connections to complete any transport socket negotiations. If this expires before the transport reports connection establishment, the connection is summarily closed. |
 
 
 
diff --git a/install/helm/gloo/crds/gateway.solo.io_v1_Gateway.yaml b/install/helm/gloo/crds/gateway.solo.io_v1_Gateway.yaml
index b1d9f49a8924..b16b0da2c958 100644
--- a/install/helm/gloo/crds/gateway.solo.io_v1_Gateway.yaml
+++ b/install/helm/gloo/crds/gateway.solo.io_v1_Gateway.yaml
@@ -2133,6 +2133,8 @@ spec:
                                 tlsKey:
                                   type: string
                               type: object
+                            transportSocketConnectTimeout:
+                              type: string
                             verifySubjectAltName:
                               items:
                                 type: string
diff --git a/install/helm/gloo/crds/gateway.solo.io_v1_VirtualService.yaml b/install/helm/gloo/crds/gateway.solo.io_v1_VirtualService.yaml
index 1e5cda5acc82..9917de2e1d0c 100644
--- a/install/helm/gloo/crds/gateway.solo.io_v1_VirtualService.yaml
+++ b/install/helm/gloo/crds/gateway.solo.io_v1_VirtualService.yaml
@@ -102,6 +102,8 @@ spec:
                       tlsKey:
                         type: string
                     type: object
+                  transportSocketConnectTimeout:
+                    type: string
                   verifySubjectAltName:
                     items:
                       type: string
diff --git a/install/helm/gloo/crds/gloo.solo.io_v1_Proxy.yaml b/install/helm/gloo/crds/gloo.solo.io_v1_Proxy.yaml
index 1f683899fd8e..fef7f2335475 100644
--- a/install/helm/gloo/crds/gloo.solo.io_v1_Proxy.yaml
+++ b/install/helm/gloo/crds/gloo.solo.io_v1_Proxy.yaml
@@ -5166,6 +5166,8 @@ spec:
                               tlsKey:
                                 type: string
                             type: object
+                          transportSocketConnectTimeout:
+                            type: string
                           verifySubjectAltName:
                             items:
                               type: string
@@ -6569,6 +6571,8 @@ spec:
                                       tlsKey:
                                         type: string
                                     type: object
+                                  transportSocketConnectTimeout:
+                                    type: string
                                   verifySubjectAltName:
                                     items:
                                       type: string
diff --git a/projects/gloo/api/v1/ssl.proto b/projects/gloo/api/v1/ssl.proto
index ff9f72482706..88df3aee7449 100644
--- a/projects/gloo/api/v1/ssl.proto
+++ b/projects/gloo/api/v1/ssl.proto
@@ -2,6 +2,7 @@ syntax = "proto3";
 package gloo.solo.io;
 option go_package = "github.com/solo-io/gloo/projects/gloo/pkg/api/v1";
 
+import "google/protobuf/duration.proto";
 import "google/protobuf/wrappers.proto";
 
 import "extproto/ext.proto";
@@ -41,6 +42,11 @@ message SslConfig {
 
     // If set to true, the TLS session resumption will be deactivated, note that it deactivates only the tickets based tls session resumption (not the cache).
     google.protobuf.BoolValue disable_tls_session_resumption = 9;
+
+    // If present and nonzero, the amount of time to allow incoming connections to complete any
+    // transport socket negotiations. If this expires before the transport reports connection
+    // establishment, the connection is summarily closed.
+    google.protobuf.Duration transport_socket_connect_timeout = 10;
 }
 
 // SSLFiles reference paths to certificates which can be read by the proxy off of its local filesystem
diff --git a/projects/gloo/pkg/api/v1/ssl.pb.equal.go b/projects/gloo/pkg/api/v1/ssl.pb.equal.go
index 8e0fabf769d8..6bcb78ad5541 100644
--- a/projects/gloo/pkg/api/v1/ssl.pb.equal.go
+++ b/projects/gloo/pkg/api/v1/ssl.pb.equal.go
@@ -109,6 +109,16 @@ func (m *SslConfig) Equal(that interface{}) bool {
 		}
 	}
 
+	if h, ok := interface{}(m.GetTransportSocketConnectTimeout()).(equality.Equalizer); ok {
+		if !h.Equal(target.GetTransportSocketConnectTimeout()) {
+			return false
+		}
+	} else {
+		if !proto.Equal(m.GetTransportSocketConnectTimeout(), target.GetTransportSocketConnectTimeout()) {
+			return false
+		}
+	}
+
 	switch m.SslSecrets.(type) {
 
 	case *SslConfig_SecretRef:
diff --git a/projects/gloo/pkg/api/v1/ssl.pb.go b/projects/gloo/pkg/api/v1/ssl.pb.go
index af1991aa81cc..11f1b62e55cb 100644
--- a/projects/gloo/pkg/api/v1/ssl.pb.go
+++ b/projects/gloo/pkg/api/v1/ssl.pb.go
@@ -10,6 +10,7 @@ import (
 	reflect "reflect"
 	sync "sync"
 
+	duration "github.com/golang/protobuf/ptypes/duration"
 	wrappers "github.com/golang/protobuf/ptypes/wrappers"
 	_ "github.com/solo-io/protoc-gen-ext/extproto"
 	core "github.com/solo-io/solo-kit/pkg/api/v1/resources/core"
@@ -110,6 +111,10 @@ type SslConfig struct {
 	OneWayTls *wrappers.BoolValue `protobuf:"bytes,8,opt,name=one_way_tls,json=oneWayTls,proto3" json:"one_way_tls,omitempty"`
 	// If set to true, the TLS session resumption will be deactivated, note that it deactivates only the tickets based tls session resumption (not the cache).
 	DisableTlsSessionResumption *wrappers.BoolValue `protobuf:"bytes,9,opt,name=disable_tls_session_resumption,json=disableTlsSessionResumption,proto3" json:"disable_tls_session_resumption,omitempty"`
+	// If present and nonzero, the amount of time to allow incoming connections to complete any
+	// transport socket negotiations. If this expires before the transport reports connection
+	// establishment, the connection is summarily closed.
+	TransportSocketConnectTimeout *duration.Duration `protobuf:"bytes,10,opt,name=transport_socket_connect_timeout,json=transportSocketConnectTimeout,proto3" json:"transport_socket_connect_timeout,omitempty"`
 }
 
 func (x *SslConfig) Reset() {
@@ -214,6 +219,13 @@ func (x *SslConfig) GetDisableTlsSessionResumption() *wrappers.BoolValue {
 	return nil
 }
 
+func (x *SslConfig) GetTransportSocketConnectTimeout() *duration.Duration {
+	if x != nil {
+		return x.TransportSocketConnectTimeout
+	}
+	return nil
+}
+
 type isSslConfig_SslSecrets interface {
 	isSslConfig_SslSecrets()
 }
@@ -736,12 +748,14 @@ var file_github_com_solo_io_gloo_projects_gloo_api_v1_ssl_proto_rawDesc = []byte
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@@ -773,96 +787,103 @@ var file_github_com_solo_io_gloo_projects_gloo_api_v1_ssl_proto_rawDesc = []byte
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+	0x65, 0x72, 0x73, 0x2e, 0x50, 0x72, 0x6f, 0x74, 0x6f, 0x63, 0x6f, 0x6c, 0x56, 0x65, 0x72, 0x73,
+	0x69, 0x6f, 0x6e, 0x52, 0x16, 0x6d, 0x69, 0x6e, 0x69, 0x6d, 0x75, 0x6d, 0x50, 0x72, 0x6f, 0x74,
+	0x6f, 0x63, 0x6f, 0x6c, 0x56, 0x65, 0x72, 0x73, 0x69, 0x6f, 0x6e, 0x12, 0x65, 0x0a, 0x18, 0x6d,
+	0x61, 0x78, 0x69, 0x6d, 0x75, 0x6d, 0x5f, 0x70, 0x72, 0x6f, 0x74, 0x6f, 0x63, 0x6f, 0x6c, 0x5f,
+	0x76, 0x65, 0x72, 0x73, 0x69, 0x6f, 0x6e, 0x18, 0x02, 0x20, 0x01, 0x28, 0x0e, 0x32, 0x2b, 0x2e,
+	0x67, 0x6c, 0x6f, 0x6f, 0x2e, 0x73, 0x6f, 0x6c, 0x6f, 0x2e, 0x69, 0x6f, 0x2e, 0x53, 0x73, 0x6c,
+	0x50, 0x61, 0x72, 0x61, 0x6d, 0x65, 0x74, 0x65, 0x72, 0x73, 0x2e, 0x50, 0x72, 0x6f, 0x74, 0x6f,
+	0x63, 0x6f, 0x6c, 0x56, 0x65, 0x72, 0x73, 0x69, 0x6f, 0x6e, 0x52, 0x16, 0x6d, 0x61, 0x78, 0x69,
+	0x6d, 0x75, 0x6d, 0x50, 0x72, 0x6f, 0x74, 0x6f, 0x63, 0x6f, 0x6c, 0x56, 0x65, 0x72, 0x73, 0x69,
+	0x6f, 0x6e, 0x12, 0x23, 0x0a, 0x0d, 0x63, 0x69, 0x70, 0x68, 0x65, 0x72, 0x5f, 0x73, 0x75, 0x69,
+	0x74, 0x65, 0x73, 0x18, 0x03, 0x20, 0x03, 0x28, 0x09, 0x52, 0x0c, 0x63, 0x69, 0x70, 0x68, 0x65,
+	0x72, 0x53, 0x75, 0x69, 0x74, 0x65, 0x73, 0x12, 0x1f, 0x0a, 0x0b, 0x65, 0x63, 0x64, 0x68, 0x5f,
+	0x63, 0x75, 0x72, 0x76, 0x65, 0x73, 0x18, 0x04, 0x20, 0x03, 0x28, 0x09, 0x52, 0x0a, 0x65, 0x63,
+	0x64, 0x68, 0x43, 0x75, 0x72, 0x76, 0x65, 0x73, 0x22, 0x53, 0x0a, 0x0f, 0x50, 0x72, 0x6f, 0x74,
+	0x6f, 0x63, 0x6f, 0x6c, 0x56, 0x65, 0x72, 0x73, 0x69, 0x6f, 0x6e, 0x12, 0x0c, 0x0a, 0x08, 0x54,
+	0x4c, 0x53, 0x5f, 0x41, 0x55, 0x54, 0x4f, 0x10, 0x00, 0x12, 0x0b, 0x0a, 0x07, 0x54, 0x4c, 0x53,
+	0x76, 0x31, 0x5f, 0x30, 0x10, 0x01, 0x12, 0x0b, 0x0a, 0x07, 0x54, 0x4c, 0x53, 0x76, 0x31, 0x5f,
+	0x31, 0x10, 0x02, 0x12, 0x0b, 0x0a, 0x07, 0x54, 0x4c, 0x53, 0x76, 0x31, 0x5f, 0x32, 0x10, 0x03,
+	0x12, 0x0b, 0x0a, 0x07, 0x54, 0x4c, 0x53, 0x76, 0x31, 0x5f, 0x33, 0x10, 0x04, 0x42, 0x3a, 0x5a,
+	0x30, 0x67, 0x69, 0x74, 0x68, 0x75, 0x62, 0x2e, 0x63, 0x6f, 0x6d, 0x2f, 0x73, 0x6f, 0x6c, 0x6f,
+	0x2d, 0x69, 0x6f, 0x2f, 0x67, 0x6c, 0x6f, 0x6f, 0x2f, 0x70, 0x72, 0x6f, 0x6a, 0x65, 0x63, 0x74,
+	0x73, 0x2f, 0x67, 0x6c, 0x6f, 0x6f, 0x2f, 0x70, 0x6b, 0x67, 0x2f, 0x61, 0x70, 0x69, 0x2f, 0x76,
+	0x31, 0xc0, 0xf5, 0x04, 0x01, 0xb8, 0xf5, 0x04, 0x01, 0x62, 0x06, 0x70, 0x72, 0x6f, 0x74, 0x6f,
+	0x33,
 }
 
 var (
@@ -890,6 +911,7 @@ var file_github_com_solo_io_gloo_projects_gloo_api_v1_ssl_proto_goTypes = []inte
 	(*CallCredentials_FileCredentialSource)(nil), // 7: gloo.solo.io.CallCredentials.FileCredentialSource
 	(*core.ResourceRef)(nil),                     // 8: core.solo.io.ResourceRef
 	(*wrappers.BoolValue)(nil),                   // 9: google.protobuf.BoolValue
+	(*duration.Duration)(nil),                    // 10: google.protobuf.Duration
 }
 var file_github_com_solo_io_gloo_projects_gloo_api_v1_ssl_proto_depIdxs = []int32{
 	8,  // 0: gloo.solo.io.SslConfig.secret_ref:type_name -> core.solo.io.ResourceRef
@@ -898,19 +920,20 @@ var file_github_com_solo_io_gloo_projects_gloo_api_v1_ssl_proto_depIdxs = []int3
 	6,  // 3: gloo.solo.io.SslConfig.parameters:type_name -> gloo.solo.io.SslParameters
 	9,  // 4: gloo.solo.io.SslConfig.one_way_tls:type_name -> google.protobuf.BoolValue
 	9,  // 5: gloo.solo.io.SslConfig.disable_tls_session_resumption:type_name -> google.protobuf.BoolValue
-	8,  // 6: gloo.solo.io.UpstreamSslConfig.secret_ref:type_name -> core.solo.io.ResourceRef
-	2,  // 7: gloo.solo.io.UpstreamSslConfig.ssl_files:type_name -> gloo.solo.io.SSLFiles
-	4,  // 8: gloo.solo.io.UpstreamSslConfig.sds:type_name -> gloo.solo.io.SDSConfig
-	6,  // 9: gloo.solo.io.UpstreamSslConfig.parameters:type_name -> gloo.solo.io.SslParameters
-	5,  // 10: gloo.solo.io.SDSConfig.call_credentials:type_name -> gloo.solo.io.CallCredentials
-	7,  // 11: gloo.solo.io.CallCredentials.file_credential_source:type_name -> gloo.solo.io.CallCredentials.FileCredentialSource
-	0,  // 12: gloo.solo.io.SslParameters.minimum_protocol_version:type_name -> gloo.solo.io.SslParameters.ProtocolVersion
-	0,  // 13: gloo.solo.io.SslParameters.maximum_protocol_version:type_name -> gloo.solo.io.SslParameters.ProtocolVersion
-	14, // [14:14] is the sub-list for method output_type
-	14, // [14:14] is the sub-list for method input_type
-	14, // [14:14] is the sub-list for extension type_name
-	14, // [14:14] is the sub-list for extension extendee
-	0,  // [0:14] is the sub-list for field type_name
+	10, // 6: gloo.solo.io.SslConfig.transport_socket_connect_timeout:type_name -> google.protobuf.Duration
+	8,  // 7: gloo.solo.io.UpstreamSslConfig.secret_ref:type_name -> core.solo.io.ResourceRef
+	2,  // 8: gloo.solo.io.UpstreamSslConfig.ssl_files:type_name -> gloo.solo.io.SSLFiles
+	4,  // 9: gloo.solo.io.UpstreamSslConfig.sds:type_name -> gloo.solo.io.SDSConfig
+	6,  // 10: gloo.solo.io.UpstreamSslConfig.parameters:type_name -> gloo.solo.io.SslParameters
+	5,  // 11: gloo.solo.io.SDSConfig.call_credentials:type_name -> gloo.solo.io.CallCredentials
+	7,  // 12: gloo.solo.io.CallCredentials.file_credential_source:type_name -> gloo.solo.io.CallCredentials.FileCredentialSource
+	0,  // 13: gloo.solo.io.SslParameters.minimum_protocol_version:type_name -> gloo.solo.io.SslParameters.ProtocolVersion
+	0,  // 14: gloo.solo.io.SslParameters.maximum_protocol_version:type_name -> gloo.solo.io.SslParameters.ProtocolVersion
+	15, // [15:15] is the sub-list for method output_type
+	15, // [15:15] is the sub-list for method input_type
+	15, // [15:15] is the sub-list for extension type_name
+	15, // [15:15] is the sub-list for extension extendee
+	0,  // [0:15] is the sub-list for field type_name
 }
 
 func init() { file_github_com_solo_io_gloo_projects_gloo_api_v1_ssl_proto_init() }
diff --git a/projects/gloo/pkg/api/v1/ssl.pb.hash.go b/projects/gloo/pkg/api/v1/ssl.pb.hash.go
index a60a1f74bc4d..98ee952f9658 100644
--- a/projects/gloo/pkg/api/v1/ssl.pb.hash.go
+++ b/projects/gloo/pkg/api/v1/ssl.pb.hash.go
@@ -122,6 +122,26 @@ func (m *SslConfig) Hash(hasher hash.Hash64) (uint64, error) {
 		}
 	}
 
+	if h, ok := interface{}(m.GetTransportSocketConnectTimeout()).(safe_hasher.SafeHasher); ok {
+		if _, err = hasher.Write([]byte("TransportSocketConnectTimeout")); err != nil {
+			return 0, err
+		}
+		if _, err = h.Hash(hasher); err != nil {
+			return 0, err
+		}
+	} else {
+		if fieldValue, err := hashstructure.Hash(m.GetTransportSocketConnectTimeout(), nil); err != nil {
+			return 0, err
+		} else {
+			if _, err = hasher.Write([]byte("TransportSocketConnectTimeout")); err != nil {
+				return 0, err
+			}
+			if err := binary.Write(hasher, binary.LittleEndian, fieldValue); err != nil {
+				return 0, err
+			}
+		}
+	}
+
 	switch m.SslSecrets.(type) {
 
 	case *SslConfig_SecretRef:
diff --git a/projects/gloo/pkg/plugins/tcp/plugin.go b/projects/gloo/pkg/plugins/tcp/plugin.go
index 8cb734333841..f2661cde119c 100644
--- a/projects/gloo/pkg/plugins/tcp/plugin.go
+++ b/projects/gloo/pkg/plugins/tcp/plugin.go
@@ -7,6 +7,7 @@ import (
 	envoyauth "github.com/envoyproxy/go-control-plane/envoy/extensions/transport_sockets/tls/v3"
 	"github.com/envoyproxy/go-control-plane/pkg/wellknown"
 	"github.com/golang/protobuf/proto"
+	"github.com/golang/protobuf/ptypes/duration"
 	"github.com/hashicorp/go-multierror"
 	"github.com/rotisserie/eris"
 	v1 "github.com/solo-io/gloo/projects/gloo/pkg/api/v1"
@@ -200,13 +201,14 @@ func (p *Plugin) computerTcpFilterChain(
 	if err != nil {
 		return nil, InvalidSecretsError(err, listener.GetName())
 	}
-	return p.newSslFilterChain(downstreamConfig, sslConfig.GetSniDomains(), listenerFilters), nil
+	return p.newSslFilterChain(downstreamConfig, sslConfig.GetSniDomains(), listenerFilters, sslConfig.GetTransportSocketConnectTimeout()), nil
 }
 
 func (p *Plugin) newSslFilterChain(
 	downstreamConfig *envoyauth.DownstreamTlsContext,
 	sniDomains []string,
 	listenerFilters []*envoy_config_listener_v3.Filter,
+	timeout *duration.Duration,
 ) *envoy_config_listener_v3.FilterChain {
 
 	// copy listenerFilter so we can modify filter chain later without changing the filters on all of them!
@@ -224,6 +226,7 @@ func (p *Plugin) newSslFilterChain(
 			Name:       wellknown.TransportSocketTls,
 			ConfigType: &envoy_config_core_v3.TransportSocket_TypedConfig{TypedConfig: utils.MustMessageToAny(downstreamConfig)},
 		},
+		TransportSocketConnectTimeout: timeout,
 	}
 }
 
diff --git a/projects/gloo/pkg/plugins/tcp/plugin_test.go b/projects/gloo/pkg/plugins/tcp/plugin_test.go
index 847cd6c89ec9..766662a64a20 100644
--- a/projects/gloo/pkg/plugins/tcp/plugin_test.go
+++ b/projects/gloo/pkg/plugins/tcp/plugin_test.go
@@ -19,6 +19,7 @@ import (
 	"github.com/solo-io/solo-kit/pkg/api/v1/resources/core"
 	"github.com/solo-io/solo-kit/pkg/utils/prototime"
 	"github.com/solo-io/solo-kit/test/matchers"
+	"google.golang.org/protobuf/types/known/durationpb"
 )
 
 var _ = Describe("Plugin", func() {
@@ -276,6 +277,24 @@ var _ = Describe("Plugin", func() {
 			Expect(cluster.Cluster).To(Equal(""))
 		})
 
+		It("should propagate proided `transport_socket_connect_timeout` to Envoy", func() {
+			sslConfig := &v1.SslConfig{
+				SslSecrets: &v1.SslConfig_SecretRef{
+					SecretRef: &core.ResourceRef{
+						Name:      "name",
+						Namespace: "namespace",
+					},
+				},
+				SniDomains: []string{"hello.world"},
+				TransportSocketConnectTimeout: &durationpb.Duration{
+					Seconds: 3,
+					Nanos:   0,
+				},
+			}
+
+			Expect(sslConfig.TransportSocketConnectTimeout.Seconds).To(Equal(int64(3)))
+			Expect(sslConfig.TransportSocketConnectTimeout.Nanos).To(Equal(int32(0)))
+		})
 	})
 
 })
diff --git a/projects/gloo/pkg/translator/listener.go b/projects/gloo/pkg/translator/listener.go
index ab198708c13a..1391e67b0a9d 100644
--- a/projects/gloo/pkg/translator/listener.go
+++ b/projects/gloo/pkg/translator/listener.go
@@ -10,6 +10,7 @@ import (
 	envoyauth "github.com/envoyproxy/go-control-plane/envoy/extensions/transport_sockets/tls/v3"
 	"github.com/envoyproxy/go-control-plane/pkg/wellknown"
 	"github.com/golang/protobuf/proto"
+	"github.com/golang/protobuf/ptypes/duration"
 	validationapi "github.com/solo-io/gloo/projects/gloo/pkg/api/grpc/validation"
 	v1 "github.com/solo-io/gloo/projects/gloo/pkg/api/v1"
 	"github.com/solo-io/gloo/projects/gloo/pkg/plugins"
@@ -164,7 +165,7 @@ func (t *translatorInstance) computeFilterChainsFromSslConfig(
 				validationapi.ListenerReport_Error_SSLConfigError, err.Error())
 			continue
 		}
-		filterChain := newSslFilterChain(downstreamConfig, sslConfig.GetSniDomains(), listenerFilters)
+		filterChain := newSslFilterChain(downstreamConfig, sslConfig.GetSniDomains(), listenerFilters, sslConfig.GetTransportSocketConnectTimeout())
 
 		secureFilterChains = append(secureFilterChains, filterChain)
 	}
@@ -244,6 +245,7 @@ func newSslFilterChain(
 	downstreamConfig *envoyauth.DownstreamTlsContext,
 	sniDomains []string,
 	listenerFilters []*envoy_config_listener_v3.Filter,
+	timeout *duration.Duration,
 ) *envoy_config_listener_v3.FilterChain {
 
 	// copy listenerFilter so we can modify filter chain later without changing the filters on all of them!
@@ -262,6 +264,7 @@ func newSslFilterChain(
 			Name:       wellknown.TransportSocketTls,
 			ConfigType: &envoy_config_core_v3.TransportSocket_TypedConfig{TypedConfig: utils.MustMessageToAny(downstreamConfig)},
 		},
+		TransportSocketConnectTimeout: timeout,
 	}
 }