diff --git a/authorize/ssh_grpc.go b/authorize/ssh_grpc.go
index 9769191d2..42bf8f49c 100644
--- a/authorize/ssh_grpc.go
+++ b/authorize/ssh_grpc.go
@@ -1,27 +1,40 @@
 package authorize
 
 import (
+	"bufio"
+	"bytes"
+	"crypto/sha256"
 	"encoding/binary"
 	"errors"
 	"fmt"
 	"io"
 	"net/url"
 	"slices"
+	"strconv"
 	"strings"
+	"sync"
 	"sync/atomic"
 	"time"
 
 	"github.com/charmbracelet/bubbles/list"
 	tea "github.com/charmbracelet/bubbletea"
 	"github.com/charmbracelet/lipgloss"
+	corev3 "github.com/envoyproxy/go-control-plane/envoy/config/core/v3"
+	"github.com/klauspost/compress/zstd"
 	extensions_ssh "github.com/pomerium/envoy-custom/api/extensions/filters/network/ssh"
+	extensions_session_recording "github.com/pomerium/envoy-custom/api/extensions/filters/network/ssh/filters/session_recording"
 	"github.com/pomerium/pomerium/config"
+	"github.com/pomerium/pomerium/internal/log"
 	"github.com/pomerium/pomerium/internal/sessions"
 	"github.com/pomerium/pomerium/pkg/identity"
 	"github.com/pomerium/pomerium/pkg/identity/oauth"
 	gossh "golang.org/x/crypto/ssh"
 	"golang.org/x/sync/errgroup"
+	"google.golang.org/grpc"
+	"google.golang.org/protobuf/encoding/protodelim"
+	"google.golang.org/protobuf/encoding/protojson"
 	"google.golang.org/protobuf/types/known/anypb"
+	"google.golang.org/protobuf/types/known/emptypb"
 	"google.golang.org/protobuf/types/known/timestamppb"
 	"google.golang.org/protobuf/types/known/wrapperspb"
 )
@@ -33,6 +46,76 @@ type StreamState struct {
 	MethodsAuthenticated []string
 }
 
+func (a *Authorize) RecordingFinalized(
+	stream grpc.ClientStreamingServer[extensions_session_recording.RecordingData, emptypb.Empty],
+) error {
+	msg, err := stream.Recv()
+	if err != nil {
+		return err
+	}
+	md := msg.GetMetadata()
+	if md == nil {
+		return fmt.Errorf("first message did not contain metadata")
+	}
+	log.Ctx(stream.Context()).Info().Str("info", protojson.Format(md)).Msg("new recording")
+
+	var recording []byte
+READ:
+	for {
+		msg, err := stream.Recv()
+		if err != nil {
+			if errors.Is(err, io.EOF) {
+				break
+			}
+			return err
+		}
+		switch data := msg.Data.(type) {
+		case *extensions_session_recording.RecordingData_Chunk:
+			recording = append(recording, data.Chunk...)
+		case *extensions_session_recording.RecordingData_Checksum:
+			actual := sha256.Sum256(recording)
+			if actual != [32]byte(data.Checksum) {
+				return fmt.Errorf("checksum mismatch")
+			}
+			break READ
+		}
+	}
+
+	r, err := zstd.NewReader(bytes.NewReader(recording))
+	if err != nil {
+		return fmt.Errorf("failed to create zstd reader: %w", err)
+	}
+
+	switch md.Format {
+	case extensions_session_recording.Format_AsciicastFormat:
+		log.Ctx(stream.Context()).Info().Int("compressed_size", len(recording)).Msg("asciicast recording received")
+	case extensions_session_recording.Format_RawFormat:
+		reader := bufio.NewReader(r)
+		var header extensions_session_recording.Header
+		if err := protodelim.UnmarshalFrom(reader, &header); err != nil {
+			return fmt.Errorf("failed to unmarshal header: %w", err)
+		}
+
+		var packets []*extensions_session_recording.Packet
+		for {
+			var packet extensions_session_recording.Packet
+			err := protodelim.UnmarshalFrom(reader, &packet)
+			if err != nil {
+				if errors.Is(err, io.EOF) {
+					break
+				}
+				return fmt.Errorf("failed to unmarshal packet: %w", err)
+			}
+			packets = append(packets, &packet)
+		}
+
+		log.Ctx(stream.Context()).Info().Int("compressed_size", len(recording)).Int("packet_count", len(packets)).Msg("recording received")
+	}
+	return nil
+}
+
+var activeStreamIds sync.Map
+
 func (a *Authorize) ManageStream(
 	server extensions_ssh.StreamManagement_ManageStreamServer,
 ) error {
@@ -72,6 +155,7 @@ func (a *Authorize) ManageStream(
 	var state StreamState
 
 	deviceAuthSuccess := &atomic.Bool{}
+	deviceAuthDone := make(chan struct{})
 
 	errC := make(chan error, 1)
 	a.activeStreamsMu.Lock()
@@ -80,7 +164,6 @@ func (a *Authorize) ManageStream(
 	for {
 		select {
 		case err := <-errC:
-
 			return err
 		case req, ok := <-recvC:
 			if !ok {
@@ -92,6 +175,10 @@ func (a *Authorize) ManageStream(
 				case *extensions_ssh.StreamEvent_DownstreamConnected:
 					fmt.Println("downstream connected")
 					_ = event
+				case *extensions_ssh.StreamEvent_UpstreamConnected:
+					fmt.Printf("upstream connected: %d\n", event.UpstreamConnected.GetStreamId())
+					activeStreamIds.Store(event.UpstreamConnected.GetStreamId(), state)
+					defer activeStreamIds.Delete(event.UpstreamConnected.GetStreamId())
 				case nil:
 				}
 			case *extensions_ssh.ClientMessage_AuthRequest:
@@ -119,32 +206,35 @@ func (a *Authorize) ManageStream(
 					state.PublicKey = pubkeyReq.PublicKey
 
 					if authReq.Username == "" && authReq.Hostname == "" {
-						pkData, _ := anypb.New(&extensions_ssh.PublicKeyAllowResponse{
-							PublicKey: state.PublicKey,
-							Permissions: &extensions_ssh.Permissions{
-								PermitPortForwarding:  true,
-								PermitAgentForwarding: true,
-								PermitX11Forwarding:   true,
-								PermitPty:             true,
-								PermitUserRc:          true,
-								ValidBefore:           timestamppb.New(time.Now().Add(-1 * time.Minute)),
-								ValidAfter:            timestamppb.New(time.Now().Add(12 * time.Hour)),
-							},
-						})
 						resp := extensions_ssh.ServerMessage{
 							Message: &extensions_ssh.ServerMessage_AuthResponse{
 								AuthResponse: &extensions_ssh.AuthenticationResponse{
 									Response: &extensions_ssh.AuthenticationResponse_Allow{
 										Allow: &extensions_ssh.AllowResponse{
 											Username: state.Username,
-											Hostname: state.Hostname,
-											AllowedMethods: []*extensions_ssh.AllowedMethod{
-												{
-													Method:     "publickey",
-													MethodData: pkData,
+											Target: &extensions_ssh.AllowResponse_Internal{
+												Internal: &extensions_ssh.InternalTarget{},
+											},
+										},
+									},
+								},
+							},
+						}
+						sendC <- &resp
+						continue
+					} else if authReq.Username == "_mirror" && authReq.Hostname != "" {
+						id, _ := strconv.ParseUint(authReq.Hostname, 10, 64)
+						resp := extensions_ssh.ServerMessage{
+							Message: &extensions_ssh.ServerMessage_AuthResponse{
+								AuthResponse: &extensions_ssh.AuthenticationResponse{
+									Response: &extensions_ssh.AuthenticationResponse_Allow{
+										Allow: &extensions_ssh.AllowResponse{
+											Target: &extensions_ssh.AllowResponse_MirrorSession{
+												MirrorSession: &extensions_ssh.MirrorSessionTarget{
+													SourceId: id,
+													Mode:     extensions_ssh.MirrorSessionTarget_ReadWrite,
 												},
 											},
-											Target: extensions_ssh.Target_Internal,
 										},
 									},
 								},
@@ -207,8 +297,8 @@ func (a *Authorize) ManageStream(
 					infoReq := extensions_ssh.KeyboardInteractiveInfoPrompts{
 						Name:        "Sign in with " + idp.GetType(),
 						Instruction: deviceAuthResp.VerificationURIComplete,
-						Prompts: []*extensions_ssh.KeyboardInteractiveInfoPrompts_Prompt{
-							{},
+						Prompts:     []*extensions_ssh.KeyboardInteractiveInfoPrompts_Prompt{
+							// {},
 						},
 					}
 
@@ -243,6 +333,7 @@ func (a *Authorize) ManageStream(
 						}
 						fmt.Println(token)
 						deviceAuthSuccess.Store(true)
+						close(deviceAuthDone)
 					}()
 				}
 			case *extensions_ssh.ClientMessage_InfoResponse:
@@ -254,31 +345,45 @@ func (a *Authorize) ManageStream(
 						fmt.Println(respInfo.Responses)
 					}
 				}
+				select {
+				case <-deviceAuthDone:
+				case <-ctx.Done():
+				}
 				if deviceAuthSuccess.Load() {
 					state.MethodsAuthenticated = append(state.MethodsAuthenticated, "keyboard-interactive")
 				} else {
-					retryReq := extensions_ssh.KeyboardInteractiveInfoPrompts{
-						Name:        "",
-						Instruction: "Login not successful yet, try again",
-						Prompts: []*extensions_ssh.KeyboardInteractiveInfoPrompts_Prompt{
-							{},
-						},
-					}
-					infoReqAny, _ := anypb.New(&retryReq)
-
 					resp := extensions_ssh.ServerMessage{
 						Message: &extensions_ssh.ServerMessage_AuthResponse{
 							AuthResponse: &extensions_ssh.AuthenticationResponse{
-								Response: &extensions_ssh.AuthenticationResponse_InfoRequest{
-									InfoRequest: &extensions_ssh.InfoRequest{
-										Method:  "keyboard-interactive",
-										Request: infoReqAny,
-									},
+								Response: &extensions_ssh.AuthenticationResponse_Deny{
+									Deny: &extensions_ssh.DenyResponse{},
 								},
 							},
 						},
 					}
 					sendC <- &resp
+					// retryReq := extensions_ssh.KeyboardInteractiveInfoPrompts{
+					// 	Name:        "",
+					// 	Instruction: "Login not successful yet, try again",
+					// 	Prompts:     []*extensions_ssh.KeyboardInteractiveInfoPrompts_Prompt{
+					// 		// {},
+					// 	},
+					// }
+					// infoReqAny, _ := anypb.New(&retryReq)
+
+					// resp := extensions_ssh.ServerMessage{
+					// 	Message: &extensions_ssh.ServerMessage_AuthResponse{
+					// 		AuthResponse: &extensions_ssh.AuthenticationResponse{
+					// 			Response: &extensions_ssh.AuthenticationResponse_InfoRequest{
+					// 				InfoRequest: &extensions_ssh.InfoRequest{
+					// 					Method:  "keyboard-interactive",
+					// 					Request: infoReqAny,
+					// 				},
+					// 			},
+					// 		},
+					// 	},
+					// }
+					// sendC <- &resp
 					continue
 				}
 				if slices.Contains(state.MethodsAuthenticated, "publickey") {
@@ -294,23 +399,35 @@ func (a *Authorize) ManageStream(
 							ValidAfter:            timestamppb.New(time.Now().Add(12 * time.Hour)),
 						},
 					})
+					sessionRecordingExt, _ := anypb.New(&extensions_session_recording.UpstreamTargetExtensionConfig{
+						RecordingName: fmt.Sprintf("session-%s-at-%s-%d.cast", state.Username, state.Hostname, time.Now().UnixNano()),
+						Format:        extensions_session_recording.Format_AsciicastFormat,
+					})
 					authResponse := extensions_ssh.ServerMessage{
 						Message: &extensions_ssh.ServerMessage_AuthResponse{
 							AuthResponse: &extensions_ssh.AuthenticationResponse{
 								Response: &extensions_ssh.AuthenticationResponse_Allow{
 									Allow: &extensions_ssh.AllowResponse{
 										Username: state.Username,
-										Hostname: state.Hostname,
-										AllowedMethods: []*extensions_ssh.AllowedMethod{
-											{
-												Method:     "publickey",
-												MethodData: pkData,
-											},
-											{
-												Method: "keyboard-interactive",
+										Target: &extensions_ssh.AllowResponse_Upstream{
+											Upstream: &extensions_ssh.UpstreamTarget{
+												Hostname: state.Hostname,
+												AllowedMethods: []*extensions_ssh.AllowedMethod{
+													{
+														Method:     "publickey",
+														MethodData: pkData,
+													},
+													{
+														Method: "keyboard-interactive",
+													},
+												},
+												Extensions: []*corev3.TypedExtensionConfig{
+													{
+														TypedConfig: sessionRecordingExt,
+													},
+												},
 											},
 										},
-										Target: extensions_ssh.Target_Upstream,
 									},
 								},
 							},
@@ -465,10 +582,17 @@ func (a *Authorize) ServeChannel(
 
 			switch msg.Request {
 			case "pty-req":
+				opts := a.currentOptions.Load()
+				var routes []string
+				for r := range opts.GetAllPolicies() {
+					if strings.HasPrefix(r.From, "ssh://") {
+						routes = append(routes, fmt.Sprintf("ubuntu@%s", strings.TrimSuffix(strings.TrimPrefix(r.From, "ssh://"), "."+opts.SSHHostname)))
+					}
+				}
 				req := parsePtyReq(msg.RequestSpecificData)
-				items := []list.Item{
-					item("ubuntu@vm"),
-					item("joe@local"),
+				items := []list.Item{}
+				for _, route := range routes {
+					items = append(items, item(route))
 				}
 				downstreamPtyInfo = &extensions_ssh.SSHDownstreamPTYInfo{
 					TermEnv:      req.TermEnv,
@@ -502,6 +626,10 @@ func (a *Authorize) ServeChannel(
 						return
 					}
 					username, hostname, _ := strings.Cut(answer.(model).choice, "@")
+					sessionRecordingExt, _ := anypb.New(&extensions_session_recording.UpstreamTargetExtensionConfig{
+						RecordingName: fmt.Sprintf("session-%s-at-%s-%d.cast", username, hostname, time.Now().UnixNano()),
+						Format:        extensions_session_recording.Format_AsciicastFormat,
+					})
 					handOff, _ := anypb.New(&extensions_ssh.SSHChannelControlAction{
 						Action: &extensions_ssh.SSHChannelControlAction_HandOff{
 							HandOff: &extensions_ssh.SSHChannelControlAction_HandOffUpstream{
@@ -509,7 +637,17 @@ func (a *Authorize) ServeChannel(
 								DownstreamPtyInfo:     downstreamPtyInfo,
 								UpstreamAuth: &extensions_ssh.AllowResponse{
 									Username: username,
-									Hostname: hostname,
+									Target: &extensions_ssh.AllowResponse_Upstream{
+										Upstream: &extensions_ssh.UpstreamTarget{
+											AllowMirrorConnections: true,
+											Hostname:               hostname,
+											Extensions: []*corev3.TypedExtensionConfig{
+												{
+													TypedConfig: sessionRecordingExt,
+												},
+											},
+										},
+									},
 								},
 							},
 						},
@@ -675,11 +813,5 @@ func (m model) Update(msg tea.Msg) (tea.Model, tea.Cmd) {
 }
 
 func (m model) View() string {
-	if m.choice != "" {
-		return quitTextStyle.Render(fmt.Sprintf("%s? Sounds good to me.", m.choice))
-	}
-	if m.quitting {
-		return quitTextStyle.Render("Not hungry? That’s cool.")
-	}
 	return "\n" + m.list.View()
 }
diff --git a/cmd/pomerium/main.go b/cmd/pomerium/main.go
index 3289a4391..48e1dbba3 100644
--- a/cmd/pomerium/main.go
+++ b/cmd/pomerium/main.go
@@ -53,9 +53,9 @@ func main() {
 }
 
 func run(ctx context.Context, configFile string) error {
-	ctx = log.WithContext(ctx, func(c zerolog.Context) zerolog.Context {
-		return c.Str("config_file_source", configFile).Bool("bootstrap", true)
-	})
+	// ctx = log.WithContext(ctx, func(c zerolog.Context) zerolog.Context {
+	// 	return c.Str("config_file_source", configFile).Bool("bootstrap", true)
+	// })
 
 	var src config.Source
 
diff --git a/config/envoyconfig/listeners_ssh.go b/config/envoyconfig/listeners_ssh.go
index 2574692c9..d1d6ce92b 100644
--- a/config/envoyconfig/listeners_ssh.go
+++ b/config/envoyconfig/listeners_ssh.go
@@ -4,6 +4,7 @@ import (
 	"context"
 	"fmt"
 	"net/url"
+	"os"
 	"strings"
 	"time"
 
@@ -11,14 +12,17 @@ import (
 	xds_matcher_v3 "github.com/cncf/xds/go/xds/type/matcher/v3"
 	envoy_config_core_v3 "github.com/envoyproxy/go-control-plane/envoy/config/core/v3"
 	envoy_config_listener_v3 "github.com/envoyproxy/go-control-plane/envoy/config/listener/v3"
+	extensions_compressor_zstd_v3 "github.com/envoyproxy/go-control-plane/envoy/extensions/compression/zstd/compressor/v3"
 	envoy_generic_proxy_action_v3 "github.com/envoyproxy/go-control-plane/envoy/extensions/filters/network/generic_proxy/action/v3"
 	envoy_generic_proxy_matcher_v3 "github.com/envoyproxy/go-control-plane/envoy/extensions/filters/network/generic_proxy/matcher/v3"
 	envoy_generic_router_v3 "github.com/envoyproxy/go-control-plane/envoy/extensions/filters/network/generic_proxy/router/v3"
 	envoy_generic_proxy_v3 "github.com/envoyproxy/go-control-plane/envoy/extensions/filters/network/generic_proxy/v3"
 	matcherv3 "github.com/envoyproxy/go-control-plane/envoy/type/matcher/v3"
 	extensions_ssh "github.com/pomerium/envoy-custom/api/extensions/filters/network/ssh"
+	extensions_ssh_session_recording "github.com/pomerium/envoy-custom/api/extensions/filters/network/ssh/filters/session_recording"
 	"github.com/pomerium/pomerium/config"
 	"google.golang.org/protobuf/types/known/durationpb"
+	"google.golang.org/protobuf/types/known/wrapperspb"
 )
 
 func (b *Builder) buildSSHListener(ctx context.Context, cfg *config.Config) (*envoy_config_listener_v3.Listener, error) {
@@ -39,6 +43,15 @@ func (b *Builder) buildSSHListener(ctx context.Context, cfg *config.Config) (*en
 	} else {
 		grpcClientTimeout = durationpb.New(30 * time.Second)
 	}
+	os.MkdirAll("/tmp/recordings", 0o755)
+	authorizeService := &envoy_config_core_v3.GrpcService{
+		Timeout: grpcClientTimeout,
+		TargetSpecifier: &envoy_config_core_v3.GrpcService_EnvoyGrpc_{
+			EnvoyGrpc: &envoy_config_core_v3.GrpcService_EnvoyGrpc{
+				ClusterName: "pomerium-authorize",
+			},
+		},
+	}
 	li := &envoy_config_listener_v3.Listener{
 		Name:    "ssh",
 		Address: buildTCPAddress(cfg.Options.SSHAddr, 22),
@@ -58,17 +71,30 @@ func (b *Builder) buildSSHListener(ctx context.Context, cfg *config.Config) (*en
 											PublicKeyFile:  cfg.Options.SSHUserCAKey.PublicKeyFile,
 											PrivateKeyFile: cfg.Options.SSHUserCAKey.PrivateKeyFile,
 										},
-										GrpcService: &envoy_config_core_v3.GrpcService{
-											Timeout: grpcClientTimeout,
-											TargetSpecifier: &envoy_config_core_v3.GrpcService_EnvoyGrpc_{
-												EnvoyGrpc: &envoy_config_core_v3.GrpcService_EnvoyGrpc{
-													ClusterName: "pomerium-authorize",
-												},
-											},
-										},
+										GrpcService: authorizeService,
 									}),
 								},
 								Filters: []*envoy_config_core_v3.TypedExtensionConfig{
+									{
+										Name: "envoy.filters.generic.ssh.session_recording",
+										TypedConfig: marshalAny(&extensions_ssh_session_recording.Config{
+											StorageDir:  "/tmp/recordings",
+											GrpcService: authorizeService,
+											CompressorLibrary: &envoy_config_core_v3.TypedExtensionConfig{
+												Name: "envoy.compression.zstd.compressor",
+												TypedConfig: marshalAny(&extensions_compressor_zstd_v3.Zstd{
+													CompressionLevel: wrapperspb.UInt32(19),
+													EnableChecksum:   false,
+													Strategy:         extensions_compressor_zstd_v3.Zstd_BTULTRA2,
+													ChunkSize:        wrapperspb.UInt32(8192),
+												}),
+											},
+										}),
+									},
+									// {
+									// 	Name:        "envoy.filters.generic.ssh.session_multiplexing",
+									// 	TypedConfig: marshalAny(&extensions_ssh_session_multiplexing.Config{}),
+									// },
 									{
 										Name: "envoy.filters.generic.router",
 										TypedConfig: marshalAny(&envoy_generic_router_v3.Router{
diff --git a/pkg/cmd/pomerium/pomerium.go b/pkg/cmd/pomerium/pomerium.go
index 98b079f83..9b2bd0fc2 100644
--- a/pkg/cmd/pomerium/pomerium.go
+++ b/pkg/cmd/pomerium/pomerium.go
@@ -10,6 +10,7 @@ import (
 
 	envoy_service_auth_v3 "github.com/envoyproxy/go-control-plane/envoy/service/auth/v3"
 	extensions_ssh "github.com/pomerium/envoy-custom/api/extensions/filters/network/ssh"
+	extensions_session_recording "github.com/pomerium/envoy-custom/api/extensions/filters/network/ssh/filters/session_recording"
 
 	"go.uber.org/automaxprocs/maxprocs"
 	"golang.org/x/sync/errgroup"
@@ -270,6 +271,7 @@ func setupAuthorize(ctx context.Context, src config.Source, controlPlane *contro
 	}
 	envoy_service_auth_v3.RegisterAuthorizationServer(controlPlane.GRPCServer, svc)
 	extensions_ssh.RegisterStreamManagementServer(controlPlane.GRPCServer, svc)
+	extensions_session_recording.RegisterRecordingServiceServer(controlPlane.GRPCServer, svc)
 
 	log.Ctx(ctx).Info().Msg("enabled authorize service")
 	src.OnConfigChange(ctx, svc.OnConfigChange)