diff --git a/internal/servers/worker/handler.go b/internal/servers/worker/handler.go
index e02f5d249b..1d74f3ff9c 100644
--- a/internal/servers/worker/handler.go
+++ b/internal/servers/worker/handler.go
@@ -232,7 +232,12 @@ func (w *Worker) handleProxy() http.HandlerFunc {
 			return
 		}
 
-		handleProxyFn(connCtx, conf)
+		if err = handleProxyFn(connCtx, conf); err != nil {
+			event.WriteError(ctx, op, err, event.WithInfoMsg("error handling proxy", "session_id", sessionId, "endpoint", endpoint))
+			if err = conn.Close(websocket.StatusInternalError, "unable to establish proxy"); err != nil {
+				event.WriteError(ctx, op, err, event.WithInfoMsg("error closing client connection"))
+			}
+		}
 	}
 }
 
diff --git a/internal/servers/worker/proxy/proxy.go b/internal/servers/worker/proxy/proxy.go
index 4fff22c82b..4c2e074f94 100644
--- a/internal/servers/worker/proxy/proxy.go
+++ b/internal/servers/worker/proxy/proxy.go
@@ -47,7 +47,7 @@ func (c Config) Validate() error {
 
 // Handler is the type that all proxies need to implement to be called by the worker
 // when a new client connection is created.
-type Handler func(ctx context.Context, config Config, opt ...Option)
+type Handler func(ctx context.Context, config Config, opt ...Option) error
 
 var (
 	// handlers is the map of registered handlers
diff --git a/internal/servers/worker/proxy/proxy_test.go b/internal/servers/worker/proxy/proxy_test.go
index 100e3fcbc3..42081cdea9 100644
--- a/internal/servers/worker/proxy/proxy_test.go
+++ b/internal/servers/worker/proxy/proxy_test.go
@@ -136,7 +136,7 @@ func TestRegisterHandler(t *testing.T) {
 	t.Parallel()
 	assert, require := assert.New(t), require.New(t)
 
-	fn := func(context.Context, Config, ...Option) { return }
+	fn := func(context.Context, Config, ...Option) error { return nil }
 
 	err := RegisterHandler("protocol", fn)
 	require.NoError(err)
@@ -154,7 +154,7 @@ func TestGetHandler(t *testing.T) {
 	t.Parallel()
 	assert, require := assert.New(t), require.New(t)
 
-	fn := func(context.Context, Config, ...Option) {}
+	fn := func(context.Context, Config, ...Option) error { return nil }
 
 	err := RegisterHandler("fn", fn)
 	require.NoError(err)
diff --git a/internal/servers/worker/proxy/tcp/tcp.go b/internal/servers/worker/proxy/tcp/tcp.go
index b07e779103..57f3c71edc 100644
--- a/internal/servers/worker/proxy/tcp/tcp.go
+++ b/internal/servers/worker/proxy/tcp/tcp.go
@@ -2,63 +2,45 @@ package tcp
 
 import (
 	"context"
+	"fmt"
 	"io"
 	"net"
 	"net/url"
 	"sync"
 
 	pbs "github.com/hashicorp/boundary/internal/gen/controller/servers/services"
-	"github.com/hashicorp/boundary/internal/observability/event"
 	"github.com/hashicorp/boundary/internal/servers/worker/proxy"
 	"github.com/hashicorp/boundary/internal/servers/worker/session"
 	"nhooyr.io/websocket"
 )
 
 func init() {
-	err := proxy.RegisterHandler("tcp", handleTcpProxyV1)
+	err := proxy.RegisterHandler("tcp", handleProxy)
 	if err != nil {
 		panic(err)
 	}
 }
 
-// handleTcpProxyV1 creates a tcp proxy between the incoming websocket conn and the
+// handleProxy creates a tcp proxy between the incoming websocket conn and the
 // connection it creates with the remote endpoint. handleTcpProxyV1 sets the connectionId
 // as connected in the repository.
 //
-// handleTcpProxyV1 blocks until an error (EOF on happy path) is received on either
+// handleProxy blocks until an error (EOF on happy path) is received on either
 // connection.
 //
 // All options are ignored.
-func handleTcpProxyV1(ctx context.Context, conf proxy.Config, _ ...proxy.Option) {
-	const op = "tcp.HandleTcpProxyV1"
-	si := conf.SessionInfo
-	si.RLock()
-	sessionId := si.LookupSessionResponse.GetAuthorization().GetSessionId()
-	si.RUnlock()
-
+func handleProxy(ctx context.Context, conf proxy.Config, _ ...proxy.Option) error {
 	conn := conf.ClientConn
 	sessionUrl, err := url.Parse(conf.RemoteEndpoint)
 	if err != nil {
-		event.WriteError(ctx, op, err, event.WithInfoMsg("error parsing endpoint information", "session_id", sessionId, "endpoint", conf.RemoteEndpoint))
-		if err = conn.Close(websocket.StatusInternalError, "cannot parse endpoint url"); err != nil {
-			event.WriteError(ctx, op, err, event.WithInfoMsg("error closing client connection"))
-		}
-		return
+		return fmt.Errorf("error parsing endpoint information: %w", err)
 	}
 	if sessionUrl.Scheme != "tcp" {
-		event.WriteError(ctx, op, err, event.WithInfo("session_id", sessionId, "endpoint", conf.RemoteEndpoint))
-		if err = conn.Close(websocket.StatusInternalError, "invalid scheme for type"); err != nil {
-			event.WriteError(ctx, op, err, event.WithInfoMsg("error closing client connection"))
-		}
-		return
+		return fmt.Errorf("invalid scheme for tcp proxy: %v", sessionUrl.Scheme)
 	}
 	remoteConn, err := net.Dial("tcp", sessionUrl.Host)
 	if err != nil {
-		event.WriteError(ctx, op, err, event.WithInfoMsg("error dialing endpoint", "endpoint", conf.RemoteEndpoint))
-		if err = conn.Close(websocket.StatusInternalError, "endpoint dialing failed"); err != nil {
-			event.WriteError(ctx, op, err, event.WithInfoMsg("error closing client connection"))
-		}
-		return
+		return fmt.Errorf("error dialing endpoint: %w", err)
 	}
 	// Assert this for better Go 1.11 splice support
 	tcpRemoteConn := remoteConn.(*net.TCPConn)
@@ -75,15 +57,13 @@ func handleTcpProxyV1(ctx context.Context, conf proxy.Config, _ ...proxy.Option)
 
 	connStatus, err := session.ConnectConnection(ctx, conf.SessionClient, connectionInfo)
 	if err != nil {
-		event.WriteError(ctx, op, err, event.WithInfoMsg("error marking connection as connected"))
-		if err = conn.Close(websocket.StatusInternalError, "failed to mark connection as connected"); err != nil {
-			event.WriteError(ctx, op, err, event.WithInfoMsg("error closing client connection"))
-		}
-		return
+		return fmt.Errorf("error marking connection as connected: %w", err)
 	}
-	si.Lock()
-	si.ConnInfoMap[conf.ConnectionId].Status = connStatus
-	si.Unlock()
+
+	// Update connection info to set connection status
+	conf.SessionInfo.Lock()
+	conf.SessionInfo.ConnInfoMap[conf.ConnectionId].Status = connStatus
+	conf.SessionInfo.Unlock()
 
 	// Get a wrapped net.Conn so we can use io.Copy
 	netConn := websocket.NetConn(ctx, conn, websocket.MessageBinary)
@@ -103,4 +83,5 @@ func handleTcpProxyV1(ctx context.Context, conf proxy.Config, _ ...proxy.Option)
 		_ = netConn.Close()
 	}()
 	connWg.Wait()
+	return nil
 }
diff --git a/internal/servers/worker/proxy/tcp/tcp_test.go b/internal/servers/worker/proxy/tcp/tcp_test.go
index 457be83b37..0a365ba6b1 100644
--- a/internal/servers/worker/proxy/tcp/tcp_test.go
+++ b/internal/servers/worker/proxy/tcp/tcp_test.go
@@ -70,7 +70,10 @@ func TestHandleTcpProxyV1(t *testing.T) {
 		ConnectionId:   "mock-connection",
 	}
 
-	go handleTcpProxyV1(ctx, conf)
+	go func() {
+		err = handleProxy(ctx, conf)
+		require.NoError(err)
+	}()
 
 	// wait for HandleTcpProxyV1 to dial endpoint
 	<-ready