diff --git a/adapter/outbound/http.go b/adapter/outbound/http.go
index 54e05f9d..543e48a1 100644
--- a/adapter/outbound/http.go
+++ b/adapter/outbound/http.go
@@ -7,11 +7,11 @@ import (
 	"encoding/base64"
 	"errors"
 	"fmt"
-	"io"
 	"net"
 	"net/http"
 	"strconv"
 
+	N "github.com/metacubex/mihomo/common/net"
 	"github.com/metacubex/mihomo/component/ca"
 	"github.com/metacubex/mihomo/component/dialer"
 	"github.com/metacubex/mihomo/component/proxydialer"
@@ -51,7 +51,7 @@ func (h *Http) StreamConnContext(ctx context.Context, c net.Conn, metadata *C.Me
 		}
 	}
 
-	if err := h.shakeHand(metadata, c); err != nil {
+	if err := h.shakeHandContext(ctx, c, metadata); err != nil {
 		return nil, err
 	}
 	return c, nil
@@ -99,7 +99,12 @@ func (h *Http) ProxyInfo() C.ProxyInfo {
 	return info
 }
 
-func (h *Http) shakeHand(metadata *C.Metadata, rw io.ReadWriter) error {
+func (h *Http) shakeHandContext(ctx context.Context, c net.Conn, metadata *C.Metadata) (err error) {
+	if ctx.Done() != nil {
+		done := N.SetupContextForConn(ctx, c)
+		defer done(&err)
+	}
+
 	addr := metadata.RemoteAddress()
 	HeaderString := "CONNECT " + addr + " HTTP/1.1\r\n"
 	tempHeaders := map[string]string{
@@ -123,13 +128,13 @@ func (h *Http) shakeHand(metadata *C.Metadata, rw io.ReadWriter) error {
 
 	HeaderString += "\r\n"
 
-	_, err := rw.Write([]byte(HeaderString))
+	_, err = c.Write([]byte(HeaderString))
 
 	if err != nil {
 		return err
 	}
 
-	resp, err := http.ReadResponse(bufio.NewReader(rw), nil)
+	resp, err := http.ReadResponse(bufio.NewReader(c), nil)
 
 	if err != nil {
 		return err
diff --git a/adapter/outbound/shadowsocks.go b/adapter/outbound/shadowsocks.go
index 11e744cc..e7c2dc2b 100644
--- a/adapter/outbound/shadowsocks.go
+++ b/adapter/outbound/shadowsocks.go
@@ -100,7 +100,7 @@ type restlsOption struct {
 }
 
 // StreamConnContext implements C.ProxyAdapter
-func (ss *ShadowSocks) StreamConnContext(ctx context.Context, c net.Conn, metadata *C.Metadata) (net.Conn, error) {
+func (ss *ShadowSocks) StreamConnContext(ctx context.Context, c net.Conn, metadata *C.Metadata) (_ net.Conn, err error) {
 	useEarly := false
 	switch ss.obfsMode {
 	case "tls":
@@ -109,7 +109,6 @@ func (ss *ShadowSocks) StreamConnContext(ctx context.Context, c net.Conn, metada
 		_, port, _ := net.SplitHostPort(ss.addr)
 		c = obfs.NewHTTPObfs(c, ss.obfsOption.Host, port)
 	case "websocket":
-		var err error
 		if ss.v2rayOption != nil {
 			c, err = v2rayObfs.NewV2rayObfs(ctx, c, ss.v2rayOption)
 		} else if ss.gostOption != nil {
@@ -121,14 +120,12 @@ func (ss *ShadowSocks) StreamConnContext(ctx context.Context, c net.Conn, metada
 			return nil, fmt.Errorf("%s connect error: %w", ss.addr, err)
 		}
 	case shadowtls.Mode:
-		var err error
 		c, err = shadowtls.NewShadowTLS(ctx, c, ss.shadowTLSOption)
 		if err != nil {
 			return nil, err
 		}
 		useEarly = true
 	case restls.Mode:
-		var err error
 		c, err = restls.NewRestls(ctx, c, ss.restlsConfig)
 		if err != nil {
 			return nil, fmt.Errorf("%s (restls) connect error: %w", ss.addr, err)
@@ -136,6 +133,12 @@ func (ss *ShadowSocks) StreamConnContext(ctx context.Context, c net.Conn, metada
 		useEarly = true
 	}
 	useEarly = useEarly || N.NeedHandshake(c)
+	if !useEarly {
+		if ctx.Done() != nil {
+			done := N.SetupContextForConn(ctx, c)
+			defer done(&err)
+		}
+	}
 	if metadata.NetWork == C.UDP && ss.option.UDPOverTCP {
 		uotDestination := uot.RequestDestination(uint8(ss.option.UDPOverTCPVersion))
 		if useEarly {
diff --git a/adapter/outbound/shadowsocksr.go b/adapter/outbound/shadowsocksr.go
index 3eefd2ac..7957d6cd 100644
--- a/adapter/outbound/shadowsocksr.go
+++ b/adapter/outbound/shadowsocksr.go
@@ -42,12 +42,15 @@ type ShadowSocksROption struct {
 }
 
 // StreamConnContext implements C.ProxyAdapter
-func (ssr *ShadowSocksR) StreamConnContext(ctx context.Context, c net.Conn, metadata *C.Metadata) (net.Conn, error) {
+func (ssr *ShadowSocksR) StreamConnContext(ctx context.Context, c net.Conn, metadata *C.Metadata) (_ net.Conn, err error) {
+	if ctx.Done() != nil {
+		done := N.SetupContextForConn(ctx, c)
+		defer done(&err)
+	}
 	c = ssr.obfs.StreamConn(c)
 	c = ssr.cipher.StreamConn(c)
 	var (
-		iv  []byte
-		err error
+		iv []byte
 	)
 	switch conn := c.(type) {
 	case *shadowstream.Conn:
diff --git a/adapter/outbound/snell.go b/adapter/outbound/snell.go
index f4b94787..98d16a2c 100644
--- a/adapter/outbound/snell.go
+++ b/adapter/outbound/snell.go
@@ -6,6 +6,7 @@ import (
 	"net"
 	"strconv"
 
+	N "github.com/metacubex/mihomo/common/net"
 	"github.com/metacubex/mihomo/common/structure"
 	"github.com/metacubex/mihomo/component/dialer"
 	"github.com/metacubex/mihomo/component/proxydialer"
@@ -41,7 +42,7 @@ type streamOption struct {
 	obfsOption *simpleObfsOption
 }
 
-func streamConn(c net.Conn, option streamOption) *snell.Snell {
+func snellStreamConn(c net.Conn, option streamOption) *snell.Snell {
 	switch option.obfsOption.Mode {
 	case "tls":
 		c = obfs.NewTLSObfs(c, option.obfsOption.Host)
@@ -54,15 +55,25 @@ func streamConn(c net.Conn, option streamOption) *snell.Snell {
 
 // StreamConnContext implements C.ProxyAdapter
 func (s *Snell) StreamConnContext(ctx context.Context, c net.Conn, metadata *C.Metadata) (net.Conn, error) {
-	c = streamConn(c, streamOption{s.psk, s.version, s.addr, s.obfsOption})
-	if metadata.NetWork == C.UDP {
-		err := snell.WriteUDPHeader(c, s.version)
-		return c, err
-	}
-	err := snell.WriteHeader(c, metadata.String(), uint(metadata.DstPort), s.version)
+	c = snellStreamConn(c, streamOption{s.psk, s.version, s.addr, s.obfsOption})
+	err := s.writeHeaderContext(ctx, c, metadata)
 	return c, err
 }
 
+func (s *Snell) writeHeaderContext(ctx context.Context, c net.Conn, metadata *C.Metadata) (err error) {
+	if ctx.Done() != nil {
+		done := N.SetupContextForConn(ctx, c)
+		defer done(&err)
+	}
+
+	if metadata.NetWork == C.UDP {
+		err = snell.WriteUDPHeader(c, s.version)
+		return
+	}
+	err = snell.WriteHeader(c, metadata.String(), uint(metadata.DstPort), s.version)
+	return
+}
+
 // DialContext implements C.ProxyAdapter
 func (s *Snell) DialContext(ctx context.Context, metadata *C.Metadata, opts ...dialer.Option) (_ C.Conn, err error) {
 	if s.version == snell.Version2 && len(opts) == 0 {
@@ -71,8 +82,8 @@ func (s *Snell) DialContext(ctx context.Context, metadata *C.Metadata, opts ...d
 			return nil, err
 		}
 
-		if err = snell.WriteHeader(c, metadata.String(), uint(metadata.DstPort), s.version); err != nil {
-			c.Close()
+		if err = s.writeHeaderContext(ctx, c, metadata); err != nil {
+			_ = c.Close()
 			return nil, err
 		}
 		return NewConn(c, s), err
@@ -120,12 +131,8 @@ func (s *Snell) ListenPacketWithDialer(ctx context.Context, dialer C.Dialer, met
 	if err != nil {
 		return nil, err
 	}
-	c = streamConn(c, streamOption{s.psk, s.version, s.addr, s.obfsOption})
 
-	err = snell.WriteUDPHeader(c, s.version)
-	if err != nil {
-		return nil, err
-	}
+	c, err = s.StreamConnContext(ctx, c, metadata)
 
 	pc := snell.PacketConn(c)
 	return newPacketConn(pc, s), nil
@@ -212,7 +219,7 @@ func NewSnell(option SnellOption) (*Snell, error) {
 				return nil, err
 			}
 
-			return streamConn(c, streamOption{psk, option.Version, addr, obfsOption}), nil
+			return snellStreamConn(c, streamOption{psk, option.Version, addr, obfsOption}), nil
 		})
 	}
 	return s, nil
diff --git a/adapter/outbound/socks5.go b/adapter/outbound/socks5.go
index f7f04d09..f42011d7 100644
--- a/adapter/outbound/socks5.go
+++ b/adapter/outbound/socks5.go
@@ -10,6 +10,7 @@ import (
 	"net/netip"
 	"strconv"
 
+	N "github.com/metacubex/mihomo/common/net"
 	"github.com/metacubex/mihomo/component/ca"
 	"github.com/metacubex/mihomo/component/dialer"
 	"github.com/metacubex/mihomo/component/proxydialer"
@@ -58,7 +59,7 @@ func (ss *Socks5) StreamConnContext(ctx context.Context, c net.Conn, metadata *C
 			Password: ss.pass,
 		}
 	}
-	if _, err := socks5.ClientHandshake(c, serializesSocksAddr(metadata), socks5.CmdConnect, user); err != nil {
+	if _, err := ss.clientHandshakeContext(ctx, c, serializesSocksAddr(metadata), socks5.CmdConnect, user); err != nil {
 		return nil, err
 	}
 	return c, nil
@@ -135,7 +136,7 @@ func (ss *Socks5) ListenPacketContext(ctx context.Context, metadata *C.Metadata,
 	}
 
 	udpAssocateAddr := socks5.AddrFromStdAddrPort(netip.AddrPortFrom(netip.IPv4Unspecified(), 0))
-	bindAddr, err := socks5.ClientHandshake(c, udpAssocateAddr, socks5.CmdUDPAssociate, user)
+	bindAddr, err := ss.clientHandshakeContext(ctx, c, udpAssocateAddr, socks5.CmdUDPAssociate, user)
 	if err != nil {
 		err = fmt.Errorf("client hanshake error: %w", err)
 		return
@@ -178,6 +179,14 @@ func (ss *Socks5) ProxyInfo() C.ProxyInfo {
 	return info
 }
 
+func (ss *Socks5) clientHandshakeContext(ctx context.Context, c net.Conn, addr socks5.Addr, command socks5.Command, user *socks5.User) (_ socks5.Addr, err error) {
+	if ctx.Done() != nil {
+		done := N.SetupContextForConn(ctx, c)
+		defer done(&err)
+	}
+	return socks5.ClientHandshake(c, addr, command, user)
+}
+
 func NewSocks5(option Socks5Option) (*Socks5, error) {
 	var tlsConfig *tls.Config
 	if option.TLS {
diff --git a/adapter/outbound/trojan.go b/adapter/outbound/trojan.go
index b37235e0..31275245 100644
--- a/adapter/outbound/trojan.go
+++ b/adapter/outbound/trojan.go
@@ -9,6 +9,7 @@ import (
 	"net/http"
 	"strconv"
 
+	N "github.com/metacubex/mihomo/common/net"
 	"github.com/metacubex/mihomo/component/ca"
 	"github.com/metacubex/mihomo/component/dialer"
 	"github.com/metacubex/mihomo/component/proxydialer"
@@ -110,14 +111,23 @@ func (t *Trojan) StreamConnContext(ctx context.Context, c net.Conn, metadata *C.
 		c = t.ssCipher.StreamConn(c)
 	}
 
-	if metadata.NetWork == C.UDP {
-		err = t.instance.WriteHeader(c, trojan.CommandUDP, serializesSocksAddr(metadata))
-		return c, err
-	}
-	err = t.instance.WriteHeader(c, trojan.CommandTCP, serializesSocksAddr(metadata))
+	err = t.writeHeaderContext(ctx, c, metadata)
 	return c, err
 }
 
+func (t *Trojan) writeHeaderContext(ctx context.Context, c net.Conn, metadata *C.Metadata) (err error) {
+	if ctx.Done() != nil {
+		done := N.SetupContextForConn(ctx, c)
+		defer done(&err)
+	}
+	command := trojan.CommandTCP
+	if metadata.NetWork == C.UDP {
+		command = trojan.CommandUDP
+	}
+	err = t.instance.WriteHeader(c, command, serializesSocksAddr(metadata))
+	return err
+}
+
 // DialContext implements C.ProxyAdapter
 func (t *Trojan) DialContext(ctx context.Context, metadata *C.Metadata, opts ...dialer.Option) (_ C.Conn, err error) {
 	// gun transport
@@ -131,7 +141,7 @@ func (t *Trojan) DialContext(ctx context.Context, metadata *C.Metadata, opts ...
 			c = t.ssCipher.StreamConn(c)
 		}
 
-		if err = t.instance.WriteHeader(c, trojan.CommandTCP, serializesSocksAddr(metadata)); err != nil {
+		if err = t.writeHeaderContext(ctx, c, metadata); err != nil {
 			c.Close()
 			return nil, err
 		}
@@ -184,7 +194,7 @@ func (t *Trojan) ListenPacketContext(ctx context.Context, metadata *C.Metadata,
 			c = t.ssCipher.StreamConn(c)
 		}
 
-		err = t.instance.WriteHeader(c, trojan.CommandUDP, serializesSocksAddr(metadata))
+		err = t.writeHeaderContext(ctx, c, metadata)
 		if err != nil {
 			return nil, err
 		}
@@ -219,7 +229,7 @@ func (t *Trojan) ListenPacketWithDialer(ctx context.Context, dialer C.Dialer, me
 		c = t.ssCipher.StreamConn(c)
 	}
 
-	err = t.instance.WriteHeader(c, trojan.CommandUDP, serializesSocksAddr(metadata))
+	err = t.writeHeaderContext(ctx, c, metadata)
 	if err != nil {
 		return nil, err
 	}
diff --git a/adapter/outbound/vless.go b/adapter/outbound/vless.go
index 1e7d1395..d4444cb0 100644
--- a/adapter/outbound/vless.go
+++ b/adapter/outbound/vless.go
@@ -155,7 +155,7 @@ func (v *Vless) StreamConnContext(ctx context.Context, c net.Conn, metadata *C.M
 			Path:  v.option.HTTP2Opts.Path,
 		}
 
-		c, err = vmess.StreamH2Conn(c, h2Opts)
+		c, err = vmess.StreamH2Conn(ctx, c, h2Opts)
 	case "grpc":
 		c, err = gun.StreamGunWithConn(c, v.gunTLSConfig, v.gunConfig, v.realityConfig)
 	default:
@@ -168,10 +168,14 @@ func (v *Vless) StreamConnContext(ctx context.Context, c net.Conn, metadata *C.M
 		return nil, err
 	}
 
-	return v.streamConn(c, metadata)
+	return v.streamConnContext(ctx, c, metadata)
 }
 
-func (v *Vless) streamConn(c net.Conn, metadata *C.Metadata) (conn net.Conn, err error) {
+func (v *Vless) streamConnContext(ctx context.Context, c net.Conn, metadata *C.Metadata) (conn net.Conn, err error) {
+	if ctx.Done() != nil {
+		done := N.SetupContextForConn(ctx, c)
+		defer done(&err)
+	}
 	if metadata.NetWork == C.UDP {
 		if v.option.PacketAddr {
 			metadata = &C.Metadata{
@@ -238,7 +242,7 @@ func (v *Vless) DialContext(ctx context.Context, metadata *C.Metadata, opts ...d
 			safeConnClose(c, err)
 		}(c)
 
-		c, err = v.client.StreamConn(c, parseVlessAddr(metadata, v.option.XUDP))
+		c, err = v.streamConnContext(ctx, c, metadata)
 		if err != nil {
 			return nil, err
 		}
@@ -292,7 +296,7 @@ func (v *Vless) ListenPacketContext(ctx context.Context, metadata *C.Metadata, o
 			safeConnClose(c, err)
 		}(c)
 
-		c, err = v.streamConn(c, metadata)
+		c, err = v.streamConnContext(ctx, c, metadata)
 		if err != nil {
 			return nil, fmt.Errorf("new vless client error: %v", err)
 		}
diff --git a/adapter/outbound/vmess.go b/adapter/outbound/vmess.go
index 00f8a31e..285fdc8e 100644
--- a/adapter/outbound/vmess.go
+++ b/adapter/outbound/vmess.go
@@ -199,7 +199,7 @@ func (v *Vmess) StreamConnContext(ctx context.Context, c net.Conn, metadata *C.M
 			Path:  v.option.HTTP2Opts.Path,
 		}
 
-		c, err = mihomoVMess.StreamH2Conn(c, h2Opts)
+		c, err = mihomoVMess.StreamH2Conn(ctx, c, h2Opts)
 	case "grpc":
 		c, err = gun.StreamGunWithConn(c, v.gunTLSConfig, v.gunConfig, v.realityConfig)
 	default:
@@ -226,17 +226,24 @@ func (v *Vmess) StreamConnContext(ctx context.Context, c net.Conn, metadata *C.M
 	if err != nil {
 		return nil, err
 	}
-	return v.streamConn(c, metadata)
+	return v.streamConnConntext(ctx, c, metadata)
 }
 
-func (v *Vmess) streamConn(c net.Conn, metadata *C.Metadata) (conn net.Conn, err error) {
+func (v *Vmess) streamConnConntext(ctx context.Context, c net.Conn, metadata *C.Metadata) (conn net.Conn, err error) {
+	useEarly := N.NeedHandshake(c)
+	if !useEarly {
+		if ctx.Done() != nil {
+			done := N.SetupContextForConn(ctx, c)
+			defer done(&err)
+		}
+	}
 	if metadata.NetWork == C.UDP {
 		if v.option.XUDP {
 			var globalID [8]byte
 			if metadata.SourceValid() {
 				globalID = utils.GlobalID(metadata.SourceAddress())
 			}
-			if N.NeedHandshake(c) {
+			if useEarly {
 				conn = v.client.DialEarlyXUDPPacketConn(c,
 					globalID,
 					M.SocksaddrFromNet(metadata.UDPAddr()))
@@ -246,7 +253,7 @@ func (v *Vmess) streamConn(c net.Conn, metadata *C.Metadata) (conn net.Conn, err
 					M.SocksaddrFromNet(metadata.UDPAddr()))
 			}
 		} else if v.option.PacketAddr {
-			if N.NeedHandshake(c) {
+			if useEarly {
 				conn = v.client.DialEarlyPacketConn(c,
 					M.ParseSocksaddrHostPort(packetaddr.SeqPacketMagicAddress, 443))
 			} else {
@@ -255,7 +262,7 @@ func (v *Vmess) streamConn(c net.Conn, metadata *C.Metadata) (conn net.Conn, err
 			}
 			conn = packetaddr.NewBindConn(conn)
 		} else {
-			if N.NeedHandshake(c) {
+			if useEarly {
 				conn = v.client.DialEarlyPacketConn(c,
 					M.SocksaddrFromNet(metadata.UDPAddr()))
 			} else {
@@ -264,7 +271,7 @@ func (v *Vmess) streamConn(c net.Conn, metadata *C.Metadata) (conn net.Conn, err
 			}
 		}
 	} else {
-		if N.NeedHandshake(c) {
+		if useEarly {
 			conn = v.client.DialEarlyConn(c,
 				M.ParseSocksaddrHostPort(metadata.String(), metadata.DstPort))
 		} else {
@@ -290,7 +297,7 @@ func (v *Vmess) DialContext(ctx context.Context, metadata *C.Metadata, opts ...d
 			safeConnClose(c, err)
 		}(c)
 
-		c, err = v.client.DialConn(c, M.ParseSocksaddrHostPort(metadata.String(), metadata.DstPort))
+		c, err = v.streamConnConntext(ctx, c, metadata)
 		if err != nil {
 			return nil, err
 		}
@@ -341,7 +348,7 @@ func (v *Vmess) ListenPacketContext(ctx context.Context, metadata *C.Metadata, o
 			safeConnClose(c, err)
 		}(c)
 
-		c, err = v.streamConn(c, metadata)
+		c, err = v.streamConnConntext(ctx, c, metadata)
 		if err != nil {
 			return nil, fmt.Errorf("new vmess client error: %v", err)
 		}
diff --git a/transport/vmess/h2.go b/transport/vmess/h2.go
index a39ec5d9..5ad24f3d 100644
--- a/transport/vmess/h2.go
+++ b/transport/vmess/h2.go
@@ -7,6 +7,8 @@ import (
 	"net/http"
 	"net/url"
 
+	N "github.com/metacubex/mihomo/common/net"
+
 	"github.com/metacubex/randv2"
 	"golang.org/x/net/http2"
 )
@@ -100,7 +102,12 @@ func (hc *h2Conn) Close() error {
 	return hc.Conn.Close()
 }
 
-func StreamH2Conn(conn net.Conn, cfg *H2Config) (net.Conn, error) {
+func StreamH2Conn(ctx context.Context, conn net.Conn, cfg *H2Config) (_ net.Conn, err error) {
+	if ctx.Done() != nil {
+		done := N.SetupContextForConn(ctx, conn)
+		defer done(&err)
+	}
+
 	transport := &http2.Transport{}
 
 	cconn, err := transport.NewClientConn(conn)