diff --git a/cli/cli.go b/cli/cli.go
index 76bc988..a34f8a1 100644
--- a/cli/cli.go
+++ b/cli/cli.go
@@ -142,7 +142,7 @@ func Run(config Config, args []string) error {
 	// Create certificate manager (if TLS interception is enabled)
 	var tlsConfig *cryptotls.Config
 	if !config.NoTLSIntercept {
-		certManager, err := tls.NewCertificateManager("", logger) // Empty configDir since it will be determined internally
+		certManager, err := tls.NewCertificateManager(logger)
 		if err != nil {
 			logger.Error("Failed to create certificate manager", "error", err)
 			return fmt.Errorf("failed to create certificate manager: %v", err)
diff --git a/namespace/linux.go b/namespace/linux.go
index 073d677..92be549 100644
--- a/namespace/linux.go
+++ b/namespace/linux.go
@@ -18,6 +18,7 @@ import (
 type Linux struct {
 	config      Config
 	namespace   string
+	vethHost    string // Host-side veth interface name for iptables rules
 	logger      *slog.Logger
 	preparedEnv map[string]string
 	procAttr    *syscall.SysProcAttr
@@ -26,9 +27,10 @@ type Linux struct {
 // newLinux creates a new Linux network jail instance
 func newLinux(config Config, logger *slog.Logger) (*Linux, error) {
 	return &Linux{
-		config:    config,
-		namespace: newNamespaceName(),
-		logger:    logger,
+		config:      config,
+		namespace:   newNamespaceName(),
+		logger:      logger,
+		preparedEnv: make(map[string]string),
 	}, nil
 }
 
@@ -63,12 +65,14 @@ func (l *Linux) Open() error {
 
 	// Prepare environment once during setup
 	l.logger.Debug("Preparing environment")
-	l.preparedEnv = make(map[string]string)
 
 	// Start with current environment
 	for _, envVar := range os.Environ() {
 		if parts := strings.SplitN(envVar, "=", 2); len(parts) == 2 {
-			l.preparedEnv[parts[0]] = parts[1]
+			// Only set if not already set by SetEnv
+			if _, exists := l.preparedEnv[parts[0]]; !exists {
+				l.preparedEnv[parts[0]] = parts[1]
+			}
 		}
 	}
 
@@ -193,6 +197,9 @@ func (l *Linux) setupNetworking() error {
 	vethHost := fmt.Sprintf("veth_h_%s", uniqueID)                // veth_h_1234567 = 14 chars
 	vethNetJail := fmt.Sprintf("veth_n_%s", uniqueID)             // veth_n_1234567 = 14 chars
 
+	// Store veth interface name for iptables rules
+	l.vethHost = vethHost
+
 	setupCmds := []struct {
 		description string
 		command     *exec.Cmd
@@ -246,42 +253,40 @@ options timeout:2 attempts:2
 	return nil
 }
 
-// setupIptables configures iptables rules for traffic redirection
+// setupIptables configures iptables rules for comprehensive TCP traffic interception
 func (l *Linux) setupIptables() error {
 	// Enable IP forwarding
 	cmd := exec.Command("sysctl", "-w", "net.ipv4.ip_forward=1")
 	cmd.Run() // Ignore error
 
-	// NAT rules for outgoing traffic
+	// NAT rules for outgoing traffic (MASQUERADE for return traffic)
 	cmd = exec.Command("iptables", "-t", "nat", "-A", "POSTROUTING", "-s", "192.168.100.0/24", "-j", "MASQUERADE")
 	err := cmd.Run()
 	if err != nil {
 		return fmt.Errorf("failed to add NAT rule: %v", err)
 	}
 
-	// Redirect HTTP traffic to proxy
-	cmd = exec.Command("ip", "netns", "exec", l.namespace, "iptables", "-t", "nat", "-A", "OUTPUT",
-		"-p", "tcp", "--dport", "80", "-j", "DNAT", "--to-destination", fmt.Sprintf("192.168.100.1:%d", l.config.HTTPPort))
-	err = cmd.Run()
-	if err != nil {
-		return fmt.Errorf("failed to add HTTP redirect rule: %v", err)
-	}
-
-	// Redirect HTTPS traffic to proxy
-	cmd = exec.Command("ip", "netns", "exec", l.namespace, "iptables", "-t", "nat", "-A", "OUTPUT",
-		"-p", "tcp", "--dport", "443", "-j", "DNAT", "--to-destination", fmt.Sprintf("192.168.100.1:%d", l.config.HTTPSPort))
+	// COMPREHENSIVE APPROACH: Intercept ALL TCP traffic from namespace
+	// Use PREROUTING on host to catch traffic after it exits namespace but before routing
+	// This ensures NO TCP traffic can bypass the proxy
+	cmd = exec.Command("iptables", "-t", "nat", "-A", "PREROUTING", "-i", l.vethHost, "-p", "tcp", "-j", "REDIRECT", "--to-ports", fmt.Sprintf("%d", l.config.HTTPSPort))
 	err = cmd.Run()
 	if err != nil {
-		return fmt.Errorf("failed to add HTTPS redirect rule: %v", err)
+		return fmt.Errorf("failed to add comprehensive TCP redirect rule: %v", err)
 	}
 
+	l.logger.Debug("Comprehensive TCP jailing enabled", "interface", l.vethHost, "proxy_port", l.config.HTTPSPort)
 	return nil
 }
 
 // removeIptables removes iptables rules
 func (l *Linux) removeIptables() error {
+	// Remove comprehensive TCP redirect rule
+	cmd := exec.Command("iptables", "-t", "nat", "-D", "PREROUTING", "-i", l.vethHost, "-p", "tcp", "-j", "REDIRECT", "--to-ports", fmt.Sprintf("%d", l.config.HTTPSPort))
+	cmd.Run() // Ignore errors during cleanup
+
 	// Remove NAT rule
-	cmd := exec.Command("iptables", "-t", "nat", "-D", "POSTROUTING", "-s", "192.168.100.0/24", "-j", "MASQUERADE")
+	cmd = exec.Command("iptables", "-t", "nat", "-D", "POSTROUTING", "-s", "192.168.100.0/24", "-j", "MASQUERADE")
 	cmd.Run() // Ignore errors during cleanup
 
 	return nil
@@ -295,4 +300,4 @@ func (l *Linux) removeNamespace() error {
 		return fmt.Errorf("failed to remove namespace: %v", err)
 	}
 	return nil
-}
+}
\ No newline at end of file
diff --git a/namespace/macos.go b/namespace/macos.go
index 88e58e0..56b904e 100644
--- a/namespace/macos.go
+++ b/namespace/macos.go
@@ -40,6 +40,7 @@ func newMacOSJail(config Config, logger *slog.Logger) (*MacOSNetJail, error) {
 		pfRulesPath:   pfRulesPath,
 		mainRulesPath: mainRulesPath,
 		logger:        logger,
+		preparedEnv:   make(map[string]string),
 	}, nil
 }
 
@@ -63,12 +64,14 @@ func (m *MacOSNetJail) Open() error {
 
 	// Prepare environment once during setup
 	m.logger.Debug("Preparing environment")
-	m.preparedEnv = make(map[string]string)
 
 	// Start with current environment
 	for _, envVar := range os.Environ() {
 		if parts := strings.SplitN(envVar, "=", 2); len(parts) == 2 {
-			m.preparedEnv[parts[0]] = parts[1]
+			// Only set if not already set by SetEnv
+			if _, exists := m.preparedEnv[parts[0]]; !exists {
+				m.preparedEnv[parts[0]] = parts[1]
+			}
 		}
 	}
 
@@ -243,7 +246,7 @@ func (m *MacOSNetJail) getDefaultInterface() (string, error) {
 	return "en0", nil
 }
 
-// createPFRules creates PF rules for traffic diversion
+// createPFRules creates PF rules for comprehensive TCP traffic diversion
 func (m *MacOSNetJail) createPFRules() (string, error) {
 	// Get the default network interface
 	iface, err := m.getDefaultInterface()
@@ -251,35 +254,34 @@ func (m *MacOSNetJail) createPFRules() (string, error) {
 		return "", fmt.Errorf("failed to get default interface: %v", err)
 	}
 
-	// Create PF rules following httpjail's working pattern
-	rules := fmt.Sprintf(`# boundary PF rules for GID %d on interface %s
-# First, redirect traffic arriving on lo0 to our proxy ports
-rdr pass on lo0 inet proto tcp from any to any port 80 -> 127.0.0.1 port %d
-rdr pass on lo0 inet proto tcp from any to any port 443 -> 127.0.0.1 port %d
+	// Create comprehensive PF rules for ALL TCP traffic interception
+	// This prevents bypass via non-standard ports (8080, 3306, 22, etc.)
+	rules := fmt.Sprintf(`# comprehensive TCP jailing PF rules for GID %d on interface %s
+# COMPREHENSIVE APPROACH: Intercept ALL TCP traffic from the jailed group
+# This ensures NO TCP traffic can bypass the proxy by using alternative ports
+
+# First, redirect ALL TCP traffic arriving on lo0 to our HTTPS proxy port
+# The HTTPS proxy can handle both HTTP and HTTPS traffic
+rdr pass on lo0 inet proto tcp from any to any -> 127.0.0.1 port %d
 
-# Route boundary group traffic to lo0 where it will be redirected
-pass out route-to (lo0 127.0.0.1) inet proto tcp from any to any port 80 group %d keep state
-pass out route-to (lo0 127.0.0.1) inet proto tcp from any to any port 443 group %d keep state
+# Route ALL TCP traffic from boundary group to lo0 where it will be redirected
+pass out route-to (lo0 127.0.0.1) inet proto tcp from any to any group %d keep state
 
-# Also handle traffic on the specific interface
-pass out on %s route-to (lo0 127.0.0.1) inet proto tcp from any to any port 80 group %d keep state
-pass out on %s route-to (lo0 127.0.0.1) inet proto tcp from any to any port 443 group %d keep state
+# Also handle ALL TCP traffic on the specific interface from the group
+pass out on %s route-to (lo0 127.0.0.1) inet proto tcp from any to any group %d keep state
 
 # Allow all loopback traffic
 pass on lo0 all
 `,
 		m.groupID,
 		iface,
-		m.config.HTTPPort,
-		m.config.HTTPSPort,
-		m.groupID,
-		m.groupID,
-		iface,
+		m.config.HTTPSPort, // Use HTTPS proxy port for all TCP traffic
 		m.groupID,
 		iface,
 		m.groupID,
 	)
 
+	m.logger.Debug("Comprehensive TCP jailing enabled for macOS", "group_id", m.groupID, "proxy_port", m.config.HTTPSPort)
 	return rules, nil
 }
 
diff --git a/tls/tls.go b/tls/tls.go
index e5ca824..4222147 100644
--- a/tls/tls.go
+++ b/tls/tls.go
@@ -30,7 +30,12 @@ type CertificateManager struct {
 }
 
 // NewCertificateManager creates a new certificate manager
-func NewCertificateManager(configDir string, logger *slog.Logger) (*CertificateManager, error) {
+func NewCertificateManager(logger *slog.Logger) (*CertificateManager, error) {
+	configDir, err := getConfigDir()
+	if err != nil {
+		return nil, fmt.Errorf("failed to determine config directory: %v", err)
+	}
+
 	cm := &CertificateManager{
 		certCache: make(map[string]*tls.Certificate),
 		logger:    logger,
@@ -38,7 +43,7 @@ func NewCertificateManager(configDir string, logger *slog.Logger) (*CertificateM
 	}
 
 	// Load or generate CA certificate
-	err := cm.loadOrGenerateCA()
+	err = cm.loadOrGenerateCA()
 	if err != nil {
 		return nil, fmt.Errorf("failed to load or generate CA: %v", err)
 	}