diff --git a/e2e_tests/landjail/landjail_test.go b/e2e_tests/landjail/landjail_test.go
index 900a85e..5d6a975 100644
--- a/e2e_tests/landjail/landjail_test.go
+++ b/e2e_tests/landjail/landjail_test.go
@@ -29,11 +29,11 @@ func TestLandjail(t *testing.T) {
 	})
 
 	// Test allowed HTTPS request
-	//	t.Run("HTTPSRequestThroughBoundary", func(t *testing.T) {
-	//		expectedResponse := `{"message":"👋"}
-	//`
-	//		lt.ExpectAllowed("https://dev.coder.com/api/v2", expectedResponse)
-	//	})
+	t.Run("HTTPSRequestThroughBoundary", func(t *testing.T) {
+		expectedResponse := `{"message":"👋"}
+`
+		lt.ExpectAllowed("https://dev.coder.com/api/v2", expectedResponse)
+	})
 
 	// Test blocked HTTP request
 	t.Run("HTTPBlockedDomainTest", func(t *testing.T) {
@@ -41,7 +41,7 @@ func TestLandjail(t *testing.T) {
 	})
 
 	// Test blocked HTTPS request
-	//t.Run("HTTPSBlockedDomainTest", func(t *testing.T) {
-	//	lt.ExpectDeny("https://example.com")
-	//})
+	t.Run("HTTPSBlockedDomainTest", func(t *testing.T) {
+		lt.ExpectDeny("https://example.com")
+	})
 }
diff --git a/proxy/connect.go b/proxy/connect.go
new file mode 100644
index 0000000..da4ce08
--- /dev/null
+++ b/proxy/connect.go
@@ -0,0 +1,207 @@
+package proxy
+
+import (
+	"bufio"
+	"bytes"
+	"crypto/tls"
+	"io"
+	"net"
+	"net/http"
+	"net/url"
+	"strconv"
+	"strings"
+
+	"github.com/coder/boundary/audit"
+)
+
+// handleCONNECT handles HTTP CONNECT requests for tunneling
+func (p *Server) handleCONNECT(conn net.Conn, req *http.Request) {
+	// Extract target from CONNECT request
+	// CONNECT requests have the target in req.Host (format: hostname:port)
+	target := req.Host
+	if target == "" {
+		target = req.URL.Host
+	}
+
+	p.logger.Debug("🔌 CONNECT request", "target", target)
+
+	// Send 200 Connection established response
+	response := "HTTP/1.1 200 Connection established\r\n\r\n"
+	_, err := conn.Write([]byte(response))
+	if err != nil {
+		p.logger.Error("Failed to send CONNECT response", "error", err)
+		return
+	}
+
+	p.logger.Debug("CONNECT tunnel established", "target", target)
+
+	// Handle the tunnel - decrypt TLS and process each HTTP request
+	p.handleCONNECTTunnel(conn, target)
+}
+
+// handleCONNECTTunnel handles the tunnel after CONNECT is established
+// It decrypts TLS traffic and processes each HTTP request separately
+func (p *Server) handleCONNECTTunnel(conn net.Conn, target string) {
+	defer func() {
+		err := conn.Close()
+		if err != nil {
+			p.logger.Error("Failed to close CONNECT tunnel", "error", err)
+		}
+	}()
+
+	// Wrap connection with TLS server to decrypt traffic
+	tlsConn := tls.Server(conn, p.tlsConfig)
+
+	// Perform TLS handshake
+	if err := tlsConn.Handshake(); err != nil {
+		p.logger.Error("TLS handshake failed in CONNECT tunnel", "error", err)
+		return
+	}
+
+	p.logger.Debug("✅ TLS handshake successful in CONNECT tunnel")
+
+	// Process HTTP requests in a loop
+	reader := bufio.NewReader(tlsConn)
+	for {
+		// Read HTTP request from tunnel
+		req, err := http.ReadRequest(reader)
+		if err != nil {
+			if err == io.EOF {
+				p.logger.Debug("CONNECT tunnel closed by client")
+				break
+			}
+			p.logger.Error("Failed to read HTTP request from CONNECT tunnel", "error", err)
+			break
+		}
+
+		p.logger.Debug("🔒 HTTP Request in CONNECT tunnel", "method", req.Method, "url", req.URL.String(), "target", target)
+
+		// Process this request - check if allowed and forward to target
+		p.processTunnelRequest(tlsConn, req, target)
+	}
+}
+
+// processTunnelRequest processes a single HTTP request from the CONNECT tunnel
+func (p *Server) processTunnelRequest(conn net.Conn, req *http.Request, targetHost string) {
+	// Check if request should be allowed
+	// Use the original request URL but evaluate against rules
+	urlStr := req.Host + req.URL.String()
+	result := p.ruleEngine.Evaluate(req.Method, urlStr)
+
+	// Audit the request
+	p.auditor.AuditRequest(audit.Request{
+		Method:  req.Method,
+		URL:     req.URL.String(),
+		Host:    req.Host,
+		Allowed: result.Allowed,
+		Rule:    result.Rule,
+	})
+
+	if !result.Allowed {
+		p.logger.Debug("Request in CONNECT tunnel blocked", "method", req.Method, "url", urlStr)
+		p.writeBlockedResponse(conn, req)
+		return
+	}
+
+	// Forward request to target
+	// The target is the original CONNECT target, but we use the request's host/path
+	p.forwardTunnelRequest(conn, req, targetHost)
+}
+
+// forwardTunnelRequest forwards a request from the tunnel to the target
+func (p *Server) forwardTunnelRequest(conn net.Conn, req *http.Request, targetHost string) {
+	// Create HTTP client
+	client := &http.Client{
+		CheckRedirect: func(req *http.Request, via []*http.Request) error {
+			return http.ErrUseLastResponse // Don't follow redirects
+		},
+	}
+
+	// Extract hostname and port from targetHost
+	hostname := targetHost
+	port := "443" // Default HTTPS port
+	if strings.Contains(targetHost, ":") {
+		parts := strings.Split(targetHost, ":")
+		hostname = parts[0]
+		port = parts[1]
+	}
+
+	scheme := "https"
+	if port == "80" {
+		scheme = "http"
+	}
+
+	// Build target URL using the request's path but the CONNECT target's host
+	// URL.Host can include port for connection, but Host header should not
+	targetURL := &url.URL{
+		Scheme:   scheme,
+		Host:     targetHost, // Include port for connection
+		Path:     req.URL.Path,
+		RawQuery: req.URL.RawQuery,
+	}
+
+	var body = req.Body
+	if req.Method == http.MethodGet || req.Method == http.MethodHead {
+		body = nil
+	}
+
+	newReq, err := http.NewRequest(req.Method, targetURL.String(), body)
+	if err != nil {
+		p.logger.Error("can't create HTTP request for tunnel", "error", err)
+		return
+	}
+
+	// Set Host header to just the hostname (without port)
+	// The Host header should not include the port number for HTTPS
+	newReq.Host = hostname
+
+	// Copy headers (but skip Host since we set it explicitly above)
+	for name, values := range req.Header {
+		// Skip connection-specific headers and Host header
+		lowerName := strings.ToLower(name)
+		if lowerName == "connection" || lowerName == "proxy-connection" || lowerName == "host" {
+			continue
+		}
+		for _, value := range values {
+			newReq.Header.Add(name, value)
+		}
+	}
+
+	// Make request to destination
+	resp, err := client.Do(newReq)
+	if err != nil {
+		p.logger.Error("Failed to forward request from CONNECT tunnel", "error", err)
+		return
+	}
+
+	p.logger.Debug("Response from target", "status", resp.StatusCode, "target", targetHost)
+
+	// Read the body and set Content-Length
+	bodyBytes, err := io.ReadAll(resp.Body)
+	if err != nil {
+		p.logger.Error("can't read response body from tunnel", "error", err)
+		return
+	}
+	resp.Header.Set("Content-Length", strconv.Itoa(len(bodyBytes)))
+	resp.ContentLength = int64(len(bodyBytes))
+	err = resp.Body.Close()
+	if err != nil {
+		p.logger.Error("Failed to close response body", "error", err)
+		return
+	}
+	resp.Body = io.NopCloser(bytes.NewBuffer(bodyBytes))
+
+	// Normalize to HTTP/1.1
+	resp.Proto = "HTTP/1.1"
+	resp.ProtoMajor = 1
+	resp.ProtoMinor = 1
+
+	// Write response back to tunnel
+	err = resp.Write(conn)
+	if err != nil {
+		p.logger.Error("Failed to write response to CONNECT tunnel", "error", err)
+		return
+	}
+
+	p.logger.Debug("Successfully forwarded response in CONNECT tunnel")
+}
diff --git a/proxy/proxy.go b/proxy/proxy.go
index 86f9e2e..9be9b5e 100644
--- a/proxy/proxy.go
+++ b/proxy/proxy.go
@@ -218,6 +218,11 @@ func (p *Server) handleHTTPConnection(conn net.Conn) {
 		return
 	}
 
+	if req.Method == http.MethodConnect {
+		p.handleCONNECT(conn, req)
+		return
+	}
+
 	p.logger.Debug("🌐 HTTP Request: %s %s", req.Method, req.URL.String())
 	p.processHTTPRequest(conn, req, false)
 }