diff --git a/clavis/clavis-vault/cmd/clavitor/main.go b/clavis/clavis-vault/cmd/clavitor/main.go
index 89cfdea..13c6765 100644
--- a/clavis/clavis-vault/cmd/clavitor/main.go
+++ b/clavis/clavis-vault/cmd/clavitor/main.go
@@ -9,6 +9,7 @@ import (
 
 	"github.com/johanj/clavitor/api"
 	"github.com/johanj/clavitor/lib"
+	"github.com/johanj/clavitor/proxy"
 )
 
 //go:embed web
@@ -28,6 +29,15 @@ func main() {
 	telemetryFreq := flag.Int("telemetry-freq", envInt("TELEMETRY_FREQ", 0), "Telemetry POST interval in seconds (0 = disabled)")
 	telemetryHost := flag.String("telemetry-host", envStr("TELEMETRY_HOST", ""), "Telemetry endpoint URL")
 	telemetryToken := flag.String("telemetry-token", envStr("TELEMETRY_TOKEN", ""), "Bearer token for telemetry endpoint")
+
+	// Proxy mode flags
+	proxyEnabled := flag.Bool("proxy", envBool("PROXY_ENABLED", false), "Enable MITM proxy mode (set HTTP_PROXY=http://127.0.0.1:19840 in agent)")
+	proxyAddr := flag.String("proxy-addr", envStr("PROXY_ADDR", "127.0.0.1:19840"), "Proxy listen address")
+	proxyLLM := flag.Bool("proxy-llm", envBool("PROXY_LLM", false), "Enable LLM policy evaluation in proxy")
+	proxyLLMURL := flag.String("proxy-llm-url", envStr("PROXY_LLM_URL", ""), "LLM API base URL for proxy policy (OpenAI-compatible)")
+	proxyLLMKey := flag.String("proxy-llm-key", envStr("PROXY_LLM_KEY", ""), "LLM API key for proxy policy")
+	proxyLLMModel := flag.String("proxy-llm-model", envStr("PROXY_LLM_MODEL", ""), "LLM model for proxy policy evaluation")
+
 	flag.Parse()
 
 	cfg, err := lib.LoadConfig()
@@ -48,6 +58,28 @@ func main() {
 	// Start automatic backup scheduler (3 weekly + 3 monthly, rotated)
 	lib.StartBackupTimer(cfg.DataDir)
 
+	// Start proxy if enabled
+	if *proxyEnabled {
+		px, err := proxy.New(proxy.Config{
+			ListenAddr: *proxyAddr,
+			DataDir:    cfg.DataDir,
+			LLMEnabled: *proxyLLM,
+			LLMBaseURL: *proxyLLMURL,
+			LLMAPIKey:  *proxyLLMKey,
+			LLMModel:   *proxyLLMModel,
+		})
+		if err != nil {
+			log.Fatalf("proxy: %v", err)
+		}
+		go func() {
+			if err := px.ListenAndServe(); err != nil {
+				log.Printf("proxy: stopped: %v", err)
+			}
+		}()
+		log.Printf("proxy: CA cert at %s — install in OS trust store", px.CACertPath())
+		log.Printf("proxy: set HTTP_PROXY=http://%s HTTPS_PROXY=http://%s in agent environment", *proxyAddr, *proxyAddr)
+	}
+
 	router := api.NewRouter(cfg, webFS)
 
 	addr := ":" + cfg.Port
@@ -64,6 +96,13 @@ func envStr(key, fallback string) string {
 	return fallback
 }
 
+func envBool(key string, fallback bool) bool {
+	if v := os.Getenv(key); v != "" {
+		return v == "1" || v == "true" || v == "yes"
+	}
+	return fallback
+}
+
 func envInt(key string, fallback int) int {
 	if v := os.Getenv(key); v != "" {
 		if n, err := strconv.Atoi(v); err == nil {
diff --git a/clavis/clavis-vault/proxy/bufconn.go b/clavis/clavis-vault/proxy/bufconn.go
new file mode 100644
index 0000000..d0b8bf7
--- /dev/null
+++ b/clavis/clavis-vault/proxy/bufconn.go
@@ -0,0 +1,10 @@
+package proxy
+
+import (
+	"bufio"
+	"net"
+)
+
+func newBufReader(conn net.Conn) *bufio.Reader {
+	return bufio.NewReader(conn)
+}
diff --git a/clavis/clavis-vault/proxy/proxy.go b/clavis/clavis-vault/proxy/proxy.go
new file mode 100644
index 0000000..a94dab8
--- /dev/null
+++ b/clavis/clavis-vault/proxy/proxy.go
@@ -0,0 +1,452 @@
+// Package proxy implements an HTTPS MITM proxy with LLM-based policy evaluation.
+//
+// Architecture:
+//   - Agent sets HTTP_PROXY=http://localhost:19840 (or configured port)
+//   - For plain HTTP: proxy injects Authorization/headers, forwards
+//   - For HTTPS: proxy performs CONNECT tunnel, generates per-host TLS cert (signed by local CA)
+//   - Before injecting credentials: optional LLM policy evaluation (intent check)
+//
+// Credential injection:
+//   - Scans request for placeholder patterns: {{clavitor.entry_title.field_label}}
+//   - Also injects via per-host credential rules stored in vault
+//   - Tier check: L2 fields are never injected (identity/card data)
+package proxy
+
+import (
+	"crypto/rand"
+	"crypto/rsa"
+	"crypto/tls"
+	"crypto/x509"
+	"crypto/x509/pkix"
+	"encoding/pem"
+	"fmt"
+	"io"
+	"log"
+	"math/big"
+	"net"
+	"net/http"
+	"net/http/httputil"
+	"os"
+	"path/filepath"
+	"strings"
+	"sync"
+	"time"
+)
+
+// Config holds proxy configuration.
+type Config struct {
+	// ListenAddr is the proxy listen address, e.g. "127.0.0.1:19840"
+	ListenAddr string
+
+	// DataDir is the vault data directory (for CA cert/key storage)
+	DataDir string
+
+	// VaultKey is the L1 decryption key (to read credentials for injection)
+	VaultKey []byte
+
+	// DBPath is path to the vault SQLite database
+	DBPath string
+
+	// LLMEnabled enables LLM-based intent evaluation before credential injection
+	LLMEnabled bool
+
+	// LLMBaseURL is the LLM API base URL (OpenAI-compatible)
+	LLMBaseURL string
+
+	// LLMAPIKey is the API key for LLM requests
+	LLMAPIKey string
+
+	// LLMModel is the model to use for policy evaluation
+	LLMModel string
+}
+
+// Proxy is the MITM proxy server.
+type Proxy struct {
+	cfg    Config
+	ca     *tls.Certificate
+	caCert *x509.Certificate
+	caKey  *rsa.PrivateKey
+	certMu sync.Mutex
+	certs  map[string]*tls.Certificate // hostname → generated cert (cache)
+}
+
+// New creates a new Proxy. Generates or loads the CA cert from DataDir.
+func New(cfg Config) (*Proxy, error) {
+	p := &Proxy{
+		cfg:   cfg,
+		certs: make(map[string]*tls.Certificate),
+	}
+	if err := p.loadOrCreateCA(); err != nil {
+		return nil, fmt.Errorf("proxy CA: %w", err)
+	}
+	return p, nil
+}
+
+// ListenAndServe starts the proxy server. Blocks until stopped.
+func (p *Proxy) ListenAndServe() error {
+	ln, err := net.Listen("tcp", p.cfg.ListenAddr)
+	if err != nil {
+		return fmt.Errorf("proxy listen %s: %w", p.cfg.ListenAddr, err)
+	}
+	log.Printf("proxy: listening on %s (LLM policy: %v)", p.cfg.ListenAddr, p.cfg.LLMEnabled)
+	srv := &http.Server{
+		Handler:      p,
+		ReadTimeout:  30 * time.Second,
+		WriteTimeout: 30 * time.Second,
+	}
+	return srv.Serve(ln)
+}
+
+// ServeHTTP handles all incoming proxy requests.
+func (p *Proxy) ServeHTTP(w http.ResponseWriter, r *http.Request) {
+	if r.Method == http.MethodConnect {
+		p.handleCONNECT(w, r)
+		return
+	}
+	p.handleHTTP(w, r)
+}
+
+// handleHTTP handles plain HTTP proxy requests.
+func (p *Proxy) handleHTTP(w http.ResponseWriter, r *http.Request) {
+	// Remove proxy-specific headers
+	r.RequestURI = ""
+	r.Header.Del("Proxy-Connection")
+	r.Header.Del("Proxy-Authenticate")
+	r.Header.Del("Proxy-Authorization")
+
+	// Inject credentials if applicable
+	if err := p.injectCredentials(r); err != nil {
+		log.Printf("proxy: credential injection error for %s: %v", r.URL.Host, err)
+		// Non-fatal: continue without injection
+	}
+
+	// Forward the request
+	rp := &httputil.ReverseProxy{
+		Director: func(req *http.Request) {},
+	}
+	rp.ServeHTTP(w, r)
+}
+
+// handleCONNECT handles HTTPS CONNECT tunnel requests.
+func (p *Proxy) handleCONNECT(w http.ResponseWriter, r *http.Request) {
+	host := r.Host
+	if !strings.Contains(host, ":") {
+		host = host + ":443"
+	}
+	hostname, _, _ := net.SplitHostPort(host)
+
+	// Acknowledge the CONNECT
+	w.WriteHeader(http.StatusOK)
+
+	// Hijack the connection
+	hijacker, ok := w.(http.Hijacker)
+	if !ok {
+		log.Printf("proxy: CONNECT hijack not supported")
+		return
+	}
+	clientConn, _, err := hijacker.Hijack()
+	if err != nil {
+		log.Printf("proxy: CONNECT hijack error: %v", err)
+		return
+	}
+	defer clientConn.Close()
+
+	// Generate a certificate for this hostname
+	cert, err := p.certForHost(hostname)
+	if err != nil {
+		log.Printf("proxy: cert generation failed for %s: %v", hostname, err)
+		return
+	}
+
+	// Wrap client connection in TLS (using our MITM cert)
+	tlsCfg := &tls.Config{
+		Certificates: []tls.Certificate{*cert},
+		MinVersion:   tls.VersionTLS12,
+	}
+	tlsClientConn := tls.Server(clientConn, tlsCfg)
+	defer tlsClientConn.Close()
+	if err := tlsClientConn.Handshake(); err != nil {
+		log.Printf("proxy: TLS handshake failed for %s: %v", hostname, err)
+		return
+	}
+
+	// Connect to real upstream
+	upstreamConn, err := tls.Dial("tcp", host, &tls.Config{
+		ServerName: hostname,
+		MinVersion: tls.VersionTLS12,
+	})
+	if err != nil {
+		log.Printf("proxy: upstream dial failed for %s: %v", host, err)
+		return
+	}
+	defer upstreamConn.Close()
+
+	// Intercept HTTP traffic between client and upstream
+	p.interceptHTTP(tlsClientConn, upstreamConn, hostname)
+}
+
+// interceptHTTP reads HTTP requests from the client, injects credentials, forwards to upstream.
+func (p *Proxy) interceptHTTP(clientConn net.Conn, upstreamConn net.Conn, hostname string) {
+	// Use Go's http.ReadRequest to parse the client's request
+	clientReader := newBufReader(clientConn)
+
+	for {
+		req, err := http.ReadRequest(clientReader)
+		if err != nil {
+			if err != io.EOF {
+				log.Printf("proxy: read request error for %s: %v", hostname, err)
+			}
+			return
+		}
+
+		// Set the correct URL for upstream forwarding
+		req.URL.Scheme = "https"
+		req.URL.Host = hostname
+		req.RequestURI = ""
+
+		// Inject credentials
+		if err := p.injectCredentials(req); err != nil {
+			log.Printf("proxy: credential injection error for %s: %v", hostname, err)
+		}
+
+		// Forward to upstream
+		if err := req.Write(upstreamConn); err != nil {
+			log.Printf("proxy: upstream write error for %s: %v", hostname, err)
+			return
+		}
+
+		// Read upstream response and forward to client
+		upstreamReader := newBufReader(upstreamConn)
+		resp, err := http.ReadResponse(upstreamReader, req)
+		if err != nil {
+			log.Printf("proxy: upstream read error for %s: %v", hostname, err)
+			return
+		}
+		defer resp.Body.Close()
+
+		if err := resp.Write(clientConn); err != nil {
+			log.Printf("proxy: client write error for %s: %v", hostname, err)
+			return
+		}
+	}
+}
+
+// injectCredentials scans the request for credential placeholders and injects them.
+// Placeholder format: {{clavitor.entry_title.field_label}} in headers, URL, or body.
+// Also applies host-based automatic injection rules from vault.
+// L2 (identity/card) fields are NEVER injected.
+func (p *Proxy) injectCredentials(r *http.Request) error {
+	if p.cfg.VaultKey == nil {
+		return nil // No vault key — skip injection
+	}
+
+	// Check for LLM policy evaluation
+	if p.cfg.LLMEnabled {
+		allowed, reason, err := p.evaluatePolicy(r)
+		if err != nil {
+			log.Printf("proxy: LLM policy eval error: %v (allowing)", err)
+		} else if !allowed {
+			log.Printf("proxy: LLM policy DENIED %s %s: %s", r.Method, r.URL, reason)
+			return fmt.Errorf("policy denied: %s", reason)
+		}
+	}
+
+	// TODO: Implement placeholder substitution once vault DB integration is wired in.
+	// Pattern: scan r.Header values, r.URL, r.Body for {{clavitor.TITLE.FIELD}}
+	// Lookup entry by title (case-insensitive), get field by label, verify Tier != L2
+	// Replace placeholder with decrypted field value.
+	//
+	// Auto-injection (host rules):
+	// Vault entries can specify "proxy_inject_hosts": ["api.github.com"] in metadata
+	// When a request matches, inject the entry's L1 fields as headers per a configured map.
+	//
+	// This stub returns nil — no injection until DB wiring is complete.
+	return nil
+}
+
+// evaluatePolicy calls the configured LLM to evaluate whether this request
+// is consistent with the expected behavior of an AI agent (vs. exfiltration/abuse).
+func (p *Proxy) evaluatePolicy(r *http.Request) (allowed bool, reason string, err error) {
+	if p.cfg.LLMBaseURL == "" || p.cfg.LLMAPIKey == "" {
+		return true, "LLM not configured", nil
+	}
+
+	// Build a concise request summary for the LLM
+	summary := fmt.Sprintf("Method: %s\nHost: %s\nPath: %s\nContent-Type: %s",
+		r.Method, r.Host, r.URL.Path,
+		r.Header.Get("Content-Type"))
+
+	prompt := `You are a security policy evaluator for an AI agent credential proxy.
+
+The following outbound HTTP request is about to have credentials injected and be forwarded.
+Evaluate whether this request is consistent with normal AI agent behavior (coding, API calls, deployment)
+vs. suspicious activity (credential exfiltration, unexpected destinations, data harvesting).
+
+Request summary:
+` + summary + `
+
+Respond with JSON only: {"allowed": true/false, "reason": "one sentence"}`
+
+	_ = prompt // Used when LLM call is implemented below
+
+	// TODO: Implement actual LLM call using cfg.LLMBaseURL + cfg.LLMAPIKey + cfg.LLMModel
+	// For now: always allow (policy eval is opt-in, not blocking by default)
+	// Real implementation: POST to /v1/chat/completions, parse JSON response
+	return true, "policy evaluation not yet implemented", nil
+}
+
+// certForHost returns a TLS certificate for the given hostname, generating one if needed.
+func (p *Proxy) certForHost(hostname string) (*tls.Certificate, error) {
+	p.certMu.Lock()
+	defer p.certMu.Unlock()
+
+	if cert, ok := p.certs[hostname]; ok {
+		// Check if cert is still valid (> 1 hour remaining)
+		if time.Until(cert.Leaf.NotAfter) > time.Hour {
+			return cert, nil
+		}
+	}
+
+	// Generate a new cert signed by our CA
+	cert, err := p.generateCert(hostname)
+	if err != nil {
+		return nil, err
+	}
+	p.certs[hostname] = cert
+	return cert, nil
+}
+
+// generateCert generates a TLS cert for the given hostname, signed by the proxy CA.
+func (p *Proxy) generateCert(hostname string) (*tls.Certificate, error) {
+	key, err := rsa.GenerateKey(rand.Reader, 2048)
+	if err != nil {
+		return nil, fmt.Errorf("generate key: %w", err)
+	}
+
+	serial, _ := rand.Int(rand.Reader, new(big.Int).Lsh(big.NewInt(1), 128))
+	tmpl := &x509.Certificate{
+		SerialNumber: serial,
+		Subject:      pkix.Name{CommonName: hostname},
+		DNSNames:     []string{hostname},
+		NotBefore:    time.Now().Add(-time.Minute),
+		NotAfter:     time.Now().Add(24 * time.Hour),
+		KeyUsage:     x509.KeyUsageDigitalSignature,
+		ExtKeyUsage:  []x509.ExtKeyUsage{x509.ExtKeyUsageServerAuth},
+	}
+
+	// Add IP SAN if hostname is an IP
+	if ip := net.ParseIP(hostname); ip != nil {
+		tmpl.IPAddresses = []net.IP{ip}
+		tmpl.DNSNames = nil
+	}
+
+	certDER, err := x509.CreateCertificate(rand.Reader, tmpl, p.caCert, &key.PublicKey, p.caKey)
+	if err != nil {
+		return nil, fmt.Errorf("create cert: %w", err)
+	}
+
+	leaf, err := x509.ParseCertificate(certDER)
+	if err != nil {
+		return nil, fmt.Errorf("parse cert: %w", err)
+	}
+
+	tlsCert := &tls.Certificate{
+		Certificate: [][]byte{certDER},
+		PrivateKey:  key,
+		Leaf:        leaf,
+	}
+	return tlsCert, nil
+}
+
+// loadOrCreateCA loads the proxy CA cert/key from DataDir, or generates new ones.
+func (p *Proxy) loadOrCreateCA() error {
+	caDir := filepath.Join(p.cfg.DataDir, "proxy")
+	if err := os.MkdirAll(caDir, 0700); err != nil {
+		return err
+	}
+	certPath := filepath.Join(caDir, "ca.crt")
+	keyPath := filepath.Join(caDir, "ca.key")
+
+	// Try to load existing CA
+	if _, err := os.Stat(certPath); err == nil {
+		certPEM, err := os.ReadFile(certPath)
+		if err != nil {
+			return fmt.Errorf("read CA cert: %w", err)
+		}
+		keyPEM, err := os.ReadFile(keyPath)
+		if err != nil {
+			return fmt.Errorf("read CA key: %w", err)
+		}
+		tlsCert, err := tls.X509KeyPair(certPEM, keyPEM)
+		if err != nil {
+			return fmt.Errorf("parse CA keypair: %w", err)
+		}
+		tlsCert.Leaf, err = x509.ParseCertificate(tlsCert.Certificate[0])
+		if err != nil {
+			return fmt.Errorf("parse CA cert: %w", err)
+		}
+		// Check expiry — regenerate if < 7 days left
+		if time.Until(tlsCert.Leaf.NotAfter) < 7*24*time.Hour {
+			log.Printf("proxy: CA cert expires soon (%s), regenerating", tlsCert.Leaf.NotAfter.Format("2006-01-02"))
+		} else {
+			p.ca = &tlsCert
+			p.caCert = tlsCert.Leaf
+			p.caKey = tlsCert.PrivateKey.(*rsa.PrivateKey)
+			log.Printf("proxy: loaded CA cert (expires %s)", tlsCert.Leaf.NotAfter.Format("2006-01-02"))
+			return nil
+		}
+	}
+
+	// Generate new CA
+	log.Printf("proxy: generating new CA cert...")
+	key, err := rsa.GenerateKey(rand.Reader, 4096)
+	if err != nil {
+		return fmt.Errorf("generate CA key: %w", err)
+	}
+
+	serial, _ := rand.Int(rand.Reader, new(big.Int).Lsh(big.NewInt(1), 128))
+	tmpl := &x509.Certificate{
+		SerialNumber:          serial,
+		Subject:               pkix.Name{CommonName: "Clavitor Proxy CA", Organization: []string{"Clavitor"}},
+		NotBefore:             time.Now().Add(-time.Minute),
+		NotAfter:              time.Now().Add(365 * 24 * time.Hour),
+		KeyUsage:              x509.KeyUsageCertSign | x509.KeyUsageCRLSign,
+		BasicConstraintsValid: true,
+		IsCA:                  true,
+		MaxPathLen:            0,
+	}
+
+	certDER, err := x509.CreateCertificate(rand.Reader, tmpl, tmpl, &key.PublicKey, key)
+	if err != nil {
+		return fmt.Errorf("create CA cert: %w", err)
+	}
+	leaf, _ := x509.ParseCertificate(certDER)
+
+	// Write to disk
+	certFile, err := os.OpenFile(certPath, os.O_CREATE|os.O_WRONLY|os.O_TRUNC, 0600)
+	if err != nil {
+		return fmt.Errorf("write CA cert: %w", err)
+	}
+	pem.Encode(certFile, &pem.Block{Type: "CERTIFICATE", Bytes: certDER})
+	certFile.Close()
+
+	keyFile, err := os.OpenFile(keyPath, os.O_CREATE|os.O_WRONLY|os.O_TRUNC, 0600)
+	if err != nil {
+		return fmt.Errorf("write CA key: %w", err)
+	}
+	pem.Encode(keyFile, &pem.Block{Type: "RSA PRIVATE KEY", Bytes: x509.MarshalPKCS1PrivateKey(key)})
+	keyFile.Close()
+
+	p.ca = &tls.Certificate{Certificate: [][]byte{certDER}, PrivateKey: key, Leaf: leaf}
+	p.caCert = leaf
+	p.caKey = key
+
+	log.Printf("proxy: CA cert generated at %s (install in OS trust store or pass --proxy-ca)", certPath)
+	log.Printf("proxy: CA cert path: %s", certPath)
+	return nil
+}
+
+// CACertPath returns the path to the proxy CA certificate (for user installation).
+func (p *Proxy) CACertPath() string {
+	return filepath.Join(p.cfg.DataDir, "proxy", "ca.crt")
+}