diff --git a/pkg/tlsx/tls/tls.go b/pkg/tlsx/tls/tls.go
index c07a5ed2..f9fb1102 100644
--- a/pkg/tlsx/tls/tls.go
+++ b/pkg/tlsx/tls/tls.go
@@ -210,8 +210,26 @@ func (c *Client) EnumerateCiphers(hostname, ip, port string, options clients.Con
 		threads = len(toEnumerate)
 	}
 
+	// Build a context that respects the global timeout so cipher enumeration
+	// cannot block forever if a host stops responding mid-scan.
+	// context.Background() was previously used here, causing pool.Acquire to
+	// hang indefinitely when all pool connections were exhausted (issue #819).
+	enumCtx := context.Background()
+	var enumCancel context.CancelFunc
+	if c.options.Timeout > 0 {
+		// Give the whole enumeration a generous per-host ceiling:
+		// timeout * (number of ciphers / concurrency + 1) keeps things moving
+		// without cutting off legitimately slow hosts.
+		perHostDeadline := time.Duration(c.options.Timeout) * time.Second *
+			time.Duration((len(toEnumerate)/threads)+1)
+		enumCtx, enumCancel = context.WithTimeout(context.Background(), perHostDeadline)
+	} else {
+		enumCtx, enumCancel = context.WithCancel(context.Background())
+	}
+	defer enumCancel()
+
 	// setup connection pool
-	pool, err := connpool.NewOneTimePool(context.Background(), address, threads)
+	pool, err := connpool.NewOneTimePool(enumCtx, address, threads)
 	if err != nil {
 		return enumeratedCiphers, errorutil.NewWithErr(err).Msgf("failed to setup connection pool") //nolint
 	}
@@ -227,8 +245,14 @@ func (c *Client) EnumerateCiphers(hostname, ip, port string, options clients.Con
 
 	for _, v := range toEnumerate {
 		// create new baseConn and pass it to tlsclient
-		baseConn, err := pool.Acquire(context.Background())
+		// Use enumCtx (with timeout) instead of context.Background() so
+		// Acquire unblocks when the overall enumeration deadline expires.
+		baseConn, err := pool.Acquire(enumCtx)
 		if err != nil {
+			if errors.Is(err, context.DeadlineExceeded) || errors.Is(err, context.Canceled) {
+				// Timeout hit: return what we have so far instead of hanging.
+				return enumeratedCiphers, nil
+			}
 			return enumeratedCiphers, errorutil.NewWithErr(err).WithTag("ctls") //nolint
 		}
 		stats.IncrementCryptoTLSConnections()
@@ -236,7 +260,9 @@ func (c *Client) EnumerateCiphers(hostname, ip, port string, options clients.Con
 
 		conn := tls.Client(baseConn, baseCfg)
 
-		if err := conn.Handshake(); err == nil {
+		// Use HandshakeContext so the enumeration deadline/cancellation is
+		// respected during the handshake itself, not just during pool.Acquire.
+		if err := conn.HandshakeContext(enumCtx); err == nil {
 			ciphersuite := conn.ConnectionState().CipherSuite
 			enumeratedCiphers = append(enumeratedCiphers, tls.CipherSuiteName(ciphersuite))
 		}
diff --git a/pkg/tlsx/ztls/ztls.go b/pkg/tlsx/ztls/ztls.go
index a03b7267..2e43c73e 100644
--- a/pkg/tlsx/ztls/ztls.go
+++ b/pkg/tlsx/ztls/ztls.go
@@ -226,8 +226,23 @@ func (c *Client) EnumerateCiphers(hostname, ip, port string, options clients.Con
 		threads = len(toEnumerate)
 	}
 
+	// Build a context that respects the global timeout so cipher enumeration
+	// cannot block forever if a host stops responding mid-scan.
+	// context.Background() / context.TODO() were previously used here, causing
+	// pool.Acquire and tlsHandshakeWithTimeout to hang indefinitely (issue #819).
+	enumCtx := context.Background()
+	var enumCancel context.CancelFunc
+	if c.options.Timeout > 0 {
+		perHostDeadline := time.Duration(c.options.Timeout) * time.Second *
+			time.Duration((len(toEnumerate)/threads)+1)
+		enumCtx, enumCancel = context.WithTimeout(context.Background(), perHostDeadline)
+	} else {
+		enumCtx, enumCancel = context.WithCancel(context.Background())
+	}
+	defer enumCancel()
+
 	// setup connection pool
-	pool, err := connpool.NewOneTimePool(context.Background(), address, threads)
+	pool, err := connpool.NewOneTimePool(enumCtx, address, threads)
 	if err != nil {
 		return enumeratedCiphers, errorutil.NewWithErr(err).Msgf("failed to setup connection pool") //nolint
 	}
@@ -249,15 +264,20 @@ func (c *Client) EnumerateCiphers(hostname, ip, port string, options clients.Con
 	gologger.Debug().Label("ztls").Msgf("Starting cipher enumeration with %v ciphers in %v", len(toEnumerate), options.VersionTLS)
 
 	for _, v := range toEnumerate {
-		baseConn, err := pool.Acquire(context.Background())
+		// Use enumCtx so Acquire unblocks when the enumeration deadline expires.
+		baseConn, err := pool.Acquire(enumCtx)
 		if err != nil {
+			if errors.Is(err, context.DeadlineExceeded) || errors.Is(err, context.Canceled) {
+				return enumeratedCiphers, nil
+			}
 			return enumeratedCiphers, errorutil.NewWithErr(err).WithTag("ztls") //nolint
 		}
 		stats.IncrementZcryptoTLSConnections()
 		conn := tls.Client(baseConn, baseCfg)
 		baseCfg.CipherSuites = []uint16{ztlsCiphers[v]}
 
-		if err := c.tlsHandshakeWithTimeout(conn, context.TODO()); err == nil {
+		// Use enumCtx instead of context.TODO() to propagate the timeout.
+		if err := c.tlsHandshakeWithTimeout(conn, enumCtx); err == nil {
 			h1 := conn.GetHandshakeLog()
 			enumeratedCiphers = append(enumeratedCiphers, h1.ServerHello.CipherSuite.String())
 		}
@@ -320,20 +340,32 @@ func (c *Client) getConfig(hostname, ip, port string, options clients.ConnectOpt
 	return config, nil
 }
 
-// tlsHandshakeWithCtx attempts tls handshake with given timeout
+// tlsHandshakeWithTimeout attempts a TLS handshake and returns when it
+// completes or when ctx is cancelled/expired, whichever comes first.
+//
+// The previous implementation had a subtle bug: the select case
+//
+//	case errChan <- tlsConn.Handshake():
+//
+// evaluates Handshake() synchronously before the select statement is
+// entered.  If the handshake blocks indefinitely (e.g. the server stops
+// responding mid-handshake) the ctx.Done() case is never evaluated and the
+// function hangs forever.  The fix runs the handshake in a goroutine so
+// that both channels can be observed concurrently.
 func (c *Client) tlsHandshakeWithTimeout(tlsConn *tls.Conn, ctx context.Context) error {
 	errChan := make(chan error, 1)
-	defer close(errChan)
+
+	go func() {
+		errChan <- tlsConn.Handshake()
+	}()
 
 	select {
 	case <-ctx.Done():
 		return errorutil.NewWithTag("ztls", "timeout while attempting handshake") //nolint
-	case errChan <- tlsConn.Handshake():
-	}
-
-	err := <-errChan
-	if err == tls.ErrCertsOnly {
-		err = nil
+	case err := <-errChan:
+		if err == tls.ErrCertsOnly {
+			return nil
+		}
+		return err
 	}
-	return err
 }