diff --git a/internal/engine/session.go b/internal/engine/session.go
index e78c999..a0adfea 100644
--- a/internal/engine/session.go
+++ b/internal/engine/session.go
@@ -168,6 +168,8 @@ func NewSession(ctx context.Context, config SessionConfig) (*Session, error) {
 	if proxyURL != nil {
 		switch proxyURL.Scheme {
 		case "psiphon", "tor", "fake":
+			config.Logger.Infof(
+				"starting '%s' tunnel; please be patient...", proxyURL.Scheme)
 			tunnel, err := tunnel.Start(ctx, &tunnel.Config{
 				Name:      proxyURL.Scheme,
 				Session:   &sessionTunnelEarlySession{},
@@ -178,6 +180,7 @@ func NewSession(ctx context.Context, config SessionConfig) (*Session, error) {
 			if err != nil {
 				return nil, err
 			}
+			config.Logger.Infof("tunnel '%s' running...", proxyURL.Scheme)
 			sess.tunnel = tunnel
 			proxyURL = tunnel.SOCKS5ProxyURL()
 		}
diff --git a/internal/engine/tunnel/tor.go b/internal/engine/tunnel/tor.go
index 71e8496..96e299c 100644
--- a/internal/engine/tunnel/tor.go
+++ b/internal/engine/tunnel/tor.go
@@ -6,6 +6,7 @@ import (
 	"fmt"
 	"io"
 	"net/url"
+	"os"
 	"path/filepath"
 	"strings"
 	"time"
@@ -45,9 +46,6 @@ func (tt *torTunnel) Stop() {
 	tt.instance.Close()
 }
 
-// TODO(bassosimone): the current design is such that we have a bunch of
-// torrc-$number and a growing tor.log file inside of stateDir.
-
 // ErrTorUnableToGetSOCKSProxyAddress indicates that we could not
 // get the SOCKS proxy address via the control port.
 var ErrTorUnableToGetSOCKSProxyAddress = errors.New(
@@ -70,6 +68,7 @@ func torStart(ctx context.Context, config *Config) (Tunnel, error) {
 	}
 	stateDir := filepath.Join(config.TunnelDir, "tor")
 	logfile := filepath.Join(stateDir, "tor.log")
+	maybeCleanupTunnelDir(stateDir, logfile)
 	extraArgs := append([]string{}, config.TorArgs...)
 	extraArgs = append(extraArgs, "Log")
 	extraArgs = append(extraArgs, "notice stderr")
@@ -112,3 +111,19 @@ func torStart(ctx context.Context, config *Config) (Tunnel, error) {
 		proxy:         &url.URL{Scheme: "socks5", Host: proxyAddress},
 	}, nil
 }
+
+// maybeCleanupTunnelDir removes stale files inside
+// of the tunnel directory.
+func maybeCleanupTunnelDir(dir, logfile string) {
+	os.Remove(logfile)
+	removeWithGlob(filepath.Join(dir, "torrc-*"))
+	removeWithGlob(filepath.Join(dir, "control-port-*"))
+}
+
+// removeWithGlob globs and removes files.
+func removeWithGlob(pattern string) {
+	files, _ := filepath.Glob(pattern)
+	for _, file := range files {
+		os.Remove(file)
+	}
+}
diff --git a/internal/engine/tunnel/tor_test.go b/internal/engine/tunnel/tor_test.go
index 8e27e5c..c180041 100644
--- a/internal/engine/tunnel/tor_test.go
+++ b/internal/engine/tunnel/tor_test.go
@@ -3,7 +3,12 @@ package tunnel
 import (
 	"context"
 	"errors"
+	"fmt"
+	"io/ioutil"
 	"net/url"
+	"os"
+	"path/filepath"
+	"strings"
 	"testing"
 
 	"github.com/cretz/bine/control"
@@ -226,3 +231,53 @@ func TestTorUnsupportedProxy(t *testing.T) {
 		t.Fatal("expected nil tunnel here")
 	}
 }
+
+func TestMaybeCleanupTunnelDir(t *testing.T) {
+	fakeTunDir := filepath.Join("testdata", "fake-tun-dir")
+	if err := os.RemoveAll(fakeTunDir); err != nil {
+		t.Fatal(err)
+	}
+	if err := os.MkdirAll(fakeTunDir, 0700); err != nil {
+		t.Fatal(err)
+	}
+	fakeData := []byte("deadbeef\n")
+	logfile := filepath.Join(fakeTunDir, "tor.log")
+	if err := ioutil.WriteFile(logfile, fakeData, 0600); err != nil {
+		t.Fatal(err)
+	}
+	for idx := 0; idx < 3; idx++ {
+		filename := filepath.Join(fakeTunDir, fmt.Sprintf("torrc-%d", idx))
+		if err := ioutil.WriteFile(filename, fakeData, 0600); err != nil {
+			t.Fatal(err)
+		}
+		filename = filepath.Join(fakeTunDir, fmt.Sprintf("control-port-%d", idx))
+		if err := ioutil.WriteFile(filename, fakeData, 0600); err != nil {
+			t.Fatal(err)
+		}
+		filename = filepath.Join(fakeTunDir, fmt.Sprintf("antani-%d", idx))
+		if err := ioutil.WriteFile(filename, fakeData, 0600); err != nil {
+			t.Fatal(err)
+		}
+	}
+	files, err := filepath.Glob(filepath.Join(fakeTunDir, "*"))
+	if err != nil {
+		t.Fatal(err)
+	}
+	if len(files) != 10 {
+		t.Fatal("unexpected number of files")
+	}
+	maybeCleanupTunnelDir(fakeTunDir, logfile)
+	files, err = filepath.Glob(filepath.Join(fakeTunDir, "*"))
+	if err != nil {
+		t.Fatal(err)
+	}
+	if len(files) != 3 {
+		t.Fatal("unexpected number of files")
+	}
+	expectPrefix := filepath.Join(fakeTunDir, "antani-")
+	for _, file := range files {
+		if !strings.HasPrefix(file, expectPrefix) {
+			t.Fatal("unexpected file name: ", file)
+		}
+	}
+}