diff --git a/.claude/settings.local.json b/.claude/settings.local.json
index a8fbbe8..5350b29 100644
--- a/.claude/settings.local.json
+++ b/.claude/settings.local.json
@@ -4,7 +4,10 @@
       "WebFetch(domain:pkg.go.dev)",
       "Bash(make:*)",
       "Bash(./out/shell-now:*)",
-      "WebFetch(domain:github.com)"
+      "WebFetch(domain:github.com)",
+      "Bash(find:*)",
+      "Bash(true)",
+      "Bash(ls:*)"
     ],
     "deny": []
   }
diff --git a/cmd/shell-now/main.go b/cmd/shell-now/main.go
index 0739bdc..25f0826 100644
--- a/cmd/shell-now/main.go
+++ b/cmd/shell-now/main.go
@@ -113,6 +113,32 @@ PowerShell:
 	}
 	rootCmd.AddCommand(versionCmd)
 
+	// Add replay command
+	replayCmd := &cobra.Command{
+		Use:   "replay [filename]",
+		Short: "Replay recorded shell sessions",
+		Long: `Replay recorded shell sessions using asciinema.
+
+Without arguments, replays the most recent recording.
+With filename argument, replays the specific recording.
+Use 'shell-now replay list' to see all available recordings.`,
+		RunE: func(cmd *cobra.Command, args []string) error {
+			if len(args) == 0 {
+				// Replay latest recording
+				return pkg.ReplayLatestRecording(ctx)
+			}
+			
+			if args[0] == "list" {
+				// List all recordings
+				return pkg.PrintRecordingsList()
+			}
+			
+			// Replay specific recording
+			return pkg.ReplayRecording(ctx, args[0])
+		},
+	}
+	rootCmd.AddCommand(replayCmd)
+
 	// Execute with context
 	if err := rootCmd.ExecuteContext(ctx); err != nil {
 		os.Exit(1)
diff --git a/pkg/bootstrap.go b/pkg/bootstrap.go
index 7ea05d8..1276fcd 100644
--- a/pkg/bootstrap.go
+++ b/pkg/bootstrap.go
@@ -6,6 +6,8 @@ import (
 	"log/slog"
 	"math/rand"
 	"net"
+	"os"
+	"path/filepath"
 	"sync"
 	"time"
 )
@@ -19,6 +21,9 @@ func Bootstrap(ctx context.Context) error {
 	if err := prepareTtyd(ctx); err != nil {
 		return err
 	}
+	if err := prepareAsciinema(ctx); err != nil {
+		return err
+	}
 
 	ttydListenPort, err := getAvailablePort()
 	if err != nil {
@@ -94,3 +99,22 @@ func randomDigitalString(length int) string {
 	}
 	return string(b)
 }
+
+func ensureRecordingsDirectory() (string, error) {
+	home, err := os.UserHomeDir()
+	if err != nil {
+		return "", err
+	}
+	
+	recordingsDir := filepath.Join(home, ".local", "share", "shell-now", "recordings")
+	err = os.MkdirAll(recordingsDir, 0755)
+	if err != nil {
+		return "", err
+	}
+	
+	return recordingsDir, nil
+}
+
+func generateRecordingFilename() string {
+	return fmt.Sprintf("shell-now-%s.cast", time.Now().Format("2006-01-02-15-04-05"))
+}
diff --git a/pkg/prepare.go b/pkg/prepare.go
index 74103d2..fbae825 100644
--- a/pkg/prepare.go
+++ b/pkg/prepare.go
@@ -20,3 +20,10 @@ func prepareCloudflared(ctx context.Context) error {
 	slog.Info("can not automatically prepare [cloudflared] on this platform, please install it manually", "platform", getPlatform())
 	return nil
 }
+
+// prepareAsciinema will check if asciinema is existed in PATH
+// if not, it will print an error message
+func prepareAsciinema(ctx context.Context) error {
+	slog.Warn("asciinema not available on this platform, session recording will be disabled", "platform", getPlatform())
+	return nil
+}
diff --git a/pkg/prepare_darwin.go b/pkg/prepare_darwin.go
index a78fd48..77a1db0 100644
--- a/pkg/prepare_darwin.go
+++ b/pkg/prepare_darwin.go
@@ -3,6 +3,7 @@ package pkg
 import (
 	"context"
 	"fmt"
+	"log/slog"
 	"os/exec"
 )
 
@@ -25,3 +26,14 @@ func prepareCloudflared(ctx context.Context) error {
 	}
 	return nil
 }
+
+// prepareAsciinema will check if asciinema is existed in PATH
+// if not, it will print an error message
+func prepareAsciinema(ctx context.Context) error {
+	// check if asciinema is existed in PATH
+	if _, err := exec.LookPath("asciinema"); err != nil {
+		slog.Warn("asciinema not found in PATH, session recording will be disabled. Execute `brew install asciinema` to enable recording.")
+		return nil
+	}
+	return nil
+}
diff --git a/pkg/prepare_linux.go b/pkg/prepare_linux.go
index 6062cba..552edf6 100644
--- a/pkg/prepare_linux.go
+++ b/pkg/prepare_linux.go
@@ -99,3 +99,15 @@ func download(ctx context.Context, url string, output string) error {
 	}
 	return nil
 }
+
+func prepareAsciinema(ctx context.Context) error {
+	// lookup command asciinema
+	_, err := lookupBinary(ctx, "asciinema")
+	if err == nil {
+		// asciinema is available
+		return nil
+	}
+
+	slog.Warn("asciinema not found in PATH, session recording will be disabled. Install asciinema to enable recording.")
+	return nil
+}
diff --git a/pkg/replay.go b/pkg/replay.go
new file mode 100644
index 0000000..0360e88
--- /dev/null
+++ b/pkg/replay.go
@@ -0,0 +1,121 @@
+package pkg
+
+import (
+	"context"
+	"fmt"
+	"log/slog"
+	"os"
+	"os/exec"
+	"path/filepath"
+	"sort"
+	"strings"
+)
+
+func ListRecordings() ([]string, error) {
+	recordingsDir, err := ensureRecordingsDirectory()
+	if err != nil {
+		return nil, fmt.Errorf("ensure recordings directory: %w", err)
+	}
+
+	// List all .cast files in the recordings directory
+	files, err := filepath.Glob(filepath.Join(recordingsDir, "*.cast"))
+	if err != nil {
+		return nil, fmt.Errorf("list recording files: %w", err)
+	}
+
+	// Sort files by modification time (newest first)
+	sort.Slice(files, func(i, j int) bool {
+		infoI, errI := os.Stat(files[i])
+		infoJ, errJ := os.Stat(files[j])
+		if errI != nil || errJ != nil {
+			return false
+		}
+		return infoI.ModTime().After(infoJ.ModTime())
+	})
+
+	// Return just the filenames without the full path
+	var recordings []string
+	for _, file := range files {
+		recordings = append(recordings, filepath.Base(file))
+	}
+
+	return recordings, nil
+}
+
+func ReplayRecording(ctx context.Context, filename string) error {
+	// Lookup asciinema binary
+	asciinema, err := lookupBinary(ctx, "asciinema")
+	if err != nil {
+		return fmt.Errorf("lookup asciinema binary: %w", err)
+	}
+
+	recordingsDir, err := ensureRecordingsDirectory()
+	if err != nil {
+		return fmt.Errorf("ensure recordings directory: %w", err)
+	}
+
+	// Construct full path to recording file
+	recordingPath := filepath.Join(recordingsDir, filename)
+	
+	// Check if file exists
+	if _, err := os.Stat(recordingPath); os.IsNotExist(err) {
+		return fmt.Errorf("recording file not found: %s", filename)
+	}
+
+	slog.Info("replaying session", "file", recordingPath)
+
+	// Execute asciinema play command
+	cmd := exec.CommandContext(ctx, asciinema, "play", recordingPath)
+	cmd.Stdout = os.Stdout
+	cmd.Stderr = os.Stderr
+	cmd.Stdin = os.Stdin
+
+	return cmd.Run()
+}
+
+func ReplayLatestRecording(ctx context.Context) error {
+	recordings, err := ListRecordings()
+	if err != nil {
+		return fmt.Errorf("list recordings: %w", err)
+	}
+
+	if len(recordings) == 0 {
+		return fmt.Errorf("no recordings found")
+	}
+
+	// Replay the most recent recording (first in sorted list)
+	return ReplayRecording(ctx, recordings[0])
+}
+
+func PrintRecordingsList() error {
+	recordings, err := ListRecordings()
+	if err != nil {
+		return fmt.Errorf("list recordings: %w", err)
+	}
+
+	if len(recordings) == 0 {
+		fmt.Println("No recordings found.")
+		return nil
+	}
+
+	fmt.Printf("Available recordings (%d):\n", len(recordings))
+	fmt.Println("----------------------------------")
+	
+	for i, recording := range recordings {
+		// Extract timestamp from filename for better display
+		displayName := recording
+		if strings.HasPrefix(recording, "shell-now-") && strings.HasSuffix(recording, ".cast") {
+			timestamp := strings.TrimPrefix(recording, "shell-now-")
+			timestamp = strings.TrimSuffix(timestamp, ".cast")
+			displayName = fmt.Sprintf("Session %s", timestamp)
+		}
+		
+		fmt.Printf("%2d. %s\n", i+1, displayName)
+	}
+	
+	fmt.Println("----------------------------------")
+	fmt.Println("Use 'shell-now replay <filename>' to replay a specific recording")
+	fmt.Println("Use 'shell-now replay' to replay the latest recording")
+	
+	return nil
+}
\ No newline at end of file
diff --git a/pkg/ttyd.go b/pkg/ttyd.go
index 5462252..8f35542 100644
--- a/pkg/ttyd.go
+++ b/pkg/ttyd.go
@@ -6,6 +6,8 @@ import (
 	"log/slog"
 	"os"
 	"os/exec"
+	"path/filepath"
+	"strings"
 )
 
 func startTtyd(ctx context.Context,
@@ -26,8 +28,21 @@ func startTtyd(ctx context.Context,
 		return fmt.Errorf("fetch available startup command: %w", err)
 	}
 
-	// execute ttyd <options> <startupCommand>
-	cmd := exec.CommandContext(ctx, ttydBinary, "--writable", "--port", fmt.Sprintf("%d", listenPort), "--credential", fmt.Sprintf("%s:%s", username, password), startupCommand)
+	// Get asciinema binary and setup recording (best-effort)
+	command, args, _ := prepareAsciinemaCommand(ctx, startupCommand)
+
+	// execute ttyd <options> <command> [args]
+	var cmd *exec.Cmd
+	if args == "" {
+		// No recording, just use the original command
+		cmd = exec.CommandContext(ctx, ttydBinary, "--writable", "--port", fmt.Sprintf("%d", listenPort), "--credential", fmt.Sprintf("%s:%s", username, password), command)
+	} else {
+		// Recording with asciinema - split args properly
+		argsList := strings.Fields(args)
+		ttydArgs := []string{"--writable", "--port", fmt.Sprintf("%d", listenPort), "--credential", fmt.Sprintf("%s:%s", username, password), command}
+		ttydArgs = append(ttydArgs, argsList...)
+		cmd = exec.CommandContext(ctx, ttydBinary, ttydArgs...)
+	}
 
 	if os.Getenv("DEBUG") != "" {
 		cmd.Stdout = os.Stdout
@@ -39,7 +54,7 @@ func startTtyd(ctx context.Context,
 
 func fetchAvailableStartupCommand(ctx context.Context) (string, error) {
 	// test commands in PATH,
-	// zsh, fish, bash, sh, login
+	// zsh, fish, bash, sh, login (login as lowest choice)
 	commands := []string{"zsh", "fish", "bash", "sh", "login"}
 	for _, command := range commands {
 		if _, err := exec.LookPath(command); err == nil {
@@ -48,3 +63,29 @@ func fetchAvailableStartupCommand(ctx context.Context) (string, error) {
 	}
 	return "", fmt.Errorf("no available startup command found, auto detect failed with zsh, fish, bash, sh, login")
 }
+
+func prepareAsciinemaCommand(ctx context.Context, originalCommand string) (string, string, error) {
+	// Lookup asciinema binary
+	asciinema, err := lookupBinary(ctx, "asciinema")
+	if err != nil {
+		// Best-effort: if asciinema is not available, just use the original command
+		slog.Debug("asciinema not available, proceeding without recording", "error", err)
+		return originalCommand, "", nil
+	}
+
+	// Ensure recordings directory exists
+	recordingsDir, err := ensureRecordingsDirectory()
+	if err != nil {
+		slog.Warn("failed to create recordings directory, proceeding without recording", "error", err)
+		return originalCommand, "", nil
+	}
+
+	// Generate recording filename
+	recordingFile := filepath.Join(recordingsDir, generateRecordingFilename())
+
+	slog.Info("recording session", "file", recordingFile)
+
+	// Use asciinema as the main command with -c flag to specify shell to record
+	// Format: asciinema rec filename.cast -c shell_command
+	return asciinema, fmt.Sprintf("rec %s -c %s", recordingFile, originalCommand), nil
+}