diff --git a/README.md b/README.md
index 9e9da99..fcd1b76 100644
--- a/README.md
+++ b/README.md
@@ -324,7 +324,7 @@ Before any destructive operation, gh-stack automatically captures a snapshot of
 - Stack configuration (parent, PR number, fork point)
 - Any auto-stashed uncommitted changes
 
-Snapshots are stored in `.git/stack-undo/` and archived to `.git/stack-undo/done/` after successful undo.
+Snapshots are stored in `.git/stack-undo/` and archived to `.git/stack-undo/done/` after successful undo. Snapshots are automatically pruned to keep at most 50 pending and 50 archived, with the oldest removed first. No manual cleanup is required.
 
 > [!NOTE]
 >
diff --git a/internal/undo/undo.go b/internal/undo/undo.go
index 6d8b3b4..ed57b80 100644
--- a/internal/undo/undo.go
+++ b/internal/undo/undo.go
@@ -15,6 +15,14 @@ const (
 	undoDir    = "stack-undo"
 	archiveDir = "done"
 	timeFormat = "20060102T150405.000000000Z" // Compact ISO8601 with nanoseconds to avoid collisions
+
+	// maxActiveSnapshots is the maximum number of pending undo snapshots to keep.
+	// Oldest snapshots are pruned automatically when this limit is exceeded.
+	maxActiveSnapshots = 50
+
+	// maxArchivedSnapshots is the maximum number of archived (used) snapshots to keep.
+	// Oldest archived snapshots are pruned automatically when this limit is exceeded.
+	maxArchivedSnapshots = 50
 )
 
 // ErrNoSnapshot is returned when no undo snapshot exists.
@@ -52,6 +60,7 @@ func NewSnapshot(operation, command, originalHead string) *Snapshot {
 }
 
 // Save persists the snapshot to .git/stack-undo/{timestamp}-{operation}.json.
+// Automatically prunes old snapshots if the count exceeds maxActiveSnapshots.
 func Save(gitDir string, snapshot *Snapshot) error {
 	dir := filepath.Join(gitDir, undoDir)
 	if err := os.MkdirAll(dir, 0755); err != nil {
@@ -65,7 +74,12 @@ func Save(gitDir string, snapshot *Snapshot) error {
 	if err != nil {
 		return err
 	}
-	return os.WriteFile(path, data, 0644)
+	if err := os.WriteFile(path, data, 0644); err != nil {
+		return err
+	}
+
+	// Prune old snapshots if we exceed the limit
+	return pruneDir(dir, maxActiveSnapshots)
 }
 
 // LoadLatest reads the most recent snapshot from .git/stack-undo/.
@@ -125,6 +139,7 @@ func Load(path string) (*Snapshot, error) {
 }
 
 // Archive moves a snapshot file to the done/ subdirectory.
+// Automatically prunes old archived snapshots if the count exceeds maxArchivedSnapshots.
 func Archive(gitDir, snapshotPath string) error {
 	archivePath := filepath.Join(gitDir, undoDir, archiveDir)
 	if err := os.MkdirAll(archivePath, 0755); err != nil {
@@ -133,7 +148,12 @@ func Archive(gitDir, snapshotPath string) error {
 
 	filename := filepath.Base(snapshotPath)
 	dest := filepath.Join(archivePath, filename)
-	return os.Rename(snapshotPath, dest)
+	if err := os.Rename(snapshotPath, dest); err != nil {
+		return err
+	}
+
+	// Prune old archived snapshots if we exceed the limit
+	return pruneDir(archivePath, maxArchivedSnapshots)
 }
 
 // List returns all available (non-archived) snapshots, sorted newest first.
@@ -195,3 +215,44 @@ func Remove(snapshotPath string) error {
 	}
 	return err
 }
+
+// pruneDir removes the oldest .json files in dir if the count exceeds max.
+// Files are sorted by name (which starts with a timestamp), so oldest are deleted first.
+func pruneDir(dir string, max int) error {
+	entries, err := os.ReadDir(dir)
+	if err != nil {
+		if os.IsNotExist(err) {
+			return nil
+		}
+		return err
+	}
+
+	// Filter to only .json files
+	var jsonFiles []os.DirEntry
+	for _, entry := range entries {
+		if !entry.IsDir() && strings.HasSuffix(entry.Name(), ".json") {
+			jsonFiles = append(jsonFiles, entry)
+		}
+	}
+
+	// Nothing to prune
+	if len(jsonFiles) <= max {
+		return nil
+	}
+
+	// Sort ascending by name (oldest first, since filenames start with timestamp)
+	sort.Slice(jsonFiles, func(i, j int) bool {
+		return jsonFiles[i].Name() < jsonFiles[j].Name()
+	})
+
+	// Delete oldest files until we're at or below max
+	toDelete := len(jsonFiles) - max
+	for i := 0; i < toDelete; i++ {
+		path := filepath.Join(dir, jsonFiles[i].Name())
+		if removeErr := os.Remove(path); removeErr != nil && !os.IsNotExist(removeErr) {
+			return removeErr
+		}
+	}
+
+	return nil
+}
diff --git a/internal/undo/undo_test.go b/internal/undo/undo_test.go
index 195a535..159ed4e 100644
--- a/internal/undo/undo_test.go
+++ b/internal/undo/undo_test.go
@@ -320,3 +320,91 @@ func TestRemove(t *testing.T) {
 		t.Errorf("Remove non-existent should not error: %v", err)
 	}
 }
+
+func TestSavePrunesOldSnapshots(t *testing.T) {
+	dir := t.TempDir()
+	gitDir := filepath.Join(dir, ".git")
+	if err := os.MkdirAll(gitDir, 0755); err != nil {
+		t.Fatal(err)
+	}
+
+	// Create 55 snapshots (exceeds the 50 limit)
+	for i := 0; i < 55; i++ {
+		snapshot := undo.NewSnapshot("cascade", "gh stack cascade", "main")
+		// Use distinct timestamps to ensure unique filenames
+		snapshot.Timestamp = time.Date(2024, 1, 1, 0, 0, i, 0, time.UTC)
+		snapshot.Branches["feature"] = undo.BranchState{SHA: "abc"}
+		if err := undo.Save(gitDir, snapshot); err != nil {
+			t.Fatalf("Save %d failed: %v", i, err)
+		}
+	}
+
+	// Verify only 50 snapshots remain
+	snapshots, err := undo.List(gitDir)
+	if err != nil {
+		t.Fatal(err)
+	}
+
+	if len(snapshots) != 50 {
+		t.Errorf("Expected 50 snapshots after pruning, got %d", len(snapshots))
+	}
+
+	// Verify the oldest 5 were pruned (timestamps 0-4 should be gone)
+	// The newest should be timestamp second=54, oldest kept should be second=5
+	if len(snapshots) > 0 {
+		newest := snapshots[0]
+		if newest.Timestamp.Second() != 54 {
+			t.Errorf("Expected newest snapshot to have second=54, got %d", newest.Timestamp.Second())
+		}
+		oldest := snapshots[len(snapshots)-1]
+		if oldest.Timestamp.Second() != 5 {
+			t.Errorf("Expected oldest kept snapshot to have second=5, got %d", oldest.Timestamp.Second())
+		}
+	}
+}
+
+func TestArchivePrunesOldSnapshots(t *testing.T) {
+	dir := t.TempDir()
+	gitDir := filepath.Join(dir, ".git")
+	if err := os.MkdirAll(gitDir, 0755); err != nil {
+		t.Fatal(err)
+	}
+
+	// Create and archive 55 snapshots (exceeds the 50 limit)
+	for i := 0; i < 55; i++ {
+		snapshot := undo.NewSnapshot("cascade", "gh stack cascade", "main")
+		snapshot.Timestamp = time.Date(2024, 1, 1, 0, 0, i, 0, time.UTC)
+		snapshot.Branches["feature"] = undo.BranchState{SHA: "abc"}
+		if err := undo.Save(gitDir, snapshot); err != nil {
+			t.Fatalf("Save %d failed: %v", i, err)
+		}
+
+		// Get the path and archive it
+		_, path, err := undo.LoadLatest(gitDir)
+		if err != nil {
+			t.Fatalf("LoadLatest %d failed: %v", i, err)
+		}
+		if err := undo.Archive(gitDir, path); err != nil {
+			t.Fatalf("Archive %d failed: %v", i, err)
+		}
+	}
+
+	// Verify only 50 archived snapshots remain
+	doneDir := filepath.Join(gitDir, "stack-undo", "done")
+	entries, err := os.ReadDir(doneDir)
+	if err != nil {
+		t.Fatalf("Failed to read done dir: %v", err)
+	}
+
+	// Count only .json files
+	jsonCount := 0
+	for _, entry := range entries {
+		if !entry.IsDir() && filepath.Ext(entry.Name()) == ".json" {
+			jsonCount++
+		}
+	}
+
+	if jsonCount != 50 {
+		t.Errorf("Expected 50 archived snapshots after pruning, got %d", jsonCount)
+	}
+}