diff --git a/README.md b/README.md
index 91c047c395..a91089e7a3 100644
--- a/README.md
+++ b/README.md
@@ -122,6 +122,7 @@ d2 --watch in.d2 out.svg
 ```
 
 A browser window will open with `out.svg` and live-reload on changes to `in.d2`.
+If you want the generated output removed on exit, use `d2 --watch --watch-cleanup in.d2 out.svg`.
 
 ## Install
 
diff --git a/d2cli/main.go b/d2cli/main.go
index 6e49ad0615..c439e97ff3 100644
--- a/d2cli/main.go
+++ b/d2cli/main.go
@@ -75,6 +75,10 @@ func Run(ctx context.Context, ms *xmain.State) (err error) {
 	if err != nil {
 		return err
 	}
+	watchCleanupFlag, err := ms.Opts.Bool("D2_WATCH_CLEANUP", "watch-cleanup", "", false, "when used with watch, remove generated output files when exiting")
+	if err != nil {
+		return err
+	}
 	layoutFlag := ms.Opts.String("D2_LAYOUT", "layout", "l", "dagre", `the layout engine used`)
 	themeFlag, err := ms.Opts.Int64("D2_THEME", "theme", "t", 0, "the diagram theme ID")
 	if err != nil {
@@ -369,6 +373,7 @@ func Run(ctx context.Context, ms *xmain.State) (err error) {
 			port:            *portFlag,
 			inputPath:       inputPath,
 			outputPath:      outputPath,
+			cleanupOutput:   *watchCleanupFlag,
 			bundle:          *bundleFlag,
 			forceAppendix:   *forceAppendixFlag,
 			pw:              pw,
diff --git a/d2cli/watch.go b/d2cli/watch.go
index 3e3db95b99..4089fc8c69 100644
--- a/d2cli/watch.go
+++ b/d2cli/watch.go
@@ -51,6 +51,7 @@ type watcherOpts struct {
 	port            string
 	inputPath       string
 	outputPath      string
+	cleanupOutput   bool
 	boardPath       string
 	pwd             string
 	bundle          bool
@@ -88,6 +89,8 @@ type watcher struct {
 
 	resMu sync.Mutex
 	res   *compileResult
+
+	cleanupOutputDir bool
 }
 
 type compileResult struct {
@@ -118,6 +121,13 @@ func newWatcher(ctx context.Context, ms *xmain.State, opts watcherOpts) (*watche
 }
 
 func (w *watcher) init() error {
+	if w.cleanupOutput && w.outputPath != "-" {
+		outputDir := watchOutputDir(w.outputPath)
+		if outputDir != "" {
+			_, err := os.Stat(outputDir)
+			w.cleanupOutputDir = errors.Is(err, os.ErrNotExist)
+		}
+	}
 	fw, err := fsnotify.NewWatcher()
 	if err != nil {
 		return err
@@ -151,20 +161,35 @@ func (w *watcher) initStaticFileServer() error {
 	return nil
 }
 
-func (w *watcher) run() error {
-	defer w.close()
+func (w *watcher) run() (err error) {
+	defer func() {
+		w.close()
+		if !w.cleanupOutput || w.outputPath == "-" {
+			return
+		}
+		cleanupErr := cleanupWatchOutput(w.outputPath, w.cleanupOutputDir)
+		if cleanupErr == nil {
+			return
+		}
+		if err == nil {
+			err = cleanupErr
+			return
+		}
+		w.ms.Log.Warn.Printf("failed to clean up watch output %s: %v", w.ms.HumanPath(w.outputPath), cleanupErr)
+	}()
 
 	w.goFunc(w.watchLoop)
 	w.goFunc(w.compileLoop)
 
-	err := w.goServe()
+	err = w.goServe()
 	if err != nil {
 		return err
 	}
 
 	w.wg.Wait()
 	w.close()
-	return w.err
+	err = w.err
+	return err
 }
 
 func (w *watcher) close() {
@@ -485,9 +510,35 @@ func (w *watcher) listen() error {
 	}
 	w.l = l
 	w.ms.Log.Success.Printf("listening on http://%v", w.l.Addr())
+	if w.cleanupOutput {
+		w.ms.Log.Info.Printf("press Ctrl-C to quit and remove %s", w.ms.HumanPath(w.outputPath))
+	} else {
+		w.ms.Log.Info.Printf("press Ctrl-C to quit")
+	}
 	return nil
 }
 
+func cleanupWatchOutput(outputPath string, removeDir bool) error {
+	err := os.Remove(outputPath)
+	if err != nil && !errors.Is(err, os.ErrNotExist) {
+		return err
+	}
+
+	outputDir := watchOutputDir(outputPath)
+	if !removeDir || outputDir == "" {
+		return nil
+	}
+	return os.RemoveAll(outputDir)
+}
+
+func watchOutputDir(outputPath string) string {
+	ext := filepath.Ext(outputPath)
+	if ext == "" {
+		return ""
+	}
+	return strings.TrimSuffix(outputPath, ext)
+}
+
 func (w *watcher) goServe() error {
 	m := http.NewServeMux()
 	// TODO: Add cmdlog logging and error reporting middleware
diff --git a/e2etests-cli/main_test.go b/e2etests-cli/main_test.go
index 8d2913f6e9..3385ed567b 100644
--- a/e2etests-cli/main_test.go
+++ b/e2etests-cli/main_test.go
@@ -1342,6 +1342,52 @@ layers: {
 				assert.Success(t, err)
 			},
 		},
+		{
+			name:   "watch-cleanup",
+			serial: true,
+			run: func(t *testing.T, ctx context.Context, dir string, env *xos.Env) {
+				writeFile(t, dir, "index.d2", `a -> b`)
+
+				stderr := &stderrWrapper{}
+				tms := testMain(dir, env, "--watch", "--watch-cleanup", "--browser=0", "index.d2", "out.svg")
+				tms.Stderr = stderr
+
+				tms.Start(t, ctx)
+				interrupted := false
+				defer func() {
+					if interrupted {
+						return
+					}
+					err := tms.Signal(ctx, os.Interrupt)
+					assert.Success(t, err)
+				}()
+
+				doneRE := regexp.MustCompile(`successfully compiled index.d2`)
+				_, err := waitLogs(ctx, stderr, doneRE)
+				assert.Success(t, err)
+
+				outputPath := filepath.Join(dir, "out.svg")
+				_, err = os.Stat(outputPath)
+				assert.Success(t, err)
+
+				err = tms.Signal(ctx, os.Interrupt)
+				assert.Success(t, err)
+				interrupted = true
+
+				deadline := time.Now().Add(2 * time.Second)
+				for {
+					_, err = os.Stat(outputPath)
+					if errors.Is(err, os.ErrNotExist) {
+						break
+					}
+					assert.Success(t, err)
+					if time.Now().After(deadline) {
+						t.Fatalf("expected %s to be removed after watch exit", outputPath)
+					}
+					time.Sleep(10 * time.Millisecond)
+				}
+			},
+		},
 		{
 			name:   "watch-ok-link",
 			serial: true,