diff --git a/htmd/cli.py b/htmd/cli.py
index 445f267..5c06305 100644
--- a/htmd/cli.py
+++ b/htmd/cli.py
@@ -2,11 +2,14 @@
 import importlib
 from pathlib import Path
 import sys
+import threading
 import warnings
 
 import click
 from flask import Flask
 from flask_flatpages import FlatPages, Page
+from watchdog.observers import Observer
+from watchdog.events import DirModifiedEvent, FileModifiedEvent, FileSystemEventHandler
 
 from .utils import (
     combine_and_minify_css,
@@ -202,6 +205,24 @@ def build(
     click.echo(click.style(msg, fg='green'))
 
 
+class StaticHandler(FileSystemEventHandler):
+    def __init__(self, static_directory: Path) -> None:
+        super().__init__()
+        self.static_directory = static_directory
+
+    def on_modified(self, event: DirModifiedEvent | FileModifiedEvent) -> None:
+        dst_css = 'combined.min.css'
+        dst_js = 'combined.min.js'
+        if event.is_directory or dst_css in event.src_path or dst_js in event.src_path:
+            return
+        if event.event_type == 'modified' and event.src_path.endswith('.css'):
+            click.echo(f'Changes detected in {event.src_path}. Recreating {dst_css}...')
+            combine_and_minify_css(self.static_directory)
+        elif event.event_type == 'modified' and event.src_path.endswith('.js'):
+            click.echo(f'Changes detected in {event.src_path}. Recreating {dst_js}...')
+            combine_and_minify_js(self.static_directory)
+
+
 @cli.command('preview', short_help='Serve files to preview site.')
 @click.pass_context
 @click.option(
@@ -245,13 +266,34 @@ def preview(
         assert app.static_folder is not None
         combine_and_minify_js(Path(app.static_folder))
 
+    def watch_static() -> None:
+        static_directory = Path(app.static_folder)
+
+        event_handler = StaticHandler(static_directory)
+        observer = Observer()
+        observer.schedule(event_handler, path=static_directory, recursive=True)
+        observer.start()
+
+        try:
+            while not exit_event.is_set():
+                observer.join(1)
+        finally:
+            observer.stop()
+            observer.join()
+
+    watch_thread = threading.Thread(target=watch_static)
+    watch_thread.start()
+
     # reload when static files change
     # werkzeug will re-run the terminal command
     # Which causes the above combine_and_minify_*() to run
     # and recreate combined.min.css/combined.min.js files
     static_path = site.project_dir / 'static'
     extra_files = static_path.iterdir()
+    exit_event = threading.Event()
     app.run(debug=True, host=host, port=port, extra_files=extra_files)
+    # After Flask has been stopped stop watchdog
+    exit_event.set()
 
 
 @cli.command('templates', short_help='Create any missing templates')
diff --git a/pyproject.toml b/pyproject.toml
index 54e599c..1f303de 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -22,6 +22,7 @@ dependencies = [
   "jsmin",
   "Pygments",
   "requests",
+  "watchdog",
 ]
 description = "Write Markdown and Jinja2 templates to create a website"
 maintainers = [
@@ -67,6 +68,7 @@ order-by-type = false
 section-order = ["future", "standard-library", "third-party", "first-party", "local-folder"]
 
 [tool.ruff.lint.per-file-ignores]
+"htmd/cli.py" = ["I001"]
 "tests/test_app.py" = ["ARG001"]
 "tests/test_build.py" = ["I001"]
 "tests/test_drafts.py" = ["ARG001", "I001"]
diff --git a/tests/test_preview.py b/tests/test_preview.py
index 48db40f..e0ae0b5 100644
--- a/tests/test_preview.py
+++ b/tests/test_preview.py
@@ -1,6 +1,7 @@
 from pathlib import Path
 import time
 from types import TracebackType
+import urllib3
 
 from click.testing import CliRunner
 from htmd.cli import preview
@@ -182,7 +183,7 @@ def test_preview_reload_js(run_start: CliRunner) -> None:  # noqa: ARG001
         while after == before:
             try:
                 response = requests.get(url, timeout=0.1)
-            except requests.exceptions.ReadTimeout:
+            except (requests.exceptions.ReadTimeout, urllib3.exceptions.IncompleteRead):
                 # happens during restart
                 read_timeout = True
             else:
@@ -191,3 +192,34 @@ def test_preview_reload_js(run_start: CliRunner) -> None:  # noqa: ARG001
         assert read_timeout
         assert before != after
         assert expected in after
+
+
+def test_preview_reload_js_new_file(run_start: CliRunner) -> None:  # noqa: ARG001
+    url = 'http://localhost:9090/static/combined.min.js'
+    new_js = 'document.getElementByTagName("body");'
+    expected = new_js
+
+    with run_preview():
+        response = requests.get(url, timeout=0.01)
+        assert response.status_code == 404
+        before = response.text
+        # Need to create before running preview since no .js files exist
+        js_path = Path('static') / 'script.js'
+        with js_path.open('w') as js_file:
+            js_file.write(new_js)
+
+        # Ensure new style is available after reload
+        read_timeout = False
+        after = before
+        while after == before:
+            try:
+                response = requests.get(url, timeout=0.1)
+            except requests.exceptions.ReadTimeout:
+                # happens during restart
+                read_timeout = True
+            else:
+                after = response.text
+
+        assert read_timeout is False
+        assert before != after
+        assert expected in after