diff --git a/assets/graphics/reload.png b/assets/graphics/reload.png
deleted file mode 100644
index 83b07e0..0000000
Binary files a/assets/graphics/reload.png and /dev/null differ
diff --git a/menus/downloader.py b/menus/downloader.py
index 81a852a..53d050a 100644
--- a/menus/downloader.py
+++ b/menus/downloader.py
@@ -1,11 +1,11 @@
 from mutagen.id3 import ID3, TIT2, TPE1, WXXX
 from mutagen.mp3 import MP3
 
-import arcade, arcade.gui, os, json, threading, subprocess, traceback
+import arcade, arcade.gui, os, json, threading, subprocess, urllib.request, platform
 
 from arcade.gui.experimental.focus import UIFocusGroup
 
-from utils.utils import ensure_yt_dlp, adjust_volume
+from utils.music_handling import adjust_volume
 from utils.constants import button_style
 from utils.preload import button_texture, button_hovered_texture
 
@@ -65,7 +65,7 @@ class Downloader(arcade.gui.UIView):
             self.status_label.update_font(font_color=arcade.color.LIGHT_GREEN)
 
     def run_yt_dlp(self, url):
-        yt_dlp_path = ensure_yt_dlp()
+        yt_dlp_path = self.ensure_yt_dlp()
 
         command = [
             yt_dlp_path, f"{url}",
@@ -161,6 +161,34 @@ class Downloader(arcade.gui.UIView):
 
         self.yt_dl_buffer = f"Successfully downloaded {title} to {path}"
 
+    def ensure_yt_dlp():
+        system = platform.system()
+
+        if system == "Windows":
+            path = os.path.join("bin", "yt-dlp.exe")
+        elif system == "Darwin":
+            path = os.path.join("bin", "yt-dlp_macos")
+        elif system == "Linux":
+            path = os.path.join("bin", "yt-dlp_linux")
+            
+        if not os.path.exists("bin"):
+            os.makedirs("bin")
+
+        if not os.path.exists(path):
+            if system == "Windows":
+                url = "https://github.com/yt-dlp/yt-dlp/releases/latest/download/yt-dlp.exe"
+            elif system == "Darwin":
+                url = "https://github.com/yt-dlp/yt-dlp/releases/latest/download/yt-dlp_macos"
+            elif system == "Linux":
+                url = "https://github.com/yt-dlp/yt-dlp/releases/latest/download/yt-dlp_linux"
+            else:
+                raise RuntimeError("Unsupported OS")
+
+            urllib.request.urlretrieve(url, path)
+            os.chmod(path, 0o755)
+
+        return path
+
     def main_exit(self):
         from menus.main import Main
         self.window.show_view(Main(self.pypresence_client, self.current_mode, self.current_music_name, self.current_length, self.current_music_player, self.queue, self.loaded_sounds, self.shuffle))
diff --git a/menus/main.py b/menus/main.py
index e7081e8..adb5a23 100644
--- a/menus/main.py
+++ b/menus/main.py
@@ -2,8 +2,10 @@ import random, asyncio, pypresence, time, copy, json, os, logging, webbrowser
 import arcade, pyglet
 
 from utils.preload import *
-from utils.constants import button_style, slider_style, audio_extensions, discord_presence_id
-from utils.utils import FakePyPresence, UIFocusTextureButton, MusicItem, extract_metadata_and_thumbnail, truncate_end, adjust_volume, convert_seconds_to_date
+from utils.constants import button_style, slider_style, audio_extensions, discord_presence_id, view_modes
+from utils.utils import FakePyPresence, UIFocusTextureButton, MusicItem, convert_seconds_to_date
+from utils.music_handling import update_last_play_statistics, extract_metadata_and_thumbnail, adjust_volume, truncate_end, convert_timestamp_to_time_ago
+from utils.file_watching import watch_directories, watch_files
 
 from thefuzz import process, fuzz
 
@@ -57,7 +59,6 @@ class Main(arcade.gui.UIView):
         self.tab_content = {}
         self.playlist_content = {}
         self.file_metadata = {}
-        self.thumbnails = {}
         self.tab_buttons = {}
         self.music_buttons = {}
 
@@ -67,6 +68,9 @@ class Main(arcade.gui.UIView):
         self.current_mode = current_mode or "files"
         self.current_playlist = None
         self.time_to_seek = None
+        self.tab_observer = None
+        self.playlist_observer = None
+        self.should_reload = False
         self.current_tab = self.tab_options[0]
         self.queue = queue if queue else []
         self.loaded_sounds = loaded_sounds if loaded_sounds else {}
@@ -117,11 +121,11 @@ class Main(arcade.gui.UIView):
 
         self.downloader_button = self.settings_box.add(UIFocusTextureButton(texture=download_icon, texture_hovered=download_icon, texture_pressed=download_icon, style=button_style))
         self.downloader_button.on_click = lambda event: self.downloader()
-
-        self.reload_button = self.settings_box.add(UIFocusTextureButton(texture=reload_icon, texture_hovered=reload_icon, texture_pressed=reload_icon, style=button_style))
-        self.reload_button.on_click = lambda event: self.reload()
-
-        mode_icon = playlist_icon if self.current_mode == "files" else files_icon
+        
+        if self.current_mode == "files":
+            mode_icon = files_icon
+        elif self.current_mode == "playlist":
+            mode_icon = playlist_icon
 
         self.mode_button = self.settings_box.add(UIFocusTextureButton(texture=mode_icon, texture_hovered=mode_icon, texture_pressed=mode_icon, style=button_style))
         self.mode_button.on_click = lambda event: self.change_mode()
@@ -178,14 +182,13 @@ class Main(arcade.gui.UIView):
 
     def update_buttons(self):
         if self.current_mode == "files":
-            self.mode_button.texture = playlist_icon
-            self.mode_button.texture_hovered = playlist_icon
-            self.mode_button.texture_pressed = playlist_icon
-
+            mode_icon = files_icon
         elif self.current_mode == "playlist":
-            self.mode_button.texture = files_icon
-            self.mode_button.texture_hovered = files_icon
-            self.mode_button.texture_pressed = files_icon
+            mode_icon = playlist_icon
+
+        self.mode_button.texture = mode_icon
+        self.mode_button.texture_hovered = mode_icon
+        self.mode_button.texture_pressed = mode_icon
 
         self.shuffle_button.texture = no_shuffle_icon if self.shuffle else shuffle_icon
         self.shuffle_button.texture_hovered = no_shuffle_icon if self.shuffle else shuffle_icon
@@ -211,7 +214,10 @@ class Main(arcade.gui.UIView):
         self.anchor.detect_focusable_widgets()
 
     def change_mode(self):
-        self.current_mode = "playlist" if self.current_mode == "files" else "files"
+        if view_modes.index(self.current_mode) == len(view_modes) - 1:
+            self.current_mode = view_modes[0]
+        else:
+            self.current_mode = view_modes[view_modes.index(self.current_mode) + 1]
 
         self.current_playlist = list(self.playlist_content.keys())[0] if self.playlist_content else None
 
@@ -219,8 +225,8 @@ class Main(arcade.gui.UIView):
         self.search_term = ""
 
         self.reload()
-
         self.load_tabs()
+        self.update_buttons()
 
     def skip_sound(self):
         if not self.current_music_player is None:
@@ -264,7 +270,15 @@ class Main(arcade.gui.UIView):
     def open_metadata(self, file_path):
         metadata = self.file_metadata[file_path]
 
-        metadata_text = f"File path: {file_path}\nArtist: {metadata['artist']}\nTitle: {metadata['title']}\nSound length: {convert_seconds_to_date(int(metadata['sound_length']))}\nBitrate: {metadata['bit_rate']}Kbps"
+        metadata_text = f'''File path: {file_path}
+File size: {metadata['file_size']}MiB
+Artist: {metadata['artist']}
+Title: {metadata['title']}
+Amount of times played: {metadata['play_count']}
+Last Played: {convert_timestamp_to_time_ago(int(metadata['last_played']))}
+Sound length: {convert_seconds_to_date(int(metadata['sound_length']))}
+Bitrate: {metadata['bitrate']}Kbps
+Sample rate: {metadata['sample_rate']}KHz'''
 
         msgbox = arcade.gui.UIMessageBox(title=f"{metadata['artist']} - {metadata['title']} Metadata", buttons=("Uploader", "Source", "Close"), message_text=metadata_text, width=self.window.width / 2, height=self.window.height / 2)
         msgbox.on_action = lambda event, metadata=metadata: self.metadata_button_action(event.action, metadata)
@@ -284,25 +298,19 @@ class Main(arcade.gui.UIView):
             if not self.search_term == "":
                 matches = process.extract(self.search_term, self.tab_content[self.current_tab], limit=5, processor=lambda text: text.lower(), scorer=fuzz.partial_token_sort_ratio)
                 self.highest_score_file = f"{self.current_tab}/{matches[0][0]}"
-                
-                for match in matches:
-                    music_filename = match[0]
-                    metadata = self.file_metadata[f"{tab}/{music_filename}"]
-                    self.music_buttons[f"{tab}/{music_filename}"] = self.music_box.add(MusicItem(metadata=metadata, texture=self.thumbnails[f"{tab}/{music_filename}"], width=self.window.width / 1.2, height=self.window.height / 11))
-                    self.music_buttons[f"{tab}/{music_filename}"].button.on_click = lambda event, music_path=f"{tab}/{music_filename}": self.music_button_click(event, music_path)
-                    self.music_buttons[f"{tab}/{music_filename}"].view_metadata_button.on_click = lambda event, music_path=f"{tab}/{music_filename}": self.open_metadata(music_path)
+                content_to_show = [match[0] for match in matches]
 
             else:
                 self.highest_score_file = ""
-
                 self.no_music_label.visible = not self.tab_content[tab]
+                content_to_show = self.tab_content[tab]
 
-                for music_filename in self.tab_content[tab]:
-                    metadata = self.file_metadata[f"{tab}/{music_filename}"]
-                    
-                    self.music_buttons[f"{tab}/{music_filename}"] = self.music_box.add(MusicItem(metadata=metadata, texture=self.thumbnails[f"{tab}/{music_filename}"], width=self.window.width / 1.2, height=self.window.height / 11))
-                    self.music_buttons[f"{tab}/{music_filename}"].button.on_click = lambda event, music_path=f"{tab}/{music_filename}": self.music_button_click(event, music_path)
-                    self.music_buttons[f"{tab}/{music_filename}"].view_metadata_button.on_click = lambda event, music_path=f"{tab}/{music_filename}": self.open_metadata(music_path)
+            for music_filename in content_to_show:
+                metadata = self.file_metadata[f"{tab}/{music_filename}"]
+                
+                self.music_buttons[f"{tab}/{music_filename}"] = self.music_box.add(MusicItem(metadata=metadata, width=self.window.width / 1.2, height=self.window.height / 11))
+                self.music_buttons[f"{tab}/{music_filename}"].button.on_click = lambda event, music_path=f"{tab}/{music_filename}": self.music_button_click(event, music_path)
+                self.music_buttons[f"{tab}/{music_filename}"].view_metadata_button.on_click = lambda event, music_path=f"{tab}/{music_filename}": self.open_metadata(music_path)
 
         elif self.current_mode == "playlist":
             self.current_playlist = tab
@@ -311,25 +319,20 @@ class Main(arcade.gui.UIView):
                 if not self.search_term == "":
                     matches = process.extract(self.search_term, self.playlist_content[tab], limit=5, processor=lambda text: text.lower(), scorer=fuzz.partial_token_sort_ratio)
                     self.highest_score_file = matches[0][0]
-                    for match in matches:
-                        music_path = match[0]
-                        metadata = self.file_metadata[music_path]
-                        self.music_buttons[music_path] = self.music_box.add(MusicItem(metadata=metadata, texture=self.thumbnails[music_path], width=self.window.width / 1.2, height=self.window.height / 11))
-                        self.music_buttons[music_path].button.on_click = lambda event, music_path=music_path: self.music_button_click(event, music_path)
-                        self.music_buttons[music_path].view_metadata_button.on_click = lambda event, music_path=music_path: self.open_metadata(music_path)
+                    content_to_show = [match[0] for match in matches]
 
                 else:
                     self.highest_score_file = ""
-
                     self.no_music_label.visible = not self.playlist_content[tab]
+                    content_to_show = self.playlist_content[tab]
 
-                    for music_path in self.playlist_content[tab]:
-                        metadata = self.file_metadata[music_path]
-                        self.music_buttons[music_path] = self.music_box.add(MusicItem(metadata=metadata, texture=self.thumbnails[music_path], width=self.window.width / 1.2, height=self.window.height / 11))
-                        self.music_buttons[music_path].button.on_click = lambda event, music_path=music_path: self.music_button_click(event, music_path)
-                        self.music_buttons[music_path].view_metadata_button.on_click = lambda event, music_path=music_path: self.open_metadata(music_filename)
+                for music_path in content_to_show:
+                    metadata = self.file_metadata[music_path]
+                    self.music_buttons[music_path] = self.music_box.add(MusicItem(metadata=metadata, width=self.window.width / 1.2, height=self.window.height / 11))
+                    self.music_buttons[music_path].button.on_click = lambda event, music_path=music_path: self.music_button_click(event, music_path)
+                    self.music_buttons[music_path].view_metadata_button.on_click = lambda event, music_path=music_path: self.open_metadata(music_path)
 
-                self.music_buttons["add_music"] = self.music_box.add(MusicItem(metadata=None, texture=music_icon, width=self.window.width / 1.2, height=self.window.height / 11))
+                self.music_buttons["add_music"] = self.music_box.add(MusicItem(metadata=None, width=self.window.width / 1.2, height=self.window.height / 11))
                 self.music_buttons["add_music"].button.on_click = lambda event: self.add_music()
 
         self.anchor.detect_focusable_widgets()
@@ -348,12 +351,11 @@ class Main(arcade.gui.UIView):
 
             self.window.show_view(Main(self.pypresence_client, self.current_mode, self.current_music_name, # temporarily fixes the issue of bad resolution after deletion with less than 2 rows
                                        self.current_length, self.current_music_player, self.queue, self.loaded_sounds, self.shuffle))
-
+            
     def load_content(self):
         self.tab_content.clear()
         self.playlist_content.clear()
         self.file_metadata.clear()
-        self.thumbnails.clear()
         
         for tab in self.tab_options:
             expanded_tab = os.path.expanduser(tab)
@@ -367,23 +369,33 @@ class Main(arcade.gui.UIView):
             for filename in os.listdir(expanded_tab):
                 if filename.split(".")[-1] in audio_extensions:
                     if f"{expanded_tab}/{filename}" not in self.file_metadata:
-                        sound_length, bit_rate, uploader_url, source_url, artist, title, thumbnail = extract_metadata_and_thumbnail(f"{expanded_tab}/{filename}", (int(self.window.width / 16), int(self.window.height / 9)))
-                        self.file_metadata[f"{expanded_tab}/{filename}"] = {"sound_length": sound_length, "bit_rate": bit_rate, "uploader_url": uploader_url, "source_url": source_url, "artist": artist, "title": title}
-                        self.thumbnails[f"{expanded_tab}/{filename}"] = thumbnail
+                        self.file_metadata[f"{expanded_tab}/{filename}"] = extract_metadata_and_thumbnail(f"{expanded_tab}/{filename}", (int(self.window.width / 16), int(self.window.height / 9)))
                     self.tab_content[expanded_tab].append(filename)
-        
+
+        if self.tab_observer:
+            self.tab_observer.stop()
+        self.tab_observer = watch_directories(self.tab_content.keys(), self.on_file_change)
+
+        playlist_files = []
         for playlist, content in self.settings_dict.get("playlists", {}).items():
             for file in content:
+                playlist_files.append(file)
+
                 if not os.path.exists(file) or not os.path.isfile(file):
                     content.remove(file) # also removes reference from self.settings_dict["playlists"]
                     continue
                 
                 if file not in self.file_metadata:
-                    sound_length, bit_rate, uploader_url, source_url, artist, title, thumbnail = extract_metadata_and_thumbnail(file, (int(self.window.width / 16), int(self.window.height / 9)))
-                    self.file_metadata[file] = {"sound_length": sound_length, "bit_rate": bit_rate, "uploader_url": uploader_url, "source_url": source_url, "artist": artist, "title": title}
-                    self.thumbnails[file] = thumbnail
+                    self.file_metadata[file] = extract_metadata_and_thumbnail(file, (int(self.window.width / 16), int(self.window.height / 9)))
             self.playlist_content[playlist] = content
 
+        if self.playlist_observer:
+            self.playlist_observer.stop()
+        self.playlist_observer = watch_files(playlist_files, self.on_file_change)
+
+    def on_file_change(self, event_type, path):
+        self.should_reload = True # needed because the observer runs in another thread and OpenGL is single-threaded.
+
     def load_tabs(self):
         self.tab_box.clear()
 
@@ -410,6 +422,10 @@ class Main(arcade.gui.UIView):
             self.current_music_player.volume = self.volume / 100
 
     def on_update(self, delta_time):
+        if self.should_reload:
+            self.should_reload = False
+            self.reload()
+
         if self.current_music_player is None or self.current_music_player.time == 0:
             if len(self.queue) > 0:
                 music_path = self.queue.pop(0)
@@ -420,12 +436,14 @@ class Main(arcade.gui.UIView):
 
                 if self.settings_dict.get("normalize_audio", True):
                     self.current_music_label.text = "Normalizing audio..."
-                    self.window.draw(delta_time)
+                    self.window.draw(delta_time) # draw before blocking
                     try:
                         adjust_volume(music_path, self.settings_dict.get("normalized_volume", -8))
                     except Exception as e:
                         logging.error(f"Couldn't normalize volume for {music_path}: {e}")
 
+                update_last_play_statistics(music_path)
+
                 if not music_name in self.loaded_sounds:
                     self.loaded_sounds[music_name] = arcade.Sound(music_path, streaming=self.settings_dict.get("music_mode", "Stream") == "Stream")
 
@@ -438,7 +456,7 @@ class Main(arcade.gui.UIView):
                 self.current_length = self.loaded_sounds[music_name].get_length()
 
                 self.current_music_name = music_name
-                self.current_music_thumbnail_image.texture = self.thumbnails[music_path]
+                self.current_music_thumbnail_image.texture = self.file_metadata[music_path]["thumbnail"]
                 self.current_music_label.text = truncate_end(music_name, int(self.window.width / 30))
                 self.time_label.text = "00:00"
                 self.progressbar.max_value = self.current_length
diff --git a/pyproject.toml b/pyproject.toml
index 6ea4653..9ccf1f5 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -10,4 +10,5 @@ dependencies = [
     "pydub>=0.25.1",
     "pypresence>=4.3.0",
     "thefuzz>=0.22.1",
+    "watchdog>=6.0.0",
 ]
diff --git a/requirements.txt b/requirements.txt
index 34b8731..5ebfefc 100644
--- a/requirements.txt
+++ b/requirements.txt
@@ -1,7 +1,32 @@
-Pillow
+# This file was autogenerated by uv via the following command:
+#    uv pip compile pyproject.toml -o requirements.txt
 arcade==3.2.0
-pypresence
-mutagen
-yt-dlp
-thefuzz
-pydub
+    # via musicplayer (pyproject.toml)
+attrs==25.3.0
+    # via pytiled-parser
+cffi==1.17.1
+    # via pymunk
+mutagen==1.47.0
+    # via musicplayer (pyproject.toml)
+pillow==11.0.0
+    # via arcade
+pycparser==2.22
+    # via cffi
+pydub==0.25.1
+    # via musicplayer (pyproject.toml)
+pyglet==2.1.6
+    # via arcade
+pymunk==6.9.0
+    # via arcade
+pypresence==4.3.0
+    # via musicplayer (pyproject.toml)
+pytiled-parser==2.2.9
+    # via arcade
+rapidfuzz==3.13.0
+    # via thefuzz
+thefuzz==0.22.1
+    # via musicplayer (pyproject.toml)
+typing-extensions==4.14.0
+    # via pytiled-parser
+watchdog==6.0.0
+    # via musicplayer (pyproject.toml)
diff --git a/run.py b/run.py
index b2b0aca..d8bff07 100644
--- a/run.py
+++ b/run.py
@@ -33,7 +33,7 @@ timestamp = datetime.datetime.now().strftime("%Y-%m-%d_%H-%M-%S")
 log_filename = f"debug_{timestamp}.log"
 logging.basicConfig(filename=f'{os.path.join(log_dir, log_filename)}', format='%(asctime)s %(name)s %(levelname)s: %(message)s', level=logging.DEBUG)
 
-for logger_name_to_disable in ['arcade', "numba"]:
+for logger_name_to_disable in ['arcade', "watchdog", "PIL"]:
     logging.getLogger(logger_name_to_disable).propagate = False
     logging.getLogger(logger_name_to_disable).disabled = True
 
diff --git a/utils/constants.py b/utils/constants.py
index 2be02a7..a8417e4 100644
--- a/utils/constants.py
+++ b/utils/constants.py
@@ -9,6 +9,8 @@ discord_presence_id = 1368277020332523530
 
 audio_extensions = ["mp3", "m4a", "aac", "flac", "ogg", "opus", "wav"]
 
+view_modes = ["files", "playlist"]
+
 DARK_GRAY = Color(45, 45, 45)
 GRAY = Color(70, 70, 70)
 LIGHT_GRAY = Color(150, 150, 150)
diff --git a/utils/file_watching.py b/utils/file_watching.py
new file mode 100644
index 0000000..93c49f5
--- /dev/null
+++ b/utils/file_watching.py
@@ -0,0 +1,46 @@
+from watchdog.events import PatternMatchingEventHandler
+from watchdog.observers import Observer
+
+from typing import Callable
+
+from utils.constants import audio_extensions
+
+import os
+
+class DirectoryWatcher(PatternMatchingEventHandler):
+    def __init__(self, trigger_function: Callable[[str, str], None]):
+        patterns = [f"*.{ext}" for ext in audio_extensions]
+        super().__init__(patterns=patterns, ignore_directories=True, case_sensitive=False)
+        self.trigger_function = trigger_function
+
+    def on_created(self, event):
+        self.trigger_function("create", event.src_path)
+        
+    def on_deleted(self, event):
+        self.trigger_function("delete", event.src_path)
+
+def watch_directories(directory_paths: list[str], func: Callable[[str, str], None]):
+    event_handler = DirectoryWatcher(func)
+    observer = Observer()
+    
+    for directory_path in directory_paths:
+        observer.schedule(event_handler, path=directory_path)
+
+    observer.start()
+    return observer
+
+def file_hit(event_type: str, file_path: str, directories: dict[str, list[str]], func: Callable[[str, str], None]):
+    directory = os.path.dirname(file_path)
+    if directory in directories and file_path in directories[directory]:
+        func(event_type, file_path)
+
+def watch_files(file_paths: list[str], func: Callable[[str, str], None]):
+    directories: dict[str, list[str]] = {}
+    for file_path in file_paths:
+        directory = os.path.dirname(file_path)
+        directories.setdefault(directory, []).append(file_path)
+
+    return watch_directories(
+        list(directories.keys()),
+        lambda event_type, file_path: file_hit(event_type, file_path, directories, func)
+    )
\ No newline at end of file
diff --git a/utils/music_handling.py b/utils/music_handling.py
new file mode 100644
index 0000000..7fe16d4
--- /dev/null
+++ b/utils/music_handling.py
@@ -0,0 +1,189 @@
+import io, base64, tempfile, struct, re, os, logging, arcade, time
+
+from mutagen.easyid3 import EasyID3
+from mutagen.id3 import ID3, TXXX, ID3NoHeaderError
+from mutagen import File
+
+from pydub import AudioSegment
+from PIL import Image
+
+from utils.utils import convert_seconds_to_date
+
+def truncate_end(text: str, max_length: int) -> str:
+    if len(text) <= max_length:
+        return text
+    if max_length <= 3:
+        return text
+    return text[:max_length - 3] + '...'
+
+def extract_metadata_and_thumbnail(file_path: str, thumb_resolution: tuple) -> tuple:
+    artist = "Unknown"
+    title = ""
+    source_url = "Unknown"
+    uploader_url = "Unknown"
+    thumb_texture = None
+    sound_length = 0
+    bitrate = 0
+    sample_rate = 0
+    last_played = 0
+    play_count = 0
+
+    basename = os.path.basename(file_path)
+    name_only = os.path.splitext(basename)[0]
+    ext = os.path.splitext(file_path)[1].lower().lstrip('.')
+
+    try:
+        thumb_audio = EasyID3(file_path)
+        try:
+            artist = str(thumb_audio["artist"][0])
+            title = str(thumb_audio["title"][0])
+        except KeyError:
+            artist_title_match = re.search(r'^.+\s*-\s*.+$', title)
+            if artist_title_match:
+                title = title.split("- ")[1]
+
+        file_audio = File(file_path)
+        if hasattr(file_audio, 'info'):
+            sound_length = round(file_audio.info.length, 2)
+            bitrate = int((file_audio.info.bitrate or 0) / 1000)
+            sample_rate = int(file_audio.info.sample_rate / 1000)
+
+        thumb_image_data = None
+        if ext == 'mp3':
+            for tag in file_audio.values():
+                if tag.FrameID == "APIC":
+                    thumb_image_data = tag.data
+                    break
+        elif ext in ('m4a', 'aac'):
+            if 'covr' in file_audio:
+                thumb_image_data = file_audio['covr'][0]
+        elif ext == 'flac':
+            if file_audio.pictures:
+                thumb_image_data = file_audio.pictures[0].data
+        elif ext in ('ogg', 'opus'):
+            if "metadata_block_picture" in file_audio:
+                pic_data = base64.b64decode(file_audio["metadata_block_picture"][0])
+                header_len = struct.unpack(">I", pic_data[0:4])[0]
+                thumb_image_data = pic_data[4 + header_len:]
+
+        id3 = ID3(file_path)
+        for frame in id3.getall("WXXX"):
+            if frame.desc.lower() == "uploader":
+                uploader_url = frame.url
+            elif frame.desc.lower() == "source":
+                source_url = frame.url
+
+        for frame in id3.getall("TXXX"):
+            if frame.desc.lower() == "last_played":
+                last_played = float(frame.text[0])
+            elif frame.desc.lower() == "play_count":
+                play_count = int(frame.text[0])
+
+        if thumb_image_data:
+            pil_image = Image.open(io.BytesIO(thumb_image_data)).convert("RGBA")
+            pil_image = pil_image.resize(thumb_resolution)
+            thumb_texture = arcade.Texture(pil_image)
+
+    except Exception as e:
+        logging.debug(f"[Metadata/Thumbnail Error] {file_path}: {e}")
+
+    if artist == "Unknown" or not title:
+        match = re.search(r'^(.*?)\s+-\s+(.*?)$', name_only)
+        if match:
+            file_path_artist, file_path_title = match.groups()
+            if artist == "Unknown":
+                artist = file_path_artist
+            if not title:
+                title = file_path_title
+
+    if not title:
+        title = name_only
+
+    if thumb_texture is None:
+        from utils.preload import music_icon
+        thumb_texture = music_icon
+
+    file_size = round(os.path.getsize(file_path) / (1024 ** 2), 2) # MiB
+
+    return {
+        "sound_length": sound_length,
+        "bitrate": bitrate,
+        "file_size": file_size,
+        "last_played": last_played,
+        "play_count": play_count,
+        "sample_rate": sample_rate,
+        "uploader_url": uploader_url,
+        "source_url": source_url,
+        "artist": artist,
+        "title": title,
+        "thumbnail": thumb_texture
+    }
+
+def adjust_volume(input_path, volume):
+    try:
+        easy_tags = EasyID3(input_path)
+        tags = dict(easy_tags)
+        tags = {k: v[0] if isinstance(v, list) else v for k, v in tags.items()}
+    except Exception as e:
+        tags = {}
+
+    try:
+        id3 = ID3(input_path)
+        apic_frames = [f for f in id3.values() if f.FrameID == "APIC"]
+        cover_path = None
+        if apic_frames:
+            apic = apic_frames[0]
+            ext = ".jpg" if apic.mime == "image/jpeg" else ".png"
+            temp_cover = tempfile.NamedTemporaryFile(delete=False, suffix=ext)
+            temp_cover.write(apic.data)
+            temp_cover.close()
+            cover_path = temp_cover.name
+        else:
+            cover_path = None
+    except Exception as e:
+        cover_path = None
+
+    audio = AudioSegment.from_file(input_path)
+    
+    if int(audio.dBFS) == volume:
+        return
+    
+    export_args = {
+        "format": "mp3",
+        "tags": tags
+    }
+    if cover_path:
+        export_args["cover"] = cover_path
+
+    change = volume - audio.dBFS
+    audio.apply_gain(change)
+    audio.export(input_path, **export_args)
+
+def update_last_play_statistics(filepath):
+    try:
+        audio = ID3(filepath)
+    except ID3NoHeaderError:
+        audio = ID3()
+
+    audio.setall("TXXX:last_played", [TXXX(desc="last_played", text=str(time.time()))])
+
+    play_count_frames = audio.getall("TXXX:play_count")
+    if play_count_frames:
+        try:
+            count = int(play_count_frames[0].text[0])
+        except (ValueError, IndexError):
+            count = 0
+    else:
+        count = 0
+
+    audio.setall("TXXX:play_count", [TXXX(desc="play_count", text=str(count + 1))])
+
+    audio.save(filepath)
+
+def convert_timestamp_to_time_ago(timestamp):
+    current_timestamp = time.time()
+    elapsed_time = current_timestamp - timestamp
+    if not timestamp == 0:
+        return convert_seconds_to_date(elapsed_time) + ' ago'
+    else:
+        return "Never"
\ No newline at end of file
diff --git a/utils/preload.py b/utils/preload.py
index f3ad475..a4512e1 100644
--- a/utils/preload.py
+++ b/utils/preload.py
@@ -14,9 +14,9 @@ shuffle_icon = arcade.load_texture("assets/graphics/shuffle.png")
 no_shuffle_icon = arcade.load_texture("assets/graphics/no_shuffle.png")
 
 settings_icon = arcade.load_texture("assets/graphics/settings.png")
-reload_icon = arcade.load_texture("assets/graphics/reload.png")
 download_icon = arcade.load_texture("assets/graphics/download.png")
 plus_icon = arcade.load_texture("assets/graphics/plus.png")
+
 playlist_icon = arcade.load_texture("assets/graphics/playlist.png")
 files_icon = arcade.load_texture("assets/graphics/files.png")
 
diff --git a/utils/utils.py b/utils/utils.py
index 29c3dc7..cc1ba1b 100644
--- a/utils/utils.py
+++ b/utils/utils.py
@@ -1,12 +1,4 @@
-import logging, sys, traceback, os, re, platform, urllib.request, io, base64, tempfile, struct
-
-from mutagen.easyid3 import EasyID3
-from mutagen.id3 import ID3
-from mutagen import File
-
-from pydub import AudioSegment
-
-from PIL import Image
+import logging, sys, traceback
 
 from utils.constants import menu_background_color, button_style
 from utils.preload import button_texture, button_hovered_texture
@@ -88,12 +80,12 @@ class UIFocusTextureButton(arcade.gui.UITextureButton):
             self.resize(width=self.width / 1.1, height=self.height / 1.1)
 
 class MusicItem(arcade.gui.UIBoxLayout):
-    def __init__(self, metadata: dict, width: int, height: int, texture: arcade.Texture, padding=10):
+    def __init__(self, metadata: dict, width: int, height: int, padding=10):
         super().__init__(width=width, height=height, space_between=padding, align="top", vertical=False)
 
         if metadata:
             self.image = self.add(arcade.gui.UIImage(
-                texture=texture,
+                texture=metadata["thumbnail"],
                 width=height * 1.5,
                 height=height,
             ))
@@ -142,167 +134,6 @@ def get_closest_resolution():
         )
     return closest_resolution
 
-def get_yt_dlp_binary_path():
-    system = platform.system()
-
-    if system == "Windows":
-        binary = "yt-dlp.exe"
-    elif system == "Darwin":
-        binary = "yt-dlp_macos"
-    elif system == "Linux":
-        binary = "yt-dlp_linux"
-
-    return os.path.join("bin", binary)
-
-def ensure_yt_dlp():
-    path = get_yt_dlp_binary_path()
-
-    if not os.path.exists("bin"):
-        os.makedirs("bin")
-
-    if not os.path.exists(path):
-        system = platform.system()
-
-        if system == "Windows":
-            url = "https://github.com/yt-dlp/yt-dlp/releases/latest/download/yt-dlp.exe"
-        elif system == "Darwin":
-            url = "https://github.com/yt-dlp/yt-dlp/releases/latest/download/yt-dlp_macos"
-        elif system == "Linux":
-            url = "https://github.com/yt-dlp/yt-dlp/releases/latest/download/yt-dlp_linux"
-        else:
-            raise RuntimeError("Unsupported OS")
-
-        urllib.request.urlretrieve(url, path)
-        os.chmod(path, 0o755)
-
-    return path
-
-def truncate_end(text: str, max_length: int) -> str:
-    if len(text) <= max_length:
-        return text
-    if max_length <= 3:
-        return text
-    return text[:max_length - 3] + '...'
-
-def extract_metadata_and_thumbnail(filename: str, thumb_resolution: tuple) -> tuple:
-    artist = "Unknown"
-    title = ""
-    source_url = "Unknown"
-    creator_url = "Unknown"
-    thumb_texture = None
-    sound_length = 0
-    bit_rate = 0
-
-    basename = os.path.basename(filename)
-    name_only = re.sub(r'\s*\[[a-zA-Z0-9\-_]{5,}\]$', '', os.path.splitext(basename)[0])
-    ext = os.path.splitext(filename)[1].lower().lstrip('.')
-
-    try:
-        thumb_audio = EasyID3(filename)
-        try:
-            artist = str(thumb_audio["artist"][0])
-            title = str(thumb_audio["title"][0])
-        except KeyError:
-            artist_title_match = re.search(r'^.+\s*-\s*.+$', title)
-            if artist_title_match:
-                title = title.split("- ")[1]
-
-        file_audio = File(filename)
-        if hasattr(file_audio, 'info'):
-            sound_length = round(file_audio.info.length, 2)
-            bit_rate = int((file_audio.info.bitrate or 0) / 1000)
-
-        thumb_image_data = None
-        if ext == 'mp3':
-            for tag in file_audio.values():
-                if tag.FrameID == "APIC":
-                    thumb_image_data = tag.data
-                    break
-        elif ext in ('m4a', 'aac'):
-            if 'covr' in file_audio:
-                thumb_image_data = file_audio['covr'][0]
-        elif ext == 'flac':
-            if file_audio.pictures:
-                thumb_image_data = file_audio.pictures[0].data
-        elif ext in ('ogg', 'opus'):
-            if "metadata_block_picture" in file_audio:
-                pic_data = base64.b64decode(file_audio["metadata_block_picture"][0])
-                header_len = struct.unpack(">I", pic_data[0:4])[0]
-                thumb_image_data = pic_data[4 + header_len:]
-
-        id3 = ID3(filename)
-        for frame in id3.getall("WXXX"):
-            if frame.desc.lower() == "creator":
-                creator_url = frame.url
-            elif frame.desc.lower() == "source":
-                source_url = frame.url
-
-        if thumb_image_data:
-            pil_image = Image.open(io.BytesIO(thumb_image_data)).convert("RGBA")
-            pil_image = pil_image.resize(thumb_resolution)
-            thumb_texture = arcade.Texture(pil_image)
-
-    except Exception as e:
-        logging.debug(f"[Metadata/Thumbnail Error] {filename}: {e}")
-
-    if artist == "Unknown" or not title:
-        match = re.search(r'^(.*?)\s+-\s+(.*?)$', name_only)
-        if match:
-            filename_artist, filename_title = match.groups()
-            if artist == "Unknown":
-                artist = filename_artist
-            if not title:
-                title = filename_title
-
-    if not title:
-        title = name_only
-
-    if thumb_texture is None:
-        from utils.preload import music_icon
-        thumb_texture = music_icon
-
-    return sound_length, bit_rate, creator_url, source_url, artist, title, thumb_texture
-
-def adjust_volume(input_path, volume):
-    try:
-        easy_tags = EasyID3(input_path)
-        tags = dict(easy_tags)
-        tags = {k: v[0] if isinstance(v, list) else v for k, v in tags.items()}
-    except Exception as e:
-        tags = {}
-
-    try:
-        id3 = ID3(input_path)
-        apic_frames = [f for f in id3.values() if f.FrameID == "APIC"]
-        cover_path = None
-        if apic_frames:
-            apic = apic_frames[0]
-            ext = ".jpg" if apic.mime == "image/jpeg" else ".png"
-            temp_cover = tempfile.NamedTemporaryFile(delete=False, suffix=ext)
-            temp_cover.write(apic.data)
-            temp_cover.close()
-            cover_path = temp_cover.name
-        else:
-            cover_path = None
-    except Exception as e:
-        cover_path = None
-
-    audio = AudioSegment.from_file(input_path)
-    
-    if int(audio.dBFS) == volume:
-        return
-    
-    export_args = {
-        "format": "mp3",
-        "tags": tags
-    }
-    if cover_path:
-        export_args["cover"] = cover_path
-
-    change = volume - audio.dBFS
-    audio.apply_gain(change)
-    audio.export(input_path, **export_args)
-
 def convert_seconds_to_date(seconds):
     days, remainder = divmod(seconds, 86400)
     hours, remainder = divmod(remainder, 3600)
diff --git a/uv.lock b/uv.lock
index 62c94d0..5f9c3cf 100644
--- a/uv.lock
+++ b/uv.lock
@@ -81,6 +81,7 @@ dependencies = [
     { name = "pydub" },
     { name = "pypresence" },
     { name = "thefuzz" },
+    { name = "watchdog" },
 ]
 
 [package.metadata]
@@ -90,6 +91,7 @@ requires-dist = [
     { name = "pydub", specifier = ">=0.25.1" },
     { name = "pypresence", specifier = ">=4.3.0" },
     { name = "thefuzz", specifier = ">=0.22.1" },
+    { name = "watchdog", specifier = ">=6.0.0" },
 ]
 
 [[package]]
@@ -313,3 +315,30 @@ sdist = { url = "https://files.pythonhosted.org/packages/d1/bc/51647cd02527e87d0
 wheels = [
     { url = "https://files.pythonhosted.org/packages/69/e0/552843e0d356fbb5256d21449fa957fa4eff3bbc135a74a691ee70c7c5da/typing_extensions-4.14.0-py3-none-any.whl", hash = "sha256:a1514509136dd0b477638fc68d6a91497af5076466ad0fa6c338e44e359944af", size = 43839, upload_time = "2025-06-02T14:52:10.026Z" },
 ]
+
+[[package]]
+name = "watchdog"
+version = "6.0.0"
+source = { registry = "https://pypi.org/simple" }
+sdist = { url = "https://files.pythonhosted.org/packages/db/7d/7f3d619e951c88ed75c6037b246ddcf2d322812ee8ea189be89511721d54/watchdog-6.0.0.tar.gz", hash = "sha256:9ddf7c82fda3ae8e24decda1338ede66e1c99883db93711d8fb941eaa2d8c282", size = 131220, upload_time = "2024-11-01T14:07:13.037Z" }
+wheels = [
+    { url = "https://files.pythonhosted.org/packages/e0/24/d9be5cd6642a6aa68352ded4b4b10fb0d7889cb7f45814fb92cecd35f101/watchdog-6.0.0-cp311-cp311-macosx_10_9_universal2.whl", hash = "sha256:6eb11feb5a0d452ee41f824e271ca311a09e250441c262ca2fd7ebcf2461a06c", size = 96393, upload_time = "2024-11-01T14:06:31.756Z" },
+    { url = "https://files.pythonhosted.org/packages/63/7a/6013b0d8dbc56adca7fdd4f0beed381c59f6752341b12fa0886fa7afc78b/watchdog-6.0.0-cp311-cp311-macosx_10_9_x86_64.whl", hash = "sha256:ef810fbf7b781a5a593894e4f439773830bdecb885e6880d957d5b9382a960d2", size = 88392, upload_time = "2024-11-01T14:06:32.99Z" },
+    { url = "https://files.pythonhosted.org/packages/d1/40/b75381494851556de56281e053700e46bff5b37bf4c7267e858640af5a7f/watchdog-6.0.0-cp311-cp311-macosx_11_0_arm64.whl", hash = "sha256:afd0fe1b2270917c5e23c2a65ce50c2a4abb63daafb0d419fde368e272a76b7c", size = 89019, upload_time = "2024-11-01T14:06:34.963Z" },
+    { url = "https://files.pythonhosted.org/packages/39/ea/3930d07dafc9e286ed356a679aa02d777c06e9bfd1164fa7c19c288a5483/watchdog-6.0.0-cp312-cp312-macosx_10_13_universal2.whl", hash = "sha256:bdd4e6f14b8b18c334febb9c4425a878a2ac20efd1e0b231978e7b150f92a948", size = 96471, upload_time = "2024-11-01T14:06:37.745Z" },
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