diff --git a/app/lib/populate.py b/app/lib/populate.py
index 3ca20946..e648e19e 100644
--- a/app/lib/populate.py
+++ b/app/lib/populate.py
@@ -77,12 +77,14 @@ class Populate:
         for _dir in dirs_to_scan:
             files = files.union(run_fast_scandir(_dir, full=True)[1])
 
-        unmodified = self.remove_modified(tracks)
+        unmodified, modified_tracks = self.remove_modified(tracks)
         untagged = files - unmodified
 
         if len(untagged) != 0:
             self.tag_untagged(untagged, key)
 
+        self.extract_thumb_with_overwrite(modified_tracks)
+
         ProcessTrackThumbnails()
         ProcessAlbumColors()
         ProcessArtistColors()
@@ -116,24 +118,26 @@ class Populate:
         since they were added to the database.
         """
 
-        unmodified = set()
-        modified = set()
+        unmodified_paths = set()
+        modified_tracks: list[Track] = []
+        modified_paths = set()
 
         for track in tracks:
             try:
                 if track.last_mod == os.path.getmtime(track.filepath):
-                    unmodified.add(track.filepath)
+                    unmodified_paths.add(track.filepath)
                     continue
             except (FileNotFoundError, OSError) as e:
                 TrackStore.remove_track_obj(track)
                 remove_tracks_by_filepaths(track.filepath)
 
-            modified.add(track.filepath)
+            modified_paths.add(track.filepath)
+            modified_tracks.append(track)
 
-        TrackStore.remove_tracks_by_filepaths(modified)
-        remove_tracks_by_filepaths(modified)
+        TrackStore.remove_tracks_by_filepaths(modified_paths)
+        remove_tracks_by_filepaths(modified_paths)
 
-        return unmodified
+        return unmodified_paths, modified_tracks
 
     @staticmethod
     def tag_untagged(untagged: set[str], key: str):
@@ -178,6 +182,19 @@ class Populate:
 
         log.info("Added %s/%s tracks", tagged_count, len(untagged))
 
+    @staticmethod
+    def extract_thumb_with_overwrite(tracks: list[Track]):
+        """
+        Extracts the thumbnail from a list of filepaths,
+        overwriting the existing thumbnail if it exists,
+        for modified files.
+        """
+        for track in tracks:
+            try:
+                extract_thumb(track.filepath, track.image, overwrite=True)
+            except FileNotFoundError:
+                continue
+
 
 def get_image(album: Album):
     """
@@ -259,7 +276,7 @@ class FetchSimilarArtistsLastFM:
                 tqdm(
                     pool.imap_unordered(save_similar_artists, artists),
                     total=len(artists),
-                    desc="Downloading similar artists",
+                    desc="Fetching similar artists",
                 )
             )
 
diff --git a/app/lib/taglib.py b/app/lib/taglib.py
index b63a6897..57a24d65 100644
--- a/app/lib/taglib.py
+++ b/app/lib/taglib.py
@@ -24,9 +24,10 @@ def parse_album_art(filepath: str):
         return None
 
 
-def extract_thumb(filepath: str, webp_path: str) -> bool:
+def extract_thumb(filepath: str, webp_path: str, overwrite=False) -> bool:
     """
-    Extracts the thumbnail from an audio file. Returns the path to the thumbnail.
+    Extracts the thumbnail from an audio file.
+    Returns the path to the thumbnail.
     """
     original_img_path = os.path.join(Paths.get_original_thumb_path(), webp_path)
     lg_img_path = os.path.join(Paths.get_lg_thumb_path(), webp_path)
@@ -40,7 +41,7 @@ def extract_thumb(filepath: str, webp_path: str) -> bool:
         img.resize((tsize, tsize), Image.ANTIALIAS).save(lg_img_path, "webp")
         img.resize((sm_tsize, sm_tsize), Image.ANTIALIAS).save(sm_img_path, "webp")
 
-    if os.path.exists(lg_img_path):
+    if not overwrite and os.path.exists(lg_img_path):
         img_size = os.path.getsize(lg_img_path)
 
         if img_size > 0:
@@ -67,7 +68,10 @@ def extract_thumb(filepath: str, webp_path: str) -> bool:
     return False
 
 
-def extract_date(date_str: str | None) -> int | None:
+def parse_date(date_str: str | None) -> int | None:
+    """
+    Extracts the date from a string and returns a timestamp.
+    """
     try:
         date = pendulum.parse(date_str, strict=False)
         return int(date.timestamp())
@@ -76,6 +80,10 @@ def extract_date(date_str: str | None) -> int | None:
 
 
 def get_tags(filepath: str):
+    """
+    Returns the tags for a given audio file.
+    """
+
     filetype = filepath.split(".")[-1]
     filename = (filepath.split("/")[-1]).replace(f".{filetype}", "")
 
@@ -149,7 +157,7 @@ def get_tags(filepath: str):
     tags.image = f"{tags.albumhash}.webp"
     tags.folder = win_replace_slash(os.path.dirname(filepath))
 
-    tags.date = extract_date(tags.year) or int(last_mod)
+    tags.date = parse_date(tags.year) or int(last_mod)
     tags.filepath = win_replace_slash(filepath)
     tags.filetype = filetype
     tags.last_mod = last_mod
diff --git a/app/lib/watchdogg.py b/app/lib/watchdogg.py
index bb77bf91..a6dce629 100644
--- a/app/lib/watchdogg.py
+++ b/app/lib/watchdogg.py
@@ -184,7 +184,7 @@ def add_track(filepath: str) -> None:
         if not ArtistStore.artist_exists(artist.artisthash):
             ArtistStore.add_artist(Artist(artist.name))
 
-    extract_thumb(filepath, track.image)
+    extract_thumb(filepath, track.image, overwrite=True)
 
 
 def remove_track(filepath: str) -> None: