diff --git a/.gitignore b/.gitignore
index 1cffda606..257924c6e 100644
--- a/.gitignore
+++ b/.gitignore
@@ -145,3 +145,6 @@ temp/
 # VS Code
 .vscode
 *.txt
+
+# Output Folder
+output/
\ No newline at end of file
diff --git a/spotdl/download/downloader.py b/spotdl/download/downloader.py
index fdf86fb70..60db8c500 100644
--- a/spotdl/download/downloader.py
+++ b/spotdl/download/downloader.py
@@ -459,6 +459,18 @@ def search_and_download(  # pylint: disable=R0911
                 restrict=self.settings["restrict"],
                 file_name_length=self.settings["max_filename_length"],
             )
+
+            # Update output path using song.album_name if valid; otherwise, use song.artist.
+            output_file = (
+                Path("output")
+                / (
+                    Path(song.album_name)
+                    if Path(song.album_name).is_dir()
+                    else Path(song.artist)
+                )
+                / output_file
+            )
+
         except Exception:
             song = reinit_song(song)
 
@@ -470,6 +482,17 @@ def search_and_download(  # pylint: disable=R0911
                 file_name_length=self.settings["max_filename_length"],
             )
 
+            # Update output path using song.album_name if valid; otherwise, use song.artist.
+            output_file = (
+                Path("output")
+                / (
+                    Path(song.album_name)
+                    if Path(song.album_name).is_dir()
+                    else Path(song.artist)
+                )
+                / output_file
+            )
+
             reinitialized = True
 
         if song.explicit is True and self.settings["skip_explicit"] is True:
@@ -488,14 +511,14 @@ def search_and_download(  # pylint: disable=R0911
             dup_song_paths: List[Path] = self.known_songs.get(song.url, [])
 
             # Remove files from the list that have the same path as the output file
-            dup_song_paths = [
-                dup_song_path
-                for dup_song_path in dup_song_paths
-                if (dup_song_path.absolute() != output_file.absolute())
-                and dup_song_path.exists()
-            ]
+            dup_song_paths = list(Path(output_file.parts[0]).rglob(output_file.name))
+
+            # Checking if file already exists in all subfolders of output directory
+            file_exists = (
+                next(Path(output_file.parts[0]).rglob(output_file.name), None)
+                or dup_song_paths
+            )
 
-            file_exists = output_file.exists() or dup_song_paths
             if not self.settings["scan_for_songs"]:
                 for file_extension in self.scan_formats:
                     ext_path = output_file.with_suffix(f".{file_extension}")
@@ -571,7 +594,7 @@ def search_and_download(  # pylint: disable=R0911
                         logger.info("Removing duplicate file: %s", dup_song_path)
 
                         dup_song_path.unlink()
-                    except (PermissionError, OSError) as exc:
+                    except (PermissionError, OSError, Exception) as exc:
                         logger.debug(
                             "Could not remove duplicate file: %s, error: %s",
                             dup_song_path,