diff --git a/src/ytdl_sub/plugins/subtitles.py b/src/ytdl_sub/plugins/subtitles.py
index de98f888..0ea85244 100644
--- a/src/ytdl_sub/plugins/subtitles.py
+++ b/src/ytdl_sub/plugins/subtitles.py
@@ -1,3 +1,4 @@
+from pathlib import Path
 from typing import Dict
 from typing import List
 from typing import Optional
@@ -7,6 +8,7 @@ from ytdl_sub.downloaders.ytdl_options_builder import YTDLOptionsBuilder
 from ytdl_sub.entries.entry import Entry
 from ytdl_sub.plugins.plugin import Plugin
 from ytdl_sub.plugins.plugin import PluginOptions
+from ytdl_sub.utils.file_handler import FileHandler
 from ytdl_sub.utils.file_handler import FileMetadata
 from ytdl_sub.utils.logger import Logger
 from ytdl_sub.validators.string_formatter_validators import StringFormatterValidator
@@ -206,4 +208,11 @@ class SubtitlesPlugin(Plugin[SubtitleOptions]):
                     entry=entry,
                 )
 
+                # Delete any possible original subtitle files before conversion
+                for possible_ext in SUBTITLE_EXTENSIONS:
+                    possible_subs_file = (
+                        Path(self.working_directory) / f"{entry.uid}.{lang}.{possible_ext}"
+                    )
+                    FileHandler.delete(possible_subs_file)
+
         return file_metadata
diff --git a/src/ytdl_sub/utils/file_handler.py b/src/ytdl_sub/utils/file_handler.py
index 2b8f1ced..ddabadd4 100644
--- a/src/ytdl_sub/utils/file_handler.py
+++ b/src/ytdl_sub/utils/file_handler.py
@@ -414,6 +414,9 @@ class FileHandler:
                 self.copy(src_file_path=source_file_path, dst_file_path=output_file_path)
             else:
                 self.move(src_file_path=source_file_path, dst_file_path=output_file_path)
+        # Simulate the file being moved during dry run by deleting it
+        elif self.dry_run and not copy_file:
+            FileHandler.delete(source_file_path)
 
     def delete_file_from_output_directory(self, file_name: str):
         """
diff --git a/src/ytdl_sub/utils/thumbnail.py b/src/ytdl_sub/utils/thumbnail.py
index 25a4b9f5..2b3ee102 100644
--- a/src/ytdl_sub/utils/thumbnail.py
+++ b/src/ytdl_sub/utils/thumbnail.py
@@ -5,6 +5,7 @@ from urllib.request import urlopen
 
 from ytdl_sub.entries.entry import Entry
 from ytdl_sub.utils.ffmpeg import FFMPEG
+from ytdl_sub.utils.file_handler import FileHandler
 from ytdl_sub.utils.retry import retry
 
 
@@ -42,6 +43,7 @@ def convert_download_thumbnail(entry: Entry, error_if_not_found: bool = True) ->
 
     if not download_thumbnail_path == download_thumbnail_path_as_jpg:
         FFMPEG.run(["-bitexact", "-i", download_thumbnail_path, download_thumbnail_path_as_jpg])
+        FileHandler.delete(download_thumbnail_path)
 
 
 @retry(times=5, exceptions=(Exception,))