diff --git a/src/ytdl_sub/cli/main.py b/src/ytdl_sub/cli/main.py
index f88f74e8..b6b93548 100644
--- a/src/ytdl_sub/cli/main.py
+++ b/src/ytdl_sub/cli/main.py
@@ -40,7 +40,7 @@ def _download_subscriptions_from_yaml_files(
     subscriptions: List[Subscription] = []
     output: List[Tuple[Subscription, FileHandlerTransactionLog]] = []
 
-    # Load all of the subscriptions first to perform all validation before downloading
+    # Load all the subscriptions first to perform all validation before downloading
     for path in subscription_paths:
         subscriptions += Subscription.from_file_path(config=config, subscription_path=path)
 
@@ -55,6 +55,7 @@ def _download_subscriptions_from_yaml_files(
 
         output.append((subscription, transaction_log))
         gc.collect()  # Garbage collect after each subscription download
+        Logger.cleanup()  # Cleanup logger after each successful subscription download
 
     return output
 
diff --git a/src/ytdl_sub/utils/logger.py b/src/ytdl_sub/utils/logger.py
index 095c86aa..3112f918 100644
--- a/src/ytdl_sub/utils/logger.py
+++ b/src/ytdl_sub/utils/logger.py
@@ -197,7 +197,7 @@ class Logger:
     @classmethod
     def cleanup(cls, delete_debug_file: bool = True):
         """
-        Cleans up any log files left behind.
+        Cleans up any log files left behind
 
         Parameters
         ----------
diff --git a/tests/unit/utils/test_logger.py b/tests/unit/utils/test_logger.py
index d46534bd..8d6ebec7 100644
--- a/tests/unit/utils/test_logger.py
+++ b/tests/unit/utils/test_logger.py
@@ -94,13 +94,28 @@ class TestLogger:
 
         assert lines == ["[ytdl-sub:name_test] info test\n", "[ytdl-sub:name_test] debug test\n"]
 
-        # Ensure the file cleans up too
-        for handler in logger.handlers:
-            handler.close()
-
         Logger.cleanup(delete_debug_file=True)
         assert not os.path.isfile(Logger._DEBUG_LOGGER_FILE.name)
 
+    def test_logger_can_be_cleaned_during_execution(self):
+        Logger._LOGGER_LEVEL = LoggerLevels.INFO
+        logger = Logger.get(name="name_test")
+
+        for _ in range(2):
+            logger.info("info test")
+            logger.debug("debug test")
+
+            with open(Logger._DEBUG_LOGGER_FILE.name, "r", encoding="utf-8") as log_file:
+                lines = log_file.readlines()
+
+            assert lines == [
+                "[ytdl-sub:name_test] info test\n",
+                "[ytdl-sub:name_test] debug test\n",
+            ]
+
+            Logger.cleanup(delete_debug_file=True)
+            assert not os.path.isfile(Logger._DEBUG_LOGGER_FILE.name)
+
     @pytest.mark.parametrize(
         "log_level, expected_stdout",
         [