diff --git a/src/ytdl_sub/cli/entrypoint.py b/src/ytdl_sub/cli/entrypoint.py
index c685fb6f..442d04c3 100644
--- a/src/ytdl_sub/cli/entrypoint.py
+++ b/src/ytdl_sub/cli/entrypoint.py
@@ -5,7 +5,6 @@ from datetime import datetime
 from pathlib import Path
 from typing import List
 from typing import Optional
-from typing import Tuple
 
 from yt_dlp.utils import sanitize_filename
 
@@ -20,7 +19,6 @@ from ytdl_sub.subscriptions.subscription import Subscription
 from ytdl_sub.utils.exceptions import ExperimentalFeatureNotEnabled
 from ytdl_sub.utils.exceptions import ValidationException
 from ytdl_sub.utils.file_handler import FileHandler
-from ytdl_sub.utils.file_handler import FileHandlerTransactionLog
 from ytdl_sub.utils.file_lock import working_directory_lock
 from ytdl_sub.utils.logger import Logger
 
@@ -31,6 +29,10 @@ logger = Logger.get()
 _VIEW_EXTRA_ARGS_FORMATTER = "--preset _view --overrides.url {}"
 
 
+def _log_time() -> str:
+    return datetime.now().strftime("%Y-%m-%d-%H%M%S")
+
+
 def _maybe_write_subscription_log_file(
     config: ConfigFile,
     subscription: Subscription,
@@ -51,15 +53,14 @@ def _maybe_write_subscription_log_file(
     if success and not config.config_options.persist_logs.keep_successful_logs:
         return
 
-    log_time = datetime.now().strftime("%Y-%m-%d-%H%M%S")
     log_subscription_name = sanitize_filename(subscription.name).lower().replace(" ", "_")
     log_success = "success" if success else "error"
 
-    log_filename = f"{log_time}.{log_subscription_name}.{log_success}.log"
+    log_filename = f"{_log_time()}.{log_subscription_name}.{log_success}.log"
     persist_log_path = Path(config.config_options.persist_logs.logs_directory) / log_filename
 
     if not success:
-        Logger.log_exit_exception(exception=exception, log_filepath=persist_log_path)
+        Logger.log_exception(exception=exception, log_filepath=persist_log_path)
 
     os.makedirs(os.path.dirname(persist_log_path), exist_ok=True)
     FileHandler.copy(Logger.debug_log_filename(), persist_log_path)
@@ -67,7 +68,7 @@ def _maybe_write_subscription_log_file(
 
 def _download_subscriptions_from_yaml_files(
     config: ConfigFile, subscription_paths: List[str], update_with_info_json: bool, dry_run: bool
-) -> List[Tuple[Subscription, FileHandlerTransactionLog]]:
+) -> List[Subscription]:
     """
     Downloads all subscriptions from one or many subscription yaml files.
 
@@ -84,7 +85,7 @@ def _download_subscriptions_from_yaml_files(
 
     Returns
     -------
-    List of (subscription, transaction_log)
+    List of subscriptions processed
 
     Raises
     ------
@@ -92,45 +93,41 @@ def _download_subscriptions_from_yaml_files(
         Any exception during download
     """
     subscriptions: List[Subscription] = []
-    output: List[Tuple[Subscription, FileHandlerTransactionLog]] = []
 
     # 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)
 
     for subscription in subscriptions:
-        logger.info(
-            "Beginning subscription %s for %s",
-            ("dry run" if dry_run else "download"),
-            subscription.name,
-        )
-        logger.debug("Subscription full yaml:\n%s", subscription.as_yaml())
+        with subscription.exception_handling():
+            logger.info(
+                "Beginning subscription %s for %s",
+                ("dry run" if dry_run else "download"),
+                subscription.name,
+            )
+            logger.debug("Subscription full yaml:\n%s", subscription.as_yaml())
 
-        try:
             if update_with_info_json:
-                transaction_log = subscription.update_with_info_json(dry_run=dry_run)
+                subscription.update_with_info_json(dry_run=dry_run)
             else:
-                transaction_log = subscription.download(dry_run=dry_run)
-        except Exception as exc:  # pylint: disable=broad-except
-            _maybe_write_subscription_log_file(
-                config=config, subscription=subscription, dry_run=dry_run, exception=exc
-            )
-            raise
-        else:
-            output.append((subscription, transaction_log))
-            _maybe_write_subscription_log_file(
-                config=config, subscription=subscription, dry_run=dry_run
-            )
-            Logger.cleanup()  # Cleanup logger after each successful subscription download
-        finally:
-            gc.collect()  # Garbage collect after each subscription download
+                subscription.download(dry_run=dry_run)
 
-    return output
+        _maybe_write_subscription_log_file(
+            config=config,
+            subscription=subscription,
+            dry_run=dry_run,
+            exception=subscription.exception,
+        )
+
+        Logger.cleanup(cleanup_error_log=False)
+        gc.collect()  # Garbage collect after each subscription download
+
+    return subscriptions
 
 
 def _download_subscription_from_cli(
     config: ConfigFile, dry_run: bool, extra_args: List[str]
-) -> Tuple[Subscription, FileHandlerTransactionLog]:
+) -> Subscription:
     """
     Downloads a one-off subscription using the CLI
 
@@ -158,12 +155,12 @@ def _download_subscription_from_cli(
     )
 
     logger.info("Beginning CLI %s", ("dry run" if dry_run else "download"))
-    return subscription, subscription.download(dry_run=dry_run)
+    subscription.download(dry_run=dry_run)
+
+    return subscription
 
 
-def _view_url_from_cli(
-    config: ConfigFile, url: str, split_chapters: bool
-) -> Tuple[Subscription, FileHandlerTransactionLog]:
+def _view_url_from_cli(config: ConfigFile, url: str, split_chapters: bool) -> Subscription:
     """
     `ytdl-sub view` dry-runs a URL to print its source variables. Use the pre-built `_view` preset,
     inject the URL argument, and dry-run.
@@ -180,10 +177,12 @@ def _view_url_from_cli(
         url,
         " with split chapters" if split_chapters else "",
     )
-    return subscription, subscription.download(dry_run=True)
+    subscription.download(dry_run=True)
+
+    return subscription
 
 
-def main() -> List[Tuple[Subscription, FileHandlerTransactionLog]]:
+def main() -> List[Subscription]:
     """
     Entrypoint for ytdl-sub, without the error handling
     """
@@ -203,7 +202,7 @@ def main() -> List[Tuple[Subscription, FileHandlerTransactionLog]]:
         logger.info("No config specified, using defaults.")
         config = ConfigFile(name="default_config", value={})
 
-    transaction_logs: List[Tuple[Subscription, FileHandlerTransactionLog]] = []
+    subscriptions: List[Subscription] = []
 
     # If transaction log file is specified, make sure we can open it
     _maybe_validate_transaction_log_file(transaction_log_file_path=args.transaction_log)
@@ -222,7 +221,7 @@ def main() -> List[Tuple[Subscription, FileHandlerTransactionLog]]:
                     "full backup before usage. You have been warned!",
                 )
 
-            transaction_logs = _download_subscriptions_from_yaml_files(
+            subscriptions = _download_subscriptions_from_yaml_files(
                 config=config,
                 subscription_paths=args.subscription_paths,
                 update_with_info_json=args.update_with_info_json,
@@ -231,13 +230,13 @@ def main() -> List[Tuple[Subscription, FileHandlerTransactionLog]]:
 
         # One-off download
         elif args.subparser == "dl":
-            transaction_logs.append(
+            subscriptions.append(
                 _download_subscription_from_cli(
                     config=config, dry_run=args.dry_run, extra_args=extra_args
                 )
             )
         elif args.subparser == "view":
-            transaction_logs.append(
+            subscriptions.append(
                 _view_url_from_cli(config=config, url=args.url, split_chapters=args.split_chapters)
             )
         else:
@@ -245,10 +244,10 @@ def main() -> List[Tuple[Subscription, FileHandlerTransactionLog]]:
 
     if not args.suppress_transaction_log:
         output_transaction_log(
-            transaction_logs=transaction_logs,
+            subscriptions=subscriptions,
             transaction_log_file_path=args.transaction_log,
         )
 
-    output_summary(transaction_logs)
+    output_summary(subscriptions)
 
-    return transaction_logs
+    return subscriptions
diff --git a/src/ytdl_sub/cli/output_summary.py b/src/ytdl_sub/cli/output_summary.py
index 607f0bf6..61cf2317 100644
--- a/src/ytdl_sub/cli/output_summary.py
+++ b/src/ytdl_sub/cli/output_summary.py
@@ -1,10 +1,8 @@
 from typing import List
-from typing import Tuple
 
 from colorama import Fore
 
 from ytdl_sub.subscriptions.subscription import Subscription
-from ytdl_sub.utils.file_handler import FileHandlerTransactionLog
 from ytdl_sub.utils.logger import Logger
 
 logger = Logger.get()
@@ -37,51 +35,52 @@ def _color_int(value: int) -> str:
     return _no_color(str_int)
 
 
-def output_summary(transaction_logs: List[Tuple[Subscription, FileHandlerTransactionLog]]) -> str:
+def output_summary(subscriptions: List[Subscription]) -> None:
     """
     Parameters
     ----------
-    transaction_logs
-        Transaction logs from downloaded subscriptions
+    subscriptions
+        Processed subscriptions
 
     Returns
     -------
     Output summary to print
     """
+    # many locals for proper output printing
+    # pylint: disable=too-many-locals
+    if len(subscriptions) == 0:
+        logger.info("No subscriptions ran")
+        return
+
     summary: List[str] = []
 
+    # Initialize totals to 0
+    total_subs: int = len(subscriptions)
+    total_subs_str = f"Total: {total_subs}"
+    total_added: int = sum(sub.num_entries_added for sub in subscriptions)
+    total_modified: int = sum(sub.num_entries_modified for sub in subscriptions)
+    total_removed: int = sum(sub.num_entries_removed for sub in subscriptions)
+    total_entries: int = sum(sub.num_entries for sub in subscriptions)
+    total_errors: int = sum(sub.exception is not None for sub in subscriptions)
+
     # Initialize widths to 0
-    width_sub_name: int = 0
-    width_num_entries_added: int = 0
-    width_num_entries_modified: int = 0
-    width_num_entries_removed: int = 0
-    width_num_entries: int = 0
-
-    # Calculate min width needed
-    for subscription, _ in transaction_logs:
-        width_sub_name = max(width_sub_name, len(subscription.name))
-        width_num_entries_added = max(
-            width_num_entries_added, len(_color_int(subscription.num_entries_added))
-        )
-        width_num_entries_modified = max(
-            width_num_entries_modified, len(_color_int(subscription.num_entries_modified))
-        )
-        width_num_entries_removed = max(
-            width_num_entries_removed, len(_color_int(subscription.num_entries_removed * -1))
-        )
-        width_num_entries = max(width_num_entries, len(str(subscription.num_entries)))
-
-    # Add spacing for aesthetics
-    width_sub_name += 4
-    width_num_entries += 4
+    width_sub_name: int = max(len(sub.name) for sub in subscriptions) + 4  # aesthetics
+    width_num_entries_added: int = len(_color_int(total_added))
+    width_num_entries_modified: int = len(_color_int(total_modified))
+    width_num_entries_removed: int = len(_color_int(total_removed))
+    width_num_entries: int = len(str(total_entries)) + 4  # aesthetics
 
     # Build the summary
-    for subscription, _ in transaction_logs:
+    for subscription in subscriptions:
         num_entries_added = _color_int(subscription.num_entries_added)
         num_entries_modified = _color_int(subscription.num_entries_modified)
         num_entries_removed = _color_int(subscription.num_entries_removed * -1)
         num_entries = str(subscription.num_entries)
-        status = _green("success")
+        status = (
+            _red(subscription.exception.__class__.__name__)
+            if subscription.exception
+            else _green("✔")
+        )
 
         summary.append(
             f"{subscription.name:<{width_sub_name}} "
@@ -92,5 +91,23 @@ def output_summary(transaction_logs: List[Tuple[Subscription, FileHandlerTransac
             f"{status}"
         )
 
+    total_errors_str = (
+        _green("Success") if total_errors == 0 else _red(f"Error{'s' if total_errors > 1 else ''}")
+    )
+
+    summary.append(
+        f"{total_subs_str:<{width_sub_name}} "
+        f"{_color_int(total_added):>{width_num_entries_added}} "
+        f"{_color_int(total_modified):>{width_num_entries_modified}} "
+        f"{_color_int(total_removed):>{width_num_entries_removed}} "
+        f"{total_entries:>{width_num_entries}} "
+        f"{total_errors_str}"
+    )
+
+    if total_errors > 0:
+        summary.append("")
+        summary.append(f"See `{Logger.error_log_filename()}` for details on errors.")
+        summary.append("Consider making a GitHub issue including the uploaded log file.")
+
     # Hack to always show download summary, even if logs are set to quiet
     logger.warning("Download Summary:\n%s", "\n".join(summary))
diff --git a/src/ytdl_sub/cli/output_transaction_log.py b/src/ytdl_sub/cli/output_transaction_log.py
index 6bf5e07b..ce46de0c 100644
--- a/src/ytdl_sub/cli/output_transaction_log.py
+++ b/src/ytdl_sub/cli/output_transaction_log.py
@@ -1,10 +1,8 @@
 from typing import List
 from typing import Optional
-from typing import Tuple
 
 from ytdl_sub.subscriptions.subscription import Subscription
 from ytdl_sub.utils.exceptions import ValidationException
-from ytdl_sub.utils.file_handler import FileHandlerTransactionLog
 from ytdl_sub.utils.logger import Logger
 
 logger = Logger.get()
@@ -23,7 +21,7 @@ def _maybe_validate_transaction_log_file(transaction_log_file_path: Optional[str
 
 
 def output_transaction_log(
-    transaction_logs: List[Tuple[Subscription, FileHandlerTransactionLog]],
+    subscriptions: List[Subscription],
     transaction_log_file_path: Optional[str],
 ) -> None:
     """
@@ -31,19 +29,19 @@ def output_transaction_log(
 
     Parameters
     ----------
-    transaction_logs
-        The transaction logs from downloaded subscriptions
+    subscriptions
+        Processed subscriptions
     transaction_log_file_path
         Optional file path to write to
     """
     transaction_log_file_contents = ""
-    for subscription, transaction_log in transaction_logs:
-        if transaction_log.is_empty:
+    for subscription in subscriptions:
+        if subscription.transaction_log.is_empty:
             transaction_log_contents = f"\nNo files changed for {subscription.name}"
         else:
             transaction_log_contents = (
                 f"Transaction log for {subscription.name}:\n"
-                f"{transaction_log.to_output_message(subscription.output_directory)}"
+                f"{subscription.transaction_log.to_output_message(subscription.output_directory)}"
             )
 
         if transaction_log_file_path:
diff --git a/src/ytdl_sub/main.py b/src/ytdl_sub/main.py
index d522049a..b4e7e776 100644
--- a/src/ytdl_sub/main.py
+++ b/src/ytdl_sub/main.py
@@ -4,7 +4,7 @@ from ytdl_sub.cli.parsers.main import parser
 from ytdl_sub.utils.logger import Logger
 
 
-def _main():
+def _main() -> int:
     # Set log level before any other ytdl-sub files are imported. That way, when loggers
     # get initialized, they will see the set log level
     args, _ = parser.parse_known_args()
@@ -15,7 +15,10 @@ def _main():
 
     # pylint: enable=import-outside-toplevel
 
-    ytdl_sub.cli.entrypoint.main()
+    subs = ytdl_sub.cli.entrypoint.main()
+    if any(sub.exception for sub in subs):
+        return 1  # Return error-code if any exceptions occurred
+    return 0
 
 
 def main():
@@ -23,14 +26,13 @@ def main():
     Entrypoint for ytdl-sub
     """
     try:
-        _main()
-        Logger.cleanup()  # Ran successfully, so we can delete the debug file
+        return_code = _main()
+        Logger.cleanup(cleanup_error_log=return_code == 0)
+        sys.exit(return_code)
     except Exception as exc:  # pylint: disable=broad-except
-        Logger.log_exit_exception(exception=exc)
+        Logger.log_exception(exception=exc)
         sys.exit(1)
 
-    sys.exit(0)
-
 
 if __name__ == "__main__":
     main()
diff --git a/src/ytdl_sub/subscriptions/base_subscription.py b/src/ytdl_sub/subscriptions/base_subscription.py
index 28f9caa6..0c61f7e1 100644
--- a/src/ytdl_sub/subscriptions/base_subscription.py
+++ b/src/ytdl_sub/subscriptions/base_subscription.py
@@ -9,6 +9,7 @@ from ytdl_sub.config.preset_options import OutputOptions
 from ytdl_sub.config.preset_options import Overrides
 from ytdl_sub.config.preset_options import YTDLOptions
 from ytdl_sub.downloaders.url.validators import MultiUrlValidator
+from ytdl_sub.utils.file_handler import FileHandlerTransactionLog
 from ytdl_sub.utils.logger import Logger
 from ytdl_sub.ytdl_additions.enhanced_download_archive import EnhancedDownloadArchive
 
@@ -59,6 +60,8 @@ class BaseSubscription(ABC):
             migrated_file_name=migrated_file_name,
         )
 
+        self._exception: Optional[Exception] = None
+
     @property
     def downloader_options(self) -> MultiUrlValidator:
         """
@@ -167,6 +170,24 @@ class BaseSubscription(ABC):
         """
         return self._enhanced_download_archive.num_entries
 
+    @property
+    def transaction_log(self) -> FileHandlerTransactionLog:
+        """
+        Returns
+        -------
+        Transaction log from the subscription
+        """
+        return self._enhanced_download_archive.get_file_handler_transaction_log()
+
+    @property
+    def exception(self) -> Optional[Exception]:
+        """
+        Returns
+        -------
+        An exception if one occurred while processing the subscription
+        """
+        return self._exception
+
     def as_yaml(self) -> str:
         """
         Returns
diff --git a/src/ytdl_sub/subscriptions/subscription_download.py b/src/ytdl_sub/subscriptions/subscription_download.py
index 4e6eebcc..366b8a6e 100644
--- a/src/ytdl_sub/subscriptions/subscription_download.py
+++ b/src/ytdl_sub/subscriptions/subscription_download.py
@@ -326,7 +326,9 @@ class SubscriptionDownload(BaseSubscription, ABC):
             If true, do not download any video/audio files or move anything to the output
             directory.
         """
+        self._exception = None
         self._enhanced_download_archive.reinitialize(dry_run=dry_run)
+
         plugins = self._initialize_plugins()
 
         subscription_ytdl_options = SubscriptionYTDLOptions(
@@ -353,6 +355,19 @@ class SubscriptionDownload(BaseSubscription, ABC):
             dry_run=dry_run,
         )
 
+    @contextlib.contextmanager
+    def exception_handling(self) -> None:
+        """
+        Try to perform something on the subscription.
+        Store the error if one occurs.
+        """
+        try:
+            yield
+        except Exception as exc:  # pylint: disable=broad-except
+            self._exception = exc
+
+        return self.transaction_log
+
     def update_with_info_json(self, dry_run: bool = False) -> FileHandlerTransactionLog:
         """
         Performs the subscription update using local info json files.
@@ -362,7 +377,9 @@ class SubscriptionDownload(BaseSubscription, ABC):
         dry_run
             If true, do not modify any video/audio files or move anything to the output directory.
         """
+        self._exception = None
         self._enhanced_download_archive.reinitialize(dry_run=dry_run)
+
         plugins = self._initialize_plugins()
 
         subscription_ytdl_options = SubscriptionYTDLOptions(
diff --git a/src/ytdl_sub/utils/logger.py b/src/ytdl_sub/utils/logger.py
index 70bde484..0b531a32 100644
--- a/src/ytdl_sub/utils/logger.py
+++ b/src/ytdl_sub/utils/logger.py
@@ -91,11 +91,9 @@ class Logger:
     # Ignore 'using with' warning since this will be cleaned up later
     # pylint: disable=R1732
     _DEBUG_LOGGER_FILE = tempfile.NamedTemporaryFile(prefix="ytdl-sub.", delete=False)
+    _ERROR_LOG_FILE = tempfile.NamedTemporaryFile(prefix="ytdl-sub.errors", delete=False)
     # pylint: enable=R1732
 
-    # Whether the final exception lines were added to the debug log
-    _LOGGED_EXIT_EXCEPTION: bool = False
-
     # Keep track of all Loggers created
     _LOGGERS: List[logging.Logger] = []
 
@@ -108,6 +106,15 @@ class Logger:
         """
         return cls._DEBUG_LOGGER_FILE.name
 
+    @classmethod
+    def error_log_filename(cls) -> str:
+        """
+        Returns
+        -------
+        File name of the error log file
+        """
+        return cls._ERROR_LOG_FILE.name
+
     @classmethod
     def set_log_level(cls, log_level_name: str):
         """
@@ -204,9 +211,12 @@ class Logger:
                 redirect_stream.flush()
 
     @classmethod
-    def log_exit_exception(cls, exception: Exception, log_filepath: Optional[Path] = None):
+    def log_exception(cls, exception: Exception, log_filepath: Optional[Path] = None):
         """
-        Performs the final log before exiting from an error
+        Logs an exception based on the exception type. Will transfer all
+        debug logs into the error log file. This allows for subscriptions to only write to the
+        error log if an error occurred - successful subscriptions will clean the debug log file
+        w/out any write to the error log.
 
         Parameters
         ----------
@@ -215,34 +225,37 @@ class Logger:
         log_filepath
             Optional. The filepath to the debug logs
         """
-        if not cls._LOGGED_EXIT_EXCEPTION:
-            logger = cls.get()
+        logger = cls.get()
 
-            # Log validation exceptions as-is
-            if isinstance(exception, ValidationException):
-                logger.error(str(exception))
-            # Log permission errors explicitly
-            elif isinstance(exception, PermissionError):
-                logger.error(
-                    "A permission error occurred:\n%s\n"
-                    "The user running ytdl-sub must have permission to this file/directory.",
-                    str(exception),
-                )
-            # For other uncaught errors, log as bug:
-            else:
-                logger.exception("An uncaught error occurred:")
-                logger.error(
-                    "Version %s\nPlease upload the error log file '%s' and make a Github "
-                    "issue at https://github.com/jmbannon/ytdl-sub/issues with your config and "
-                    "command/subscription yaml file to reproduce. Thanks for trying ytdl-sub!",
-                    __local_version__,
-                    log_filepath if log_filepath else Logger.debug_log_filename(),
-                )
+        # Log validation exceptions as-is
+        if isinstance(exception, ValidationException):
+            logger.error(str(exception))
+        # Log permission errors explicitly
+        elif isinstance(exception, PermissionError):
+            logger.error(
+                "A permission error occurred:\n%s\n"
+                "The user running ytdl-sub must have permission to this file/directory.",
+                str(exception),
+            )
+        # For other uncaught errors, log as bug:
+        else:
+            logger.exception("An uncaught error occurred:")
+            logger.error(
+                "Version %s\nPlease upload the error log file '%s' and make a Github "
+                "issue at https://github.com/jmbannon/ytdl-sub/issues with your config and "
+                "command/subscription yaml file to reproduce. Thanks for trying ytdl-sub!",
+                __local_version__,
+                log_filepath if log_filepath else Logger.error_log_filename(),
+            )
 
-            cls._LOGGED_EXIT_EXCEPTION = True
+        # Any time an exception occurs, dump all debug logs into the error log
+        with open(cls.debug_log_filename(), mode="r", encoding="utf-8") as debug_logs, open(
+            cls.error_log_filename(), mode="a", encoding="utf-8"
+        ) as error_logs:
+            error_logs.writelines(debug_logs.readlines())
 
     @classmethod
-    def cleanup(cls):
+    def cleanup(cls, cleanup_error_log: bool = False):
         """
         Cleans up debug log file left behind
         """
@@ -251,6 +264,8 @@ class Logger:
                 handler.close()
 
         cls._DEBUG_LOGGER_FILE.close()
-
         FileHandler.delete(cls.debug_log_filename())
-        cls._LOGGED_EXIT_EXCEPTION = False
+
+        if cleanup_error_log:
+            cls._ERROR_LOG_FILE.close()
+            FileHandler.delete(cls.error_log_filename())
diff --git a/tests/e2e/conftest.py b/tests/e2e/conftest.py
index 8cb6b9cd..b2a883f7 100644
--- a/tests/e2e/conftest.py
+++ b/tests/e2e/conftest.py
@@ -2,7 +2,6 @@ import json
 import sys
 import tempfile
 from typing import List
-from typing import Tuple
 from unittest.mock import patch
 
 import pytest
@@ -10,7 +9,6 @@ import pytest
 from ytdl_sub.cli.entrypoint import main
 from ytdl_sub.subscriptions.subscription import Subscription
 from ytdl_sub.utils.file_handler import FileHandler
-from ytdl_sub.utils.file_handler import FileHandlerTransactionLog
 
 
 @pytest.fixture()
@@ -46,7 +44,7 @@ def timestamps_file_path():
         FileHandler.delete(tmp.name)
 
 
-def mock_run_from_cli(args: str) -> List[Tuple[Subscription, FileHandlerTransactionLog]]:
+def mock_run_from_cli(args: str) -> List[Subscription]:
     args_list = ["ytdl-sub"] + args.split()
     with patch.object(sys, "argv", args_list):
         return main()
diff --git a/tests/e2e/plugins/internal/test_view.py b/tests/e2e/plugins/internal/test_view.py
index e3838e6f..dbfcd13b 100644
--- a/tests/e2e/plugins/internal/test_view.py
+++ b/tests/e2e/plugins/internal/test_view.py
@@ -17,10 +17,10 @@ class TestView:
         args = f"view "
         args += "--split-chapters " if split_chapters else ""
         args += f"https://www.youtube.com/playlist?list=PLBsm_SagFMmdWnCnrNtLjA9kzfrRkto4i"
-        subscription_transaction_log = mock_run_from_cli(args=args)
+        subscriptions = mock_run_from_cli(args=args)
 
-        assert len(subscription_transaction_log) == 1
-        transaction_log = subscription_transaction_log[0][1]
+        assert len(subscriptions) == 1
+        transaction_log = subscriptions[0].transaction_log
 
         # Ensure the video and thumbnail are recognized
         assert len(transaction_log.files_created) == 2
diff --git a/tests/e2e/youtube/test_playlist.py b/tests/e2e/youtube/test_playlist.py
index 4ec810f9..fa9df4c4 100644
--- a/tests/e2e/youtube/test_playlist.py
+++ b/tests/e2e/youtube/test_playlist.py
@@ -163,10 +163,10 @@ class TestPlaylist:
         ) as subscription_path:
             args = "--dry-run " if dry_run else ""
             args += f"sub {subscription_path}"
-            subscription_transaction_log = mock_run_from_cli(args=args)
+            subscriptions = mock_run_from_cli(args=args)
 
-            assert len(subscription_transaction_log) == 1
-            transaction_log = subscription_transaction_log[0][1]
+            assert len(subscriptions) == 1
+            transaction_log = subscriptions[0].transaction_log
 
             assert_transaction_log_matches(
                 output_directory=output_directory,
@@ -186,7 +186,7 @@ class TestPlaylist:
                     expected_message="ExistingVideoReached, stopping additional downloads",
                     log_level="debug",
                 ):
-                    transaction_log = mock_run_from_cli(args=args)[0][1]
+                    transaction_log = mock_run_from_cli(args=args)[0].transaction_log
 
                 assert transaction_log.is_empty
                 assert_expected_downloads(
diff --git a/tests/e2e/youtube/test_video.py b/tests/e2e/youtube/test_video.py
index f9fd9e33..8dd29583 100644
--- a/tests/e2e/youtube/test_video.py
+++ b/tests/e2e/youtube/test_video.py
@@ -187,14 +187,12 @@ class TestYoutubeVideo:
         args = "--dry-run " if dry_run else ""
         args += f"--config {music_video_config_path} "
         args += f"dl {single_video_preset_dict_dl_args}"
-        subscription_transaction_log = mock_run_from_cli(args=args)
-
-        assert len(subscription_transaction_log) == 1
-        transaction_log = subscription_transaction_log[0][1]
+        subscriptions = mock_run_from_cli(args=args)
 
+        assert len(subscriptions) == 1
         assert_transaction_log_matches(
             output_directory=output_directory,
-            transaction_log=transaction_log,
+            transaction_log=subscriptions[0].transaction_log,
             transaction_log_summary_file_name="youtube/test_video_cli.txt",
         )
         assert_expected_downloads(
diff --git a/tests/unit/cli/conftest.py b/tests/unit/cli/conftest.py
new file mode 100644
index 00000000..09a27d8c
--- /dev/null
+++ b/tests/unit/cli/conftest.py
@@ -0,0 +1,87 @@
+import datetime
+import os
+import shutil
+import tempfile
+import time
+from typing import Callable
+from unittest.mock import patch
+
+import mergedeep
+import pytest
+
+from ytdl_sub.config.config_file import ConfigFile
+from ytdl_sub.subscriptions.subscription import Subscription
+from ytdl_sub.utils.file_handler import FileHandlerTransactionLog
+from ytdl_sub.utils.file_handler import FileMetadata
+from ytdl_sub.utils.logger import Logger
+
+
+@pytest.fixture
+def mock_subscription_download_factory():
+    def _mock_subscription_download_factory(mock_success_output: bool) -> Callable:
+        def _mock_download(self: Subscription, dry_run: bool) -> FileHandlerTransactionLog:
+            Logger.get().info(
+                "name=%s success=%s dry_run=%s", self.name, mock_success_output, dry_run
+            )
+
+            if not mock_success_output:
+                raise ValueError("error")
+
+            (
+                self._enhanced_download_archive.get_file_handler_transaction_log()
+                .log_created_file("created_file.txt", FileMetadata())
+                .log_modified_file("modified_file.txt", FileMetadata())
+                .log_removed_file("deleted_file.txt")
+            )
+
+            return self._enhanced_download_archive.get_file_handler_transaction_log()
+
+        return _mock_download
+
+    return _mock_subscription_download_factory
+
+
+@pytest.fixture
+def mock_subscription_download_success(mock_subscription_download_factory: Callable):
+    with patch.object(
+        Subscription,
+        "download",
+        new=mock_subscription_download_factory(mock_success_output=True),
+    ):
+        yield
+
+
+@pytest.fixture
+def persist_logs_directory() -> str:
+    # Delete the temp_dir on creation
+    with tempfile.TemporaryDirectory() as temp_dir:
+        pass
+
+    yield temp_dir
+
+    if os.path.isdir(temp_dir):
+        shutil.rmtree(temp_dir)
+
+
+@pytest.fixture
+def persist_logs_config_factory(
+    music_video_config: ConfigFile, persist_logs_directory: str
+) -> Callable:
+    def _persist_logs_config_factory(keep_successful_logs: bool) -> ConfigFile:
+        return ConfigFile.from_dict(
+            dict(
+                mergedeep.merge(
+                    music_video_config.as_dict(),
+                    {
+                        "configuration": {
+                            "persist_logs": {
+                                "logs_directory": persist_logs_directory,
+                                "keep_successful_logs": keep_successful_logs,
+                            },
+                        }
+                    },
+                )
+            )
+        )
+
+    return _persist_logs_config_factory
diff --git a/tests/unit/cli/test_entrypoint.py b/tests/unit/cli/test_entrypoint.py
index bc6cdb68..13fb9569 100644
--- a/tests/unit/cli/test_entrypoint.py
+++ b/tests/unit/cli/test_entrypoint.py
@@ -1,110 +1,24 @@
-import os.path
 import re
-import shutil
 import sys
-import tempfile
-import time
 from pathlib import Path
 from typing import Callable
-from typing import List
-from typing import Optional
-from typing import Tuple
-from unittest.mock import MagicMock
-from unittest.mock import Mock
 from unittest.mock import patch
 
-import mergedeep
 import pytest
-from conftest import assert_logs
 
 from ytdl_sub.cli.entrypoint import _download_subscriptions_from_yaml_files
 from ytdl_sub.cli.entrypoint import main
-from ytdl_sub.cli.output_summary import output_summary
-from ytdl_sub.cli.output_transaction_log import logger as transaction_logger
-from ytdl_sub.config.config_file import ConfigFile
 from ytdl_sub.subscriptions.subscription import Subscription
 from ytdl_sub.utils.exceptions import ExperimentalFeatureNotEnabled
-from ytdl_sub.utils.file_handler import FileHandler
-from ytdl_sub.utils.file_handler import FileHandlerTransactionLog
-from ytdl_sub.utils.file_handler import FileMetadata
-from ytdl_sub.utils.logger import Logger
 
 ####################################################################################################
 # SHARED FIXTURES
 
 
-@pytest.fixture
-def mock_subscription_download_factory():
-    def _mock_subscription_download_factory(mock_success_output: bool) -> Callable:
-        def _mock_download(self: Subscription, dry_run: bool) -> FileHandlerTransactionLog:
-            Logger.get().info(
-                "name=%s success=%s dry_run=%s", self.name, mock_success_output, dry_run
-            )
-            time.sleep(1)
-            if not mock_success_output:
-                raise ValueError("error")
-            return (
-                FileHandlerTransactionLog()
-                .log_created_file("created_file.txt", FileMetadata())
-                .log_modified_file("modified_file.txt", FileMetadata())
-                .log_removed_file("deleted_file.txt")
-            )
-
-        return _mock_download
-
-    return _mock_subscription_download_factory
-
-
-@pytest.fixture
-def mock_subscription_download_success(mock_subscription_download_factory: Callable):
-    with patch.object(
-        Subscription,
-        "download",
-        new=mock_subscription_download_factory(mock_success_output=True),
-    ):
-        yield
-
-
 ####################################################################################################
 # PERSIST LOGS FIXTURES + TESTS
 
 
-@pytest.fixture
-def persist_logs_directory() -> str:
-    # Delete the temp_dir on creation
-    with tempfile.TemporaryDirectory() as temp_dir:
-        pass
-
-    yield temp_dir
-
-    if os.path.isdir(temp_dir):
-        shutil.rmtree(temp_dir)
-
-
-@pytest.fixture
-def persist_logs_config_factory(
-    music_video_config: ConfigFile, persist_logs_directory: str
-) -> Callable:
-    def _persist_logs_config_factory(keep_successful_logs: bool) -> ConfigFile:
-        return ConfigFile.from_dict(
-            dict(
-                mergedeep.merge(
-                    music_video_config.as_dict(),
-                    {
-                        "configuration": {
-                            "persist_logs": {
-                                "logs_directory": persist_logs_directory,
-                                "keep_successful_logs": keep_successful_logs,
-                            },
-                        }
-                    },
-                )
-            )
-        )
-
-    return _persist_logs_config_factory
-
-
 @pytest.mark.parametrize("dry_run", [True, False])
 @pytest.mark.parametrize("mock_success_output", [True, False])
 @pytest.mark.parametrize("keep_successful_logs", [True, False])
@@ -125,7 +39,8 @@ def test_subscription_logs_write_to_file(
         Subscription,
         "download",
         new=mock_subscription_download_factory(mock_success_output=mock_success_output),
-    ):
+        # mock datetime to be an index to be able to run instantly
+    ), patch("ytdl_sub.cli.entrypoint._log_time", side_effect=[str(idx) for idx in range(10)]):
         try:
             _download_subscriptions_from_yaml_files(
                 config=config,
@@ -142,24 +57,22 @@ def test_subscription_logs_write_to_file(
     if dry_run or (mock_success_output and not keep_successful_logs):
         assert len(log_directory_files) == 0
         return
-    # If not success, expect 1 log file
+    # If not success, expect 2 log files for both sub errors
     elif not mock_success_output:
-        assert len(log_directory_files) == 1
-        log_path = log_directory_files[0]
-        assert bool(re.match(r"\d{4}-\d{2}-\d{2}-\d{6}\.john_smith\.error\.log", log_path.name))
-        with open(log_path, "r", encoding="utf-8") as log_file:
-            assert log_file.readlines()[-1] == (
-                f"Please upload the error log file '{str(log_path)}' and make a Github issue "
-                f"at https://github.com/jmbannon/ytdl-sub/issues with your config and "
-                f"command/subscription yaml file to reproduce. Thanks for trying ytdl-sub!\n"
-            )
+        assert len(log_directory_files) == 2
+        for log_path in log_directory_files:
+            assert bool(re.match(r"\d\.john_smith\.error\.log", log_path.name))
+            with open(log_path, "r", encoding="utf-8") as log_file:
+                assert log_file.readlines()[-1] == (
+                    f"Please upload the error log file '{str(log_path)}' and make a Github issue "
+                    f"at https://github.com/jmbannon/ytdl-sub/issues with your config and "
+                    f"command/subscription yaml file to reproduce. Thanks for trying ytdl-sub!\n"
+                )
     # If success and success logging, expect 3 log files
     else:
         assert len(log_directory_files) == num_subscriptions
         for log_file_path in log_directory_files:
-            assert bool(
-                re.match(r"\d{4}-\d{2}-\d{2}-\d{6}\.john_smith\.success\.log", log_file_path.name)
-            )
+            assert bool(re.match(r"\d\.john_smith\.success\.log", log_file_path.name))
             with open(log_file_path, "r", encoding="utf-8") as log_file:
                 assert (
                     log_file.readlines()[-1]
@@ -167,122 +80,6 @@ def test_subscription_logs_write_to_file(
                 )
 
 
-####################################################################################################
-# TRANSACTION LOGS FIXTURES + TESTS
-
-
-@pytest.fixture
-def transaction_log_file_path() -> str:
-    # Delete the temp_file on creation
-    with tempfile.NamedTemporaryFile() as temp_file:
-        pass
-
-    yield temp_file.name
-
-    if os.path.isfile(temp_file.name):
-        FileHandler.delete(temp_file.name)
-
-
-@pytest.mark.parametrize("file_transaction_log", [None, "output.log"])
-def test_suppress_transaction_log(
-    mock_subscription_download_success,
-    music_video_config_path: Path,
-    music_video_subscription_path: Path,
-    file_transaction_log: Optional[str],
-) -> None:
-    with patch.object(
-        sys,
-        "argv",
-        [
-            "ytdl-sub",
-            "--config",
-            str(music_video_config_path),
-            "sub",
-            str(music_video_subscription_path),
-            "--suppress-transaction-log",
-        ]
-        + (["--transaction-log", file_transaction_log] if file_transaction_log else []),
-    ), patch("ytdl_sub.cli.output_transaction_log.output_transaction_log") as mock_transaction_log:
-        transaction_logs = main()
-
-        assert transaction_logs
-        assert mock_transaction_log.call_count == 0
-
-
-def test_transaction_log_to_file(
-    mock_subscription_download_success,
-    music_video_config_path: Path,
-    music_video_subscription_path: Path,
-    transaction_log_file_path: Path,
-) -> None:
-    with patch.object(
-        sys,
-        "argv",
-        [
-            "ytdl-sub",
-            "--config",
-            str(music_video_config_path),
-            "sub",
-            str(music_video_subscription_path),
-            "--transaction-log",
-            str(transaction_log_file_path),
-        ],
-    ):
-        transaction_logs = main()
-        assert transaction_logs
-
-    with open(transaction_log_file_path, "r", encoding="utf-8") as transaction_log_file:
-        assert transaction_log_file.readlines()[0] == "Transaction log for john_smith:\n"
-
-
-def test_transaction_log_to_logger(
-    mock_subscription_download_success,
-    music_video_config_path: Path,
-    music_video_subscription_path: Path,
-) -> None:
-    with patch.object(
-        sys,
-        "argv",
-        [
-            "ytdl-sub",
-            "--config",
-            str(music_video_config_path),
-            "sub",
-            str(music_video_subscription_path),
-        ],
-    ), assert_logs(
-        logger=transaction_logger,
-        expected_message="Transaction log for john_smith:\n",
-        log_level="info",
-    ):
-        transaction_logs = main()
-        assert transaction_logs
-
-
-def test_output_summary():
-    subscription_values: List[Tuple[str, int, int, int, int]] = [
-        ("long_name_but_lil_values", 0, 0, 0, 6),
-        ("john_smith", 1, 0, 0, 52),
-        ("david_gore", 0, 0, 0, 4),
-        ("christopher_snoop", 50, 0, 3, 518),
-        ("beyond funk", 0, 0, 0, 176),
-    ]
-
-    mock_subscriptions: List[Tuple[MagicMock, FileHandlerTransactionLog]] = []
-    for values in subscription_values:
-        sub = Mock()
-        sub.name = values[0]
-        sub.num_entries_added = values[1]
-        sub.num_entries_modified = values[2]
-        sub.num_entries_removed = values[3]
-        sub.num_entries = values[4]
-
-        mock_subscriptions.append((sub, FileHandlerTransactionLog()))
-
-    _ = output_summary(transaction_logs=mock_subscriptions)
-    assert True  # Test used for manual inspection - too hard to test ansi color codes
-
-
 def test_update_with_info_json_requires_experimental_flag(
     music_video_config_path: Path,
     music_video_subscription_path: Path,
diff --git a/tests/unit/cli/test_output_summary.py b/tests/unit/cli/test_output_summary.py
new file mode 100644
index 00000000..67422532
--- /dev/null
+++ b/tests/unit/cli/test_output_summary.py
@@ -0,0 +1,67 @@
+from typing import List
+from typing import Optional
+from typing import Tuple
+from unittest.mock import MagicMock
+from unittest.mock import Mock
+
+from ytdl_sub.cli.output_summary import output_summary
+
+
+def _to_mock_subscriptions(
+    subscription_values: List[Tuple[str, int, int, int, int, Optional[Exception]]]
+) -> List[MagicMock]:
+    mock_subscriptions: List[MagicMock] = []
+    for values in subscription_values:
+        sub = Mock()
+        sub.name = values[0]
+        sub.num_entries_added = values[1]
+        sub.num_entries_modified = values[2]
+        sub.num_entries_removed = values[3]
+        sub.num_entries = values[4]
+        sub.exception = values[5]
+
+        mock_subscriptions.append(sub)
+
+    return mock_subscriptions
+
+
+def test_output_summary_no_errors():
+    mock_subscriptions = _to_mock_subscriptions(
+        [
+            ("long_name_but_lil_values", 0, 0, 0, 6, None),
+            ("john_smith", 1, 0, 0, 52, None),
+            ("david_gore", 0, 0, 0, 4, None),
+            ("christopher_snoop", 50, 0, 3, 518, None),
+            ("beyond funk", 352, 0, 0, 2342, None),
+        ]
+    )
+
+    output_summary(subscriptions=mock_subscriptions)
+
+
+def test_output_summary_one_error():
+    mock_subscriptions = _to_mock_subscriptions(
+        [
+            ("long_name_but_lil_values", 0, 0, 0, 6, None),
+            ("john_smith", 1, 0, 0, 52, None),
+            ("david_gore", 0, 0, 0, 4, None),
+            ("christopher_snoop", 50, 0, 3, 518, None),
+            ("beyond funk", 0, 0, 0, 176, ValueError("lol")),
+        ]
+    )
+
+    output_summary(subscriptions=mock_subscriptions)
+
+
+def test_output_summary_multiple_errors():
+    mock_subscriptions = _to_mock_subscriptions(
+        [
+            ("long_name_but_lil_values", 0, 0, 0, 6, None),
+            ("john_smith", 1, 0, 0, 52, None),
+            ("david_gore", 0, 0, 0, 4, PermissionError("ack")),
+            ("christopher_snoop", 50, 0, 3, 518, None),
+            ("beyond funk", 0, 0, 0, 176, ValueError("lol")),
+        ]
+    )
+
+    output_summary(subscriptions=mock_subscriptions)
diff --git a/tests/unit/cli/test_output_transaction_log.py b/tests/unit/cli/test_output_transaction_log.py
new file mode 100644
index 00000000..2bf8a39d
--- /dev/null
+++ b/tests/unit/cli/test_output_transaction_log.py
@@ -0,0 +1,101 @@
+import os
+import sys
+import tempfile
+from pathlib import Path
+from typing import Optional
+from unittest.mock import patch
+
+import pytest
+from conftest import assert_logs
+
+from ytdl_sub.cli.entrypoint import main
+from ytdl_sub.cli.output_transaction_log import logger as transaction_logger
+from ytdl_sub.utils.file_handler import FileHandler
+
+
+@pytest.fixture
+def transaction_log_file_path() -> str:
+    # Delete the temp_file on creation
+    with tempfile.NamedTemporaryFile() as temp_file:
+        pass
+
+    yield temp_file.name
+
+    if os.path.isfile(temp_file.name):
+        FileHandler.delete(temp_file.name)
+
+
+@pytest.mark.parametrize("file_transaction_log", [None, "output.log"])
+def test_suppress_transaction_log(
+    mock_subscription_download_success,
+    music_video_config_path: Path,
+    music_video_subscription_path: Path,
+    file_transaction_log: Optional[str],
+) -> None:
+    with patch.object(
+        sys,
+        "argv",
+        [
+            "ytdl-sub",
+            "--config",
+            str(music_video_config_path),
+            "sub",
+            str(music_video_subscription_path),
+            "--suppress-transaction-log",
+        ]
+        + (["--transaction-log", file_transaction_log] if file_transaction_log else []),
+    ), patch("ytdl_sub.cli.output_transaction_log.output_transaction_log") as mock_transaction_log:
+        subscriptions = main()
+
+        assert subscriptions
+        assert mock_transaction_log.call_count == 0
+
+
+def test_transaction_log_to_file(
+    mock_subscription_download_success,
+    music_video_config_path: Path,
+    music_video_subscription_path: Path,
+    transaction_log_file_path: Path,
+) -> None:
+    with patch.object(
+        sys,
+        "argv",
+        [
+            "ytdl-sub",
+            "--config",
+            str(music_video_config_path),
+            "sub",
+            str(music_video_subscription_path),
+            "--transaction-log",
+            str(transaction_log_file_path),
+        ],
+    ):
+        subscriptions = main()
+        assert subscriptions
+
+    with open(transaction_log_file_path, "r", encoding="utf-8") as transaction_log_file:
+        assert transaction_log_file.readlines()[0] == "Transaction log for john_smith:\n"
+
+
+def test_transaction_log_to_logger(
+    mock_subscription_download_success,
+    music_video_config_path: Path,
+    music_video_subscription_path: Path,
+) -> None:
+    with patch.object(
+        sys,
+        "argv",
+        [
+            "ytdl-sub",
+            "--config",
+            str(music_video_config_path),
+            "sub",
+            str(music_video_subscription_path),
+        ],
+    ), assert_logs(
+        logger=transaction_logger,
+        expected_message="Transaction log for john_smith:\n",
+        log_level="info",
+    ):
+        subscriptions = main()
+        assert subscriptions
diff --git a/tests/unit/main/test_main.py b/tests/unit/main/test_main.py
index cea92901..5f4b2d5a 100644
--- a/tests/unit/main/test_main.py
+++ b/tests/unit/main/test_main.py
@@ -38,10 +38,18 @@ def mock_sys_exit():
     return _mock_sys_exit
 
 
-def test_main_success(mock_sys_exit):
-    with mock_sys_exit(expected_exit_code=0):
-        with patch("src.ytdl_sub.main._main"):
-            main()
+@pytest.mark.parametrize("return_code", [0, 1])
+def test_main_exit_code(mock_sys_exit, return_code: int):
+    with mock_sys_exit(expected_exit_code=return_code), patch(
+        "src.ytdl_sub.main._main"
+    ) as mock_inner_main, patch.object(Logger, "cleanup") as mock_logger_cleanup:
+        mock_inner_main.return_value = return_code
+        main()
+
+        assert mock_logger_cleanup.call_count == 1
+        assert mock_logger_cleanup.call_args.kwargs["cleanup_error_log"] == (
+            True if return_code == 0 else False
+        )
 
 
 def test_main_validation_error(capsys, mock_sys_exit):
@@ -70,7 +78,7 @@ def test_main_uncaught_error(capsys, mock_sys_exit, expected_uncaught_error_mess
     assert mock_error.call_count == 1
     assert mock_error.call_args.args[0] == expected_uncaught_error_message
     assert mock_error.call_args.args[1] == __local_version__
-    assert mock_error.call_args.args[2] == Logger.debug_log_filename()
+    assert mock_error.call_args.args[2] == Logger.error_log_filename()
 
 
 def test_main_permission_error(capsys, mock_sys_exit, expected_uncaught_error_message):
diff --git a/tests/unit/utils/test_logger.py b/tests/unit/utils/test_logger.py
index 64415a60..5a75e5c3 100644
--- a/tests/unit/utils/test_logger.py
+++ b/tests/unit/utils/test_logger.py
@@ -111,11 +111,12 @@ class TestLogger:
         Logger.cleanup()
         assert not os.path.isfile(Logger._DEBUG_LOGGER_FILE.name)
 
-    def test_logger_can_be_cleaned_during_execution(self):
+    @pytest.mark.parametrize("clean_error_log", [True, False])
+    def test_logger_can_be_cleaned_during_execution(self, clean_error_log: bool):
         Logger._LOGGER_LEVEL = LoggerLevels.INFO
         logger = Logger.get(name="name_test")
 
-        for _ in range(2):
+        for iteration in range(2):
             logger.info("info test")
             logger.debug("debug test")
 
@@ -127,8 +128,39 @@ class TestLogger:
                 "[ytdl-sub:name_test] debug test\n",
             ]
 
-            Logger.cleanup()
-            assert not os.path.isfile(Logger._DEBUG_LOGGER_FILE.name)
+            try:
+                raise ValueError("some error")
+            except ValueError as exc:
+                Logger.log_exception(exception=exc)
+
+            Logger.cleanup(cleanup_error_log=clean_error_log)
+            assert not os.path.isfile(Logger.debug_log_filename())
+
+            assert clean_error_log == (not os.path.isfile(Logger.error_log_filename()))
+            if not clean_error_log:
+                with open(Logger.error_log_filename(), mode="r", encoding="utf-8") as err_file:
+                    err_logs = err_file.readlines()
+                    expected = [
+                        "[ytdl-sub:name_test] info test\n",
+                        "[ytdl-sub:name_test] debug test\n",
+                        "[ytdl-sub] An uncaught error occurred:\n",
+                        "Traceback (most recent call last):\n",
+                        '  File "/home/j/workspace/ytdl-sub/tests/unit/utils/test_logger.py", line 132, in test_logger_can_be_cleaned_during_execution\n',
+                        '    raise ValueError("some error")\n',
+                        "ValueError: some error\n",
+                        "[ytdl-sub] Version 2023.03.24+14e4a4b\n",
+                        f"Please upload the error log file '{Logger.error_log_filename()}' and make a Github issue at https://github.com/jmbannon/ytdl-sub/issues with your config and command/subscription yaml file to reproduce. Thanks for trying ytdl-sub!\n",
+                    ]
+
+                    assert err_logs[0:4] == expected[0:4]
+                    assert err_logs[8] == expected[8]
+
+                    if iteration == 1:
+                        err_lines = len(expected)
+
+                        # Two errors occurred, error log should contain 2
+                        assert err_logs[err_lines : err_lines + 4] == expected[0:4]
+                        assert err_logs[err_lines + 8] == expected[8]
 
     @pytest.mark.parametrize(
         "log_level, expected_stdout",