diff --git a/ytdl_subscribe/entries/entry.py b/ytdl_subscribe/entries/entry.py
index 10219a3c..edffac3c 100644
--- a/ytdl_subscribe/entries/entry.py
+++ b/ytdl_subscribe/entries/entry.py
@@ -80,6 +80,13 @@ class Entry:
         """Returns the entry's upload month as an int"""
         return int(self.upload_day_padded.lstrip("0"))
 
+    @property
+    def standardized_upload_date(self) -> str:
+        """
+        :return: upload date as YYYY-MM-DD
+        """
+        return f"{self.upload_year}-{self.upload_month_padded}-{self.upload_day_padded}"
+
     @property
     def description(self) -> str:
         return self.kwargs("description")
@@ -126,6 +133,7 @@ class Entry:
             "upload_month_padded": self.upload_month_padded,
             "upload_day": self.upload_day,
             "upload_day_padded": self.upload_day_padded,
+            "standardized_upload_date": self.standardized_upload_date,
             "thumbnail": self.thumbnail,
             "thumbnail_ext": self.thumbnail_ext,
         }
diff --git a/ytdl_subscribe/subscriptions/subscription.py b/ytdl_subscribe/subscriptions/subscription.py
index 06d624b1..dd2c7fba 100644
--- a/ytdl_subscribe/subscriptions/subscription.py
+++ b/ytdl_subscribe/subscriptions/subscription.py
@@ -1,3 +1,4 @@
+import contextlib
 import os
 import shutil
 from abc import ABC
@@ -126,6 +127,10 @@ class Subscription(Generic[S], ABC):
     def _post_process_nfo(self, nfo_options: NFOValidator, entry: Optional[Entry] = None):
         """
         Creates an entry's NFO file using values defined in the metadata options
+
+        :param nfo_options: Options for the NFO
+        :param entry: Optional. Will pass entry values to nfo string formatters. If None, will only
+        use override variables that must resolve.
         """
         nfo = {}
 
@@ -151,21 +156,27 @@ class Subscription(Generic[S], ABC):
         with open(nfo_file_path, "wb") as nfo_file:
             nfo_file.write(xml)
 
+    @contextlib.contextmanager
+    def _maintain_archive_file(self):
+        if not self.output_options.maintain_download_archive:
+            return
+
+        existing_download_archive = Path(self.output_directory) / self.download_archive_file_name
+        working_directory_archive = Path(self.working_directory) / self.download_archive_file_name
+
+        if os.path.exists(existing_download_archive):
+            shutil.copy(existing_download_archive, working_directory_archive)
+
+        yield
+
+        shutil.copy(working_directory_archive, existing_download_archive)
+
     def download(self):
         """
         Performs the subscription download.
         """
-        existing_download_archive = Path(self.output_directory) / self.download_archive_file_name
-        working_directory_archive = Path(self.working_directory) / self.download_archive_file_name
-
-        if self.output_options.maintain_download_archive:
-            if os.path.exists(existing_download_archive):
-                shutil.copy(existing_download_archive, working_directory_archive)
-
-        self._extract_info()
-
-        if self.output_options.maintain_download_archive:
-            shutil.copy(working_directory_archive, existing_download_archive)
+        with self._maintain_archive_file():
+            self._extract_info()
 
     def _extract_info(self):
         """
diff --git a/ytdl_subscribe/ytdl_additions/__init__.py b/ytdl_subscribe/ytdl_additions/__init__.py
new file mode 100644
index 00000000..e69de29b
diff --git a/ytdl_subscribe/ytdl_additions/enhanced_download_archive.py b/ytdl_subscribe/ytdl_additions/enhanced_download_archive.py
new file mode 100644
index 00000000..ad45ad71
--- /dev/null
+++ b/ytdl_subscribe/ytdl_additions/enhanced_download_archive.py
@@ -0,0 +1,92 @@
+import json
+from dataclasses import dataclass
+from pathlib import Path
+from typing import Dict
+from typing import List
+
+from ytdl_subscribe.entries.entry import Entry
+
+
+@dataclass
+class DownloadMapping:
+    upload_date: str
+    file_paths: List[str]
+
+
+class DownloadMappings:
+    def __init__(self):
+        self._entry_mappings: Dict[str, DownloadMapping] = {}
+
+    @classmethod
+    def from_json(cls, file_path: str) -> "DownloadMappings":
+        entry_mappings = DownloadMappings()
+        entry_mappings._entry_mappings = json.load(open(file_path, "r", encoding="utf8"))
+        return entry_mappings
+
+    def to_json(self) -> str:
+        return json.dumps(
+            {
+                uid: mapping
+                for uid, mapping in sorted(
+                    self._entry_mappings.items(),
+                    key=lambda item: item[1]["upload_date"],
+                    reverse=True,
+                )
+            }
+        )
+
+
+class DownloadArchive:
+    """
+    Class to handle any operations to the ytdl download archive. Try to keep it as barebones as
+    possible in case of future changes.
+    """
+
+    def __init__(
+        self,
+    ):
+        self._download_archive_lines: List[str] = []
+
+    @classmethod
+    def from_file(cls, file_path: str) -> "DownloadArchive":
+        lines = open(file_path, "r", encoding="utf8").readlines()
+        download_archive = DownloadArchive()
+        download_archive._download_archive_lines = lines
+        return download_archive
+
+
+class EnhancedDownloadArchive:
+    """
+    Maintains ytdl's download archive file as well as create an additional mapping file to map
+    ytdl ids to multiple files
+    """
+
+    def __init__(self, name: str):
+        self.name = name
+        self._download_archive = None
+        self._download_mapping = None
+        self._appended_entries: List[Entry] = []
+
+    @property
+    def download_archive_file_name(self):
+        return f".ytdl-subscribe-{self.name}-download-archive.txt"
+
+    @property
+    def download_mapping_file_name(self):
+        return f".ytdl-subscribe-{self.name}-download-mapping.json"
+
+    def load(self, directory: str) -> "EnhancedDownloadArchive":
+        self._download_archive = DownloadArchive.from_file(
+            file_path=str(Path(directory) / self.download_archive_file_name)
+        )
+
+        self._download_mapping = DownloadMappings.from_json(
+            file_path=str(Path(directory) / self.download_mapping_file_name)
+        )
+
+        return self
+
+    # def append(self, entry: Entry, relative_file_path: str):
+    #     self._appended_entries.append(
+    #         EntryMapping(entry=entry, relative_file_path=relative_file_path))
+    #