diff --git a/README.md b/README.md
index 9cf668b..9eadb71 100644
--- a/README.md
+++ b/README.md
@@ -51,6 +51,16 @@ If a release was already saved to directory '0.0.1-1', then a new release direct
 #### Next Step
 Simply double-click the .streamDeckPlugin file, which will load up the plugin in the Stream Deck application.
 
+#### Pack for debug mode
+To pack the plugin in debug mode, which enables remote debugging capabilities, use the `--debug` flag:
+
+```bash
+streamdeck-cli pack /path/to/plugin --debug --debug-port 5679
+```
+
+This will create a flag file named `.debug` in the packed plugin containing the specified port.
+
+When this file is included, the plugin will wait for a debugger to attach at that port before starting. You can use tools like VS Code's Python debugger or PyCharm's remote debugger to connect to it.
 
 ## Contributing
 Contributions are welcome! Please open an issue or submit a pull request on GitHub.
diff --git a/streamdeck_cli/commands/pack/__init__.py b/streamdeck_cli/commands/pack/__init__.py
index eb8bd91..298aff8 100644
--- a/streamdeck_cli/commands/pack/__init__.py
+++ b/streamdeck_cli/commands/pack/__init__.py
@@ -1,6 +1,4 @@
 """Pack/build a Stream Deck plugin into a .streamDeckPlugin file."""
-from __future__ import annotations
-
 import logging
 from pathlib import Path
 from typing import Optional
@@ -35,6 +33,12 @@ def pack(
         help="Output directory",
     ),
     version: Optional[str] = None,  # noqa: UP007
+    debug_port: Optional[int] = typer.Option(
+        None,
+        "--debug",
+        "-d",
+        help="Enable debug mode in the packed plugin to listen for debug messages on the specified port",
+    ),
 ) -> None:
     """Pack/build a Stream Deck plugin into a .streamDeckPlugin file."""
     # Validate the manifest by initiating its model.
@@ -49,7 +53,7 @@ def pack(
     # Define the full output file path for the plugin.
     # The output file at this path will be a .streamDeckPlugin file, which will open the plugin in the Stream Deck app.
     # The output file at this path is a zip file containing the files of the plugin, which the Stream Deck software unzips to a specific app directory.
-    output_filepath = output_dirpath / f"{manifest.uuid}.streamDeckPlugin"
+    output_filepath = versioned_output_dirpath / f"{manifest.uuid}.streamDeckPlugin"
     logger.info("Output plugin file will be created at: %s", output_filepath)
 
     # Create the package directory
@@ -59,7 +63,13 @@ def pack(
     pathignore_spec: pathspec.PathSpec = get_packignore_specification(plugin_dirpath)
 
     # Create the zip file and add the plugin files
-    archive_plugin_files(plugin_dirpath, output_filepath, plugin_uuid=manifest.uuid, packignore_spec=pathignore_spec)
+    archive_plugin_files(
+        plugin_dirpath,
+        output_filepath,
+        plugin_uuid=manifest.uuid,
+        packignore_spec=pathignore_spec,
+        debug_port=debug_port,
+    )
 
 
 if __name__ == "__main__":
diff --git a/streamdeck_cli/commands/pack/zip.py b/streamdeck_cli/commands/pack/zip.py
index 3991269..9c329b8 100644
--- a/streamdeck_cli/commands/pack/zip.py
+++ b/streamdeck_cli/commands/pack/zip.py
@@ -19,7 +19,13 @@
 logger = logging.getLogger("streamdeck-cli")
 
 
-def archive_plugin_files(plugin_dirpath: Path, output_filepath: Path, plugin_uuid: str, packignore_spec: pathspec.PathSpec) -> None:
+def archive_plugin_files(
+    plugin_dirpath: Path,
+    output_filepath: Path,
+    plugin_uuid: str,
+    packignore_spec: pathspec.PathSpec,
+    debug_port: int | None = None,
+) -> None:
     """Archive the plugin files into a a new zip file."""
     with zipfile.ZipFile(output_filepath, "w", zipfile.ZIP_DEFLATED) as zip_file:
         # Files should be stuffed in the zip file under a base directory with the name of the plugin UUID found in the manifest.
@@ -37,6 +43,12 @@ def archive_plugin_files(plugin_dirpath: Path, output_filepath: Path, plugin_uui
             zip_file.write(full_filepath, arcname=arcname)
 
 
+        # Add a file `.debug` containing the debug port number if debug mode is enabled to the zip file
+        if debug_port:
+            print("YOOO")
+            zip_file.writestr(f"{entry_prefix}/.debug", str(debug_port))
+
+
 def walk_filtered_plugin_files(source_dirpath: Path, packignore_spec: pathspec.PathSpec) -> Generator[Path, None, None]:
     """Walk through the plugin directory and yield files that are not ignored."""
     # Walk through the directory and yield files that are not ignored