diff --git a/src/jcloud_docsgen/core/python/_core.py b/src/jcloud_docsgen/core/python/_core.py
index 73b6b26..af783b3 100644
--- a/src/jcloud_docsgen/core/python/_core.py
+++ b/src/jcloud_docsgen/core/python/_core.py
@@ -22,7 +22,13 @@ from typing import TypeAlias
 
 import docstring_parser
 
-from ...exceptions import InvalidNamespaceError, PythonArgumentStructureError
+import shutil
+
+from ...exceptions import (
+    DirectoryNotEmptyError,
+    InvalidNamespaceError,
+    PythonArgumentStructureError,
+)
 from ...utils import get_relative_path_segments, non_empty_str
 from .arguments import PythonArgumentKind, PythonFunctionArgument
 from .definitions import (
@@ -1114,12 +1120,29 @@ class PythonDocumentationGenerator:
 
         return self._namespace(self.project_directory)
 
-    def generate_documentation(self) -> None:
+    def generate_documentation(self, force: bool = False) -> None:
         """
         Generates the full project documentation and writes it to the
         documentation directory.
+
+        :param force: Indicates whether existing contents of the output
+                      directory shall be overwritten. If ``True``, all
+                      contents of the output directory will be deleted
+                      first.
+        :type force: bool
+
+        :raises DirectoryNotEmptyError: If ``force`` is ``False`` and
+                                        the output directory is not
+                                        empty.
         """
 
+        if self.docs_directory.exists() and list(
+            self.docs_directory.iterdir()
+        ):
+            if force:
+                shutil.rmtree(self.docs_directory)
+            else:
+                raise DirectoryNotEmptyError(str(self.docs_directory))
         self.docs_directory.mkdir(parents=True, exist_ok=True)
 
         _generate_package_namespace_documentation(