diff --git a/.gitignore b/.gitignore
index dfb652b..cb3f739 100644
--- a/.gitignore
+++ b/.gitignore
@@ -176,3 +176,5 @@ pyrightconfig.json
 # End of https://www.toptal.com/developers/gitignore/api/python
 
 cache/
+
+/collected-content-media
diff --git a/content/core.page/test.yaml b/content/core.Page/test.yaml
similarity index 100%
rename from content/core.page/test.yaml
rename to content/core.Page/test.yaml
diff --git a/content/core.Page/testdir/media.txt b/content/core.Page/testdir/media.txt
new file mode 100644
index 0000000..02258db
--- /dev/null
+++ b/content/core.Page/testdir/media.txt
@@ -0,0 +1 @@
+Imagine this is an image.
diff --git a/content/core.page/test2.md b/content/core.Page/testdir/test2.md
similarity index 86%
rename from content/core.page/test2.md
rename to content/core.Page/testdir/test2.md
index 00f9c82..3038be5 100644
--- a/content/core.page/test2.md
+++ b/content/core.Page/testdir/test2.md
@@ -3,6 +3,7 @@ title: Test
 tags:
     - tag-1
 runtime_render: false
+media: ./media.txt
 ---
 
 # Heading
diff --git a/content/core.tag/tags.yml b/content/core.Tag/tags.yml
similarity index 100%
rename from content/core.tag/tags.yml
rename to content/core.Tag/tags.yml
diff --git a/requirements.txt b/requirements.txt
index d055c3e..4880143 100644
--- a/requirements.txt
+++ b/requirements.txt
@@ -1,5 +1,5 @@
 django
-git+https://github.com/andrewgodwin/yamdl@8d34d7397f3564a550042e81ea79cca7d2f3777e
+git+https://github.com/andrewgodwin/yamdl@237d3607a8e611c723ee45a7b1726c00b1648451
 gunicorn
 markdown
 chrono
diff --git a/yamdl_playground/core/apps.py b/yamdl_playground/core/apps.py
index 8200b13..9f64914 100644
--- a/yamdl_playground/core/apps.py
+++ b/yamdl_playground/core/apps.py
@@ -4,6 +4,8 @@ from django.db.models.signals import post_save
 import warnings
 from django.utils.html import strip_tags
 from django.core.management import call_command
+from django.core.files.storage import storages
+import shutil
 
 
 class CoreConfig(AppConfig):
@@ -15,6 +17,9 @@ class CoreConfig(AppConfig):
         from .models import Page
 
         if not self.loaded:
+            # Clear storage to ensure files are always fresh
+            shutil.rmtree(storages["yamdl"].location, ignore_errors=True)
+
             connection = connections["yamdl"]
 
             with warnings.catch_warnings():
diff --git a/yamdl_playground/core/models.py b/yamdl_playground/core/models.py
index 1c40d8e..86116a3 100644
--- a/yamdl_playground/core/models.py
+++ b/yamdl_playground/core/models.py
@@ -2,6 +2,11 @@ from django.db import models
 import markdown
 from django.utils.functional import cached_property
 from django.template import Template, Context
+from django.core.files.storage import storages
+from django.core.files import File
+from pathlib import Path
+import os.path
+
 
 class Tag(models.Model):
     __yamdl__ = True
@@ -11,6 +16,8 @@ class Tag(models.Model):
 
     content = models.TextField()
 
+def get_page_upload_to(instance, filename):
+    return f"{instance._meta.verbose_name}/{instance.slug}/{os.path.basename(filename)}"
 
 class Page(models.Model):
     __yamdl__ = True
@@ -26,6 +33,8 @@ class Page(models.Model):
     slug = models.CharField(max_length=128, unique=True, db_index=True, default=None, null=True)
     file_path = models.CharField(max_length=255)
 
+    media = models.FileField(null=True, default=None, storage=storages["yamdl"], upload_to=get_page_upload_to)
+
     tags = models.ManyToManyField(Tag)
 
     @classmethod
@@ -44,6 +53,11 @@ class Page(models.Model):
             "tokens": md.toc_tokens
         }
 
+        if data.get("media"):
+            source_dir = Path(data["file_path"]).parent
+
+            data["media"] = File((source_dir / data["media"]).open("rb"))
+
         instance = cls(**data)
 
         if not instance.runtime_render:
diff --git a/yamdl_playground/settings.py b/yamdl_playground/settings.py
index 4dc00e4..6a659ca 100644
--- a/yamdl_playground/settings.py
+++ b/yamdl_playground/settings.py
@@ -144,6 +144,22 @@ USE_TZ = True
 
 STATIC_URL = 'static/'
 
+STORAGES = {
+    "default": {
+        "BACKEND": "django.core.files.storage.FileSystemStorage",
+    },
+    "staticfiles": {
+        "BACKEND": "django.contrib.staticfiles.storage.StaticFilesStorage",
+    },
+    "yamdl": {
+        "BACKEND": "django.core.files.storage.FileSystemStorage",
+        "OPTIONS": {
+            "location": BASE_DIR / "collected-content-media",
+            "base_url": "/yamdl-media/"
+        }
+    }
+}
+
 # Default primary key field type
 # https://docs.djangoproject.com/en/5.0/ref/settings/#default-auto-field