diff --git a/Makefile b/Makefile
index 1bc336bf8..ec98d90a5 100644
--- a/Makefile
+++ b/Makefile
@@ -61,5 +61,8 @@ gen-outpost:
 
 gen: gen-build gen-clean gen-web gen-outpost
 
+migrate:
+	python -m lifecycle.migrate
+
 run:
 	go run -v cmd/server/main.go
diff --git a/authentik/core/migrations/0026_alter_application_meta_icon.py b/authentik/core/migrations/0026_alter_application_meta_icon.py
new file mode 100644
index 000000000..d2a0aed56
--- /dev/null
+++ b/authentik/core/migrations/0026_alter_application_meta_icon.py
@@ -0,0 +1,20 @@
+# Generated by Django 3.2.5 on 2021-07-09 17:27
+
+from django.db import migrations, models
+
+
+class Migration(migrations.Migration):
+
+    dependencies = [
+        ("authentik_core", "0025_alter_application_meta_icon"),
+    ]
+
+    operations = [
+        migrations.AlterField(
+            model_name="application",
+            name="meta_icon",
+            field=models.FileField(
+                default=None, max_length=500, null=True, upload_to="application-icons/"
+            ),
+        ),
+    ]
diff --git a/authentik/core/models.py b/authentik/core/models.py
index df003cc54..866ec374c 100644
--- a/authentik/core/models.py
+++ b/authentik/core/models.py
@@ -228,7 +228,10 @@ class Application(PolicyBindingModel):
     )
     # For template applications, this can be set to /static/authentik/applications/*
     meta_icon = models.FileField(
-        upload_to="application-icons/", default=None, null=True
+        upload_to="application-icons/",
+        default=None,
+        null=True,
+        max_length=500,
     )
     meta_description = models.TextField(default="", blank=True)
     meta_publisher = models.TextField(default="", blank=True)
diff --git a/authentik/flows/migrations/0023_alter_flow_background.py b/authentik/flows/migrations/0023_alter_flow_background.py
new file mode 100644
index 000000000..e7ee64008
--- /dev/null
+++ b/authentik/flows/migrations/0023_alter_flow_background.py
@@ -0,0 +1,24 @@
+# Generated by Django 3.2.5 on 2021-07-09 17:27
+
+from django.db import migrations, models
+
+
+class Migration(migrations.Migration):
+
+    dependencies = [
+        ("authentik_flows", "0022_alter_flowstagebinding_invalid_response_action"),
+    ]
+
+    operations = [
+        migrations.AlterField(
+            model_name="flow",
+            name="background",
+            field=models.FileField(
+                default=None,
+                help_text="Background shown during execution",
+                max_length=500,
+                null=True,
+                upload_to="flow-backgrounds/",
+            ),
+        ),
+    ]
diff --git a/authentik/flows/models.py b/authentik/flows/models.py
index df713dba2..d4821ec27 100644
--- a/authentik/flows/models.py
+++ b/authentik/flows/models.py
@@ -121,6 +121,7 @@ class Flow(SerializerModel, PolicyBindingModel):
         default=None,
         null=True,
         help_text=_("Background shown during execution"),
+        max_length=500,
     )
 
     compatibility_mode = models.BooleanField(