diff --git a/authentik/core/migrations/0046_session_and_more.py b/authentik/core/migrations/0046_session_and_more.py
index 1a681ea1f5..1b52b1d65f 100644
--- a/authentik/core/migrations/0046_session_and_more.py
+++ b/authentik/core/migrations/0046_session_and_more.py
@@ -79,6 +79,7 @@ def _migrate_session(
         AuthenticatedSession.objects.using(db_alias).create(
             session=session,
             user=old_auth_session.user,
+            uuid=old_auth_session.uuid,
         )
 
 
diff --git a/authentik/core/migrations/0048_delete_oldauthenticatedsession_content_type.py b/authentik/core/migrations/0048_delete_oldauthenticatedsession_content_type.py
index d79f14a74a..09a1027e39 100644
--- a/authentik/core/migrations/0048_delete_oldauthenticatedsession_content_type.py
+++ b/authentik/core/migrations/0048_delete_oldauthenticatedsession_content_type.py
@@ -1,10 +1,81 @@
 # Generated by Django 5.1.9 on 2025-05-14 11:15
 
-from django.apps.registry import Apps
+from django.apps.registry import Apps, apps as global_apps
 from django.db import migrations
+from django.contrib.contenttypes.management import create_contenttypes
+from django.contrib.auth.management import create_permissions
 from django.db.backends.base.schema import BaseDatabaseSchemaEditor
 
 
+def migrate_authenticated_session_permissions(apps: Apps, schema_editor: BaseDatabaseSchemaEditor):
+    """Migrate permissions from OldAuthenticatedSession to AuthenticatedSession"""
+    db_alias = schema_editor.connection.alias
+
+    # `apps` here is just an instance of `django.db.migrations.state.AppConfigStub`, we need the
+    # real config for creating permissions and content types
+    authentik_core_config = global_apps.get_app_config("authentik_core")
+    # These are only ran by django after all migrations, but we need them right now.
+    # `global_apps` is needed,
+    create_permissions(authentik_core_config, using=db_alias, verbosity=1)
+    create_contenttypes(authentik_core_config, using=db_alias, verbosity=1)
+
+    # But from now on, this is just a regular migration, so use `apps`
+    Permission = apps.get_model("auth", "Permission")
+    ContentType = apps.get_model("contenttypes", "ContentType")
+
+    try:
+        old_ct = ContentType.objects.using(db_alias).get(
+            app_label="authentik_core", model="oldauthenticatedsession"
+        )
+        new_ct = ContentType.objects.using(db_alias).get(
+            app_label="authentik_core", model="authenticatedsession"
+        )
+    except ContentType.DoesNotExist:
+        # This should exist at this point, but if not, let's cut our losses
+        return
+
+    # Get all permissions for the old content type
+    old_perms = Permission.objects.using(db_alias).filter(content_type=old_ct)
+
+    # Create equivalent permissions for the new content type
+    for old_perm in old_perms:
+        new_perm = (
+            Permission.objects.using(db_alias)
+            .filter(
+                content_type=new_ct,
+                codename=old_perm.codename,
+            )
+            .first()
+        )
+        if not new_perm:
+            # This should exist at this point, but if not, let's cut our losses
+            continue
+
+        # Global user permissions
+        User = apps.get_model("authentik_core", "User")
+        User.user_permissions.through.objects.using(db_alias).filter(
+            permission=old_perm
+        ).all().update(permission=new_perm)
+
+        # Global role permissions
+        DjangoGroup = apps.get_model("auth", "Group")
+        DjangoGroup.permissions.through.objects.using(db_alias).filter(
+            permission=old_perm
+        ).all().update(permission=new_perm)
+
+        # Object user permissions
+        UserObjectPermission = apps.get_model("guardian", "UserObjectPermission")
+        UserObjectPermission.objects.using(db_alias).filter(permission=old_perm).all().update(
+            permission=new_perm, content_type=new_ct
+        )
+
+        # Object role permissions
+        GroupObjectPermission = apps.get_model("guardian", "GroupObjectPermission")
+        GroupObjectPermission.objects.using(db_alias).filter(permission=old_perm).all().update(
+            permission=new_perm, content_type=new_ct
+        )
+
+
 def remove_old_authenticated_session_content_type(
     apps: Apps, schema_editor: BaseDatabaseSchemaEditor
 ):
@@ -21,7 +92,12 @@ class Migration(migrations.Migration):
     ]
 
     operations = [
+        migrations.RunPython(
+            code=migrate_authenticated_session_permissions,
+            reverse_code=migrations.RunPython.noop,
+        ),
         migrations.RunPython(
             code=remove_old_authenticated_session_content_type,
+            reverse_code=migrations.RunPython.noop,
         ),
     ]