diff --git a/app/models/appearance.rb b/app/models/appearance.rb
index e114c435b67..ff1ecfda684 100644
--- a/app/models/appearance.rb
+++ b/app/models/appearance.rb
@@ -44,7 +44,11 @@ class Appearance < ActiveRecord::Base
   private
 
   def logo_system_path(logo, mount_type)
-    return unless logo&.upload
+    # Legacy attachments may not have have an associated Upload record,
+    # so fallback to the AttachmentUploader#url if this is the
+    # case. AttachmentUploader#path doesn't work because for a local
+    # file, this is an absolute path to the file.
+    return logo&.url unless logo&.upload
 
     # If we're using a CDN, we need to use the full URL
     asset_host = ActionController::Base.asset_host
diff --git a/changelogs/unreleased/sh-fix-issue-9357.yml b/changelogs/unreleased/sh-fix-issue-9357.yml
new file mode 100644
index 00000000000..756cd6047b8
--- /dev/null
+++ b/changelogs/unreleased/sh-fix-issue-9357.yml
@@ -0,0 +1,5 @@
+---
+title: Fix 500 errors with legacy appearance logos
+merge_request: 24615
+author:
+type: fixed
diff --git a/spec/models/appearance_spec.rb b/spec/models/appearance_spec.rb
index ec2e7d672f0..cc76a2019ec 100644
--- a/spec/models/appearance_spec.rb
+++ b/spec/models/appearance_spec.rb
@@ -36,6 +36,13 @@ describe Appearance do
       expect(subject.send("#{logo_type}_path")).to be_nil
     end
 
+    it 'returns the path when the upload has been orphaned' do
+      appearance.send(logo_type).upload.destroy
+      appearance.reload
+
+      expect(appearance.send("#{logo_type}_path")).to eq(expected_path)
+    end
+
     it 'returns a local path using the system route' do
       expect(appearance.send("#{logo_type}_path")).to eq(expected_path)
     end