diff --git a/spec/tasks/themes_spec.rb b/spec/tasks/themes_spec.rb
index 4a1c4a84ecf..ff454dac007 100644
--- a/spec/tasks/themes_spec.rb
+++ b/spec/tasks/themes_spec.rb
@@ -18,7 +18,20 @@ RSpec.describe "tasks/themes" do
       }
       JSON
 
-      setup_git_repo("about.json" => about_json, "common/header.html" => "I AM A HEADER")
+      settings_yaml = <<~YAML
+      some_setting:
+        type: string
+        default: some default value
+      string_setting:
+        type: string
+        default: default value
+      YAML
+
+      setup_git_repo(
+        "about.json" => about_json,
+        "common/header.html" => "I AM A HEADER",
+        "settings.yml" => settings_yaml,
+      )
     end
 
     let(:initial_repo_url) do
@@ -31,6 +44,57 @@ RSpec.describe "tasks/themes" do
 
     after { `rm -fr #{initial_repo}` }
 
+    it "should retain a theme's settings and not update the theme when a theme's setting fails to save" do
+      theme.update_setting(:some_setting, "some setting value")
+
+      migration_content = <<~JS
+      export default function migrate(settings) {
+        const oldSetting = settings.get("string_setting");
+        settings.set("string_setting", [{}]);
+        return settings;
+      }
+      JS
+
+      settings_yaml = <<~YAML
+      string_setting:
+        type: objects
+        default: []
+        schema:
+          name: some object
+          properties:
+            title:
+              type: string
+              required: true
+      YAML
+
+      add_to_git_repo(
+        initial_repo,
+        "migrations/settings/0001-a-migration.js" => migration_content,
+        "settings.yml" => settings_yaml,
+        "common/header.html" => "I AM UPDATED HEADER",
+      )
+
+      original_remote_version = theme.remote_theme.remote_version
+      original_local_version = theme.remote_theme.local_version
+
+      stderr = capture_stderr { capture_stdout { Rake::Task["themes:update"].invoke } }
+
+      expect(stderr.chomp).to eq(
+        "[default] Failed to update 'awesome theme' (#{theme.id}): The property at JSON Pointer '/0/title' must be present.",
+      )
+
+      theme.reload
+
+      expect(theme.theme_fields.count).to eq(2)
+      expect(theme.theme_fields.where(name: "header").first.value).to eq("I AM A HEADER")
+      expect(theme.theme_settings_migrations.count).to eq(0)
+      expect(theme.remote_theme.commits_behind).to eq(0)
+      expect(theme.remote_theme.remote_version).to eq(original_remote_version)
+      expect(theme.remote_theme.local_version).to eq(original_local_version)
+      expect(theme.settings[:some_setting].value).to eq("some setting value")
+      expect(theme.settings[:string_setting].value).to eq("default value")
+    end
+
     it "should not update the theme if a theme setting migration fails during the update" do
       migration_content = <<~JS
       export default function migrate(settings) {
@@ -51,7 +115,7 @@ RSpec.describe "tasks/themes" do
 
       theme.reload
 
-      expect(theme.theme_fields.count).to eq(1)
+      expect(theme.theme_fields.count).to eq(2)
       expect(theme.theme_fields.where(name: "header").first.value).to eq("I AM A HEADER")
       expect(theme.theme_settings_migrations.count).to eq(0)
       expect(theme.remote_theme.commits_behind).to eq(0)