diff --git a/apps/web/src/app/config.json/extras.ts b/apps/web/src/app/config.json/extras.ts
index a79f181115..1662d90f91 100644
--- a/apps/web/src/app/config.json/extras.ts
+++ b/apps/web/src/app/config.json/extras.ts
@@ -36,6 +36,10 @@ const agentConfig = {
 
 export const kiloExtras = {
   top: {
+    auto_expand_history: {
+      description: 'Automatically expand command history when searching',
+      type: 'boolean',
+    },
     model: {
       description: 'Model to use in the format of provider/model, eg anthropic/claude-2',
       ...nullableModel,
diff --git a/apps/web/src/tests/cli-config-schema.test.ts b/apps/web/src/tests/cli-config-schema.test.ts
index dcc5f0d543..a1affd755e 100644
--- a/apps/web/src/tests/cli-config-schema.test.ts
+++ b/apps/web/src/tests/cli-config-schema.test.ts
@@ -32,6 +32,7 @@ describe('kilo config.json schema merge', () => {
   test('adds kilo-only top-level keys', () => {
     expect(props.commit_message).toBeDefined();
     expect(props.remote_control).toBeDefined();
+    expect(props.auto_expand_history).toBeDefined();
   });
 
   test('commit_message has a prompt string property', () => {