diff --git a/extension/package-lock.json b/extension/package-lock.json
index 0b126fd..2af6c18 100644
--- a/extension/package-lock.json
+++ b/extension/package-lock.json
@@ -1,12 +1,12 @@
 {
   "name": "gravity-bridge",
-  "version": "0.5.57",
+  "version": "0.5.58",
   "lockfileVersion": 3,
   "requires": true,
   "packages": {
     "": {
       "name": "gravity-bridge",
-      "version": "0.5.57",
+      "version": "0.5.58",
       "dependencies": {
         "cheerio": "^1.2.0",
         "ws": "^8.19.0"
diff --git a/extension/package.json b/extension/package.json
index 3f8914b..42fbd55 100644
--- a/extension/package.json
+++ b/extension/package.json
@@ -2,7 +2,7 @@
   "name": "gravity-bridge",
   "displayName": "Gravity Bridge",
   "description": "Discord-based unified approval system for Antigravity AI interactions.",
-  "version": "0.5.57",
+  "version": "0.5.58",
   "publisher": "variet",
   "engines": {
     "vscode": "^1.100.0"
diff --git a/extension/src/http-bridge.ts b/extension/src/http-bridge.ts
index ec18cfe..036adb8 100644
--- a/extension/src/http-bridge.ts
+++ b/extension/src/http-bridge.ts
@@ -361,11 +361,22 @@ function _handlePending(req: any, res: any, ctx: HttpBridgeContext) {
                 buttons: data.buttons,
                 step_index: ctx.lastPendingStepIndex >= 0 ? ctx.lastPendingStepIndex : undefined,
             };
-            // v17: "Always run" auto-approve — click button immediately without Discord roundtrip
-            // rawCmd is the original button text before enrichment. "Always run" means the user
-            // already trusts this command pattern, so we auto-approve at the bridge level.
+            // v17+: "Always run" auto-approve — click button immediately without Discord roundtrip
+            // Check rawCmd first, then fall back to scanning the buttons array
+            // (Observer may detect "Run" first while "Always run" is a sibling button)
+            let alwaysRunIndex = -1;
             if (/^Always\s+run$/i.test(rawCmd)) {
-                ctx.logToFile(`[HTTP] AUTO-APPROVE "Always run": enriched="${enrichedCmd.substring(0, 80)}"`);
+                alwaysRunIndex = 0;
+            } else if (Array.isArray(data.buttons)) {
+                for (let bi = 0; bi < data.buttons.length; bi++) {
+                    if (/^Always\s+run$/i.test((data.buttons[bi].text || '').trim())) {
+                        alwaysRunIndex = bi;
+                        break;
+                    }
+                }
+            }
+            if (alwaysRunIndex >= 0) {
+                ctx.logToFile(`[HTTP] AUTO-APPROVE "Always run" (btnIdx=${alwaysRunIndex}): enriched="${enrichedCmd.substring(0, 80)}"`);
                 // Write response file so observer's pollResponseGroup picks it up and clicks the button
                 const responseDir = path.join(ctx.bridgePath, 'response');
                 if (!fs.existsSync(responseDir)) {
@@ -374,7 +385,7 @@ function _handlePending(req: any, res: any, ctx: HttpBridgeContext) {
                 const respPayload = {
                     request_id: rid,
                     approved: true,
-                    button_index: 0,  // "Always run" is always the first button
+                    button_index: alwaysRunIndex,
                     step_type: data.step_type || 'command',
                     project_name: ctx.projectName,
                 };