diff --git a/extension/package-lock.json b/extension/package-lock.json
index 1b36257..8af4ff4 100644
--- a/extension/package-lock.json
+++ b/extension/package-lock.json
@@ -1,12 +1,12 @@
 {
   "name": "gravity-bridge",
-  "version": "0.5.59",
+  "version": "0.5.60",
   "lockfileVersion": 3,
   "requires": true,
   "packages": {
     "": {
       "name": "gravity-bridge",
-      "version": "0.5.59",
+      "version": "0.5.60",
       "dependencies": {
         "cheerio": "^1.2.0",
         "ws": "^8.19.0"
diff --git a/extension/package.json b/extension/package.json
index fa3759b..d532a47 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": "0.5.59",
+  "version": "0.5.60",
   "publisher": "variet",
   "engines": {
     "vscode": "^1.100.0"
diff --git a/extension/src/http-bridge.ts b/extension/src/http-bridge.ts
index 036adb8..55d57a7 100644
--- a/extension/src/http-bridge.ts
+++ b/extension/src/http-bridge.ts
@@ -266,6 +266,64 @@ function _handlePending(req: any, res: any, ctx: HttpBridgeContext) {
             const GENERIC_BTN_RE = /^(?:Always\s*)?(?:Run|Allow|Accept|Approve)$/i;
             let enrichedCmd = rawCmd;
             let enrichedDesc = rawDesc;
+
+            // v19: "Always run" auto-approve — MUST run BEFORE any filter can reject it
+            // Detects from rawCmd OR from buttons array (Observer may detect sibling first)
+            let alwaysRunDetected = /^Always\s+run$/i.test(rawCmd);
+            let alwaysRunBtnIndex = alwaysRunDetected ? 0 : -1;
+            if (!alwaysRunDetected && Array.isArray(data.buttons)) {
+                for (let bi = 0; bi < data.buttons.length; bi++) {
+                    if (/^Always\s+run$/i.test((data.buttons[bi].text || '').trim())) {
+                        alwaysRunDetected = true;
+                        alwaysRunBtnIndex = bi;
+                        break;
+                    }
+                }
+            }
+            if (alwaysRunDetected) {
+                // Try enrichment for better Discord display text
+                let displayCmd = rawCmd;
+                if (GENERIC_BTN_RE.test(rawCmd) && rawDesc.length > 10 && rawDesc !== rawCmd) {
+                    const promptMatch = rawDesc.match(/[>»]\s*(.+)/);
+                    if (promptMatch && promptMatch[1].trim().length > 3) {
+                        displayCmd = promptMatch[1].trim().substring(0, 200);
+                    }
+                }
+                const rid = data.request_id || Date.now().toString();
+                ctx.logToFile(`[HTTP] AUTO-APPROVE "Always run" (btnIdx=${alwaysRunBtnIndex}): cmd="${displayCmd.substring(0, 80)}"`);
+                // Write response file so observer's pollResponseGroup picks it up and clicks the button
+                const responseDir = path.join(ctx.bridgePath, 'response');
+                if (!fs.existsSync(responseDir)) {
+                    fs.mkdirSync(responseDir, { recursive: true });
+                }
+                const respPayload = {
+                    request_id: rid,
+                    approved: true,
+                    button_index: alwaysRunBtnIndex >= 0 ? alwaysRunBtnIndex : 0,
+                    step_type: data.step_type || 'command',
+                    project_name: ctx.projectName,
+                };
+                fs.writeFileSync(
+                    path.join(responseDir, `${rid}.json`),
+                    JSON.stringify(respPayload),
+                    'utf-8'
+                );
+                // Notify Discord (non-interactive "자동 승인" embed)
+                if (ctx.wsBridge && ctx.wsBridge.isConnected()) {
+                    ctx.wsBridge.sendPending({
+                        request_id: rid,
+                        command: displayCmd,
+                        description: rawDesc ? `[${rawCmd}] ${rawDesc}` : rawCmd,
+                        step_type: data.step_type || 'command',
+                        status: 'auto_approved',
+                        buttons: data.buttons,
+                        project_name: ctx.projectName,
+                    });
+                }
+                res.writeHead(200, { 'Content-Type': 'application/json' });
+                res.end(JSON.stringify({ ok: true, request_id: rid, auto_approved: true }));
+                return;
+            }
             if (GENERIC_BTN_RE.test(rawCmd) && rawDesc.length > 10 && rawDesc !== rawCmd) {
                 // Extract the actual command from description (often includes terminal prompt)
                 // Pattern: "…\project_name > actual_command"
@@ -361,55 +419,8 @@ function _handlePending(req: any, res: any, ctx: HttpBridgeContext) {
                 buttons: data.buttons,
                 step_index: ctx.lastPendingStepIndex >= 0 ? ctx.lastPendingStepIndex : undefined,
             };
-            // v17+: "Always run" auto-approve — click button immediately without Discord roundtrip
-            // Check rawCmd first, then fall back to scanning the buttons array
-            // (Observer may detect "Run" first while "Always run" is a sibling button)
-            let alwaysRunIndex = -1;
-            if (/^Always\s+run$/i.test(rawCmd)) {
-                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="${enrichedCmd.substring(0, 80)}"`);
-                // Write response file so observer's pollResponseGroup picks it up and clicks the button
-                const responseDir = path.join(ctx.bridgePath, 'response');
-                if (!fs.existsSync(responseDir)) {
-                    fs.mkdirSync(responseDir, { recursive: true });
-                }
-                const respPayload = {
-                    request_id: rid,
-                    approved: true,
-                    button_index: alwaysRunIndex,
-                    step_type: data.step_type || 'command',
-                    project_name: ctx.projectName,
-                };
-                fs.writeFileSync(
-                    path.join(responseDir, `${rid}.json`),
-                    JSON.stringify(respPayload),
-                    'utf-8'
-                );
-                // Notify Discord (non-interactive "자동 승인" embed)
-                if (ctx.wsBridge && ctx.wsBridge.isConnected()) {
-                    ctx.wsBridge.sendPending({
-                        request_id: rid,
-                        command: enrichedCmd || rawCmd,
-                        description: enrichedDesc,
-                        step_type: pending.step_type,
-                        status: 'auto_approved',
-                        buttons: pending.buttons,
-                        project_name: ctx.projectName,
-                    });
-                }
-                res.writeHead(200, { 'Content-Type': 'application/json' });
-                res.end(JSON.stringify({ ok: true, request_id: rid, auto_approved: true }));
-                return;
-            }
+            // v19: "Always run" auto-approve was already handled above (before filter chain)
+            // No need for duplicate check here.
             // File permission: inject multi-choice buttons
             const cmdLower = enrichedCmd.toLowerCase();
             if (cmdLower.includes('allow') && !pending.buttons) {