diff --git a/apps/server/src/routes/health/routes/environment.ts b/apps/server/src/routes/health/routes/environment.ts
index ee5f7d53..8e5a89c9 100644
--- a/apps/server/src/routes/health/routes/environment.ts
+++ b/apps/server/src/routes/health/routes/environment.ts
@@ -9,12 +9,14 @@ import type { Request, Response } from 'express';
 
 export interface EnvironmentResponse {
   isContainerized: boolean;
+  skipSandboxWarning?: boolean;
 }
 
 export function createEnvironmentHandler() {
   return (_req: Request, res: Response): void => {
     res.json({
       isContainerized: process.env.IS_CONTAINERIZED === 'true',
+      skipSandboxWarning: process.env.AUTOMAKER_SKIP_SANDBOX_WARNING === 'true',
     } satisfies EnvironmentResponse);
   };
 }
diff --git a/apps/ui/src/lib/http-api-client.ts b/apps/ui/src/lib/http-api-client.ts
index d7ac5280..cd0e6739 100644
--- a/apps/ui/src/lib/http-api-client.ts
+++ b/apps/ui/src/lib/http-api-client.ts
@@ -483,6 +483,7 @@ export const verifySession = async (): Promise<boolean> => {
  */
 export const checkSandboxEnvironment = async (): Promise<{
   isContainerized: boolean;
+  skipSandboxWarning?: boolean;
   error?: string;
 }> => {
   try {
@@ -498,7 +499,10 @@ export const checkSandboxEnvironment = async (): Promise<{
     }
 
     const data = await response.json();
-    return { isContainerized: data.isContainerized ?? false };
+    return {
+      isContainerized: data.isContainerized ?? false,
+      skipSandboxWarning: data.skipSandboxWarning ?? false,
+    };
   } catch (error) {
     logger.error('Sandbox environment check failed:', error);
     return { isContainerized: false, error: 'Network error' };
diff --git a/apps/ui/src/routes/__root.tsx b/apps/ui/src/routes/__root.tsx
index f3a662e8..9c118967 100644
--- a/apps/ui/src/routes/__root.tsx
+++ b/apps/ui/src/routes/__root.tsx
@@ -252,15 +252,16 @@ function RootLayoutContent() {
     setIsMounted(true);
   }, []);
 
-  // Check sandbox environment only after user is authenticated and setup is complete
+  // Check sandbox environment only after user is authenticated, setup is complete, and settings are loaded
   useEffect(() => {
     // Skip if already decided
     if (sandboxStatus !== 'pending') {
       return;
     }
 
-    // Don't check sandbox until user is authenticated and has completed setup
-    if (!authChecked || !isAuthenticated || !setupComplete) {
+    // Don't check sandbox until user is authenticated, has completed setup, and settings are loaded
+    // CRITICAL: settingsLoaded must be true to ensure skipSandboxWarning has been hydrated from server
+    if (!authChecked || !isAuthenticated || !setupComplete || !settingsLoaded) {
       return;
     }
 
@@ -271,8 +272,8 @@ function RootLayoutContent() {
         if (result.isContainerized) {
           // Running in a container, no warning needed
           setSandboxStatus('containerized');
-        } else if (skipSandboxWarning) {
-          // User opted to skip the warning, auto-confirm
+        } else if (result.skipSandboxWarning || skipSandboxWarning) {
+          // Skip if env var is set OR if user preference is set
           setSandboxStatus('confirmed');
         } else {
           // Not containerized, show warning dialog
@@ -290,7 +291,14 @@ function RootLayoutContent() {
     };
 
     checkSandbox();
-  }, [sandboxStatus, skipSandboxWarning, authChecked, isAuthenticated, setupComplete]);
+  }, [
+    sandboxStatus,
+    skipSandboxWarning,
+    authChecked,
+    isAuthenticated,
+    setupComplete,
+    settingsLoaded,
+  ]);
 
   // Handle sandbox risk confirmation
   const handleSandboxConfirm = useCallback(