diff --git a/relay_client.py b/relay_client.py
index 4ce4677..af1935e 100644
--- a/relay_client.py
+++ b/relay_client.py
@@ -141,6 +141,8 @@ class RelayClient:
 
         if response.get("type") == "auth_response":
             if response.get("success"):
+                # Mark as connected before callbacks so update_ip_label works
+                self._connected = True
                 new_session_id = response.get("sessionId")
                 if new_session_id and new_session_id != self.session_id:
                     self.session_id = new_session_id
diff --git a/web/js/app.js b/web/js/app.js
index c7fbbd5..b20f7bf 100644
--- a/web/js/app.js
+++ b/web/js/app.js
@@ -308,9 +308,16 @@ class MacroPadApp {
         }
 
         container.innerHTML = macroEntries.map(([id, macro]) => {
-            const imageSrc = macro.image_path
-                ? `/api/image/${macro.image_path}`
-                : null;
+            let imageSrc = null;
+            if (macro.image_path) {
+                const basePath = this.getApiUrl(`/api/image/${macro.image_path}`);
+                // Add password as query param for relay mode (img tags can't use headers)
+                if (this.relayMode && this.password) {
+                    imageSrc = `${basePath}?password=${encodeURIComponent(this.password)}`;
+                } else {
+                    imageSrc = basePath;
+                }
+            }
             const firstChar = macro.name.charAt(0).toUpperCase();
 
             return `