diff --git a/assistant/src/daemon/server.ts b/assistant/src/daemon/server.ts
index ef530e9ba48..b28040cecb4 100644
--- a/assistant/src/daemon/server.ts
+++ b/assistant/src/daemon/server.ts
@@ -373,7 +373,28 @@ export class DaemonServer {
       { channelId: transport.channelId },
       "Transport metadata received",
     );
-    conversation.setTransportHints(transport.hints);
+
+    // Build enriched hints: interface ID first, then host environment (macOS
+    // only), then any client-provided hints.
+    const enrichedHints: string[] = [];
+
+    const interfaceLabel = parseInterfaceId(transport.interfaceId) ?? "vellum";
+    enrichedHints.push(`User is messaging from interface: ${interfaceLabel}`);
+
+    if (transport.interfaceId === "macos") {
+      if (transport.hostHomeDir) {
+        enrichedHints.push(`Host home directory: ${transport.hostHomeDir}`);
+      }
+      if (transport.hostUsername) {
+        enrichedHints.push(`Host username: ${transport.hostUsername}`);
+      }
+    }
+
+    if (transport.hints) {
+      enrichedHints.push(...transport.hints);
+    }
+
+    conversation.setTransportHints(enrichedHints);
   }
 
   constructor() {