diff --git a/cli/src/lib/local.ts b/cli/src/lib/local.ts
index 3d3e422aeac..eb60b4807d6 100644
--- a/cli/src/lib/local.ts
+++ b/cli/src/lib/local.ts
@@ -193,6 +193,7 @@ export async function startLocalDaemon(): Promise<void> {
       for (const key of [
         "ANTHROPIC_API_KEY",
         "BASE_DATA_DIR",
+        "RUNTIME_HTTP_PORT",
         "VELLUM_DAEMON_TCP_PORT",
         "VELLUM_DAEMON_TCP_HOST",
         "VELLUM_DAEMON_SOCKET",
diff --git a/clients/macos/vellum-assistant/App/AppDelegate.swift b/clients/macos/vellum-assistant/App/AppDelegate.swift
index df71e9ca5d5..390234393f5 100644
--- a/clients/macos/vellum-assistant/App/AppDelegate.swift
+++ b/clients/macos/vellum-assistant/App/AppDelegate.swift
@@ -557,12 +557,10 @@ public final class AppDelegate: NSObject, NSApplicationDelegate {
 
         let assistant = loadAssistantFromLockfile()
 
-        // Ensure the daemon starts its runtime HTTP server so the app
-        // can communicate over HTTP instead of IPC.
-        if FeatureFlagManager.shared.isEnabled(.localHttpEnabled) {
-            if ProcessInfo.processInfo.environment["RUNTIME_HTTP_PORT"] == nil {
-                setenv("RUNTIME_HTTP_PORT", "7821", 0)
-            }
+        // Ensure the daemon starts its runtime HTTP server so the
+        // gateway can proxy iOS traffic to it.
+        if ProcessInfo.processInfo.environment["RUNTIME_HTTP_PORT"] == nil {
+            setenv("RUNTIME_HTTP_PORT", "7821", 0)
         }
 
         configureDaemonTransport(for: assistant)
diff --git a/clients/macos/vellum-assistant/App/AssistantCli.swift b/clients/macos/vellum-assistant/App/AssistantCli.swift
index 197e44e8b2e..20afdb18f9a 100644
--- a/clients/macos/vellum-assistant/App/AssistantCli.swift
+++ b/clients/macos/vellum-assistant/App/AssistantCli.swift
@@ -602,10 +602,9 @@ final class AssistantCli {
                     env[key] = val
                 }
             }
-            // Forward RUNTIME_HTTP_PORT only when the localHttpEnabled flag
-            // is active, so the daemon doesn't start its HTTP server by default.
-            if FeatureFlagManager.shared.isEnabled(.localHttpEnabled),
-               let port = fullEnv["RUNTIME_HTTP_PORT"] ?? getenv("RUNTIME_HTTP_PORT").flatMap({ String(cString: $0) }) {
+            // Always forward RUNTIME_HTTP_PORT so the daemon starts its
+            // HTTP server — required for iOS pairing via the gateway.
+            if let port = fullEnv["RUNTIME_HTTP_PORT"] ?? getenv("RUNTIME_HTTP_PORT").flatMap({ String(cString: $0) }) {
                 env["RUNTIME_HTTP_PORT"] = port
             }
             proc.environment = env