diff --git a/src/discord/monitor.ts b/src/discord/monitor.ts
index b45434d61..4cc98a169 100644
--- a/src/discord/monitor.ts
+++ b/src/discord/monitor.ts
@@ -396,6 +396,11 @@ export async function monitorDiscordProvider(opts: MonitorDiscordOpts = {}) {
         MediaType: media?.contentType,
         MediaUrl: media?.path,
       };
+      const replyTarget = ctxPayload.To ?? undefined;
+      if (!replyTarget) {
+        runtime.error?.(danger("discord: missing reply target"));
+        return;
+      }
 
       if (isDirectMessage) {
         const sessionCfg = cfg.session;
@@ -430,7 +435,7 @@ export async function monitorDiscordProvider(opts: MonitorDiscordOpts = {}) {
           .then(async () => {
             await deliverReplies({
               replies: [payload],
-              target: ctxPayload.To,
+              target: replyTarget,
               token,
               runtime,
               replyToMode,
@@ -473,7 +478,7 @@ export async function monitorDiscordProvider(opts: MonitorDiscordOpts = {}) {
 
       await deliverReplies({
         replies,
-        target: ctxPayload.To,
+        target: replyTarget,
         token,
         runtime,
         replyToMode,
@@ -482,7 +487,7 @@ export async function monitorDiscordProvider(opts: MonitorDiscordOpts = {}) {
       didSendReply = true;
       if (isVerbose()) {
         logVerbose(
-          `discord: delivered ${replies.length} reply${replies.length === 1 ? "" : "ies"} to ${ctxPayload.To}`,
+          `discord: delivered ${replies.length} reply${replies.length === 1 ? "" : "ies"} to ${replyTarget}`,
         );
       }
       if (
diff --git a/src/gateway/call.ts b/src/gateway/call.ts
index bcef4c613..9f2989523 100644
--- a/src/gateway/call.ts
+++ b/src/gateway/call.ts
@@ -27,6 +27,7 @@ export async function callGateway<T = unknown>(
   const config = loadConfig();
   const isRemoteMode = config.gateway?.mode === "remote";
   const remote = isRemoteMode ? config.gateway?.remote : undefined;
+  const authToken = config.gateway?.auth?.token;
   const url =
     (typeof opts.url === "string" && opts.url.trim().length > 0
       ? opts.url.trim()
@@ -44,9 +45,8 @@ export async function callGateway<T = unknown>(
         ? remote.token.trim()
         : undefined
       : process.env.CLAWDIS_GATEWAY_TOKEN?.trim() ||
-        (typeof config.gateway?.auth?.token === "string" &&
-        config.gateway.auth.token.trim().length > 0
-          ? config.gateway.auth.token.trim()
+        (typeof authToken === "string" && authToken.trim().length > 0
+          ? authToken.trim()
           : undefined));
   const password =
     (typeof opts.password === "string" && opts.password.trim().length > 0