diff --git a/plugin/web/server.ts b/plugin/web/server.ts
index 82aa2e8..efceb67 100644
--- a/plugin/web/server.ts
+++ b/plugin/web/server.ts
@@ -276,9 +276,37 @@ export function createBridgeServer(config: BridgeServerConfig): http.Server {
       // updated `claudeSessionId` and we want to resume into the latest
       // one rather than a stale snapshot from request-arrival time.
       existingEntry = sessionKey ? getSession(workspace, sessionKey) : null;
-      if (bareSessionReset && existingEntry && sessionKey) {
+
+      // Detect a fresh OpenClaw session even when the bare-reset marker is
+      // absent. The marker only arrives when `/new` is the body of *this*
+      // user turn (see get-reply isBareSessionReset). When `/new` is sent
+      // as a separate slash command (e.g. via Discord's slash UI), OpenClaw
+      // processes the reset in a side lane that doesn't hit the bridge —
+      // it just renames the prior session file aside. The follow-up real
+      // message then arrives on a brand-new OpenClaw session, but as a
+      // normal turn with no marker. Without this check, the bridge happily
+      // resumes the long-stale claudeSessionId from before the reset.
+      //
+      // OpenClaw sends the full conversation history every turn (system +
+      // user/assistant pairs + latest user). A request with zero assistant
+      // turns is therefore a positive signal that the OpenClaw session is
+      // brand-new and any prior claudeSessionId we hold is from a previous
+      // OpenClaw session that the user already abandoned.
+      const hasAssistantHistory = body.messages.some((m) => {
+        if (m.role !== "assistant") return false;
+        if (typeof m.content === "string") return m.content.trim().length > 0;
+        return m.content.some(
+          (c) => c.type === "text" && (c.text ?? "").trim().length > 0,
+        );
+      });
+      const isFreshOpenClawSession = !hasAssistantHistory;
+
+      if ((bareSessionReset || isFreshOpenClawSession) && existingEntry && sessionKey) {
+        const reason = bareSessionReset
+          ? "bare /new detected"
+          : "fresh OpenClaw session (no assistant history in messages[])";
         logger.info(
-          `[contractor-bridge] bare /new detected — dropping prior CLI session sessionKey=${sessionKey} prevClaudeSessionId=${existingEntry.claudeSessionId}`,
+          `[contractor-bridge] ${reason} — dropping prior CLI session sessionKey=${sessionKey} prevClaudeSessionId=${existingEntry.claudeSessionId}`,
         );
         removeSession(workspace, sessionKey);
         existingEntry = null;