diff --git a/open-sse/executors/chatgpt-web.ts b/open-sse/executors/chatgpt-web.ts
index 673495449d..9a4eb3cf36 100644
--- a/open-sse/executors/chatgpt-web.ts
+++ b/open-sse/executors/chatgpt-web.ts
@@ -649,28 +649,37 @@ function buildConversationBody(
   conversationId: string | null,
   parentMessageId: string
 ): Record<string, unknown> {
-  const messages: ChatGptMessage[] = [];
+  // Critical: do NOT send prior turns as separate `assistant` and `user`
+  // messages in the `messages` array. ChatGPT's web API ("action: next")
+  // treats those as in-progress turns and the model will literally CONTINUE
+  // a prior assistant response in the new generation — observed as
+  // `[1] -> [12] -> [1123]` across three turns.
+  //
+  // Instead, fold all prior history into the system message and send only
+  // the current user message as a single new turn. The model then sees a
+  // single prompt with full context and responds fresh.
+  const systemParts: string[] = [];
+  if (parsed.systemMsg.trim()) {
+    systemParts.push(parsed.systemMsg.trim());
+  }
+  if (parsed.history.length > 0 && !conversationId) {
+    const formatted = parsed.history
+      .map((h) => `${h.role === "assistant" ? "Assistant" : "User"}: ${h.content}`)
+      .join("\n\n");
+    systemParts.push(
+      `Prior conversation (for context — answer only the new user message below):\n\n${formatted}`
+    );
+  }
 
-  if (parsed.systemMsg.trim() && !conversationId) {
+  const messages: ChatGptMessage[] = [];
+  if (systemParts.length > 0 && !conversationId) {
     messages.push({
       id: randomUUID(),
       author: { role: "system" },
-      content: { content_type: "text", parts: [parsed.systemMsg.trim()] },
+      content: { content_type: "text", parts: [systemParts.join("\n\n")] },
     });
   }
 
-  // Replay history only on a brand-new conversation; ChatGPT remembers prior turns
-  // server-side once a conversation_id exists.
-  if (!conversationId) {
-    for (const h of parsed.history) {
-      messages.push({
-        id: randomUUID(),
-        author: { role: h.role },
-        content: { content_type: "text", parts: [h.content] },
-      });
-    }
-  }
-
   messages.push({
     id: randomUUID(),
     author: { role: "user" },
diff --git a/tests/unit/chatgpt-web.test.ts b/tests/unit/chatgpt-web.test.ts
index 081e9b42fe..1f1ec730b3 100644
--- a/tests/unit/chatgpt-web.test.ts
+++ b/tests/unit/chatgpt-web.test.ts
@@ -805,9 +805,15 @@ test("Session continuity: each call starts a fresh conversation (Temporary Chat
     assert.equal(convIndices.length, 2);
     const secondBody = JSON.parse(m.calls.bodies[convIndices[1]]);
     assert.equal(secondBody.conversation_id, null, "should start a fresh conversation");
-    // The full history should be replayed in the messages array.
+    // History is folded into the system message (so the model doesn't try to
+    // continue prior assistant turns); only the latest user message is sent.
     const userMessages = secondBody.messages.filter((m) => m.author?.role === "user");
-    assert.equal(userMessages.length, 2, "should include First question + Follow-up");
+    assert.equal(userMessages.length, 1, "only the latest user message is in the messages array");
+    assert.equal(userMessages[0].content.parts[0], "Follow-up");
+    const systemMsg = secondBody.messages.find((m) => m.author?.role === "system");
+    assert.ok(systemMsg, "history should be packaged in a system message");
+    assert.match(systemMsg.content.parts[0], /First question/);
+    assert.match(systemMsg.content.parts[0], /Hello, world!/);
   } finally {
     m.restore();
   }
@@ -864,9 +870,10 @@ test("Request: payload has correct ChatGPT shape", async () => {
     assert.equal(body.action, "next");
     assert.equal(body.model, "gpt-5-3");
     assert.equal(body.history_and_training_disabled, true);
-    // System + user in messages
+    // System message preserves the user-supplied system prompt; the user
+    // message is the latest query.
     assert.equal(body.messages[0].author.role, "system");
-    assert.equal(body.messages[0].content.parts[0], "Be concise");
+    assert.match(body.messages[0].content.parts[0], /Be concise/);
     assert.equal(body.messages[body.messages.length - 1].author.role, "user");
     assert.equal(body.messages[body.messages.length - 1].content.parts[0], "What is 2+2?");
   } finally {