diff --git a/packages/relay/src/cloudflare-adapter.test.ts b/packages/relay/src/cloudflare-adapter.test.ts
index eeca70e700..e9aed32013 100644
--- a/packages/relay/src/cloudflare-adapter.test.ts
+++ b/packages/relay/src/cloudflare-adapter.test.ts
@@ -230,6 +230,39 @@ describe("RelayDurableObject control nudge/reset behavior", () => {
   });
 });
 
+describe("RelayDurableObject data forwarding", () => {
+  it("forwards a client frame only to the newest daemon socket during replacement", () => {
+    const connectionId = "clt_replacing_daemon";
+    const client = createMockSocket({
+      version: "2",
+      role: "client",
+      connectionId,
+      serverId: "srv_test",
+      createdAt: 1,
+    });
+    const daemonSockets = Array.from({ length: 6 }, (_, index) =>
+      createMockSocket({
+        version: "2",
+        role: "server",
+        connectionId,
+        serverId: "srv_test",
+        createdAt: index + 1,
+      }),
+    );
+    const { state, setTagSockets } = createMockState();
+    setTagSockets(`server:${connectionId}`, daemonSockets);
+
+    const relay = new RelayDurableObject(state as unknown as DurableObjectStateArg);
+    relay.webSocketMessage(client as unknown as WebSocket, "create_agent_request");
+
+    for (const staleSocket of daemonSockets.slice(0, -1)) {
+      expect(staleSocket.send).not.toHaveBeenCalled();
+    }
+    expect(daemonSockets.at(-1)?.send).toHaveBeenCalledOnce();
+    expect(daemonSockets.at(-1)?.send).toHaveBeenCalledWith("create_agent_request");
+  });
+});
+
 describe("relay worker endpoint routing", () => {
   it("routes missing v to legacy v1 isolated DO ids", async () => {
     const fetch = vi.fn(
diff --git a/packages/relay/src/cloudflare-adapter.ts b/packages/relay/src/cloudflare-adapter.ts
index e7e50c2309..4d77034649 100644
--- a/packages/relay/src/cloudflare-adapter.ts
+++ b/packages/relay/src/cloudflare-adapter.ts
@@ -86,6 +86,25 @@ function getString(record: Record<string, unknown>, key: string): string | undef
   return typeof value === "string" ? value : undefined;
 }
 
+function getSocketCreatedAt(ws: WebSocket): number {
+  const attachment = deserializeAttachment(ws);
+  if (!isRecord(attachment)) return 0;
+  return typeof attachment.createdAt === "number" ? attachment.createdAt : 0;
+}
+
+function selectNewestSocket(sockets: WebSocket[]): WebSocket | null {
+  let newest: WebSocket | null = null;
+  let newestCreatedAt = Number.NEGATIVE_INFINITY;
+  for (const socket of sockets) {
+    const createdAt = getSocketCreatedAt(socket);
+    if (createdAt >= newestCreatedAt) {
+      newest = socket;
+      newestCreatedAt = createdAt;
+    }
+  }
+  return newest;
+}
+
 function getGlobalWebSocketPair(): (new () => WebSocketPair) | undefined {
   // Access WebSocketPair from global scope (Cloudflare Workers runtime)
   // Use Reflect to access global property without type assertions
@@ -484,12 +503,11 @@ export class RelayDurableObject {
         this.bufferFrame(connectionId, message);
         return;
       }
-      for (const target of servers) {
-        try {
-          target.send(message);
-        } catch (error) {
-          console.error(`[Relay DO] Failed to forward client->server(${connectionId}):`, error);
-        }
+      const target = selectNewestSocket(servers);
+      try {
+        target?.send(message);
+      } catch (error) {
+        console.error(`[Relay DO] Failed to forward client->server(${connectionId}):`, error);
       }
       return;
     }