diff --git a/packages/chat-core/src/index.ts b/packages/chat-core/src/index.ts
index 265a4521..f1dacb51 100644
--- a/packages/chat-core/src/index.ts
+++ b/packages/chat-core/src/index.ts
@@ -1,6 +1,6 @@
 import fetch from "isomorphic-fetch";
 import ReconnectingWebSocket from "reconnecting-websocket";
-import { equals, adjust, omit } from "ramda";
+import { equals, adjust, omit, findLast } from "ramda";
 import { v4 as uuid } from "uuid";
 
 // Bot response
@@ -208,6 +208,20 @@ export const shouldReinitialize = (
   );
 };
 
+const getLastExpirationTimestamp = (
+  responses: Response[],
+): number | undefined => {
+  const lastExpirationResponse = findLast(
+    (response) =>
+      response.type === "bot" &&
+      typeof response.payload.expirationTimestamp === "number",
+    responses,
+  );
+  return lastExpirationResponse?.type === "bot"
+    ? lastExpirationResponse.payload.expirationTimestamp
+    : undefined;
+};
+
 export const createConversation = (config: Config): ConversationHandler => {
   let socket: ReconnectingWebSocket | undefined;
 
@@ -303,6 +317,15 @@ export const createConversation = (config: Config): ConversationHandler => {
     null;
 
   const sendToBot = async (body: BotRequest): Promise<void> => {
+    const lastExpirationTimestamp = getLastExpirationTimestamp(state.responses);
+    if (
+      typeof lastExpirationTimestamp === "number" &&
+      new Date().getTime() > lastExpirationTimestamp
+    ) {
+      setState({
+        conversationId: uuid(),
+      });
+    }
     const bodyWithContext = {
       userId: state.userId,
       conversationId: state.conversationId,
diff --git a/packages/chat-widget/src/index.tsx b/packages/chat-widget/src/index.tsx
index ee13aee2..3872aca6 100644
--- a/packages/chat-widget/src/index.tsx
+++ b/packages/chat-widget/src/index.tsx
@@ -258,29 +258,11 @@ export const retrieveSession = (storeIn: StorageType): SessionData | null => {
   try {
     const storage =
       storeIn === "sessionStorage" ? sessionStorage : localStorage;
-    // initial eslint integration
-    // eslint-disable-next-line @typescript-eslint/strict-boolean-expressions, @typescript-eslint/prefer-nullish-coalescing
-    const data = JSON.parse(storage.getItem(storageKey) || "");
+    const data = JSON.parse(storage.getItem(storageKey) ?? "");
     const responses: Response[] | undefined = data?.responses;
     const conversationId: string | undefined = data?.conversationId;
-    // initial eslint integration
-    // eslint-disable-next-line @typescript-eslint/strict-boolean-expressions
-    if (responses) {
-      let expirationTimestamp: number | undefined;
-      responses.forEach((response) => {
-        // initial eslint integration
-        // eslint-disable-next-line @typescript-eslint/strict-boolean-expressions
-        if (response.type === "bot" && response.payload.expirationTimestamp) {
-          expirationTimestamp = response.payload.expirationTimestamp;
-        }
-      });
-      // initial eslint integration
-      // eslint-disable-next-line @typescript-eslint/strict-boolean-expressions
-      if (!expirationTimestamp || new Date().getTime() < expirationTimestamp) {
-        return { responses, conversationId };
-      } else {
-        return { responses };
-      }
+    if (responses != null) {
+      return { responses, conversationId };
     }
     return null;
   } catch (err) {