diff --git a/core/index.d.ts b/core/index.d.ts
index d88feb60bf2..c3eabdd953b 100644
--- a/core/index.d.ts
+++ b/core/index.d.ts
@@ -290,6 +290,7 @@ export interface BaseSessionMetadata {
   title: string;
   dateCreated: string;
   workspaceDirectory: string;
+  messageCount?: number;
 }
 
 export interface RangeInFile {
diff --git a/core/util/history.ts b/core/util/history.ts
index cc1cf69cbf6..44241c4201e 100644
--- a/core/util/history.ts
+++ b/core/util/history.ts
@@ -141,10 +141,14 @@ export class HistoryManager {
       }
 
       let found = false;
+      const messageCount = session.history.filter(
+        (item) => item.message.role === "assistant",
+      ).length;
       for (const sessionMetadata of sessionsList) {
         if (sessionMetadata.sessionId === session.sessionId) {
           sessionMetadata.title = session.title;
           sessionMetadata.workspaceDirectory = session.workspaceDirectory;
+          sessionMetadata.messageCount = messageCount;
           found = true;
           break;
         }
@@ -156,6 +160,7 @@ export class HistoryManager {
           title: session.title,
           dateCreated: String(Date.now()),
           workspaceDirectory: session.workspaceDirectory,
+          messageCount,
         };
         sessionsList.push(sessionMetadata);
       }
diff --git a/gui/src/components/History/HistoryTableRow.tsx b/gui/src/components/History/HistoryTableRow.tsx
index 4c6fa2417f2..45c7f130976 100644
--- a/gui/src/components/History/HistoryTableRow.tsx
+++ b/gui/src/components/History/HistoryTableRow.tsx
@@ -1,8 +1,8 @@
 import {
   ArrowDownOnSquareIcon,
+  CloudIcon,
   PencilSquareIcon,
   TrashIcon,
-  CloudIcon,
 } from "@heroicons/react/24/outline";
 import { BaseSessionMetadata } from "core";
 import type { RemoteSessionMetadata } from "core/control-plane/client";
@@ -22,6 +22,7 @@ import {
 } from "../../redux/thunks/session";
 import { isShareSessionSupported } from "../../util";
 import HeaderButtonWithToolTip from "../gui/HeaderButtonWithToolTip";
+import { ToolTip } from "../gui/Tooltip";
 
 const shareSessionSupported = isShareSessionSupported();
 
@@ -144,6 +145,18 @@ export function HistoryTableRow({
                 Remote
               </span>
             )}
+
+            {sessionMetadata.messageCount !== undefined && (
+              <ToolTip
+                content={`${sessionMetadata.messageCount} message${
+                  sessionMetadata.messageCount === 1 ? " is" : "s are"
+                } present in this session`}
+              >
+                <span className="bg-vsc-background text-secondary-foreground ml-auto inline-flex items-center rounded-full px-2 py-1 text-xs font-medium">
+                  {sessionMetadata.messageCount}
+                </span>
+              </ToolTip>
+            )}
           </div>
         )}
 
@@ -166,7 +179,7 @@ export function HistoryTableRow({
       </td>
 
       {hovered && !editing && (
-        <td className="bg-input absolute right-2 top-1/2 ml-auto flex -translate-y-1/2 transform items-center gap-x-1 rounded-full px-2 py-1 shadow-md">
+        <td className="bg-input absolute right-2 top-12 ml-auto flex -translate-y-1/2 transform items-center gap-x-1 rounded-full px-2 py-1 shadow-md">
           {isRemote ? (
             <HeaderButtonWithToolTip
               text="Open in browser"