diff --git a/.changeset/history-context-menu-size.md b/.changeset/history-context-menu-size.md
new file mode 100644
index 00000000000..80a0fb90dd8
--- /dev/null
+++ b/.changeset/history-context-menu-size.md
@@ -0,0 +1,5 @@
+---
+"kilo-code": patch
+---
+
+Improve the size and readability of the local History session context menu.
diff --git a/packages/kilo-vscode/webview-ui/src/components/history/SessionList.tsx b/packages/kilo-vscode/webview-ui/src/components/history/SessionList.tsx
index 7a99fa4e48a..d0047e53aa7 100644
--- a/packages/kilo-vscode/webview-ui/src/components/history/SessionList.tsx
+++ b/packages/kilo-vscode/webview-ui/src/components/history/SessionList.tsx
@@ -115,7 +115,7 @@ const SessionList: Component<SessionListProps> = (props) => {
           {node}
         </ContextMenu.Trigger>
         <ContextMenu.Portal>
-          <ContextMenu.Content>
+          <ContextMenu.Content class="session-list-menu">
             <ContextMenu.Item onSelect={() => startRename(item)}>
               <ContextMenu.ItemLabel>{language.t("common.rename")}</ContextMenu.ItemLabel>
             </ContextMenu.Item>
diff --git a/packages/kilo-vscode/webview-ui/src/styles/history.css b/packages/kilo-vscode/webview-ui/src/styles/history.css
index b41b8b9473f..7a523e2942a 100644
--- a/packages/kilo-vscode/webview-ui/src/styles/history.css
+++ b/packages/kilo-vscode/webview-ui/src/styles/history.css
@@ -61,6 +61,26 @@ body.vscode-light
   opacity: 1;
 }
 
+.session-list-menu {
+  min-width: 180px;
+  border: 1px solid color-mix(in oklch, var(--border-base) 50%, transparent);
+  box-shadow: var(--shadow-md);
+
+  [data-slot="context-menu-item"] {
+    padding: 6px 10px;
+    line-height: var(--line-height-large);
+    transition: none;
+
+    &[data-highlighted] {
+      background: var(--surface-raised-base-hover);
+    }
+  }
+
+  [data-slot="context-menu-separator"] {
+    margin: 4px 0;
+  }
+}
+
 /* History View (unified Local + Cloud tabs) */
 .history-view {
   display: flex;