diff --git a/src/components/Chats.tsx b/src/components/Chats.tsx
index 5f15bf0..0da49af 100644
--- a/src/components/Chats.tsx
+++ b/src/components/Chats.tsx
@@ -1,5 +1,13 @@
 import { ActionIcon, Flex, Menu } from "@mantine/core";
-import { IconDotsVertical, IconMessages } from "@tabler/icons-react";
+import {
+	IconDotsVertical,
+	IconMessages,
+	IconPencil,
+	IconPin,
+	IconPinned,
+	IconPinnedOff,
+	IconTrash
+} from "@tabler/icons-react";
 import { Link } from "@tanstack/react-location";
 import { useLiveQuery } from "dexie-react-hooks";
 import { useMemo } from "react";
@@ -8,6 +16,7 @@ import { useChatId } from "../hooks/useChatId";
 import { DeleteChatModal } from "./DeleteChatModal";
 import { EditChatModal } from "./EditChatModal";
 import { MainLink } from "./MainLink";
+import { notifications } from "@mantine/notifications";
 
 export function Chats({ search }: { search: string }) {
   const chatId = useChatId();
@@ -23,47 +32,79 @@ export function Chats({ search }: { search: string }) {
     [chats, search]
   );
 
+  const toggleChatPin = async (chatId: string, event: React.UIEvent) => {
+    try {
+      event.preventDefault();
+      await db.chats.where({ id: chatId }).modify((chat) => {
+        chat.pinned = !chat.pinned;
+      });
+    } catch (error: any) {
+      if (error.toJSON().message === "Network Error") {
+        notifications.show({
+          title: "Error",
+          color: "red",
+          message: "No internet connection.",
+        });
+      }
+      const message = error.response?.data?.error?.message;
+      if (message) {
+        notifications.show({
+          title: "Error",
+          color: "red",
+          message,
+        });
+      }
+    }
+  };
+
   return (
     <>
-      {filteredChats.map((chat) => (
-        <Flex
-          key={chat.id}
-          className={chatId === chat.id ? "active" : undefined}
-          sx={(theme) => ({
-            marginTop: 1,
-            "&:hover, &.active": {
-              backgroundColor:
-                theme.colorScheme === "dark"
-                  ? theme.colors.dark[6]
-                  : theme.colors.gray[1],
-            },
-          })}
-        >
-          <Link to={`/chats/${chat.id}`} style={{ flex: 1 }}>
-            <MainLink
-              icon={<IconMessages size="1rem" />}
-              color="teal"
-              chat={chat}
-              label={chat.description}
-            />
-          </Link>
-          <Menu shadow="md" width={200} keepMounted>
-            <Menu.Target>
-              <ActionIcon sx={{ height: "auto" }}>
-                <IconDotsVertical size={20} />
-              </ActionIcon>
-            </Menu.Target>
-            <Menu.Dropdown>
-              <EditChatModal chat={chat}>
-                <Menu.Item>Edit</Menu.Item>
-              </EditChatModal>
-              <DeleteChatModal chat={chat}>
-                <Menu.Item>Delete</Menu.Item>
-              </DeleteChatModal>
-            </Menu.Dropdown>
-          </Menu>
-        </Flex>
-      ))}
+      {filteredChats
+        .sort((chat) => (chat.pinned ? -1 : 1))
+        .map((chat) => (
+          <Flex
+            key={chat.id}
+            className={chatId === chat.id ? "active" : undefined}
+            sx={(theme) => ({
+              marginTop: 1,
+              "&:hover, &.active": {
+                backgroundColor: theme.colorScheme === "dark" ? theme.colors.dark[6] : theme.colors.gray[1],
+              },
+            })}
+          >
+            <Link to={`/chats/${chat.id}`} style={{ flex: 1 }}>
+              <MainLink
+                icon={chat.pinned ? <IconPinned size="1rem" /> : <IconMessages size="1rem" />}
+                color="teal"
+                chat={chat}
+                label={chat.description}
+              />
+            </Link>
+            <Menu shadow="md" width={200} keepMounted>
+              <Menu.Target>
+                <ActionIcon sx={{ height: "auto" }}>
+                  <IconDotsVertical size={20} />
+                </ActionIcon>
+              </Menu.Target>
+              <Menu.Dropdown>
+                <Menu.Item
+                  icon={chat.pinned ? <IconPinnedOff size="1rem" /> : <IconPin size="1rem" />}
+                  onClick={(event) => toggleChatPin(chat.id, event)}
+                >
+                  {chat.pinned ? "Remove pin" : "Pin this"}
+                </Menu.Item>
+                <EditChatModal chat={chat}>
+                  <Menu.Item icon={<IconPencil size="1rem" />}>Edit</Menu.Item>
+                </EditChatModal>
+                <DeleteChatModal chat={chat}>
+                  <Menu.Item color="red" icon={<IconTrash size="1rem" />}>
+                    Delete
+                  </Menu.Item>
+                </DeleteChatModal>
+              </Menu.Dropdown>
+            </Menu>
+          </Flex>
+        ))}
     </>
   );
 }
diff --git a/src/db/index.ts b/src/db/index.ts
index f4f1288..9e5e9ad 100644
--- a/src/db/index.ts
+++ b/src/db/index.ts
@@ -7,6 +7,7 @@ export interface Chat {
   description: string;
   totalTokens: number;
   createdAt: Date;
+  pinned: boolean;
 }
 
 export interface Message {