diff --git a/api/chatbot/models.py b/api/chatbot/models.py
index eaab0bcc..6046e104 100644
--- a/api/chatbot/models.py
+++ b/api/chatbot/models.py
@@ -8,6 +8,7 @@
 class Conversation(JsonModel):
     title: str
     owner: str = Field(index=True)
+    pinned: bool = False
     created_at: datetime = Field(default_factory=utcnow)
     updated_at: datetime = created_at
 
diff --git a/api/chatbot/routers/conversation.py b/api/chatbot/routers/conversation.py
index f80c9044..03a794c0 100644
--- a/api/chatbot/routers/conversation.py
+++ b/api/chatbot/routers/conversation.py
@@ -28,7 +28,7 @@ async def get_conversations(
     userid: Annotated[str | None, UserIdHeader()] = None
 ) -> list[Conversation]:
     convs = await ORMConversation.find(ORMConversation.owner == userid).all()
-    convs.sort(key=lambda x: x.updated_at, reverse=True)
+    convs.sort(key=lambda x: (x.pinned, x.updated_at), reverse=True)
     return [Conversation(**conv.dict()) for conv in convs]
 
 
@@ -72,9 +72,16 @@ async def update_conversation(
     payload: UpdateConversation,
     userid: Annotated[str | None, UserIdHeader()] = None,
 ) -> ConversationDetail:
+    modified = False
     conv = await ORMConversation.get(conversation_id)
-    conv.title = payload.title
-    await conv.save()
+    if payload.title is not None:
+        conv.title = payload.title
+        modified = True
+    if payload.pinned is not None:
+        conv.pinned = payload.pinned
+        modified = True
+    if modified:
+        await conv.save()
     return ConversationDetail(**conv.dict())
 
 
diff --git a/api/chatbot/schemas.py b/api/chatbot/schemas.py
index df64224e..2e8f676f 100644
--- a/api/chatbot/schemas.py
+++ b/api/chatbot/schemas.py
@@ -70,6 +70,7 @@ class Conversation(BaseModel):
     id: Optional[str] = None
     title: str
     owner: str
+    pinned: bool = False
     created_at: datetime = Field(default_factory=utcnow)
     updated_at: datetime = created_at
 
@@ -92,7 +93,8 @@ class CreateConversation(BaseModel):
 
 
 class UpdateConversation(BaseModel):
-    title: str
+    title: Optional[str] = None
+    pinned: Optional[bool] = None
 
 
 class UserProfile(BaseModel):
diff --git a/web/src/routes/conversation/index.jsx b/web/src/routes/conversation/index.jsx
index 012d120c..3a30ddc9 100644
--- a/web/src/routes/conversation/index.jsx
+++ b/web/src/routes/conversation/index.jsx
@@ -21,6 +21,7 @@ export async function action({ params, request }) {
             },
             body: JSON.stringify({
                 title: conversation.title,
+                pinned: conversation.pinned,
             }),
         })
         if (!resp.ok) {
diff --git a/web/src/routes/root/SideMenuButton/index.jsx b/web/src/routes/root/SideMenuButton/index.jsx
index e3886221..93f16122 100644
--- a/web/src/routes/root/SideMenuButton/index.jsx
+++ b/web/src/routes/root/SideMenuButton/index.jsx
@@ -1,13 +1,14 @@
 import "./index.css";
 
 import { useState, useRef } from "react";
-import { useSubmit } from "react-router-dom";
+import { useFetcher } from "react-router-dom";
 import Tooltip from "@mui/material/Tooltip";
 
+import AutoAwesomeIcon from '@mui/icons-material/AutoAwesome';
 import DeleteOutlineIcon from "@mui/icons-material/DeleteOutline";
 import DriveFileRenameOutlineIcon from "@mui/icons-material/DriveFileRenameOutline";
 import MoreVertIcon from '@mui/icons-material/MoreVert';
-import AutoAwesomeIcon from '@mui/icons-material/AutoAwesome';
+import PushPinOutlinedIcon from '@mui/icons-material/PushPinOutlined';
 
 import { DropdownMenu, DropdownHeader, DropdownList } from "components/DropdownMenu";
 import { summarizeConversation } from "requests";
@@ -21,7 +22,7 @@ import { summarizeConversation } from "requests";
  * @returns
  */
 const ChatTab = ({ chat, isActive, onDeleteClick }) => {
-  const submit = useSubmit();
+  const fetcher = useFetcher();
 
   const titleRef = useRef(null);
   const [titleEditable, setTitleEditable] = useState("false");
@@ -36,8 +37,8 @@ const ChatTab = ({ chat, isActive, onDeleteClick }) => {
 
   const renameChat = async (title) => {
     setTitleEditable("false");
-    submit(
-      { title: title },
+    fetcher.submit(
+      { ...chat, title: title },
       { method: "put", action: `/conversations/${chat.id}`, encType: "application/json" }
     );
     // Maybe set snackbar to inform user?
@@ -63,6 +64,13 @@ const ChatTab = ({ chat, isActive, onDeleteClick }) => {
       });
   }
 
+  const flipPin = () => {
+    fetcher.submit(
+      { ...chat, pinned: !chat.pinned },
+      { method: "put", action: `/conversations/${chat.id}`, encType: "application/json" }
+    );
+  };
+
   return (
     <>
       <Tooltip title={titleRef.current?.innerText}>
@@ -84,6 +92,14 @@ const ChatTab = ({ chat, isActive, onDeleteClick }) => {
             <MoreVertIcon />
           </DropdownHeader>
           <DropdownList className="chat-op-menu-list">
+          <li>
+              <button className="chat-op-menu-item" onClick={flipPin}>
+                {/* TODO: there's no 'unpin' icon in material icons for now. */}
+                {/* Please see <https://github.com/google/material-design-icons/issues/1595> */}
+                {chat.pinned ? <PushPinOutlinedIcon /> : <PushPinOutlinedIcon />}
+                <span className="chat-op-menu-item-text">{chat.pinned ? "Unpin" : "Pin"}</span>
+              </button>
+            </li>
             <li>
               <button className="chat-op-menu-item" onClick={onSummarizeClick}>
                 <AutoAwesomeIcon />
diff --git a/web/src/routes/root/index.jsx b/web/src/routes/root/index.jsx
index 36f7720f..c2de326a 100644
--- a/web/src/routes/root/index.jsx
+++ b/web/src/routes/root/index.jsx
@@ -33,6 +33,9 @@ export async function loader() {
   lastSevenDays.setDate(lastSevenDays.getDate() - 7);
 
   const groupedConvs = Object.groupBy(conversations, (item) => {
+    if (item.pinned) {
+      return "pinned";
+    }
     const itemDate = new Date(item.updated_at);
     if (itemDate.toDateString() === today.toDateString()) {
       return "Today";