diff --git a/src/core/chorus/api/ChatAPI.ts b/src/core/chorus/api/ChatAPI.ts
index e9122dfe..284ad4e6 100644
--- a/src/core/chorus/api/ChatAPI.ts
+++ b/src/core/chorus/api/ChatAPI.ts
@@ -36,8 +36,7 @@ export type Chat = {
     projectContextSummaryIsStale: boolean;
     replyToId: string | null;
     gcPrototype: boolean;
-
-    pinned: boolean; // deprecated
+    pinned: boolean;
 
     // Cost tracking
     totalCostUsd?: number;
@@ -103,7 +102,7 @@ export async function fetchChats(): Promise<Chat[]> {
             project_context_summary, project_context_summary_is_stale, reply_to_id, gc_prototype_chat, total_cost_usd
             FROM chats
             WHERE reply_to_id IS NULL
-            ORDER BY updated_at DESC`,
+            ORDER BY pinned DESC, updated_at DESC`,
         )
         .then((rows) => rows.map(readChat));
 }
@@ -141,9 +140,13 @@ export function useCacheUpdateChat() {
                     updateFn(chat);
                     // NOTE: We don't always need to sort, if this becomes expensive we could gate
                     // this behind a flag
-                    draft.sort((a, b) =>
-                        b.updatedAt.localeCompare(a.updatedAt),
-                    );
+                    draft.sort((a, b) => {
+                        // Sort pinned chats first, then by updatedAt
+                        if (a.pinned !== b.pinned) {
+                            return b.pinned ? 1 : -1;
+                        }
+                        return b.updatedAt.localeCompare(a.updatedAt);
+                    });
                 }
             }),
         );
@@ -396,3 +399,25 @@ export function useRenameChat() {
         },
     });
 }
+
+export function useTogglePinChat() {
+    const queryClient = useQueryClient();
+    const cacheUpdateChat = useCacheUpdateChat();
+
+    return useMutation({
+        mutationKey: ["togglePinChat"] as const,
+        mutationFn: async ({ chatId, pinned }: { chatId: string; pinned: boolean }) => {
+            await db.execute("UPDATE chats SET pinned = $1 WHERE id = $2", [
+                pinned ? 1 : 0,
+                chatId,
+            ]);
+            return { chatId, pinned };
+        },
+        onSuccess: async (_data, variables) => {
+            cacheUpdateChat(variables.chatId, (chat) => {
+                chat.pinned = variables.pinned;
+            });
+            await queryClient.invalidateQueries(chatQueries.list());
+        },
+    });
+}
diff --git a/src/core/chorus/api/ExportAPI.ts b/src/core/chorus/api/ExportAPI.ts
new file mode 100644
index 00000000..5e795525
--- /dev/null
+++ b/src/core/chorus/api/ExportAPI.ts
@@ -0,0 +1,163 @@
+import { db } from "../DB";
+import { fetchChat } from "./ChatAPI";
+import { save } from "@tauri-apps/plugin-dialog";
+import { writeTextFile } from "@tauri-apps/plugin-fs";
+
+interface MessageRow {
+    message_id: string;
+    message_set_id: string;
+    model: string;
+    text: string;
+    created_at: string;
+}
+
+interface Turn {
+    messageSetId: string;
+    user: {
+        content: string;
+        timestamp: string;
+    };
+    responses: Array<{
+        model: string;
+        content: string;
+        timestamp: string;
+    }>;
+}
+
+interface ExportData {
+    chatId: string;
+    title: string;
+    createdAt: string;
+    turns: Turn[];
+}
+
+async function fetchChatMessages(chatId: string): Promise<MessageRow[]> {
+    const messages = await db.select<MessageRow[]>(
+        `SELECT
+            m.id as message_id,
+            m.message_set_id,
+            m.model,
+            CASE
+                WHEN m.model = 'user' THEN COALESCE(m.text, '')
+                ELSE COALESCE(NULLIF(m.text, ''), mp.content, '')
+            END as text,
+            m.created_at
+        FROM messages m
+        LEFT JOIN message_parts mp ON m.id = mp.message_id AND m.chat_id = mp.chat_id
+        WHERE m.chat_id = ?
+        ORDER BY m.created_at ASC`,
+        [chatId],
+    );
+    return messages;
+}
+
+function groupMessagesByTurns(messages: MessageRow[]): Turn[] {
+    const turnMap = new Map<string, Turn>();
+
+    for (const message of messages) {
+        if (!turnMap.has(message.message_set_id)) {
+            turnMap.set(message.message_set_id, {
+                messageSetId: message.message_set_id,
+                user: {
+                    content: "",
+                    timestamp: "",
+                },
+                responses: [],
+            });
+        }
+
+        const turn = turnMap.get(message.message_set_id)!;
+
+        if (message.model === "user") {
+            turn.user = {
+                content: message.text,
+                timestamp: message.created_at,
+            };
+        } else {
+            turn.responses.push({
+                model: message.model,
+                content: message.text,
+                timestamp: message.created_at,
+            });
+        }
+    }
+
+    return Array.from(turnMap.values());
+}
+
+async function fetchExportData(chatId: string): Promise<ExportData> {
+    const chat = await fetchChat(chatId);
+    const messages = await fetchChatMessages(chatId);
+    const turns = groupMessagesByTurns(messages);
+
+    return {
+        chatId: chat.id,
+        title: chat.title,
+        createdAt: chat.createdAt,
+        turns,
+    };
+}
+
+function formatAsJSON(data: ExportData): string {
+    return JSON.stringify(data, null, 2);
+}
+
+function formatAsMarkdown(data: ExportData): string {
+    let md = `# ${data.title}\n`;
+    md += `Created: ${new Date(data.createdAt).toLocaleDateString()}\n\n`;
+    md += `---\n\n`;
+
+    for (const turn of data.turns) {
+        // User message
+        if (turn.user.content) {
+            md += `### You\n${turn.user.content}\n\n`;
+        }
+
+        // AI responses
+        for (const response of turn.responses) {
+            md += `### ${response.model}\n${response.content}\n\n`;
+        }
+
+        md += `---\n\n`;
+    }
+
+    return md;
+}
+
+export async function exportChatAsJSON(chatId: string): Promise<void> {
+    const data = await fetchExportData(chatId);
+    const jsonContent = formatAsJSON(data);
+
+    const filePath = await save({
+        defaultPath: `${data.title || "chat"}.json`,
+        filters: [
+            {
+                name: "JSON",
+                extensions: ["json"],
+            },
+        ],
+    });
+
+    if (filePath) {
+        await writeTextFile(filePath, jsonContent);
+    }
+}
+
+export async function exportChatAsMarkdown(chatId: string): Promise<void> {
+    const data = await fetchExportData(chatId);
+    const mdContent = formatAsMarkdown(data);
+
+    const filePath = await save({
+        defaultPath: `${data.title || "chat"}.md`,
+        filters: [
+            {
+                name: "Markdown",
+                extensions: ["md"],
+            },
+        ],
+    });
+
+    if (filePath) {
+        await writeTextFile(filePath, mdContent);
+    }
+}
diff --git a/src/ui/components/AppSidebar.tsx b/src/ui/components/AppSidebar.tsx
index e48bf694..a3a40d11 100644
--- a/src/ui/components/AppSidebar.tsx
+++ b/src/ui/components/AppSidebar.tsx
@@ -9,6 +9,9 @@ import {
     SquarePlusIcon,
     ArrowBigUpIcon,
     EllipsisIcon,
+    Pin,
+    PinOff,
+    Download,
 } from "lucide-react";
 import {
     Sidebar,
@@ -54,9 +57,16 @@ import {
     DialogHeader,
     DialogTitle,
 } from "./ui/dialog";
+import {
+    DropdownMenu,
+    DropdownMenuContent,
+    DropdownMenuItem,
+    DropdownMenuTrigger,
+} from "./ui/dropdown-menu";
 import * as ChatAPI from "@core/chorus/api/ChatAPI";
 import * as ProjectAPI from "@core/chorus/api/ProjectAPI";
 import { formatCost } from "@core/chorus/api/CostAPI";
+import * as ExportAPI from "@core/chorus/api/ExportAPI";
 import RetroSpinner from "./ui/retro-spinner";
 import FeedbackButton from "./FeedbackButton";
 import { SpeakerLoudIcon } from "@radix-ui/react-icons";
@@ -821,6 +831,7 @@ function ChatListItem({ chat, isActive }: { chat: Chat; isActive: boolean }) {
         mutateAsync: deleteChatMutateAsync,
         isPending: deleteChatIsPending,
     } = ChatAPI.useDeleteChat();
+    const { mutate: togglePinChat } = ChatAPI.useTogglePinChat();
     const { data: parentChat } = useQuery(
         ChatAPI.chatQueries.detail(chat.parentChatId ?? undefined),
     );
@@ -883,11 +894,54 @@ function ChatListItem({ chat, isActive }: { chat: Chat; isActive: boolean }) {
     );
     const showCost = settings?.showCost ?? false;
 
+    const handleTogglePin = useCallback(
+        (e: React.MouseEvent) => {
+            e.preventDefault();
+            e.stopPropagation();
+            togglePinChat({
+                chatId: chat.id,
+                pinned: !chat.pinned,
+            });
+        },
+        [chat.id, chat.pinned, togglePinChat],
+    );
+
+    const handleExportJSON = useCallback(
+        async (e: React.MouseEvent) => {
+            e.preventDefault();
+            e.stopPropagation();
+            try {
+                await ExportAPI.exportChatAsJSON(chat.id);
+                toast.success("Chat exported as JSON");
+            } catch (error) {
+                toast.error("Failed to export chat");
+                console.error(error);
+            }
+        },
+        [chat.id],
+    );
+
+    const handleExportMarkdown = useCallback(
+        async (e: React.MouseEvent) => {
+            e.preventDefault();
+            e.stopPropagation();
+            try {
+                await ExportAPI.exportChatAsMarkdown(chat.id);
+                toast.success("Chat exported as Markdown");
+            } catch (error) {
+                toast.error("Failed to export chat");
+                console.error(error);
+            }
+        },
+        [chat.id],
+    );
+
     return (
         <ChatListItemView
             chatId={chat.id}
             chatTitle={chat.title || ""}
             isNewChat={chat.isNewChat}
+            isPinned={chat.pinned}
             parentChatId={parentChat?.id ?? null}
             parentChatTitle={parentChat?.title || null}
             isActive={isActive}
@@ -895,6 +949,9 @@ function ChatListItem({ chat, isActive }: { chat: Chat; isActive: boolean }) {
             onStartEdit={handleStartEdit}
             onStopEdit={handleStopEdit}
             onSubmitEdit={handleSubmitEdit}
+            onTogglePin={handleTogglePin}
+            onExportJSON={handleExportJSON}
+            onExportMarkdown={handleExportMarkdown}
             onDelete={handleOpenDeleteDialog}
             onConfirmDelete={handleConfirmDelete}
             deleteIsPending={deleteChatIsPending}
@@ -910,6 +967,7 @@ type ChatListItemViewProps = {
     chatId: string;
     chatTitle: string;
     isNewChat: boolean;
+    isPinned: boolean;
     parentChatId: string | null;
     parentChatTitle: string | null;
     isActive: boolean;
@@ -917,6 +975,9 @@ type ChatListItemViewProps = {
     onStartEdit: () => void;
     onStopEdit: () => void;
     onSubmitEdit: (newTitle: string) => Promise<void>;
+    onTogglePin: (e: React.MouseEvent) => void;
+    onExportJSON: (e: React.MouseEvent) => void;
+    onExportMarkdown: (e: React.MouseEvent) => void;
     onDelete: () => void;
     onConfirmDelete: () => void;
     deleteIsPending: boolean;
@@ -931,6 +992,7 @@ const ChatListItemView = React.memo(
         chatId,
         chatTitle,
         isNewChat,
+        isPinned,
         parentChatId,
         parentChatTitle,
         isActive,
@@ -938,6 +1000,9 @@ const ChatListItemView = React.memo(
         onStartEdit,
         onStopEdit,
         onSubmitEdit,
+        onTogglePin,
+        onExportJSON,
+        onExportMarkdown,
         onDelete,
         onConfirmDelete,
         deleteIsPending,
@@ -1021,6 +1086,40 @@ const ChatListItemView = React.memo(
 
                         {/* chat actions */}
                         <div className="flex items-center gap-2 absolute right-3 z-10">
+                            <Tooltip>
+                                <TooltipTrigger asChild>
+                                    <div onClick={onTogglePin}>
+                                        {isPinned ? (
+                                            <PinOff className="h-[13px] w-[13px] opacity-100 transition-opacity text-muted-foreground hover:text-foreground" />
+                                        ) : (
+                                            <Pin className="h-[13px] w-[13px] opacity-0 group-hover/chat-button:opacity-100 transition-opacity text-muted-foreground hover:text-foreground" />
+                                        )}
+                                    </div>
+                                </TooltipTrigger>
+                                <TooltipContent side="bottom">
+                                    {isPinned ? "Unpin chat" : "Pin chat"}
+                                </TooltipContent>
+                            </Tooltip>
+                            <DropdownMenu>
+                                <DropdownMenuTrigger asChild>
+                                    <div
+                                        onClick={(e) => {
+                                            e.preventDefault();
+                                            e.stopPropagation();
+                                        }}
+                                    >
+                                        <Download className="h-[13px] w-[13px] opacity-0 group-hover/chat-button:opacity-100 transition-opacity text-muted-foreground hover:text-foreground cursor-pointer" />
+                                    </div>
+                                </DropdownMenuTrigger>
+                                <DropdownMenuContent align="end" onClick={(e) => e.stopPropagation()}>
+                                    <DropdownMenuItem onClick={onExportJSON}>
+                                        Export as JSON
+                                    </DropdownMenuItem>
+                                    <DropdownMenuItem onClick={onExportMarkdown}>
+                                        Export as Markdown
+                                    </DropdownMenuItem>
+                                </DropdownMenuContent>
+                            </DropdownMenu>
                             <Tooltip>
                                 <TooltipTrigger asChild>
                                     <PencilOptimized