diff --git a/tools/ui/src/lib/components/app/navigation/SidebarNavigation/SidebarNavigation.svelte b/tools/ui/src/lib/components/app/navigation/SidebarNavigation/SidebarNavigation.svelte
index ddaf4d5b87..1fa7722f24 100644
--- a/tools/ui/src/lib/components/app/navigation/SidebarNavigation/SidebarNavigation.svelte
+++ b/tools/ui/src/lib/components/app/navigation/SidebarNavigation/SidebarNavigation.svelte
@@ -1,7 +1,7 @@
 <script lang="ts">
 	import { goto } from '$app/navigation';
 	import { page } from '$app/state';
-	import { Trash2, Pencil, X } from '@lucide/svelte';
+	import { Trash2, Pencil, Pin, X } from '@lucide/svelte';
 	import { Button } from '$lib/components/ui/button';
 	import { DialogConfirmation } from '$lib/components/app';
 	import SidebarNavigationActions from './SidebarNavigationActions.svelte';
@@ -52,6 +52,14 @@
 
 	let conversationTree = $derived(buildConversationTree(filteredConversations));
 
+	let pinnedConversations = $derived.by(() => {
+		return conversationTree.filter(({ conversation }) => conversation.pinned);
+	});
+
+	let unpinnedConversations = $derived.by(() => {
+		return conversationTree.filter(({ conversation }) => !conversation.pinned);
+	});
+
 	let selectedConversationHasDescendants = $derived.by(() => {
 		if (!selectedConversation) return false;
 
@@ -199,6 +207,41 @@
 			/>
 		</Sidebar.Header>
 
+		{#if !isSearchModeActive && pinnedConversations.length > 0}
+			<Sidebar.Group class="p-0 px-4">
+				<Sidebar.GroupLabel>
+					<div class="flex items-center gap-1">
+						<Pin class="h-3.5 w-3.5" />
+						<span>Pinned</span>
+					</div>
+				</Sidebar.GroupLabel>
+				<Sidebar.GroupContent>
+					<Sidebar.Menu>
+						{#each pinnedConversations as { conversation, depth } (conversation.id)}
+							<Sidebar.MenuItem class="mb-1 p-0">
+								<SidebarNavigationConversationItem
+									conversation={{
+										id: conversation.id,
+										name: conversation.name,
+										lastModified: conversation.lastModified,
+										currNode: conversation.currNode,
+										forkedFromConversationId: conversation.forkedFromConversationId,
+										pinned: conversation.pinned
+									}}
+									{depth}
+									isActive={currentChatId === conversation.id}
+									onSelect={selectConversation}
+									onEdit={handleEditConversation}
+									onDelete={handleDeleteConversation}
+									onStop={handleStopGeneration}
+								/>
+							</Sidebar.MenuItem>
+						{/each}
+					</Sidebar.Menu>
+				</Sidebar.GroupContent>
+			</Sidebar.Group>
+		{/if}
+
 		<Sidebar.Group class="mt-2 h-[calc(100vh-21rem)] space-y-2 p-0 px-3">
 			{#if (filteredConversations.length > 0 && isSearchModeActive) || !isSearchModeActive}
 				<Sidebar.GroupLabel>
@@ -208,7 +251,7 @@
 
 			<Sidebar.GroupContent>
 				<Sidebar.Menu>
-					{#each conversationTree as { conversation, depth } (conversation.id)}
+					{#each isSearchModeActive ? conversationTree : unpinnedConversations as { conversation, depth } (conversation.id)}
 						<Sidebar.MenuItem class="mb-1 p-0">
 							<SidebarNavigationConversationItem
 								conversation={{
@@ -216,7 +259,8 @@
 									name: conversation.name,
 									lastModified: conversation.lastModified,
 									currNode: conversation.currNode,
-									forkedFromConversationId: conversation.forkedFromConversationId
+									forkedFromConversationId: conversation.forkedFromConversationId,
+									pinned: conversation.pinned
 								}}
 								{depth}
 								isActive={currentChatId === conversation.id}
@@ -228,7 +272,7 @@
 						</Sidebar.MenuItem>
 					{/each}
 
-					{#if conversationTree.length === 0}
+					{#if (isSearchModeActive ? conversationTree : unpinnedConversations).length === 0}
 						<div class="px-2 py-4 text-center">
 							<p class="mb-4 p-4 text-sm text-muted-foreground">
 								{searchQuery.length > 0
diff --git a/tools/ui/src/lib/components/app/navigation/SidebarNavigation/SidebarNavigationConversationItem.svelte b/tools/ui/src/lib/components/app/navigation/SidebarNavigation/SidebarNavigationConversationItem.svelte
index e38a937385..b1c2b78f65 100644
--- a/tools/ui/src/lib/components/app/navigation/SidebarNavigation/SidebarNavigationConversationItem.svelte
+++ b/tools/ui/src/lib/components/app/navigation/SidebarNavigation/SidebarNavigationConversationItem.svelte
@@ -6,7 +6,9 @@
 		Download,
 		Loader2,
 		Square,
-		GitBranch
+		GitBranch,
+		Pin,
+		PinOff
 	} from '@lucide/svelte';
 	import { DropdownMenuActions } from '$lib/components/app';
 	import * as Tooltip from '$lib/components/ui/tooltip';
@@ -57,6 +59,10 @@
 		onStop?.(conversation.id);
 	}
 
+	function handleTogglePin() {
+		conversationsStore.toggleConversationPin(conversation.id);
+	}
+
 	function handleGlobalEditEvent(event: Event) {
 		const customEvent = event as CustomEvent<{ conversationId: string }>;
 
@@ -170,6 +176,14 @@
 				triggerTooltip="More actions"
 				bind:open={dropdownOpen}
 				actions={[
+					{
+						icon: conversation.pinned ? PinOff : Pin,
+						label: conversation.pinned ? 'Unpin' : 'Pin',
+						onclick: (e: Event) => {
+							e.stopPropagation();
+							handleTogglePin();
+						}
+					},
 					{
 						icon: Pencil,
 						label: 'Edit',
diff --git a/tools/ui/src/lib/services/database.service.ts b/tools/ui/src/lib/services/database.service.ts
index 457867d984..3338439bbe 100644
--- a/tools/ui/src/lib/services/database.service.ts
+++ b/tools/ui/src/lib/services/database.service.ts
@@ -344,6 +344,22 @@ export class DatabaseService {
 	 *
 	 */
 
+	/**
+	 * Toggles the pinned status of a conversation.
+	 *
+	 * @param id - Conversation ID
+	 * @returns The new pinned status
+	 */
+	static async toggleConversationPin(id: string): Promise<boolean> {
+		const conversation = await db.conversations.get(id);
+		if (!conversation) {
+			throw new Error(`Conversation ${id} not found`);
+		}
+		const newPinnedState = !conversation.pinned;
+		await this.updateConversation(id, { pinned: newPinnedState });
+		return newPinnedState;
+	}
+
 	/**
 	 * Updates the conversation's current node (active branch).
 	 * This determines which conversation path is currently being viewed.
diff --git a/tools/ui/src/lib/stores/conversations.svelte.ts b/tools/ui/src/lib/stores/conversations.svelte.ts
index cab6f59fae..bba5191ed5 100644
--- a/tools/ui/src/lib/stores/conversations.svelte.ts
+++ b/tools/ui/src/lib/stores/conversations.svelte.ts
@@ -506,6 +506,33 @@ class ConversationsStore {
 		}
 	}
 
+	/**
+	 * Toggles the pinned status of a conversation.
+	 * @param convId - The conversation ID to toggle
+	 * @returns The new pinned status
+	 */
+	async toggleConversationPin(convId: string): Promise<boolean> {
+		try {
+			const newPinnedState = await DatabaseService.toggleConversationPin(convId);
+
+			const convIndex = this.conversations.findIndex((c) => c.id === convId);
+
+			if (convIndex !== -1) {
+				this.conversations[convIndex].pinned = newPinnedState;
+				this.conversations = [...this.conversations];
+			}
+
+			if (this.activeConversation?.id === convId) {
+				this.activeConversation = { ...this.activeConversation, pinned: newPinnedState };
+			}
+
+			return newPinnedState;
+		} catch (error) {
+			console.error('Failed to toggle conversation pin:', error);
+			return false;
+		}
+	}
+
 	/**
 	 * Updates conversation title with optional confirmation dialog based on settings
 	 * @param convId - The conversation ID to update
@@ -1057,6 +1084,14 @@ export const isConversationsInitialized = () => conversationsStore.isInitialized
  * Builds a flat tree of conversations with depth levels for nested forks.
  * Accepts a pre-filtered list so search filtering stays in the component.
  */
+
+// Pinned conversations first, then by lastModified descending
+const comparePinnedThenRecent = (a: DatabaseConversation, b: DatabaseConversation) => {
+	if (a.pinned && !b.pinned) return -1;
+	if (!a.pinned && b.pinned) return 1;
+	return b.lastModified - a.lastModified;
+};
+
 export function buildConversationTree(convs: DatabaseConversation[]): ConversationTreeItem[] {
 	const childrenByParent = new SvelteMap<string, DatabaseConversation[]>();
 	const forkIds = new SvelteSet<string>();
@@ -1081,7 +1116,7 @@ export function buildConversationTree(convs: DatabaseConversation[]): Conversati
 
 		const children = childrenByParent.get(conv.id);
 		if (children) {
-			children.sort((a, b) => b.lastModified - a.lastModified);
+			children.sort(comparePinnedThenRecent);
 
 			for (const child of children) {
 				walk(child, depth + 1);
@@ -1089,7 +1124,7 @@ export function buildConversationTree(convs: DatabaseConversation[]): Conversati
 		}
 	}
 
-	const roots = convs.filter((c) => !forkIds.has(c.id));
+	const roots = convs.filter((c) => !forkIds.has(c.id)).sort(comparePinnedThenRecent);
 	for (const root of roots) {
 		walk(root, 0);
 	}
diff --git a/tools/ui/src/lib/types/database.d.ts b/tools/ui/src/lib/types/database.d.ts
index add628476b..b01a7b9649 100644
--- a/tools/ui/src/lib/types/database.d.ts
+++ b/tools/ui/src/lib/types/database.d.ts
@@ -15,6 +15,7 @@ export interface DatabaseConversation {
 	thinkingEnabled?: boolean;
 	reasoningEffort?: ReasoningEffort;
 	forkedFromConversationId?: string;
+	pinned?: boolean;
 }
 
 export interface DatabaseMessageExtraAudioFile {