diff --git a/site/src/pages/AgentsPage/components/ChatsSidebar/ChatsSidebar.stories.tsx b/site/src/pages/AgentsPage/components/ChatsSidebar/ChatsSidebar.stories.tsx
index 5294ba61c0..a15c7cee8c 100644
--- a/site/src/pages/AgentsPage/components/ChatsSidebar/ChatsSidebar.stories.tsx
+++ b/site/src/pages/AgentsPage/components/ChatsSidebar/ChatsSidebar.stories.tsx
@@ -1,6 +1,7 @@
 import type { Meta, StoryObj } from "@storybook/react-vite";
 import type { ComponentProps } from "react";
 import { useEffect, useState } from "react";
+import { useLocation } from "react-router";
 import { expect, fn, userEvent, waitFor, within } from "storybook/test";
 import { reactRouterParameters } from "storybook-addon-remix-react-router";
 import { userChatProviderConfigsKey } from "#/api/queries/chats";
@@ -12,10 +13,25 @@ import {
 	withDashboardProvider,
 } from "#/testHelpers/storybook";
 import { useAgentsPageKeybindings } from "../../hooks/useAgentsPageKeybindings";
-import type { AgentSidebarFilters } from "../../utils/agentSidebarFilters";
+import { DEFAULT_AGENT_SIDEBAR_FILTERS as defaultSidebarFilters } from "../../utils/agentSidebarFilters";
 import type { ModelSelectorOption } from "../ChatElements";
 import { ChatsSidebar } from "./ChatsSidebar";
 
+// Probe element used by the archived-filter preservation story to surface the
+// search string of whatever child route the sidebar's NavLink ends up at.
+const ChildSearchProbe = () => {
+	const location = useLocation();
+	return <div data-testid="child-search">{location.search}</div>;
+};
+
+// Probe element used by the settings-link preservation story to surface the
+// state.from value passed when navigating to settings.
+const SettingsStateProbe = () => {
+	const location = useLocation();
+	const from = (location.state as { from?: string })?.from ?? "";
+	return <div data-testid="settings-state-from">{from}</div>;
+};
+
 const defaultModelOptions: ModelSelectorOption[] = [
 	{
 		id: "openai:gpt-4o",
@@ -25,13 +41,6 @@ const defaultModelOptions: ModelSelectorOption[] = [
 	},
 ];
 
-const defaultSidebarFilters: AgentSidebarFilters = {
-	archiveStatus: "active",
-	groupBy: "date",
-	prStatuses: [],
-	chatStatuses: ["unread", "read"],
-};
-
 const defaultModelConfigs: TypesGen.ChatModelConfig[] = [
 	{
 		id: "config-openai-gpt-4o",
@@ -106,8 +115,8 @@ const meta: Meta<typeof ChatsSidebar> = {
 		isCreating: false,
 		regeneratingTitleChatIds: [],
 		sidebarFilters: defaultSidebarFilters,
-		onSidebarFiltersChange: fn(),
 		isPersonalModelOverridesEnabled: true,
+		onSidebarFiltersChange: fn(),
 	},
 	parameters: {
 		layout: "fullscreen",
@@ -724,6 +733,68 @@ export const SectionHeadersCollapse: Story = {
 	},
 };
 
+export const MobileHeaderActions: Story = {
+	render: ChatsSidebarWithKeybindings,
+	args: {
+		chats: sectionHeaderChats,
+	},
+	parameters: {
+		viewport: { defaultViewport: "mobile1" },
+		reactRouter: reactRouterParameters({
+			location: { path: "/agents" },
+			routing: agentsRouting,
+		}),
+	},
+	decorators: [
+		(Story) => (
+			<div style={{ height: 500, width: 360 }}>
+				<Story />
+			</div>
+		),
+	],
+	play: async ({ canvasElement }) => {
+		const canvas = within(canvasElement);
+		const searchButton = canvas.getByRole("button", { name: "Search chats" });
+		const filterButton = canvas.getByRole("button", { name: "Filter agents" });
+		const searchRect = searchButton.getBoundingClientRect();
+		const filterRect = filterButton.getBoundingClientRect();
+
+		await expect(searchButton).not.toHaveTextContent("Search");
+		expect(Math.round(searchRect.width)).toBeGreaterThanOrEqual(28);
+		expect(Math.round(filterRect.width)).toBeGreaterThanOrEqual(28);
+		expect(searchRect.right).toBeLessThan(filterRect.left);
+	},
+};
+
+export const SidebarFilterMenu: Story = {
+	args: {
+		chats: sectionHeaderChats,
+	},
+	parameters: {
+		reactRouter: reactRouterParameters({
+			location: { path: "/agents" },
+			routing: agentsRouting,
+		}),
+	},
+	play: async ({ canvasElement }) => {
+		const canvas = within(canvasElement);
+		const body = within(document.body);
+
+		await userEvent.click(
+			canvas.getByRole("button", { name: "Filter agents" }),
+		);
+		await expect(
+			await body.findByRole("radio", { name: /Archived/i }),
+		).toBeInTheDocument();
+		await userEvent.keyboard("{Escape}");
+		await waitFor(() => {
+			expect(
+				body.queryByRole("radio", { name: /Archived/i }),
+			).not.toBeInTheDocument();
+		});
+	},
+};
+
 export const SearchDialogKeyboardShortcut: Story = {
 	render: ChatsSidebarWithKeybindings,
 	args: {
@@ -740,11 +811,23 @@ export const SearchDialogKeyboardShortcut: Story = {
 		const body = within(document.body);
 		const searchButton = canvas.getByRole("button", { name: "Search chats" });
 
-		await userEvent.hover(searchButton);
-		const tooltip = await body.findByRole("tooltip");
-		await expect(tooltip).toHaveTextContent("Search chats");
-		await expect(tooltip).toHaveTextContent("Ctrl");
-		await expect(tooltip).toHaveTextContent("K");
+		await expect(searchButton).toHaveTextContent("Search");
+		await expect(searchButton).toHaveTextContent("Ctrl");
+		await expect(searchButton).toHaveTextContent("K");
+
+		await userEvent.click(searchButton);
+		const clickedSearchInput = await body.findByRole("combobox", {
+			name: "Search chats",
+		});
+		await waitFor(() => {
+			expect(clickedSearchInput).toHaveFocus();
+		});
+		await userEvent.keyboard("{Escape}");
+		await waitFor(() => {
+			expect(
+				body.queryByRole("combobox", { name: "Search chats" }),
+			).not.toBeInTheDocument();
+		});
 
 		await userEvent.keyboard("{Control>}k{/Control}");
 
@@ -1346,10 +1429,7 @@ export const ArchivedFilterShowsArchivedAgents: Story = {
 				updated_at: recentTimestamp,
 			}),
 		],
-		sidebarFilters: {
-			...defaultSidebarFilters,
-			archiveStatus: "archived",
-		},
+		sidebarFilters: { ...defaultSidebarFilters, archiveStatus: "archived" },
 	},
 	parameters: {
 		reactRouter: reactRouterParameters({
@@ -1367,6 +1447,44 @@ export const ArchivedFilterShowsArchivedAgents: Story = {
 	},
 };
 
+export const PreservesArchivedFilterOnChatNavigation: Story = {
+	args: {
+		chats: [
+			buildChat({
+				id: "archived-nav-1",
+				title: "Archived nav target",
+				archived: true,
+				updated_at: recentTimestamp,
+			}),
+		],
+		sidebarFilters: { ...defaultSidebarFilters, archiveStatus: "archived" },
+	},
+	parameters: {
+		reactRouter: reactRouterParameters({
+			location: {
+				path: "/agents",
+				searchParams: { archived: "archived" },
+			},
+			routing: [
+				{ path: "/agents", useStoryElement: true },
+				{ path: "/agents/:agentId", element: <ChildSearchProbe /> },
+			],
+		}),
+	},
+	play: async ({ canvasElement }) => {
+		const canvas = within(canvasElement);
+		const link = await canvas.findByRole("link", {
+			name: /Archived nav target/,
+		});
+		await userEvent.click(link);
+		await waitFor(() => {
+			expect(canvas.getByTestId("child-search")).toHaveTextContent(
+				"archived=archived",
+			);
+		});
+	},
+};
+
 export const NoArchivedSection: Story = {
 	args: {
 		chats: [
@@ -1757,10 +1875,7 @@ export const ArchivedAgentUnarchiveOption: Story = {
 				updated_at: recentTimestamp,
 			}),
 		],
-		sidebarFilters: {
-			...defaultSidebarFilters,
-			archiveStatus: "archived",
-		},
+		sidebarFilters: { ...defaultSidebarFilters, archiveStatus: "archived" },
 	},
 	parameters: {
 		reactRouter: reactRouterParameters({
@@ -2100,3 +2215,43 @@ export const SettingsAdminAgentsEntryPreserved: Story = {
 		expect(canvas.getByText("Manage Agents")).toBeInTheDocument();
 	},
 };
+
+export const PreservesArchivedFilterOnSettingsNavigation: Story = {
+	args: {
+		chats: [
+			buildChat({
+				id: "archived-settings-1",
+				title: "Archived settings target",
+				archived: true,
+				updated_at: recentTimestamp,
+			}),
+		],
+		sidebarFilters: { ...defaultSidebarFilters, archiveStatus: "archived" },
+	},
+	parameters: {
+		reactRouter: reactRouterParameters({
+			location: {
+				path: "/agents",
+				searchParams: { archived: "archived" },
+			},
+			routing: [
+				{
+					path: "/agents/settings",
+					element: <SettingsStateProbe />,
+				},
+				...agentsRouting,
+			],
+		}),
+	},
+	play: async ({ canvasElement }) => {
+		const canvas = within(canvasElement);
+		const settingsLink = await canvas.findByRole("link", { name: "Settings" });
+		await userEvent.click(settingsLink);
+		await waitFor(() => {
+			const fromValue =
+				canvas.getByTestId("settings-state-from").textContent ?? "";
+			expect(fromValue).toContain("/agents");
+			expect(fromValue).toContain("archived=archived");
+		});
+	},
+};
diff --git a/site/src/pages/AgentsPage/components/ChatsSidebar/chats/ChatsPanel.tsx b/site/src/pages/AgentsPage/components/ChatsSidebar/chats/ChatsPanel.tsx
index d3190229ec..dca8dfb6d3 100644
--- a/site/src/pages/AgentsPage/components/ChatsSidebar/chats/ChatsPanel.tsx
+++ b/site/src/pages/AgentsPage/components/ChatsSidebar/chats/ChatsPanel.tsx
@@ -30,11 +30,6 @@ import { ProductLogo } from "#/components/Icons/ProductLogo";
 import { Kbd, KbdGroup } from "#/components/Kbd/Kbd";
 import { ScrollArea } from "#/components/ScrollArea/ScrollArea";
 import { Skeleton } from "#/components/Skeleton/Skeleton";
-import {
-	Tooltip,
-	TooltipContent,
-	TooltipTrigger,
-} from "#/components/Tooltip/Tooltip";
 import { cn } from "#/utils/cn";
 import { getOSKey } from "#/utils/platform";
 import {
@@ -350,8 +345,11 @@ export const ChatsPanel: FC<ChatsPanelProps> = ({
 			aria-hidden={isSettingsPanel}
 			inert={isSettingsPanel ? true : undefined}
 		>
-			<div className="hidden border-b border-border-default px-2 py-1.5 sm:block">
-				<div className="flex items-center justify-between mb-2.5">
+			<nav
+				aria-label="Sidebar"
+				className="hidden border-b border-border-default px-2 py-1.5 sm:flex sm:flex-col sm:gap-1"
+			>
+				<div className="flex items-center justify-between mb-2.5 ml-2.5">
 					<div className="flex items-center gap-2">
 						<NavLink to="/workspaces" className="inline-flex">
 							<ProductLogo className="size-6" />
@@ -397,10 +395,50 @@ export const ChatsPanel: FC<ChatsPanelProps> = ({
 					onClick={onBeforeNewAgent}
 					disabled={isCreating}
 				/>
-			</div>
-			<div className="relative min-h-0 flex-1">
+				{onOpenSearchDialog && (
+					<SettingsNavItem
+						icon={SearchIcon}
+						label="Search"
+						active={false}
+						ariaLabel="Search chats"
+						onClick={onOpenSearchDialog}
+						className="group focus-visible:bg-surface-tertiary/50 focus-visible:text-content-primary"
+						trailing={
+							<KbdGroup className="opacity-0 transition-opacity group-hover:opacity-100 group-focus-visible:opacity-100">
+								<Kbd>{getOSKey()}</Kbd>
+								<Kbd>K</Kbd>
+							</KbdGroup>
+						}
+					/>
+				)}
+			</nav>
+			<div className="relative min-h-0 flex-1 flex flex-col">
+				<div className="mx-2 mt-4 mb-2">
+					<div className="ml-2.5 mr-2 flex h-7 items-center justify-between">
+						<h2 className="m-0 text-sm font-normal leading-6 text-content-primary">
+							Chats
+						</h2>
+						<div className="flex items-center gap-1">
+							{onOpenSearchDialog && (
+								<Button
+									variant="subtle"
+									size="icon"
+									aria-label="Search chats"
+									onClick={onOpenSearchDialog}
+									className="h-7 w-7 sm:hidden"
+								>
+									<SearchIcon />
+								</Button>
+							)}
+							<FilterPopover
+								filters={sidebarFilters}
+								onFiltersChange={onSidebarFiltersChange}
+							/>
+						</div>
+					</div>
+				</div>
 				<ScrollArea
-					className="h-full [&_[data-radix-scroll-area-viewport]>div]:!block"
+					className="min-h-0 flex-1 [&_[data-radix-scroll-area-viewport]>div]:!block"
 					scrollBarClassName="w-1.5"
 					viewportClassName={cn(
 						"[mask-image:linear-gradient(to_bottom,transparent_0,black_20px,black_calc(100%-20px),transparent_100%)]",
@@ -408,40 +446,7 @@ export const ChatsPanel: FC<ChatsPanelProps> = ({
 						"sm:[mask-image:none] sm:[-webkit-mask-image:none]",
 					)}
 				>
-					<div className="flex flex-col gap-2 px-2 pb-3 pt-6">
-						<div className="ml-2.5 mr-2 flex h-7 items-center justify-between">
-							<h2 className="m-0 text-sm font-normal leading-6 text-content-primary">
-								Chats
-							</h2>
-							<div className="flex flex-row -space-x-1">
-								<Tooltip delayDuration={500}>
-									<TooltipTrigger asChild>
-										<Button
-											variant="subtle"
-											size="icon"
-											aria-label="Search chats"
-											onClick={onOpenSearchDialog}
-											className="size-7 justify-end px-0"
-										>
-											<SearchIcon />
-										</Button>
-									</TooltipTrigger>
-									<TooltipContent side="bottom" align="end">
-										<span className="flex items-center gap-1">
-											<KbdGroup>
-												<Kbd>{getOSKey()}</Kbd>
-												<Kbd>K</Kbd>
-											</KbdGroup>
-											<span>Search chats</span>
-										</span>
-									</TooltipContent>
-								</Tooltip>
-								<FilterPopover
-									filters={sidebarFilters}
-									onFiltersChange={onSidebarFiltersChange}
-								/>
-							</div>
-						</div>
+					<div className="flex flex-col gap-2 px-2 pb-3 pt-5">
 						{loadError ? (
 							<div className="space-y-3 px-1">
 								<ErrorAlert error={loadError} />
diff --git a/site/src/pages/AgentsPage/components/ChatsSidebar/filters/FilterPopover.tsx b/site/src/pages/AgentsPage/components/ChatsSidebar/filters/FilterPopover.tsx
index 4241209507..9c017a0e74 100644
--- a/site/src/pages/AgentsPage/components/ChatsSidebar/filters/FilterPopover.tsx
+++ b/site/src/pages/AgentsPage/components/ChatsSidebar/filters/FilterPopover.tsx
@@ -226,7 +226,7 @@ export const FilterPopover: FC<FilterPopoverProps> = ({
 					size="icon"
 					aria-label="Filter agents"
 					className={cn(
-						"h-7 w-7 min-w-0 justify-end rounded-none px-0 text-content-secondary hover:text-content-primary",
+						"h-7 w-7 min-w-0 -mr-0.5 justify-end px-0 text-content-secondary hover:text-content-primary",
 						hasActiveFilters(filters) && "text-content-primary",
 					)}
 				>
diff --git a/site/src/pages/AgentsPage/components/ChatsSidebar/settings/SettingsNavItem.tsx b/site/src/pages/AgentsPage/components/ChatsSidebar/settings/SettingsNavItem.tsx
index 83566ff389..3282b6596f 100644
--- a/site/src/pages/AgentsPage/components/ChatsSidebar/settings/SettingsNavItem.tsx
+++ b/site/src/pages/AgentsPage/components/ChatsSidebar/settings/SettingsNavItem.tsx
@@ -1,6 +1,6 @@
 import { ShieldIcon } from "lucide-react";
-import type { FC } from "react";
-import { Link, type To } from "react-router";
+import type { ComponentProps, FC, ReactNode } from "react";
+import { Link } from "react-router";
 import {
 	Tooltip,
 	TooltipContent,
@@ -13,32 +13,52 @@ type SettingsNavItemProps = {
 	label: string;
 	active: boolean;
 	adminOnly?: boolean;
+	ariaLabel?: string;
+	className?: string;
 	disabled?: boolean;
+	trailing?: ReactNode;
 	trailingIcon?: FC<{ className?: string }>;
 } & (
-	| { to: To; replace?: boolean; state?: unknown; onClick?: () => void }
+	| {
+			to: ComponentProps<typeof Link>["to"];
+			replace?: boolean;
+			state?: unknown;
+			onClick?: () => void;
+	  }
 	| { to?: never; replace?: never; state?: never; onClick: () => void }
 );
 
-const navItemClassName = (active: boolean, disabled: boolean | undefined) =>
+const navItemClassName = (
+	active: boolean,
+	disabled: boolean | undefined,
+	className: string | undefined,
+) =>
 	cn(
 		"flex w-full items-center gap-2.5 rounded-md border-0 px-2.5 py-2 text-left text-sm cursor-pointer transition-colors no-underline",
 		active
 			? "bg-surface-quaternary/25 text-content-primary font-medium"
 			: "bg-transparent text-content-secondary hover:bg-surface-tertiary/50 hover:text-content-primary",
 		disabled && "opacity-50 pointer-events-none",
+		className,
 	);
 
 const NavItemContent: FC<{
 	icon: FC<{ className?: string }>;
 	label: string;
 	adminOnly?: boolean;
+	trailing?: ReactNode;
 	trailingIcon?: FC<{ className?: string }>;
-}> = ({ icon: Icon, label, adminOnly, trailingIcon: TrailingIcon }) => (
+}> = ({
+	icon: Icon,
+	label,
+	adminOnly,
+	trailing,
+	trailingIcon: TrailingIcon,
+}) => (
 	<>
 		<Icon className="size-4 shrink-0" />
 		<span className="min-w-0 flex-1">{label}</span>
-		{(adminOnly || TrailingIcon) && (
+		{(adminOnly || trailing || TrailingIcon) && (
 			<span className="ml-auto flex items-center gap-2">
 				{adminOnly && (
 					<Tooltip>
@@ -51,6 +71,7 @@ const NavItemContent: FC<{
 					</Tooltip>
 				)}
 				{TrailingIcon && <TrailingIcon className="size-4 shrink-0" />}
+				{trailing}
 			</span>
 		)}
 	</>
@@ -61,7 +82,10 @@ export const SettingsNavItem: FC<SettingsNavItemProps> = ({
 	label,
 	active,
 	adminOnly,
+	ariaLabel,
+	className,
 	disabled,
+	trailing,
 	trailingIcon,
 	...rest
 }) => {
@@ -72,14 +96,16 @@ export const SettingsNavItem: FC<SettingsNavItemProps> = ({
 				replace={rest.replace}
 				state={rest.state}
 				onClick={rest.onClick}
-				className={navItemClassName(active, disabled)}
+				className={navItemClassName(active, disabled, className)}
 				aria-current={active ? "page" : undefined}
+				aria-label={ariaLabel}
 				tabIndex={disabled ? -1 : undefined}
 			>
 				<NavItemContent
 					icon={icon}
 					label={label}
 					adminOnly={adminOnly}
+					trailing={trailing}
 					trailingIcon={trailingIcon}
 				/>
 			</Link>
@@ -91,13 +117,15 @@ export const SettingsNavItem: FC<SettingsNavItemProps> = ({
 			type="button"
 			onClick={rest.onClick}
 			disabled={disabled}
-			className={navItemClassName(active, disabled)}
+			className={navItemClassName(active, disabled, className)}
 			aria-current={active ? "page" : undefined}
+			aria-label={ariaLabel}
 		>
 			<NavItemContent
 				icon={icon}
 				label={label}
 				adminOnly={adminOnly}
+				trailing={trailing}
 				trailingIcon={trailingIcon}
 			/>
 		</button>