diff --git a/site/src/components/Command/Command.tsx b/site/src/components/Command/Command.tsx
index 8973154f1d..ff26e960f5 100644
--- a/site/src/components/Command/Command.tsx
+++ b/site/src/components/Command/Command.tsx
@@ -54,7 +54,7 @@ export const CommandInput = forwardRef<
 			ref={ref}
 			className={cn(
 				`flex h-10 w-full rounded-md bg-transparent py-3 text-sm outline-none border-none
-				placeholder:text-content-secondary
+				placeholder:text-content-secondary text-content-primary
 				disabled:cursor-not-allowed disabled:opacity-50`,
 				className,
 			)}
diff --git a/site/src/modules/tasks/TasksSidebar/UserCombobox.stories.tsx b/site/src/modules/tasks/TasksSidebar/UserCombobox.stories.tsx
new file mode 100644
index 0000000000..3f4900000a
--- /dev/null
+++ b/site/src/modules/tasks/TasksSidebar/UserCombobox.stories.tsx
@@ -0,0 +1,102 @@
+import { MockUserOwner } from "testHelpers/entities";
+import { withAuthProvider } from "testHelpers/storybook";
+import type { Meta, StoryObj } from "@storybook/react-vite";
+import { waitFor } from "@testing-library/react";
+import { API } from "api/api";
+import { MockUsers } from "pages/UsersPage/storybookData/users";
+import { useState } from "react";
+import { expect, spyOn, userEvent, within } from "storybook/test";
+import { UserCombobox } from "./UserCombobox";
+
+const meta: Meta<typeof UserCombobox> = {
+	title: "modules/tasks/TasksSidebar/UserCombobox",
+	component: UserCombobox,
+	decorators: [withAuthProvider],
+	parameters: {
+		user: MockUserOwner,
+	},
+	render: (args) => {
+		const [value, setValue] = useState("");
+		return <UserCombobox {...args} value={value} onValueChange={setValue} />;
+	},
+};
+
+export default meta;
+type Story = StoryObj<typeof UserCombobox>;
+
+export const Loading: Story = {
+	beforeEach: () => {
+		spyOn(API, "getUsers").mockImplementation(() => {
+			return new Promise(() => {
+				// never resolves
+			});
+		});
+	},
+};
+
+export const AllUsers: Story = {
+	parameters: {
+		queries: [{ key: ["users"], data: MockUsers }],
+	},
+};
+
+export const SelectUser: Story = {
+	beforeEach: () => {
+		spyOn(API, "getUsers").mockResolvedValue({
+			count: MockUsers.length,
+			users: MockUsers,
+		});
+	},
+	play: async ({ canvasElement, step }) => {
+		const canvas = within(canvasElement);
+		const body = within(canvasElement.ownerDocument.body);
+		const user = userEvent.setup();
+
+		await step("open combobox", async () => {
+			const trigger = await canvas.findByText(/all users/i, { exact: false });
+			await user.click(trigger);
+		});
+
+		await step("select user", async () => {
+			const option = await body.findByText(MockUsers[1].name!, {
+				exact: false,
+			});
+			await user.click(option);
+		});
+	},
+};
+
+export const SearchUser: Story = {
+	beforeEach: () => {
+		spyOn(API, "getUsers").mockImplementation((options) => {
+			let users = MockUsers;
+
+			if (options.q?.includes("Ivan")) {
+				users = users.filter((u) => u.name?.includes("Ivan"));
+			}
+
+			return Promise.resolve({
+				count: MockUsers.length,
+				users: MockUsers,
+			});
+		});
+	},
+	play: async ({ canvasElement, step }) => {
+		const canvas = within(canvasElement);
+		const body = within(canvasElement.ownerDocument.body);
+		const user = userEvent.setup();
+
+		await step("open combobox", async () => {
+			const trigger = await canvas.findByText(/all users/i, { exact: false });
+			await user.click(trigger);
+		});
+
+		await step("search user", async () => {
+			const searchInput = await body.findByLabelText("Search user");
+			await user.type(searchInput, "Ivan");
+			await waitFor(() => {
+				expect(API.getUsers).toHaveBeenCalledTimes(2);
+			});
+		});
+	},
+};
diff --git a/site/src/modules/tasks/TasksSidebar/UserCombobox.tsx b/site/src/modules/tasks/TasksSidebar/UserCombobox.tsx
new file mode 100644
index 0000000000..af5c199c99
--- /dev/null
+++ b/site/src/modules/tasks/TasksSidebar/UserCombobox.tsx
@@ -0,0 +1,167 @@
+import { users } from "api/queries/users";
+import type { User } from "api/typesGenerated";
+import { Avatar } from "components/Avatar/Avatar";
+import { Button } from "components/Button/Button";
+import {
+	Command,
+	CommandEmpty,
+	CommandGroup,
+	CommandInput,
+	CommandItem,
+	CommandList,
+} from "components/Command/Command";
+import {
+	Popover,
+	PopoverContent,
+	PopoverTrigger,
+} from "components/Popover/Popover";
+import { useAuthenticated } from "hooks";
+import { useDebouncedValue } from "hooks/debounce";
+import { CheckIcon, ChevronsUpDownIcon } from "lucide-react";
+import { type FC, useState } from "react";
+import { keepPreviousData, useQuery } from "react-query";
+import { cn } from "utils/cn";
+
+type UserOption = {
+	label: string;
+	/**
+	 * The username of the user.
+	 */
+	value: string;
+	avatarUrl?: string;
+};
+
+type UserComboboxProps = {
+	value: string;
+	onValueChange: (value: string) => void;
+};
+
+export const UserCombobox: FC<UserComboboxProps> = ({
+	value,
+	onValueChange,
+}) => {
+	const [open, setOpen] = useState(false);
+	const [search, setSearch] = useState("");
+	const debouncedSearch = useDebouncedValue(search, 250);
+	const { user } = useAuthenticated();
+	const { data: options, isFetched } = useQuery({
+		...users({ q: debouncedSearch }),
+		select: (res) => mapUsersToOptions(res.users, user, value),
+		placeholderData: keepPreviousData,
+	});
+	const selectedOption = options?.find((o) => o.value === value);
+
+	return (
+		<Popover open={open} onOpenChange={setOpen}>
+			<PopoverTrigger asChild>
+				<Button
+					disabled={!isFetched}
+					role="combobox"
+					aria-expanded={open}
+					className="justify-between rounded-full bg-surface-tertiary border border-border hover:bg-surface-quaternary text-content-primary pl-3 w-full"
+					size="sm"
+				>
+					{isFetched ? (
+						selectedOption ? (
+							<UserItem option={selectedOption} className="-ml-2" />
+						) : (
+							"All users"
+						)
+					) : (
+						"Loading users..."
+					)}
+
+					<ChevronsUpDownIcon className="h-4 w-4 shrink-0 opacity-50" />
+				</Button>
+			</PopoverTrigger>
+			<PopoverContent className="w-[280px] p-0 " side="bottom" align="start">
+				<Command>
+					<CommandInput
+						placeholder="Search user..."
+						value={search}
+						onValueChange={setSearch}
+						aria-label="Search user"
+					/>
+					<CommandList>
+						<CommandEmpty>No users found.</CommandEmpty>
+						<CommandGroup>
+							{options?.map((option) => (
+								<CommandItem
+									keywords={[option.label]}
+									key={option.value}
+									value={option.value}
+									onSelect={() => {
+										onValueChange(option.value);
+										setOpen(false);
+									}}
+								>
+									<UserItem option={option} />
+									<CheckIcon
+										className={cn(
+											"ml-2 h-4 w-4",
+											option.value === selectedOption?.value
+												? "opacity-100"
+												: "opacity-0",
+										)}
+									/>
+								</CommandItem>
+							))}
+						</CommandGroup>
+					</CommandList>
+				</Command>
+			</PopoverContent>
+		</Popover>
+	);
+};
+
+type UserItemProps = {
+	option: UserOption;
+	className?: string;
+};
+
+const UserItem: FC<UserItemProps> = ({ option, className }) => {
+	return (
+		<div className={cn("flex flex-1 items-center gap-2", className)}>
+			<Avatar
+				src={option.avatarUrl}
+				fallback={option.label}
+				className="rounded-full"
+			/>
+			{option.label}
+		</div>
+	);
+};
+
+function mapUsersToOptions(
+	users: readonly User[],
+	/**
+	 * Includes the authenticated user in the list if they are not already
+	 * present. So the current user can always select themselves easily.
+	 */
+	authUser: User,
+	/**
+	 * Username of the currently selected user.
+	 */
+	selectedValue: string,
+): UserOption[] {
+	const includeAuthenticatedUser = (users: readonly User[]) => {
+		const hasAuthenticatedUser = users.some(
+			(u) => u.username === authUser.username,
+		);
+		if (hasAuthenticatedUser) {
+			return users;
+		}
+		return [authUser, ...users];
+	};
+
+	const sortSelectedFirst = (a: User) =>
+		selectedValue && a.username === selectedValue ? -1 : 0;
+
+	return includeAuthenticatedUser(users)
+		.toSorted(sortSelectedFirst)
+		.map((user) => ({
+			label: user.name || user.username,
+			value: user.username,
+			avatarUrl: user.avatar_url,
+		}));
+}