diff --git a/site/src/components/Dialog/DeleteDialog.stories.tsx b/site/src/components/Dialog/DeleteDialog.stories.tsx
new file mode 100644
index 0000000000000..d2a6c86ba5e62
--- /dev/null
+++ b/site/src/components/Dialog/DeleteDialog.stories.tsx
@@ -0,0 +1,114 @@
+import type { Meta, StoryObj } from "@storybook/react-vite";
+import { expect, fn, userEvent, within } from "storybook/test";
+import { DeleteDialog } from "./DeleteDialog";
+import dayjs from "dayjs";
+
+const meta: Meta<typeof DeleteDialog> = {
+	title: "components/Dialog/DeleteDialog",
+	component: DeleteDialog,
+	args: {
+		open: true,
+		description: (
+			<>
+				Deleting this workspace will permanently destroy all of its Terraform
+				resources.
+			</>
+		),
+
+		resourceKind: "workspace",
+		resourceName: "coffee-tahr-38",
+
+		onDelete: fn(),
+
+		onCancel: fn(),
+	},
+};
+
+export default meta;
+
+type Story = StoryObj<typeof DeleteDialog>;
+
+export const Example: Story = {};
+
+export const WithTimeAndOwner: Story = {
+	args: {
+		resourceLastUsed: dayjs().subtract(5, "minutes"),
+		resourceOwnedBy: "Pumpkaboo",
+	},
+};
+
+export const Archive: Story = {
+	args: {
+		description: (
+			<>
+				Archiving this workspace will permanently destroy all of its Terraform
+				resources.
+			</>
+		),
+		deleteAction: "Archive",
+	},
+};
+
+export const Deleting: Story = {
+	args: {
+		deleteLoading: true,
+	},
+};
+
+export const AdditionalInfo: Story = {
+	args: {
+		additionalInfo: "Oh hell yeah",
+	},
+};
+
+export const WithNameInput: Story = {
+	args: {
+		requireAcknowledgingName: true,
+	},
+	play: async ({ canvasElement }) => {
+		const user = userEvent.setup();
+		const body = within(canvasElement.ownerDocument.body);
+		const confirmButton = await body.findByRole("button", { name: "Delete" });
+		await expect(confirmButton).toBeDisabled();
+		const input = await body.findByLabelText(
+			`Confirm the name of the workspace`,
+		);
+		await user.type(input, "coffee-tahr-38");
+		await expect(confirmButton).toBeEnabled();
+	},
+};
+
+export const AdditionalInfoWithNameInput: Story = {
+	args: {
+		requireAcknowledgingName: true,
+		additionalInfo: "Oh hell yeah",
+	},
+	play: async ({ canvasElement }) => {
+		const user = userEvent.setup();
+		const body = within(canvasElement.ownerDocument.body);
+		const confirmButton = await body.findByRole("button", { name: "Delete" });
+		await expect(confirmButton).toBeDisabled();
+		const input = await body.findByLabelText(
+			`Confirm the name of the workspace`,
+		);
+		await user.type(input, "coffee-tahr-38");
+		await expect(confirmButton).toBeEnabled();
+	},
+};
+
+export const WithNameInputFilledWrong: Story = {
+	args: {
+		requireAcknowledgingName: true,
+	},
+	play: async ({ canvasElement }) => {
+		const user = userEvent.setup();
+		const body = within(canvasElement.ownerDocument.body);
+		const confirmButton = await body.findByRole("button", { name: "Delete" });
+		await expect(confirmButton).toBeDisabled();
+		const input = await body.findByLabelText(
+			`Confirm the name of the workspace`,
+		);
+		await user.type(input, "tahr-coffee-83");
+		await expect(confirmButton).toBeEnabled();
+	},
+};
diff --git a/site/src/components/Dialog/DeleteDialog.tsx b/site/src/components/Dialog/DeleteDialog.tsx
new file mode 100644
index 0000000000000..e9c5fb008778a
--- /dev/null
+++ b/site/src/components/Dialog/DeleteDialog.tsx
@@ -0,0 +1,157 @@
+import { TimerIcon, UserIcon } from "lucide-react";
+import { useId, useState } from "react";
+import { Alert } from "#/components/Alert/Alert";
+import { Input } from "#/components/Input/Input";
+import { Label } from "#/components/Label/Label";
+import {
+	Dialog,
+	DialogActions,
+	DialogContent,
+	DialogDescription,
+	DialogFooter,
+	DialogHeader,
+	DialogTitle,
+} from "./Dialog";
+import { type DateTimeInput, relativeTime } from "#/utils/time";
+
+type DeleteDialogProps = {
+	open: boolean;
+	description: React.ReactNode;
+	requireAcknowledgingName?: boolean;
+	additionalInfo?: React.ReactNode;
+
+	resourceKind: string;
+	resourceName: string;
+	resourceLastUsed?: DateTimeInput;
+	resourceOwnedBy?: string;
+
+	deleteAction: React.ReactNode;
+	deleteLoading?: boolean;
+	onDelete: () => void;
+
+	onCancel: () => void;
+};
+
+export const DeleteDialog: React.FC<DeleteDialogProps> = ({
+	open,
+	description,
+	requireAcknowledgingName,
+	additionalInfo,
+
+	resourceKind,
+	resourceName,
+	resourceLastUsed,
+	resourceOwnedBy,
+
+	deleteAction = "Delete",
+	deleteLoading,
+	onDelete,
+
+	onCancel,
+}) => {
+	const [acknowledged, setAcknowledged] = useState(false);
+
+	const includeSubtitle = resourceLastUsed || resourceOwnedBy;
+
+	return (
+		<Dialog
+			open={open}
+			onOpenChange={(nextOpen) => {
+				if (!nextOpen) {
+					onCancel();
+				}
+			}}
+		>
+			<DialogContent>
+				<DialogHeader>
+					<DialogTitle>
+						{deleteAction} {resourceName}?
+					</DialogTitle>
+					{includeSubtitle && (
+						<div className="flex flex-row gap-3 text-sm">
+							{resourceLastUsed && (
+								<div className="flex flex-row items-center gap-1">
+									<TimerIcon className="size-4" />
+									<span>last used {relativeTime(resourceLastUsed)}</span>
+								</div>
+							)}
+							{resourceOwnedBy && (
+								<div className="flex flex-row items-center gap-1">
+									<UserIcon className="size-4" />
+									<span>owned by {resourceOwnedBy}</span>
+								</div>
+							)}
+						</div>
+					)}
+				</DialogHeader>
+				<form action={onDelete} className="flex flex-col gap-6 [&_*]:m-0">
+					<div className="flex flex-col gap-3">
+						<DialogDescription>{description}</DialogDescription>
+						{Boolean(additionalInfo) && (
+							<Alert severity="warning" prominent>
+								{additionalInfo}
+							</Alert>
+						)}
+					</div>
+					{requireAcknowledgingName && (
+						<DeleteDialogAcknowledgmentInput
+							resourceName={resourceName}
+							resourceKind={resourceKind}
+							setAcknowledged={setAcknowledged}
+						/>
+					)}
+					<DialogFooter>
+						<DialogActions
+							confirmAction={deleteAction}
+							confirmLoading={deleteLoading}
+							confirmDisabled={requireAcknowledgingName && !acknowledged}
+							confirmVariant="destructive"
+							onConfirm={onDelete}
+							onCancel={onCancel}
+						/>
+					</DialogFooter>
+				</form>
+			</DialogContent>
+		</Dialog>
+	);
+};
+
+type DeleteDialogAcknowledgmentInputProps = {
+	resourceName: string;
+	resourceKind: string;
+	setAcknowledged: (acknowledged: boolean) => void;
+};
+
+const DeleteDialogAcknowledgmentInput: React.FC<
+	DeleteDialogAcknowledgmentInputProps
+> = ({ resourceName, resourceKind, setAcknowledged }) => {
+	const inputId = useId();
+	const errorId = useId();
+	const [showError, setShowError] = useState(false);
+
+	return (
+		<div className="flex flex-col gap-3">
+			<Label htmlFor={inputId}>Confirm the name of the {resourceKind}</Label>
+			<Input
+				id={inputId}
+				onChange={(event) => {
+					const inputValue = event.target.value;
+					setAcknowledged(inputValue === resourceName);
+				}}
+				onFocus={() => setShowError(false)}
+				onBlur={(event) => {
+					const inputValue = event.target.value;
+					setShowError(inputValue.length > 0 && inputValue !== resourceName);
+				}}
+				aria-invalid={showError}
+				aria-describedby={showError ? errorId : undefined}
+				autoFocus
+			/>
+			{showError && (
+				<Alert severity="error">
+					Please enter the name of the {resourceKind}
+				</Alert>
+			)}
+		</div>
+	);
+};
diff --git a/site/src/components/Dialog/Dialog.stories.tsx b/site/src/components/Dialog/Dialog.stories.tsx
index b0f732bf643f3..f45aa4694ddc2 100644
--- a/site/src/components/Dialog/Dialog.stories.tsx
+++ b/site/src/components/Dialog/Dialog.stories.tsx
@@ -26,7 +26,7 @@ const meta: Meta<typeof Dialog> = {
 						<DialogDescription>Dialog Description text</DialogDescription>
 					</DialogHeader>
 					<DialogFooter>
-						<Button>Ok</Button>
+						<Button>OK</Button>
 					</DialogFooter>
 				</DialogContent>
 			</>
diff --git a/site/src/components/Dialog/Dialog.tsx b/site/src/components/Dialog/Dialog.tsx
index d1cbfeb10b814..20cf0e091c513 100644
--- a/site/src/components/Dialog/Dialog.tsx
+++ b/site/src/components/Dialog/Dialog.tsx
@@ -110,7 +110,7 @@ export const DialogFooter: React.FC<React.ComponentPropsWithRef<"div">> = ({
 
 type DialogActionsProps = {
 	/** Text to display in the confirm button */
-	confirmText?: React.ReactNode;
+	confirmAction?: React.ReactNode;
 	/** Whether or not confirm is loading, also disables cancel when true */
 	confirmLoading?: boolean;
 	/** Whether or not the submit button is disabled */
@@ -130,7 +130,7 @@ type DialogActionsProps = {
  * Quickly handles most modals actions, some combination of a cancel and confirm button
  */
 export const DialogActions: React.FC<DialogActionsProps> = ({
-	confirmText = "Confirm",
+	confirmAction = "Confirm",
 	confirmLoading = false,
 	confirmDisabled = false,
 	confirmVariant,
@@ -163,7 +163,7 @@ export const DialogActions: React.FC<DialogActionsProps> = ({
 					type="submit"
 				>
 					<Spinner loading={confirmLoading} />
-					{confirmText}
+					{confirmAction}
 				</Button>
 			)}
 		</>
diff --git a/site/src/pages/UsersPage/UsersPage.tsx b/site/src/pages/UsersPage/UsersPage.tsx
index 3e70e8f01fd83..cd7baa2380d2b 100644
--- a/site/src/pages/UsersPage/UsersPage.tsx
+++ b/site/src/pages/UsersPage/UsersPage.tsx
@@ -16,7 +16,7 @@ import {
 } from "#/api/queries/users";
 import type { User } from "#/api/typesGenerated";
 import { ConfirmDialog } from "#/components/Dialogs/ConfirmDialog/ConfirmDialog";
-import { DeleteDialog } from "#/components/Dialogs/DeleteDialog/DeleteDialog";
+import { DeleteDialog } from "#/components/Dialog/DeleteDialog";
 import { useFilter } from "#/components/Filter/Filter";
 import { useStatusFilterMenu } from "#/components/Filter/UsersFilter";
 import { useAuthenticated } from "#/hooks/useAuthenticated";
@@ -157,36 +157,54 @@ const UsersPage: React.FC = () => {
 				isUpdatingRoles={updateUserRolesMutation.isPending}
 			/>
 
-			<DeleteDialog
-				key={userToDelete?.username}
-				isOpen={userToDelete !== undefined}
-				confirmLoading={deleteUserMutation.isPending}
-				name={userToDelete?.username ?? ""}
-				entity="user"
-				onCancel={() => setUserToDelete(undefined)}
-				onConfirm={async () => {
-					if (!userToDelete) {
-						return;
+			{userToDelete && (
+				<DeleteDialog
+					key={userToDelete.username}
+					open
+					description={
+						<>
+							<strong>{userToDelete.name ?? userToDelete.username}</strong> will
+							immediately lose access once
+							{userToDelete.is_service_account ? " it has " : " they have "}
+							been deleted.
+						</>
 					}
-					try {
-						await deleteUserMutation.mutateAsync(userToDelete.id);
-						setUserToDelete(undefined);
-						toast.success(
-							`User "${userToDelete.username}" deleted successfully.`,
-						);
-					} catch (e) {
-						toast.error(
-							getErrorMessage(
-								e,
-								`Error deleting user "${userToDelete.username}".`,
-							),
-							{
-								description: getErrorDetail(e),
-							},
-						);
+					additionalInfo={
+						<>
+							To delete a
+							{userToDelete.is_service_account
+								? " service account, it "
+								: " user, they "}
+							must not have any workspaces.
+						</>
 					}
-				}}
-			/>
+					resourceKind="user"
+					resourceName={userToDelete.username}
+					deleteAction="Delete"
+					onDelete={async () => {
+						if (!userToDelete) {
+							return;
+						}
+						try {
+							await deleteUserMutation.mutateAsync(userToDelete.id);
+							setUserToDelete(undefined);
+							toast.success(`${userToDelete.username} has been deleted.`);
+						} catch (e) {
+							toast.error(
+								getErrorMessage(
+									e,
+									`Error deleting user "${userToDelete.username}".`,
+								),
+								{
+									description: getErrorDetail(e),
+								},
+							);
+						}
+					}}
+					deleteLoading={deleteUserMutation.isPending}
+					onCancel={() => setUserToDelete(undefined)}
+				/>
+			)}
 
 			<ConfirmDialog
 				type="delete"
@@ -220,7 +238,7 @@ const UsersPage: React.FC = () => {
 				}}
 				description={
 					<>
-						Do you want to suspend the user{" "}
+						Do you want to suspend{" "}
 						<strong>{userToSuspend?.username ?? ""}</strong>?
 					</>
 				}
diff --git a/site/src/pages/WorkspacesPage/WorkspacesTable.tsx b/site/src/pages/WorkspacesPage/WorkspacesTable.tsx
index bcf0571d90a10..a1d0f1dd09568 100644
--- a/site/src/pages/WorkspacesPage/WorkspacesTable.tsx
+++ b/site/src/pages/WorkspacesPage/WorkspacesTable.tsx
@@ -588,14 +588,19 @@ const WorkspaceActionsCell: FC<WorkspaceActionsCellProps> = ({
 			<ConfirmDialog
 				open={isStopConfirmOpen}
 				title="Stop workspace"
-				description={`Are you sure you want to stop the workspace "${workspace.name}"? This will terminate all running processes and disconnect any active sessions.`}
+				description={
+					<>
+						Are you sure you want to stop the workspace "{workspace.name}"? This
+						will terminate all running processes and disconnect any active
+						sessions.
+					</>
+				}
 				confirmText="Stop"
 				onClose={() => setIsStopConfirmOpen(false)}
 				onConfirm={() => {
 					stopWorkspaceMutation.mutate({});
 					setIsStopConfirmOpen(false);
 				}}
-				type="delete"
 			/>
 
 			<WorkspaceBuildCancelDialog
diff --git a/site/src/utils/time.ts b/site/src/utils/time.ts
index faa13a20e6403..9ba7a963f75f2 100644
--- a/site/src/utils/time.ts
+++ b/site/src/utils/time.ts
@@ -24,7 +24,7 @@ const TIME_CONSTANTS = {
 };
 
 export type TimeUnit = "days" | "hours";
-type DateTimeInput = Date | string | number | Dayjs | null | undefined;
+export type DateTimeInput = Date | string | number | Dayjs | null | undefined;
 
 // Standard format strings
 // https://day.js.org/docs/en/display/format