diff --git a/site/src/components/Badge/Badge.tsx b/site/src/components/Badge/Badge.tsx
index 8995222027ed0..e6b23b8a4dd94 100644
--- a/site/src/components/Badge/Badge.tsx
+++ b/site/src/components/Badge/Badge.tsx
@@ -19,7 +19,7 @@ const badgeVariants = cva(
 				warning:
 					"border border-solid border-border-warning bg-surface-orange text-content-warning shadow",
 				destructive:
-					"border border-solid border-border-destructive bg-surface-red text-content-highlight-red shadow",
+					"border border-solid border-border-destructive bg-surface-red text-highlight-red shadow",
 			},
 			size: {
 				xs: "text-2xs font-regular h-5 [&_svg]:hidden rounded px-1.5",
diff --git a/site/src/hooks/usePagination.ts b/site/src/hooks/usePagination.ts
index 2ab409e85c9d8..72ea70868fb30 100644
--- a/site/src/hooks/usePagination.ts
+++ b/site/src/hooks/usePagination.ts
@@ -9,7 +9,7 @@ export const usePagination = ({
 	const [searchParams, setSearchParams] = searchParamsResult;
 	const page = searchParams.get("page") ? Number(searchParams.get("page")) : 1;
 	const limit = DEFAULT_RECORDS_PER_PAGE;
-	const offset = calcOffset(page, limit);
+	const offset = page <= 0 ? 0 : (page - 1) * limit;
 
 	const goToPage = (page: number) => {
 		searchParams.set("page", page.toString());
@@ -23,7 +23,3 @@ export const usePagination = ({
 		offset,
 	};
 };
-
-export const calcOffset = (page: number, limit: number) => {
-	return page <= 0 ? 0 : (page - 1) * limit;
-};
diff --git a/site/src/modules/workspaces/WorkspaceOutdatedTooltip/WorkspaceOutdatedTooltip.stories.tsx b/site/src/modules/workspaces/WorkspaceOutdatedTooltip/WorkspaceOutdatedTooltip.stories.tsx
index bb0c93e74c8c6..843f8131b793f 100644
--- a/site/src/modules/workspaces/WorkspaceOutdatedTooltip/WorkspaceOutdatedTooltip.stories.tsx
+++ b/site/src/modules/workspaces/WorkspaceOutdatedTooltip/WorkspaceOutdatedTooltip.stories.tsx
@@ -1,7 +1,10 @@
-import { action } from "@storybook/addon-actions";
 import type { Meta, StoryObj } from "@storybook/react";
 import { expect, userEvent, waitFor, within } from "@storybook/test";
-import { MockTemplate, MockTemplateVersion } from "testHelpers/entities";
+import {
+	MockTemplate,
+	MockTemplateVersion,
+	MockWorkspace,
+} from "testHelpers/entities";
 import { withDashboardProvider } from "testHelpers/storybook";
 import { WorkspaceOutdatedTooltip } from "./WorkspaceOutdatedTooltip";
 
@@ -18,9 +21,11 @@ const meta: Meta<typeof WorkspaceOutdatedTooltip> = {
 		],
 	},
 	args: {
-		onUpdateVersion: action("onUpdateVersion"),
-		templateName: MockTemplate.display_name,
-		latestVersionId: MockTemplateVersion.id,
+		workspace: {
+			...MockWorkspace,
+			template_name: MockTemplate.display_name,
+			template_active_version_id: MockTemplateVersion.id,
+		},
 	},
 };
 
@@ -29,14 +34,12 @@ type Story = StoryObj<typeof WorkspaceOutdatedTooltip>;
 
 const Example: Story = {
 	play: async ({ canvasElement, step }) => {
-		const screen = within(canvasElement);
+		const body = within(canvasElement.ownerDocument.body);
 
 		await step("activate hover trigger", async () => {
-			await userEvent.hover(screen.getByRole("button"));
+			await userEvent.hover(body.getByRole("button"));
 			await waitFor(() =>
-				expect(
-					screen.getByText(MockTemplateVersion.message),
-				).toBeInTheDocument(),
+				expect(body.getByText(MockTemplateVersion.message)).toBeInTheDocument(),
 			);
 		});
 	},
diff --git a/site/src/modules/workspaces/WorkspaceOutdatedTooltip/WorkspaceOutdatedTooltip.tsx b/site/src/modules/workspaces/WorkspaceOutdatedTooltip/WorkspaceOutdatedTooltip.tsx
index ada4c63d9a0bb..9615560840c59 100644
--- a/site/src/modules/workspaces/WorkspaceOutdatedTooltip/WorkspaceOutdatedTooltip.tsx
+++ b/site/src/modules/workspaces/WorkspaceOutdatedTooltip/WorkspaceOutdatedTooltip.tsx
@@ -3,7 +3,10 @@ import InfoIcon from "@mui/icons-material/InfoOutlined";
 import RefreshIcon from "@mui/icons-material/Refresh";
 import Link from "@mui/material/Link";
 import Skeleton from "@mui/material/Skeleton";
+import { getErrorDetail, getErrorMessage } from "api/errors";
 import { templateVersion } from "api/queries/templates";
+import type { Workspace } from "api/typesGenerated";
+import { displayError } from "components/GlobalSnackbar/utils";
 import {
 	HelpTooltip,
 	HelpTooltipAction,
@@ -17,102 +20,99 @@ import { usePopover } from "components/deprecated/Popover/Popover";
 import { linkToTemplate, useLinks } from "modules/navigation";
 import type { FC } from "react";
 import { useQuery } from "react-query";
-
-const Language = {
-	outdatedLabel: "Outdated",
-	versionTooltipText:
-		"This workspace version is outdated and a newer version is available.",
-	updateVersionLabel: "Update",
-};
+import {
+	WorkspaceUpdateDialogs,
+	useWorkspaceUpdate,
+} from "../WorkspaceUpdateDialogs";
 
 interface TooltipProps {
-	organizationName: string;
-	templateName: string;
-	latestVersionId: string;
-	onUpdateVersion: () => void;
-	ariaLabel?: string;
+	workspace: Workspace;
 }
 
 export const WorkspaceOutdatedTooltip: FC<TooltipProps> = (props) => {
 	return (
 		<HelpTooltip>
-			<HelpTooltipTrigger
-				size="small"
-				aria-label="More info"
-				hoverEffect={false}
-			>
+			<HelpTooltipTrigger size="small" hoverEffect={false}>
 				<InfoIcon css={styles.icon} />
+				<span className="sr-only">Outdated info</span>
 			</HelpTooltipTrigger>
-
 			<WorkspaceOutdatedTooltipContent {...props} />
 		</HelpTooltip>
 	);
 };
 
-const WorkspaceOutdatedTooltipContent: FC<TooltipProps> = ({
-	organizationName,
-	templateName,
-	latestVersionId,
-	onUpdateVersion,
-	ariaLabel,
-}) => {
+const WorkspaceOutdatedTooltipContent: FC<TooltipProps> = ({ workspace }) => {
 	const getLink = useLinks();
 	const theme = useTheme();
 	const popover = usePopover();
 	const { data: activeVersion } = useQuery({
-		...templateVersion(latestVersionId),
+		...templateVersion(workspace.template_active_version_id),
 		enabled: popover.open,
 	});
+	const updateWorkspace = useWorkspaceUpdate({
+		workspace,
+		latestVersion: activeVersion,
+		onError: (error) => {
+			displayError(
+				getErrorMessage(error, "Error updating workspace"),
+				getErrorDetail(error),
+			);
+		},
+	});
 
 	const versionLink = `${getLink(
-		linkToTemplate(organizationName, templateName),
+		linkToTemplate(workspace.organization_name, workspace.template_name),
 	)}`;
 
 	return (
-		<HelpTooltipContent>
-			<HelpTooltipTitle>{Language.outdatedLabel}</HelpTooltipTitle>
-			<HelpTooltipText>{Language.versionTooltipText}</HelpTooltipText>
+		<>
+			<HelpTooltipContent disablePortal={false}>
+				<HelpTooltipTitle>Outdated</HelpTooltipTitle>
+				<HelpTooltipText>
+					This workspace version is outdated and a newer version is available.
+				</HelpTooltipText>
 
-			<div css={styles.container}>
-				<div css={{ lineHeight: "1.6" }}>
-					<div css={styles.bold}>New version</div>
-					<div>
-						{activeVersion ? (
-							<Link
-								href={`${versionLink}/versions/${activeVersion.name}`}
-								target="_blank"
-								css={{ color: theme.palette.primary.light }}
-							>
-								{activeVersion.name}
-							</Link>
-						) : (
-							<Skeleton variant="text" height={20} width={100} />
-						)}
+				<div css={styles.container}>
+					<div css={{ lineHeight: "1.6" }}>
+						<div css={styles.bold}>New version</div>
+						<div>
+							{activeVersion ? (
+								<Link
+									href={`${versionLink}/versions/${activeVersion.name}`}
+									target="_blank"
+									css={{ color: theme.palette.primary.light }}
+								>
+									{activeVersion.name}
+								</Link>
+							) : (
+								<Skeleton variant="text" height={20} width={100} />
+							)}
+						</div>
 					</div>
-				</div>
 
-				<div css={{ lineHeight: "1.6" }}>
-					<div css={styles.bold}>Message</div>
-					<div>
-						{activeVersion ? (
-							activeVersion.message || "No message"
-						) : (
-							<Skeleton variant="text" height={20} width={150} />
-						)}
+					<div css={{ lineHeight: "1.6" }}>
+						<div css={styles.bold}>Message</div>
+						<div>
+							{activeVersion ? (
+								activeVersion.message || "No message"
+							) : (
+								<Skeleton variant="text" height={20} width={150} />
+							)}
+						</div>
 					</div>
 				</div>
-			</div>
 
-			<HelpTooltipLinksGroup>
-				<HelpTooltipAction
-					icon={RefreshIcon}
-					onClick={onUpdateVersion}
-					ariaLabel={ariaLabel}
-				>
-					{Language.updateVersionLabel}
-				</HelpTooltipAction>
-			</HelpTooltipLinksGroup>
-		</HelpTooltipContent>
+				<HelpTooltipLinksGroup>
+					<HelpTooltipAction
+						icon={RefreshIcon}
+						onClick={updateWorkspace.update}
+					>
+						Update
+					</HelpTooltipAction>
+				</HelpTooltipLinksGroup>
+			</HelpTooltipContent>
+			<WorkspaceUpdateDialogs {...updateWorkspace.dialogs} />
+		</>
 	);
 };
 
diff --git a/site/src/pages/TemplateSettingsPage/TemplateSchedulePage/useWorkspacesToBeDeleted.ts b/site/src/pages/TemplateSettingsPage/TemplateSchedulePage/useWorkspacesToBeDeleted.ts
index 5a974d5d8fe31..d55f0b6c54fff 100644
--- a/site/src/pages/TemplateSettingsPage/TemplateSchedulePage/useWorkspacesToBeDeleted.ts
+++ b/site/src/pages/TemplateSettingsPage/TemplateSchedulePage/useWorkspacesToBeDeleted.ts
@@ -1,7 +1,7 @@
+import { workspaces } from "api/queries/workspaces";
 import type { Template, Workspace } from "api/typesGenerated";
 import { compareAsc } from "date-fns";
-import { calcOffset } from "hooks/usePagination";
-import { useWorkspacesData } from "pages/WorkspacesPage/data";
+import { useQuery } from "react-query";
 import type { TemplateScheduleFormValues } from "./formHelpers";
 
 export const useWorkspacesToGoDormant = (
@@ -9,11 +9,11 @@ export const useWorkspacesToGoDormant = (
 	formValues: TemplateScheduleFormValues,
 	fromDate: Date,
 ) => {
-	const { data } = useWorkspacesData({
-		offset: calcOffset(0, 0),
-		limit: 0,
-		q: `template:${template.name}`,
-	});
+	const { data } = useQuery(
+		workspaces({
+			q: `template:${template.name}`,
+		}),
+	);
 
 	return data?.workspaces?.filter((workspace: Workspace) => {
 		if (!formValues.time_til_dormant_ms) {
@@ -40,11 +40,12 @@ export const useWorkspacesToBeDeleted = (
 	formValues: TemplateScheduleFormValues,
 	fromDate: Date,
 ) => {
-	const { data } = useWorkspacesData({
-		offset: calcOffset(0, 0),
-		limit: 0,
-		q: `template:${template.name} dormant:true`,
-	});
+	const { data } = useQuery(
+		workspaces({
+			q: `template:${template.name} dormant:true`,
+		}),
+	);
+
 	return data?.workspaces?.filter((workspace: Workspace) => {
 		if (!workspace.dormant_at || !formValues.time_til_dormant_autodelete_ms) {
 			return false;
diff --git a/site/src/pages/WorkspacesPage/WorkspacesPage.tsx b/site/src/pages/WorkspacesPage/WorkspacesPage.tsx
index 551c554fd5ee3..d0439be0f0462 100644
--- a/site/src/pages/WorkspacesPage/WorkspacesPage.tsx
+++ b/site/src/pages/WorkspacesPage/WorkspacesPage.tsx
@@ -1,6 +1,7 @@
 import { getErrorDetail, getErrorMessage } from "api/errors";
 import { workspacePermissionsByOrganization } from "api/queries/organizations";
 import { templates } from "api/queries/templates";
+import { workspaces } from "api/queries/workspaces";
 import type { Workspace } from "api/typesGenerated";
 import { useFilter } from "components/Filter/Filter";
 import { useUserFilterMenu } from "components/Filter/UserFilter";
@@ -19,7 +20,6 @@ import { BatchDeleteConfirmation } from "./BatchDeleteConfirmation";
 import { BatchUpdateConfirmation } from "./BatchUpdateConfirmation";
 import { WorkspacesPageView } from "./WorkspacesPageView";
 import { useBatchActions } from "./batchActions";
-import { useWorkspaceUpdate, useWorkspacesData } from "./data";
 import { useStatusFilterMenu, useTemplateFilterMenu } from "./filter/menus";
 
 function useSafeSearchParams() {
@@ -45,9 +45,7 @@ const WorkspacesPage: FC = () => {
 	const pagination = usePagination({ searchParamsResult });
 	const { permissions, user: me } = useAuthenticated();
 	const { entitlements } = useDashboard();
-
 	const templatesQuery = useQuery(templates());
-
 	const workspacePermissionsQuery = useQuery(
 		workspacePermissionsByOrganization(
 			templatesQuery.data?.map((template) => template.organization_id),
@@ -73,12 +71,17 @@ const WorkspacesPage: FC = () => {
 		onFilterChange: () => pagination.goToPage(1),
 	});
 
-	const { data, error, queryKey, refetch } = useWorkspacesData({
+	const workspacesQueryOptions = workspaces({
 		...pagination,
 		q: filterProps.filter.query,
 	});
+	const { data, error, refetch } = useQuery({
+		...workspacesQueryOptions,
+		refetchInterval: (_, query) => {
+			return query.state.error ? false : 5_000;
+		},
+	});
 
-	const updateWorkspace = useWorkspaceUpdate(queryKey);
 	const [checkedWorkspaces, setCheckedWorkspaces] = useState<
 		readonly Workspace[]
 	>([]);
@@ -123,9 +126,6 @@ const WorkspacesPage: FC = () => {
 				limit={pagination.limit}
 				onPageChange={pagination.goToPage}
 				filterProps={filterProps}
-				onUpdateWorkspace={(workspace) => {
-					updateWorkspace.mutate(workspace);
-				}}
 				isRunningBatchAction={batchActions.isLoading}
 				onDeleteAll={() => setConfirmingBatchAction("delete")}
 				onUpdateAll={() => setConfirmingBatchAction("update")}
@@ -133,7 +133,7 @@ const WorkspacesPage: FC = () => {
 				onStopAll={() => batchActions.stopAll(checkedWorkspaces)}
 				onActionSuccess={async () => {
 					await queryClient.invalidateQueries({
-						queryKey,
+						queryKey: workspacesQueryOptions.queryKey,
 					});
 				}}
 				onActionError={(error) => {
diff --git a/site/src/pages/WorkspacesPage/WorkspacesPageView.tsx b/site/src/pages/WorkspacesPage/WorkspacesPageView.tsx
index 6db41fef8fa6c..6633f884e1263 100644
--- a/site/src/pages/WorkspacesPage/WorkspacesPageView.tsx
+++ b/site/src/pages/WorkspacesPage/WorkspacesPageView.tsx
@@ -53,7 +53,6 @@ export interface WorkspacesPageViewProps {
 	page: number;
 	limit: number;
 	onPageChange: (page: number) => void;
-	onUpdateWorkspace: (workspace: Workspace) => void;
 	onCheckChange: (checkedWorkspaces: readonly Workspace[]) => void;
 	isRunningBatchAction: boolean;
 	onDeleteAll: () => void;
@@ -76,7 +75,6 @@ export const WorkspacesPageView: FC<WorkspacesPageViewProps> = ({
 	count,
 	filterProps,
 	onPageChange,
-	onUpdateWorkspace,
 	page,
 	checkedWorkspaces,
 	onCheckChange,
@@ -223,7 +221,6 @@ export const WorkspacesPageView: FC<WorkspacesPageViewProps> = ({
 					canCreateTemplate={canCreateTemplate}
 					workspaces={workspaces}
 					isUsingFilter={filterProps.filter.used}
-					onUpdateWorkspace={onUpdateWorkspace}
 					checkedWorkspaces={checkedWorkspaces}
 					onCheckChange={onCheckChange}
 					canCheckWorkspaces={canCheckWorkspaces}
diff --git a/site/src/pages/WorkspacesPage/WorkspacesTable.tsx b/site/src/pages/WorkspacesPage/WorkspacesTable.tsx
index 92dcee60dec96..b4f1c98b27261 100644
--- a/site/src/pages/WorkspacesPage/WorkspacesTable.tsx
+++ b/site/src/pages/WorkspacesPage/WorkspacesTable.tsx
@@ -97,7 +97,6 @@ export interface WorkspacesTableProps {
 	checkedWorkspaces: readonly Workspace[];
 	error?: unknown;
 	isUsingFilter: boolean;
-	onUpdateWorkspace: (workspace: Workspace) => void;
 	onCheckChange: (checkedWorkspaces: readonly Workspace[]) => void;
 	canCheckWorkspaces: boolean;
 	templates?: Template[];
@@ -110,7 +109,6 @@ export const WorkspacesTable: FC<WorkspacesTableProps> = ({
 	workspaces,
 	checkedWorkspaces,
 	isUsingFilter,
-	onUpdateWorkspace,
 	onCheckChange,
 	canCheckWorkspaces,
 	templates,
@@ -243,16 +241,7 @@ export const WorkspacesTable: FC<WorkspacesTableProps> = ({
 												{workspace.name}
 												{workspace.favorite && <Star className="w-4 h-4" />}
 												{workspace.outdated && (
-													<WorkspaceOutdatedTooltip
-														organizationName={workspace.organization_name}
-														templateName={workspace.template_name}
-														latestVersionId={
-															workspace.template_active_version_id
-														}
-														onUpdateVersion={() => {
-															onUpdateWorkspace(workspace);
-														}}
-													/>
+													<WorkspaceOutdatedTooltip workspace={workspace} />
 												)}
 											</Stack>
 										}
diff --git a/site/src/pages/WorkspacesPage/data.ts b/site/src/pages/WorkspacesPage/data.ts
deleted file mode 100644
index 764ea218aa96c..0000000000000
--- a/site/src/pages/WorkspacesPage/data.ts
+++ /dev/null
@@ -1,112 +0,0 @@
-import { API } from "api/api";
-import { getErrorMessage } from "api/errors";
-import { workspaces } from "api/queries/workspaces";
-import type {
-	Workspace,
-	WorkspaceBuild,
-	WorkspacesRequest,
-	WorkspacesResponse,
-} from "api/typesGenerated";
-import { displayError } from "components/GlobalSnackbar/utils";
-import { useState } from "react";
-import {
-	type QueryKey,
-	useMutation,
-	useQuery,
-	useQueryClient,
-} from "react-query";
-
-export const useWorkspacesData = (req: WorkspacesRequest) => {
-	const [shouldRefetch, setShouldRefetch] = useState(true);
-	const workspacesQueryOptions = workspaces(req);
-	const result = useQuery({
-		...workspacesQueryOptions,
-		onSuccess: () => {
-			setShouldRefetch(true);
-		},
-		onError: () => {
-			setShouldRefetch(false);
-		},
-		refetchInterval: shouldRefetch ? 5_000 : undefined,
-	});
-
-	return {
-		...result,
-		queryKey: workspacesQueryOptions.queryKey,
-	};
-};
-
-export const useWorkspaceUpdate = (queryKey: QueryKey) => {
-	const queryClient = useQueryClient();
-
-	return useMutation({
-		mutationFn: API.updateWorkspaceVersion,
-		onMutate: async (workspace) => {
-			await queryClient.cancelQueries({ queryKey });
-			queryClient.setQueryData<WorkspacesResponse>(queryKey, (oldResponse) => {
-				if (oldResponse) {
-					return assignPendingStatus(oldResponse, workspace);
-				}
-			});
-		},
-		onSuccess: (workspaceBuild) => {
-			queryClient.setQueryData<WorkspacesResponse>(queryKey, (oldResponse) => {
-				if (oldResponse) {
-					return assignLatestBuild(oldResponse, workspaceBuild);
-				}
-			});
-		},
-		onError: (error) => {
-			const message = getErrorMessage(
-				error,
-				"Error updating workspace version",
-			);
-			displayError(message);
-		},
-	});
-};
-
-const assignLatestBuild = (
-	oldResponse: WorkspacesResponse,
-	build: WorkspaceBuild,
-): WorkspacesResponse => {
-	return {
-		...oldResponse,
-		workspaces: oldResponse.workspaces.map((workspace) => {
-			if (workspace.id === build.workspace_id) {
-				return {
-					...workspace,
-					latest_build: build,
-				};
-			}
-
-			return workspace;
-		}),
-	};
-};
-
-const assignPendingStatus = (
-	oldResponse: WorkspacesResponse,
-	workspace: Workspace,
-): WorkspacesResponse => {
-	return {
-		...oldResponse,
-		workspaces: oldResponse.workspaces.map((workspaceItem) => {
-			if (workspaceItem.id === workspace.id) {
-				return {
-					...workspace,
-					latest_build: {
-						...workspace.latest_build,
-						status: "pending",
-						job: {
-							...workspace.latest_build.job,
-							status: "pending",
-						},
-					},
-				} as Workspace;
-			}
-
-			return workspaceItem;
-		}),
-	};
-};

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