diff --git a/site/src/api/api.ts b/site/src/api/api.ts
index 7e50291a9b995..ae26b8b0cbb80 100644
--- a/site/src/api/api.ts
+++ b/site/src/api/api.ts
@@ -1287,6 +1287,15 @@ export const updateWorkspace = async (
   });
 };
 
+export const getWorkspaceResolveAutostart = async (
+  workspaceId: string,
+): Promise<TypesGen.ResolveAutostartResponse> => {
+  const response = await axios.get(
+    `/api/v2/workspaces/${workspaceId}/resolve-autostart`,
+  );
+  return response.data;
+};
+
 const getMissingParameters = (
   oldBuildParameters: TypesGen.WorkspaceBuildParameter[],
   newBuildParameters: TypesGen.WorkspaceBuildParameter[],
diff --git a/site/src/api/queries/workspaceQuota.ts b/site/src/api/queries/workspaceQuota.ts
index 72aaf5c716af3..b8d627783838b 100644
--- a/site/src/api/queries/workspaceQuota.ts
+++ b/site/src/api/queries/workspaceQuota.ts
@@ -11,3 +11,15 @@ export const workspaceQuota = (username: string) => {
     queryFn: () => API.getWorkspaceQuota(username),
   };
 };
+
+const getWorkspaceResolveAutostartQueryKey = (workspaceId: string) => [
+  workspaceId,
+  "workspaceResolveAutostart",
+];
+
+export const workspaceResolveAutostart = (workspaceId: string) => {
+  return {
+    queryKey: getWorkspaceResolveAutostartQueryKey(workspaceId),
+    queryFn: () => API.getWorkspaceResolveAutostart(workspaceId),
+  };
+};
diff --git a/site/src/pages/WorkspacePage/Workspace.stories.tsx b/site/src/pages/WorkspacePage/Workspace.stories.tsx
index d77bff78c5875..a455812f125eb 100644
--- a/site/src/pages/WorkspacePage/Workspace.stories.tsx
+++ b/site/src/pages/WorkspacePage/Workspace.stories.tsx
@@ -212,6 +212,14 @@ export const Outdated: Story = {
   },
 };
 
+export const CantAutostart: Story = {
+  args: {
+    ...Running.args,
+    canAutostart: false,
+    workspace: Mocks.MockOutdatedRunningWorkspaceRequireActiveVersion,
+  },
+};
+
 export const GetBuildsError: Story = {
   args: {
     ...Running.args,
diff --git a/site/src/pages/WorkspacePage/Workspace.tsx b/site/src/pages/WorkspacePage/Workspace.tsx
index 761592d32f25b..b8d49bf17ded1 100644
--- a/site/src/pages/WorkspacePage/Workspace.tsx
+++ b/site/src/pages/WorkspacePage/Workspace.tsx
@@ -73,6 +73,7 @@ export interface WorkspaceProps {
   onLoadMoreBuilds: () => void;
   isLoadingMoreBuilds: boolean;
   hasMoreBuilds: boolean;
+  canAutostart: boolean;
 }
 
 /**
@@ -111,6 +112,7 @@ export const Workspace: FC<React.PropsWithChildren<WorkspaceProps>> = ({
   onLoadMoreBuilds,
   isLoadingMoreBuilds,
   hasMoreBuilds,
+  canAutostart,
 }) => {
   const navigate = useNavigate();
   const serverVersion = buildInfo?.version || "";
@@ -168,6 +170,14 @@ export const Workspace: FC<React.PropsWithChildren<WorkspaceProps>> = ({
       clearTimeout(showTimer);
     };
   }, [workspace, now, showAlertPendingInQueue]);
+
+  const updateRequired =
+    (workspace.template_require_active_version ||
+      workspace.automatic_updates === "always") &&
+    workspace.outdated;
+  const autoStartFailing = workspace.autostart_schedule && !canAutostart;
+  const requiresManualUpdate = updateRequired && autoStartFailing;
+
   return (
     <>
       <FullWidthPageHeader>
@@ -220,12 +230,25 @@ export const Workspace: FC<React.PropsWithChildren<WorkspaceProps>> = ({
 
       <Margins css={styles.content}>
         <Stack direction="column" css={styles.firstColumnSpacer} spacing={4}>
-          {workspace.outdated && (
-            <Alert severity="info">
-              <AlertTitle>An update is available for your workspace</AlertTitle>
-              {updateMessage && <AlertDetail>{updateMessage}</AlertDetail>}
-            </Alert>
-          )}
+          {workspace.outdated &&
+            (requiresManualUpdate ? (
+              <Alert severity="warning">
+                <AlertTitle>
+                  Autostart has been disabled for your workspace.
+                </AlertTitle>
+                <AlertDetail>
+                  Autostart is unable to automatically update your workspace.
+                  Manually update your workspace to reenable Autostart.
+                </AlertDetail>
+              </Alert>
+            ) : (
+              <Alert severity="info">
+                <AlertTitle>
+                  An update is available for your workspace
+                </AlertTitle>
+                {updateMessage && <AlertDetail>{updateMessage}</AlertDetail>}
+              </Alert>
+            ))}
           {buildError}
           {cancellationError}
           {workspace.latest_build.status === "running" &&
diff --git a/site/src/pages/WorkspacePage/WorkspaceActions/constants.ts b/site/src/pages/WorkspacePage/WorkspaceActions/constants.ts
index 4d49df9d0b0a1..4209f15f48f1e 100644
--- a/site/src/pages/WorkspacePage/WorkspaceActions/constants.ts
+++ b/site/src/pages/WorkspacePage/WorkspaceActions/constants.ts
@@ -45,7 +45,7 @@ export const actionsByWorkspaceStatus = (
   }
   if (
     workspace.outdated &&
-    workspaceUpdatePolicy(workspace, canChangeVersions)
+    workspaceUpdatePolicy(workspace, canChangeVersions) === "always"
   ) {
     if (status === "running") {
       return {
diff --git a/site/src/pages/WorkspacePage/WorkspacePage.tsx b/site/src/pages/WorkspacePage/WorkspacePage.tsx
index 2c8dc3d8b9d7d..01bd83075f793 100644
--- a/site/src/pages/WorkspacePage/WorkspacePage.tsx
+++ b/site/src/pages/WorkspacePage/WorkspacePage.tsx
@@ -9,7 +9,10 @@ import { ErrorAlert } from "components/Alert/ErrorAlert";
 import { useOrganizationId } from "hooks";
 import { isAxiosError } from "axios";
 import { Margins } from "components/Margins/Margins";
-import { workspaceQuota } from "api/queries/workspaceQuota";
+import {
+  workspaceQuota,
+  workspaceResolveAutostart,
+} from "api/queries/workspaceQuota";
 import { useInfiniteQuery, useQuery } from "react-query";
 import { infiniteWorkspaceBuilds } from "api/queries/workspaceBuilds";
 
@@ -41,6 +44,12 @@ export const WorkspacePage: FC = () => {
     enabled: Boolean(workspace),
   });
 
+  const canAutostartResponse = useQuery(
+    workspaceResolveAutostart(workspace?.id ?? ""),
+  );
+
+  const canAutostart = !canAutostartResponse.data?.parameter_mismatch ?? false;
+
   if (pageError) {
     return (
       <Margins>
@@ -70,6 +79,7 @@ export const WorkspacePage: FC = () => {
           await buildsQuery.fetchNextPage();
         }}
         hasMoreBuilds={Boolean(buildsQuery.hasNextPage)}
+        canAutostart={canAutostart}
       />
     </RequirePermission>
   );
diff --git a/site/src/pages/WorkspacePage/WorkspaceReadyPage.tsx b/site/src/pages/WorkspacePage/WorkspaceReadyPage.tsx
index 34cbb665c85a8..766d7a356e5f3 100644
--- a/site/src/pages/WorkspacePage/WorkspaceReadyPage.tsx
+++ b/site/src/pages/WorkspacePage/WorkspaceReadyPage.tsx
@@ -46,6 +46,7 @@ interface WorkspaceReadyPageProps {
   onLoadMoreBuilds: () => void;
   isLoadingMoreBuilds: boolean;
   hasMoreBuilds: boolean;
+  canAutostart: boolean;
 }
 
 export const WorkspaceReadyPage = ({
@@ -57,6 +58,7 @@ export const WorkspaceReadyPage = ({
   onLoadMoreBuilds,
   isLoadingMoreBuilds,
   hasMoreBuilds,
+  canAutostart,
 }: WorkspaceReadyPageProps): JSX.Element => {
   const { buildInfo } = useDashboard();
   const featureVisibility = useFeatureVisibility();
@@ -213,6 +215,7 @@ export const WorkspaceReadyPage = ({
             <WorkspaceBuildLogsSection logs={buildLogs} />
           )
         }
+        canAutostart={canAutostart}
       />
       <DeleteDialog
         entity="workspace"