diff --git a/app/pages/system/UpdatePage.tsx b/app/pages/system/UpdatePage.tsx
index f3dccf67d..c5f490909 100644
--- a/app/pages/system/UpdatePage.tsx
+++ b/app/pages/system/UpdatePage.tsx
@@ -280,10 +280,26 @@ export default function UpdatePage() {
                               }),
                             modalTitle: 'Set target release',
                             modalContent: (
-                              <p>
-                                Are you sure you want to set <HL>{repo.systemVersion}</HL>{' '}
-                                as the target release?
-                              </p>
+                              <div className="space-y-4">
+                                {status.contactSupport && (
+                                  <Message
+                                    variant="notice"
+                                    // title="Support required"
+                                    content={
+                                      <>
+                                        The system has detected known conditions that
+                                        require Oxide support to resolve. Starting an update
+                                        before talking to support is{' '}
+                                        <HL>strongly discouraged</HL>.
+                                      </>
+                                    }
+                                  />
+                                )}
+                                <p>
+                                  Are you sure you want to set <HL>{repo.systemVersion}</HL>{' '}
+                                  as the target release?
+                                </p>
+                              </div>
                             ),
                             errorTitle: `Error setting target release to ${repo.systemVersion}`,
                           })
diff --git a/mock-api/msw/handlers.ts b/mock-api/msw/handlers.ts
index d5515b895..170d96b3b 100644
--- a/mock-api/msw/handlers.ts
+++ b/mock-api/msw/handlers.ts
@@ -58,6 +58,7 @@ import {
   internalError,
   invalidRequest,
   ipRangeLen,
+  mockFlags,
   NotImplemented,
   paginated,
   randomHex,
@@ -2121,7 +2122,10 @@ export const handlers = makeHandlers({
   },
   systemUpdateStatus: ({ cookies }) => {
     requireFleetViewer(cookies)
-    return db.updateStatus
+    return {
+      ...db.updateStatus,
+      contact_support: db.updateStatus.contact_support || mockFlags(cookies).contactSupport,
+    }
   },
   targetReleaseUpdate: ({ body, cookies }) => {
     requireFleetAdmin(cookies)
diff --git a/mock-api/msw/util.ts b/mock-api/msw/util.ts
index f3f88a2f1..cca972ede 100644
--- a/mock-api/msw/util.ts
+++ b/mock-api/msw/util.ts
@@ -9,6 +9,7 @@ import { differenceInSeconds, subHours } from 'date-fns'
 // Works without the .js for dev server and prod build in MSW mode, but
 // playwright wants the .js. No idea why, let's just add the .js.
 import { IPv4, IPv6 } from 'ip-num/IPNumber.js'
+import * as R from 'remeda'
 import { match } from 'ts-pattern'
 
 import {
@@ -334,6 +335,30 @@ export function handleMetrics({ path: { metricName }, query }: MetricParams) {
 }
 
 export const MSW_USER_COOKIE = 'msw-user'
+export const MSW_FLAGS_COOKIE = 'msw-flags'
+
+/**
+ * Test-only fleet-state overrides, serialized into the `msw-flags` cookie as a
+ * comma-separated list of the enabled keys. Some server-computed signals (e.g.
+ * update status's `contact_support`) have no operator UI to flip, so there's no
+ * user-controlled request input to drive them through the real UI. Rather than
+ * reach for `page.route`, a test enables a flag and the relevant handler ORs it
+ * in. Inert in normal use (cookie unset), and reproducible in the dev server
+ * via `document.cookie = 'msw-flags=contactSupport'`.
+ *
+ * This array is the single source of truth for valid flag names; both the e2e
+ * helper that sets the cookie and `mockFlags` that reads it derive their types
+ * from it, so a typo in a handler or test is a type error.
+ */
+export const MOCK_FLAGS = [
+  'contactSupport', // db.updateStatus.contact_support = true
+] as const
+export type MockFlag = (typeof MOCK_FLAGS)[number]
+
+export function mockFlags(cookies: Record<string, string>): Record<MockFlag, boolean> {
+  const present = (cookies[MSW_FLAGS_COOKIE] ?? '').split(',')
+  return R.fromKeys(MOCK_FLAGS, (flag) => present.includes(flag))
+}
 
 /**
  * Look up user by display name in cookie. If cookie is empty, return the first
diff --git a/mock-api/system-update.ts b/mock-api/system-update.ts
index fd127164a..ec88544c2 100644
--- a/mock-api/system-update.ts
+++ b/mock-api/system-update.ts
@@ -36,7 +36,10 @@ export const updateStatus: Json<UpdateStatus> = {
     '17.0.0': 12,
     '16.0.0': 5,
   },
-  contact_support: true,
+  // Default to false so the normal "set target release" confirmation is the
+  // default path. The scary "support required" path is exercised in e2e via the
+  // contactSupport mock flag.
+  contact_support: false,
   suspended: false,
   target_release: {
     version: '17.0.0',
diff --git a/test/e2e/system-update.e2e.ts b/test/e2e/system-update.e2e.ts
index b68f1ddd0..66fb3222d 100644
--- a/test/e2e/system-update.e2e.ts
+++ b/test/e2e/system-update.e2e.ts
@@ -66,6 +66,8 @@ test('Set target release', async ({ page }) => {
   await expect(
     modal.getByText('Are you sure you want to set 18.0.0 as the target release?')
   ).toBeVisible()
+  // no support-required warning when contact_support is false
+  await expect(modal.getByText('strongly discouraged')).toBeHidden()
 
   await page.getByRole('button', { name: 'Confirm' }).click()
 
@@ -112,6 +114,30 @@ test('Cannot downgrade to older release', async ({ page }) => {
   await expect(release16.getByText('Target')).toBeHidden()
 })
 
+test('Support required warning in set target confirmation', async ({ browser }) => {
+  // The contact-support flag makes systemUpdateStatus report support is needed
+  // (see mockFlags). Hannah Arendt is a fleet admin, so she can also open the
+  // set-target confirmation.
+  const page = await getPageAsUser(browser, 'Hannah Arendt', ['contactSupport'])
+  await page.goto('/system/update')
+
+  // the support-required banner is shown on the page
+  await expect(page.getByText('Support required')).toBeVisible()
+
+  // opening the set-target confirmation surfaces the strong warning
+  await page.getByRole('button', { name: '18.0.0 actions' }).click()
+  await page.getByRole('menuitem', { name: 'Set as target release' }).click()
+
+  const modal = page.getByRole('dialog', { name: 'Set target release' })
+  await expect(modal).toBeVisible()
+  await expect(modal.getByText(/require Oxide support to resolve/)).toBeVisible()
+  await expect(modal.getByText('strongly discouraged')).toBeVisible()
+
+  // dismiss without setting the target
+  await page.getByRole('button', { name: 'Cancel' }).click()
+  await expect(modal).toBeHidden()
+})
+
 test('Fleet viewer cannot set target release', async ({ browser }) => {
   const page = await getPageAsUser(browser, 'Jane Austen')
   await page.goto('/system/update')
diff --git a/test/e2e/utils.ts b/test/e2e/utils.ts
index 0ee45106a..a0d6edfe5 100644
--- a/test/e2e/utils.ts
+++ b/test/e2e/utils.ts
@@ -9,7 +9,7 @@ import { expect, test, type Browser, type Locator, type Page } from '@playwright
 
 import { MiB } from '~/util/units'
 
-import { MSW_USER_COOKIE } from '../../mock-api/msw/util'
+import { MSW_FLAGS_COOKIE, MSW_USER_COOKIE, type MockFlag } from '../../mock-api/msw/util'
 
 export * from '@playwright/test'
 
@@ -221,11 +221,22 @@ export async function selectOption(
   }
 }
 
-export async function getPageAsUser(browser: Browser, user: string): Promise<Page> {
+function cookie(name: string, value: string) {
+  return { name, value, domain: 'localhost', path: '/' }
+}
+
+export async function getPageAsUser(
+  browser: Browser,
+  user: string,
+  // fleet-level overrides; see mockFlags in mock-api/msw/util.ts
+  flags: MockFlag[] = []
+): Promise<Page> {
   const browserContext = await browser.newContext()
-  await browserContext.addCookies([
-    { name: MSW_USER_COOKIE, value: user, domain: 'localhost', path: '/' },
-  ])
+  const cookies = [cookie(MSW_USER_COOKIE, user)]
+  if (flags.length) {
+    cookies.push(cookie(MSW_FLAGS_COOKIE, flags.join(',')))
+  }
+  await browserContext.addCookies(cookies)
   return await browserContext.newPage()
 }