diff --git a/frontend/public/locales/en-GB/translation.json b/frontend/public/locales/en-GB/translation.json
index ee542e2dd8..1e8ea95d48 100644
--- a/frontend/public/locales/en-GB/translation.json
+++ b/frontend/public/locales/en-GB/translation.json
@@ -5104,7 +5104,8 @@
     "planOverview": {
       "adminTitle": "Admin Overview",
       "userTitle": "Plan Overview",
-      "adminBody": "As an admin, you can manage users, configure settings, and monitor server health. The first <strong>{{freeTierLimit}}</strong> people on your server get to use Stirling free of charge.",
+      "adminBodyLoginEnabled": "As an admin, you can manage users, configure settings, and monitor server health. The first <strong>{{freeTierLimit}}</strong> people on your server get to use Stirling free of charge.",
+      "adminBodyLoginDisabled": "Once you enable login mode, you can manage users, configure settings, and monitor server health. The first <strong>{{freeTierLimit}}</strong> people on your server get to use Stirling free of charge.",
       "userBody": "Invite teammates, assign roles, and keep your documents organized in one secure workspace. Enable login mode whenever you're ready to grow beyond solo use."
     },
     "securityCheck": {
diff --git a/frontend/public/locales/en-US/translation.json b/frontend/public/locales/en-US/translation.json
index ceb0cb2adf..c0390af772 100644
--- a/frontend/public/locales/en-US/translation.json
+++ b/frontend/public/locales/en-US/translation.json
@@ -4914,7 +4914,8 @@
     "planOverview": {
       "adminTitle": "Admin Overview",
       "userTitle": "Plan Overview",
-      "adminBody": "As an admin, you can manage users, configure settings, and monitor server health. The first <strong>{{freeTierLimit}}</strong> people on your server get to use Stirling free of charge.",
+      "adminBodyLoginEnabled": "As an admin, you can manage users, configure settings, and monitor server health. The first <strong>{{freeTierLimit}}</strong> people on your server get to use Stirling free of charge.",
+      "adminBodyLoginDisabled": "Once you enable login mode, you can manage users, configure settings, and monitor server health. The first <strong>{{freeTierLimit}}</strong> people on your server get to use Stirling free of charge.",
       "userBody": "Invite teammates, assign roles, and keep your documents organized in one secure workspace. Enable login mode whenever you're ready to grow beyond solo use."
     },
     "securityCheck": {
diff --git a/frontend/src/core/components/onboarding/InitialOnboardingModal/useInitialOnboardingState.ts b/frontend/src/core/components/onboarding/InitialOnboardingModal/useInitialOnboardingState.ts
index c57b0990b0..a7ffb426f5 100644
--- a/frontend/src/core/components/onboarding/InitialOnboardingModal/useInitialOnboardingState.ts
+++ b/frontend/src/core/components/onboarding/InitialOnboardingModal/useInitialOnboardingState.ts
@@ -42,6 +42,7 @@ export function useInitialOnboardingState({
     hasPaidLicense,
     scenarioKey,
     setSelfReportedAdmin,
+    isNewServer,
   } = useServerExperience();
   const osType = useOs();
   const navigate = useNavigate();
@@ -93,6 +94,13 @@ export function useInitialOnboardingState({
 
   const effectiveEnableLogin = enableLogin;
   const effectiveIsAdmin = isAdmin;
+  const shouldAssumeAdminForNewServer = Boolean(isNewServer) && !effectiveEnableLogin;
+
+  useEffect(() => {
+    if (shouldAssumeAdminForNewServer && !state.selfReportedAdmin) {
+      handleRoleSelect('admin');
+    }
+  }, [handleRoleSelect, shouldAssumeAdminForNewServer, state.selfReportedAdmin]);
 
   const shouldUseServerCount =
     (effectiveEnableLogin && effectiveIsAdmin) || !effectiveEnableLogin;
@@ -127,11 +135,19 @@ export function useInitialOnboardingState({
     return options.filter(opt => opt.url);
   }, []);
 
-  const { ids: flowSlideIds, type: flowType } = resolveFlow(
-    effectiveEnableLogin,
-    effectiveIsAdmin,
-    state.selfReportedAdmin,
+  const resolvedFlow = useMemo(
+    () => resolveFlow(effectiveEnableLogin, effectiveIsAdmin, state.selfReportedAdmin),
+    [effectiveEnableLogin, effectiveIsAdmin, state.selfReportedAdmin],
   );
+  const shouldSkipSecurityCheck = shouldAssumeAdminForNewServer;
+  const flowSlideIds = useMemo(
+    () =>
+      shouldSkipSecurityCheck
+        ? resolvedFlow.ids.filter((id) => id !== 'security-check')
+        : resolvedFlow.ids,
+    [resolvedFlow.ids, shouldSkipSecurityCheck],
+  );
+  const flowType = resolvedFlow.type;
   const totalSteps = flowSlideIds.length;
   const maxIndex = Math.max(totalSteps - 1, 0);
 
@@ -212,6 +228,7 @@ export function useInitialOnboardingState({
     selectedRole: state.selectedRole,
     onRoleSelect: handleRoleSelect,
     licenseNotice,
+    loginEnabled: effectiveEnableLogin,
   });
 
   const goNext = useCallback(() => {
diff --git a/frontend/src/core/components/onboarding/onboardingFlowConfig.ts b/frontend/src/core/components/onboarding/onboardingFlowConfig.ts
index a7617a1755..30967691dc 100644
--- a/frontend/src/core/components/onboarding/onboardingFlowConfig.ts
+++ b/frontend/src/core/components/onboarding/onboardingFlowConfig.ts
@@ -45,6 +45,7 @@ export interface SlideFactoryParams {
   selectedRole: 'admin' | 'user' | null;
   onRoleSelect: (role: 'admin' | 'user' | null) => void;
   licenseNotice?: LicenseNotice;
+  loginEnabled?: boolean;
 }
 
 export interface HeroDefinition {
@@ -142,7 +143,8 @@ export const SLIDE_DEFINITIONS: Record<SlideId, SlideDefinition> = {
   },
   'admin-overview': {
     id: 'admin-overview',
-    createSlide: ({ licenseNotice }) => PlanOverviewSlide({ isAdmin: true, licenseNotice }),
+    createSlide: ({ licenseNotice, loginEnabled }) =>
+      PlanOverviewSlide({ isAdmin: true, licenseNotice, loginEnabled }),
     hero: { type: 'diamond' },
     buttons: [
       {
diff --git a/frontend/src/core/components/onboarding/slides/PlanOverviewSlide.tsx b/frontend/src/core/components/onboarding/slides/PlanOverviewSlide.tsx
index 39287c8b51..e777aeff87 100644
--- a/frontend/src/core/components/onboarding/slides/PlanOverviewSlide.tsx
+++ b/frontend/src/core/components/onboarding/slides/PlanOverviewSlide.tsx
@@ -1,36 +1,58 @@
 import React from 'react';
-import { useTranslation, Trans } from 'react-i18next';
+import { useTranslation } from 'react-i18next';
 import { SlideConfig, LicenseNotice } from '../../../types/types';
 import { UNIFIED_CIRCLE_CONFIG } from './unifiedBackgroundConfig';
 
 interface PlanOverviewSlideProps {
   isAdmin: boolean;
   licenseNotice?: LicenseNotice;
+  loginEnabled?: boolean;
 }
 
 const DEFAULT_FREE_TIER_LIMIT = 5;
 
-export default function PlanOverviewSlide({ isAdmin, licenseNotice }: PlanOverviewSlideProps): SlideConfig {
+export default function PlanOverviewSlide({
+  isAdmin,
+  licenseNotice,
+  loginEnabled = false,
+}: PlanOverviewSlideProps): SlideConfig {
   const { t } = useTranslation();
   const freeTierLimit = licenseNotice?.freeTierLimit ?? DEFAULT_FREE_TIER_LIMIT;
 
-  const adminBody = (
-    <span>
-      <Trans
-        i18nKey="onboarding.planOverview.adminBody"
-        components={{ strong: <strong /> }}
-        values={{ freeTierLimit }}
-        defaults="As an admin, you can manage users, configure settings, and monitor server health. The first <strong>{{freeTierLimit}}</strong> people on your server get to use Stirling free of charge."
-      />
-    </span>
-  );
+  const adminBodyKey = loginEnabled
+    ? 'onboarding.planOverview.adminBodyLoginEnabled'
+    : 'onboarding.planOverview.adminBodyLoginDisabled';
+  const adminBodyTemplate = t(adminBodyKey, {
+    freeTierLimit: '{{freeTierLimit}}',
+    defaultValue: loginEnabled
+      ? 'As an admin, you can manage users, configure settings, and monitor server health. The first {{freeTierLimit}} people on your server get to use Stirling free of charge.'
+      : 'Once you enable login mode, you can manage users, configure settings, and monitor server health. The first {{freeTierLimit}} people on your server get to use Stirling free of charge.',
+  });
+
+  const renderAdminBody = () => {
+    const [before, after] = adminBodyTemplate.split('{{freeTierLimit}}');
+    if (after !== undefined) {
+      return (
+        <span>
+          {before}
+          <strong>{freeTierLimit}</strong>
+          {after}
+        </span>
+      );
+    }
+    return (
+      <span>
+        {adminBodyTemplate.replace('{{freeTierLimit}}', String(freeTierLimit))}
+      </span>
+    );
+  };
 
   return {
     key: isAdmin ? 'admin-overview' : 'plan-overview',
     title: isAdmin 
       ? t('onboarding.planOverview.adminTitle', 'Admin Overview')
       : t('onboarding.planOverview.userTitle', 'Plan Overview'),
-    body: isAdmin ? adminBody : (
+    body: isAdmin ? renderAdminBody() : (
       <span>
         {t('onboarding.planOverview.userBody', 'Invite teammates, assign roles, and keep your documents organized in one secure workspace. Enable login mode whenever you\'re ready to grow beyond solo use.')}
       </span>
diff --git a/frontend/src/core/contexts/CookieConsentContext.tsx b/frontend/src/core/contexts/CookieConsentContext.tsx
index 4d46bcd013..530f99a2a3 100644
--- a/frontend/src/core/contexts/CookieConsentContext.tsx
+++ b/frontend/src/core/contexts/CookieConsentContext.tsx
@@ -13,7 +13,7 @@ const CookieConsentContext = createContext<CookieConsentContextValue | undefined
 
 export const CookieConsentProvider: React.FC<{ children: React.ReactNode }> = ({ children }) => {
   const { config } = useAppConfig();
-  const analyticsEnabled = config?.enableAnalytics === true;
+  const analyticsEnabled = config ? config.enableAnalytics !== false : false;
   const {
     showCookieConsent,
     showCookiePreferences,
diff --git a/frontend/src/core/pages/HomePage.tsx b/frontend/src/core/pages/HomePage.tsx
index c77e352963..77fc519086 100644
--- a/frontend/src/core/pages/HomePage.tsx
+++ b/frontend/src/core/pages/HomePage.tsx
@@ -9,6 +9,7 @@ import { useBaseUrl } from "@app/hooks/useBaseUrl";
 import { useIsMobile } from "@app/hooks/useIsMobile";
 import { useAppConfig } from "@app/contexts/AppConfigContext";
 import { useLogoPath } from "@app/hooks/useLogoPath";
+import { useCookieConsentContext } from "@app/contexts/CookieConsentContext";
 import AppsIcon from '@mui/icons-material/AppsRounded';
 
 import ToolPanel from "@app/components/tools/ToolPanel";
@@ -45,6 +46,7 @@ export default function HomePage() {
   const { openFilesModal } = useFilesModalContext();
   const { colorScheme } = useMantineColorScheme();
   const { config } = useAppConfig();
+  const { hasResponded: cookieConsentResponded } = useCookieConsentContext();
   const isMobile = useIsMobile();
   const sliderRef = useRef<HTMLDivElement | null>(null);
   const [activeMobileView, setActiveMobileView] = useState<MobileView>("tools");
@@ -54,10 +56,10 @@ export default function HomePage() {
 
   // Show admin analytics choice modal if analytics settings not configured
   useEffect(() => {
-    if (config && config.enableAnalytics === null) {
+    if (config && config.enableAnalytics === null && cookieConsentResponded) {
       setShowAnalyticsModal(true);
     }
-  }, [config]);
+  }, [config, cookieConsentResponded]);
 
   const brandAltText = t("home.mobile.brandAlt", "Stirling PDF logo");
   const brandIconSrc = useLogoPath();
diff --git a/frontend/src/proprietary/contexts/ServerExperienceContext.tsx b/frontend/src/proprietary/contexts/ServerExperienceContext.tsx
index 272238bce7..338dc159a4 100644
--- a/frontend/src/proprietary/contexts/ServerExperienceContext.tsx
+++ b/frontend/src/proprietary/contexts/ServerExperienceContext.tsx
@@ -158,6 +158,15 @@ export function ServerExperienceProvider({ children }: { children: ReactNode })
     return () => window.removeEventListener('storage', handleStorage);
   }, []);
 
+  useEffect(() => {
+    if (!config) {
+      return;
+    }
+    if (config.isNewServer && !loginEnabled && !selfReportedAdmin) {
+      setSelfReportedAdmin(true);
+    }
+  }, [config, loginEnabled, selfReportedAdmin, setSelfReportedAdmin]);
+
   const fetchUserCounts = useCallback(async () => {
     if (!config) {
       return;