diff --git a/frontend/app/admin/SettingsPage.tsx b/frontend/app/admin/SettingsPage.tsx
index e795bd4..16abf91 100644
--- a/frontend/app/admin/SettingsPage.tsx
+++ b/frontend/app/admin/SettingsPage.tsx
@@ -33,14 +33,15 @@ const SECTION_LABELS: Record<string, string> = {
   jellyseerr: 'Seerr',
   jellyfin: 'Jellyfin',
   artwork: 'Artwork cache',
-  cache: 'Cache Control',
+  cache: 'Request cache',
   sonarr: 'Sonarr',
   radarr: 'Radarr',
   prowlarr: 'Prowlarr',
   qbittorrent: 'qBittorrent',
-  log: 'Activity log',
-  requests: 'Request sync',
-  site: 'Site',
+  logs: 'Activity log',
+  maintenance: 'Maintenance',
+  requests: 'Request pipeline',
+  site: 'Site & login',
 }
 
 const BOOL_SETTINGS = new Set([
@@ -114,7 +115,8 @@ const SECTION_DESCRIPTIONS: Record<string, string> = {
   prowlarr: 'Prowlarr connection used by Sonarr and Radarr for release searches.',
   qbittorrent: 'qBittorrent connection used for collector-owned download progress and diagnostics.',
   requests: 'Control how often requests are refreshed and cleaned up.',
-  log: 'Activity log for troubleshooting.',
+  logs: 'Control log output and inspect recent application activity for troubleshooting.',
+  maintenance: 'Repair cached data, clean historical records, and run recovery operations.',
   site: 'Sitewide banner, login page visibility, and version details. The changelog is generated from git history during release builds.',
 }
 
@@ -233,10 +235,14 @@ const MAGENT_SECTION_GROUPS: Array<{
       'magent_notify_push_token',
       'magent_notify_push_user_key',
       'magent_notify_push_device',
-      'magent_notify_webhook_enabled',
-      'magent_notify_webhook_url',
     ],
   },
+  {
+    key: 'magent-notify-webhook',
+    title: 'Generic Webhook',
+    description: 'Send notifications to a custom automation or integration endpoint.',
+    keys: ['magent_notify_webhook_enabled', 'magent_notify_webhook_url'],
+  },
 ]
 
 const MAGENT_GROUPS_BY_SECTION: Record<string, Set<string>> = {
@@ -247,6 +253,7 @@ const MAGENT_GROUPS_BY_SECTION: Record<string, Set<string>> = {
     'magent-notify-discord',
     'magent-notify-telegram',
     'magent-notify-push',
+    'magent-notify-webhook',
   ]),
 }
 
@@ -281,6 +288,130 @@ const SITE_SECTION_GROUPS: Array<{
   },
 ]
 
+const STANDARD_SECTION_GROUPS: Record<
+  string,
+  Array<{ key: string; title: string; description: string; keys: string[] }>
+> = {
+  seerr: [
+    {
+      key: 'seerr-connection',
+      title: 'Connection',
+      description: 'The Seerr endpoint and API credential Magent uses for request discovery and status.',
+      keys: ['jellyseerr_base_url', 'jellyseerr_api_key'],
+    },
+  ],
+  jellyseerr: [
+    {
+      key: 'seerr-connection',
+      title: 'Connection',
+      description: 'The Seerr endpoint and API credential Magent uses for request discovery and status.',
+      keys: ['jellyseerr_base_url', 'jellyseerr_api_key'],
+    },
+  ],
+  jellyfin: [
+    {
+      key: 'jellyfin-connection',
+      title: 'Connection',
+      description: 'Internal Jellyfin endpoint and administrator API credential used for lookups and user sync.',
+      keys: ['jellyfin_base_url', 'jellyfin_api_key'],
+    },
+    {
+      key: 'jellyfin-playback',
+      title: 'Playback Links',
+      description: 'Public address used when a viewer opens an available title from Magent.',
+      keys: ['jellyfin_public_url'],
+    },
+    {
+      key: 'jellyfin-users',
+      title: 'Library and User Sync',
+      description: 'Control cross-service library reconciliation and manually import Jellyfin users.',
+      keys: ['jellyfin_sync_to_arr'],
+    },
+  ],
+  sonarr: [
+    {
+      key: 'sonarr-connection',
+      title: 'Connection',
+      description: 'Sonarr endpoint and API credential used for TV collection operations.',
+      keys: ['sonarr_base_url', 'sonarr_api_key'],
+    },
+    {
+      key: 'sonarr-library',
+      title: 'TV Collection Defaults',
+      description: 'Default quality profile and destination folder used for TV requests.',
+      keys: ['sonarr_quality_profile_id', 'sonarr_root_folder'],
+    },
+  ],
+  radarr: [
+    {
+      key: 'radarr-connection',
+      title: 'Connection',
+      description: 'Radarr endpoint and API credential used for movie collection operations.',
+      keys: ['radarr_base_url', 'radarr_api_key'],
+    },
+    {
+      key: 'radarr-library',
+      title: 'Movie Collection Defaults',
+      description: 'Default quality profile and destination folder used for movie requests.',
+      keys: ['radarr_quality_profile_id', 'radarr_root_folder'],
+    },
+  ],
+  prowlarr: [
+    {
+      key: 'prowlarr-connection',
+      title: 'Connection',
+      description: 'Prowlarr endpoint and API credential used for indexer health and release discovery.',
+      keys: ['prowlarr_base_url', 'prowlarr_api_key'],
+    },
+  ],
+  qbittorrent: [
+    {
+      key: 'qbittorrent-connection',
+      title: 'Connection and Sign-in',
+      description: 'qBittorrent Web UI endpoint and credentials used for live download progress and recovery.',
+      keys: ['qbittorrent_base_url', 'qbittorrent_username', 'qbittorrent_password'],
+    },
+  ],
+  requests: [
+    {
+      key: 'requests-sync',
+      title: 'Synchronization Schedule',
+      description: 'Control incremental checks and the scheduled full request-cache rebuild.',
+      keys: [
+        'requests_poll_interval_seconds',
+        'requests_delta_sync_interval_minutes',
+        'requests_full_sync_time',
+      ],
+    },
+    {
+      key: 'requests-retention',
+      title: 'History Retention',
+      description: 'Choose when old status history is cleaned up and how long it is retained.',
+      keys: ['requests_cleanup_time', 'requests_cleanup_days'],
+    },
+  ],
+  logs: [
+    {
+      key: 'logs-output',
+      title: 'Log Output',
+      description: 'Set the default application verbosity and the active log-file destination.',
+      keys: ['log_level', 'log_file'],
+    },
+    {
+      key: 'logs-rotation',
+      title: 'File Rotation',
+      description: 'Limit log-file growth and choose how many historical files remain on disk.',
+      keys: ['log_file_max_bytes', 'log_file_backup_count'],
+    },
+    {
+      key: 'logs-components',
+      title: 'Component Verbosity',
+      description: 'Tune noisy outbound-service and scheduled-background messages independently.',
+      keys: ['log_http_client_level', 'log_background_sync_level'],
+    },
+  ],
+}
+
 const SETTING_LABEL_OVERRIDES: Record<string, string> = {
   jellyseerr_base_url: 'Seerr base URL',
   jellyseerr_api_key: 'Seerr API key',
@@ -322,6 +453,33 @@ const SETTING_LABEL_OVERRIDES: Record<string, string> = {
   magent_notify_push_device: 'Device / target',
   magent_notify_webhook_enabled: 'Generic webhook notifications enabled',
   magent_notify_webhook_url: 'Generic webhook URL',
+  jellyfin_base_url: 'Internal server URL',
+  jellyfin_api_key: 'Administrator API key',
+  jellyfin_public_url: 'Public playback URL',
+  jellyfin_sync_to_arr: 'Reconcile Jellyfin with Sonarr and Radarr',
+  sonarr_base_url: 'Sonarr server URL',
+  sonarr_api_key: 'Sonarr API key',
+  sonarr_quality_profile_id: 'Default TV quality profile',
+  sonarr_root_folder: 'Default TV root folder',
+  radarr_base_url: 'Radarr server URL',
+  radarr_api_key: 'Radarr API key',
+  radarr_quality_profile_id: 'Default movie quality profile',
+  radarr_root_folder: 'Default movie root folder',
+  prowlarr_base_url: 'Prowlarr server URL',
+  prowlarr_api_key: 'Prowlarr API key',
+  qbittorrent_base_url: 'Web UI URL',
+  qbittorrent_username: 'Web UI username',
+  qbittorrent_password: 'Web UI password',
+  requests_sync_ttl_minutes: 'Request cache freshness (minutes)',
+  requests_poll_interval_seconds: 'Full-sync eligibility check (seconds)',
+  requests_delta_sync_interval_minutes: 'Recent-change sync interval (minutes)',
+  requests_full_sync_time: 'Daily full-sync time',
+  requests_cleanup_time: 'Daily history cleanup time',
+  requests_cleanup_days: 'History retention (days)',
+  requests_data_source: 'Request read source',
+  artwork_cache_mode: 'Artwork delivery mode',
+  log_level: 'Application log level',
+  log_file: 'Active log file',
   site_login_show_jellyfin_login: 'Login page: Jellyfin sign-in',
   site_login_show_local_login: 'Login page: local Magent sign-in',
   site_login_show_forgot_password: 'Login page: forgot password',
@@ -390,12 +548,12 @@ type SectionFeedback = {
 }
 
 const SERVICE_TEST_ENDPOINTS: Record<string, string> = {
-  jellyseerr: 'seerr',
-  jellyfin: 'jellyfin',
-  sonarr: 'sonarr',
-  radarr: 'radarr',
-  prowlarr: 'prowlarr',
-  qbittorrent: 'qbittorrent',
+  'seerr-connection': 'seerr',
+  'jellyfin-connection': 'jellyfin',
+  'sonarr-connection': 'sonarr',
+  'radarr-connection': 'radarr',
+  'prowlarr-connection': 'prowlarr',
+  'qbittorrent-connection': 'qbittorrent',
 }
 
 export default function SettingsPage({ section }: SettingsPageProps) {
@@ -633,8 +791,8 @@ export default function SettingsPage({ section }: SettingsPageProps) {
     : null
   const isMagentGroupedSection = section === 'magent' || section === 'general' || section === 'notifications'
   const isSiteGroupedSection = section === 'site'
-  const visibleSections = settingsSection ? [settingsSection] : []
   const isCacheSection = section === 'cache'
+  const isArtworkSection = section === 'artwork'
   const cacheSettingKeys = new Set(['requests_sync_ttl_minutes', 'requests_data_source'])
   const artworkSettingKeys = new Set(['artwork_cache_mode'])
   const generatedSettingKeys = new Set(['site_changelog'])
@@ -643,111 +801,91 @@ export default function SettingsPage({ section }: SettingsPageProps) {
     'sonarr_qbittorrent_category',
     'radarr_qbittorrent_category',
   ])
-  const requestSettingOrder = [
-    'requests_poll_interval_seconds',
-    'requests_delta_sync_interval_minutes',
-    'requests_full_sync_time',
-    'requests_cleanup_time',
-    'requests_cleanup_days',
-  ]
-  const siteSettingOrder = [
-    'site_banner_enabled',
-    'site_banner_message',
-    'site_banner_tone',
-    'site_login_show_jellyfin_login',
-    'site_login_show_local_login',
-    'site_login_show_forgot_password',
-    'site_login_show_signup_link',
-    'site_nav_show_requests',
-  ]
-  const sortByOrder = (items: AdminSetting[], order: string[]) => {
-    const position = new Map(order.map((key, index) => [key, index]))
-    return [...items].sort((a, b) => {
-      const aIndex = position.get(a.key) ?? Number.POSITIVE_INFINITY
-      const bIndex = position.get(b.key) ?? Number.POSITIVE_INFINITY
-      if (aIndex !== bIndex) return aIndex - bIndex
-      return a.key.localeCompare(b.key)
-    })
-  }
   const cacheSettings = settings.filter((setting) => cacheSettingKeys.has(setting.key))
   const artworkSettings = settings.filter((setting) => artworkSettingKeys.has(setting.key))
+  const buildDefinedSections = (
+    definitions: Array<{ key: string; title: string; description: string; keys: string[] }>,
+    sourceItems: AdminSetting[],
+    includeUnassigned = true,
+  ): SettingsSectionGroup[] => {
+    const byKey = new Map(sourceItems.map((item) => [item.key, item]))
+    const assignedKeys = new Set(definitions.flatMap((group) => group.keys))
+    const groups = definitions.map((group) => ({
+      key: group.key,
+      title: group.title,
+      description: group.description,
+      items: group.keys
+        .map((key) => byKey.get(key))
+        .filter((item): item is AdminSetting => Boolean(item)),
+    }))
+    if (includeUnassigned) {
+      const unassigned = sourceItems.filter((item) => !assignedKeys.has(item.key))
+      if (unassigned.length > 0) {
+        groups.push({
+          key: `${section}-additional`,
+          title: 'Additional Settings',
+          description: 'Settings returned by Magent that do not yet belong to a dedicated subsection.',
+          items: unassigned.sort((a, b) => a.key.localeCompare(b.key)),
+        })
+      }
+    }
+    return groups
+  }
+  const standardDefinitions = STANDARD_SECTION_GROUPS[section]
+  const standardItems = settingsSection
+    ? (groupedSettings[settingsSection] ?? []).filter(
+        (setting) => !obsoleteSettingKeys.has(setting.key) && !hiddenSettingKeys.has(setting.key),
+      )
+    : []
   const settingsSections: SettingsSectionGroup[] = isCacheSection
     ? [
-        { key: 'cache', title: 'Cache control', items: cacheSettings },
-        { key: 'artwork', title: 'Artwork cache', items: artworkSettings },
+        {
+          key: 'cache',
+          title: 'Request Cache Strategy',
+          description: 'Choose where request pages read from and how long cached request records remain fresh.',
+          items: cacheSettings,
+        },
       ]
+    : isArtworkSection
+      ? [
+          {
+            key: 'artwork',
+            title: 'Artwork Delivery and Storage',
+            description: 'Choose how posters and backdrops are delivered, then inspect or rebuild the local artwork cache.',
+            items: artworkSettings,
+          },
+        ]
     : isMagentGroupedSection
       ? (() => {
           if (section === 'magent') {
             return []
           }
           const magentItems = groupedSettings.magent ?? []
-          const byKey = new Map(magentItems.map((item) => [item.key, item]))
           const allowedGroupKeys = MAGENT_GROUPS_BY_SECTION[section] ?? new Set<string>()
-          const groups: SettingsSectionGroup[] = MAGENT_SECTION_GROUPS.filter((group) =>
-            allowedGroupKeys.has(group.key),
-          ).map((group) => {
-            const items = group.keys
-              .map((key) => byKey.get(key))
-              .filter((item): item is AdminSetting => Boolean(item))
-            return {
-              key: group.key,
-              title: group.title,
-              description: group.description,
-              items,
-            }
-          })
-          return groups
+          const definitions = MAGENT_SECTION_GROUPS.filter((group) => allowedGroupKeys.has(group.key))
+          return buildDefinedSections(definitions, magentItems, false)
         })()
       : isSiteGroupedSection
-        ? (() => {
-            const siteItems = groupedSettings.site ?? []
-            const byKey = new Map(siteItems.map((item) => [item.key, item]))
-            return SITE_SECTION_GROUPS.map((group) => {
-              const items = group.keys
-                .map((key) => byKey.get(key))
-                .filter((item): item is AdminSetting => Boolean(item))
-              return {
-                key: group.key,
-                title: group.title,
-                description: group.description,
-                items,
-              }
-            })
-          })()
-      : visibleSections.map((sectionKey) => ({
-          key: sectionKey,
-          title: SECTION_LABELS[sectionKey] ?? sectionKey,
-          items: (() => {
-            const sectionItems = groupedSettings[sectionKey] ?? []
-            const filtered = sectionItems.filter((setting) => {
-              if (obsoleteSettingKeys.has(setting.key)) return false
-              if (sectionKey === 'requests' || sectionKey === 'artwork' || sectionKey === 'site') {
-                return !hiddenSettingKeys.has(setting.key)
-              }
-              return true
-            })
-            if (sectionKey === 'requests') {
-              return sortByOrder(filtered, requestSettingOrder)
-            }
-            if (sectionKey === 'site') {
-              return sortByOrder(filtered, siteSettingOrder)
-            }
-            return filtered
-          })(),
-        }))
+        ? buildDefinedSections(
+            SITE_SECTION_GROUPS,
+            (groupedSettings.site ?? []).filter((setting) => !hiddenSettingKeys.has(setting.key)),
+          )
+        : standardDefinitions
+          ? buildDefinedSections(standardDefinitions, standardItems)
+          : []
   const showLogs = section === 'logs'
   const showMaintenance = section === 'maintenance'
   const showRequestsExtras = section === 'requests'
-  const showArtworkExtras = section === 'cache'
+  const showArtworkExtras = section === 'artwork'
   const showCacheExtras = section === 'cache'
   const shouldRenderSection = (sectionGroup: { key: string; items?: AdminSetting[] }) => {
     if (sectionGroup.items && sectionGroup.items.length > 0) return true
     if (showArtworkExtras && sectionGroup.key === 'artwork') return true
     if (showCacheExtras && sectionGroup.key === 'cache') return true
-    if (showRequestsExtras && sectionGroup.key === 'requests') return true
+    if (showRequestsExtras && sectionGroup.key === 'requests-sync') return true
     return false
   }
+  const renderedSettingsSections = settingsSections.filter(shouldRenderSection)
 
   useEffect(() => {
     requestsSyncRef.current = requestsSync
@@ -1632,10 +1770,6 @@ export default function SettingsPage({ section }: SettingsPageProps) {
             <span>Maintenance job</span>
             <strong>{maintenanceBusy ? 'Running' : 'Idle'}</strong>
           </div>
-          <div className="cache-rail-metric">
-            <span>Live updates</span>
-            <strong>{liveStreamConnected ? 'Connected' : 'Polling'}</strong>
-          </div>
           <div className="cache-rail-metric">
             <span>Log lines in view</span>
             <strong>{logsLines.length}</strong>
@@ -1649,8 +1783,7 @@ export default function SettingsPage({ section }: SettingsPageProps) {
     </div>
   ) : undefined
   const cacheRail = showCacheExtras ? (
-    <div className="admin-rail-stack">
-      <div className="admin-rail-card cache-rail-card">
+    <div className="admin-rail-card cache-rail-card">
         <span className="admin-rail-eyebrow">Cache control</span>
         <h2>Saved requests</h2>
         <p>Load and inspect cached request entries from the right rail.</p>
@@ -1695,8 +1828,10 @@ export default function SettingsPage({ section }: SettingsPageProps) {
           )}
         </button>
         {cacheStatus && <div className="error-banner">{cacheStatus}</div>}
-      </div>
-      <div className="admin-rail-card cache-rail-card">
+    </div>
+  ) : undefined
+  const artworkRail = showArtworkExtras ? (
+    <div className="admin-rail-card cache-rail-card">
         <span className="admin-rail-eyebrow">Artwork</span>
         <h2>Cache stats</h2>
         <div className="cache-rail-metrics">
@@ -1717,7 +1852,6 @@ export default function SettingsPage({ section }: SettingsPageProps) {
             <strong>{artworkSummary?.cache_mode ?? '--'}</strong>
           </div>
         </div>
-      </div>
     </div>
   ) : undefined
 
@@ -1729,7 +1863,7 @@ export default function SettingsPage({ section }: SettingsPageProps) {
     <AdminShell
       title={SECTION_LABELS[section] ?? 'Settings'}
       subtitle={SECTION_DESCRIPTIONS[section] ?? 'Manage settings.'}
-      rail={maintenanceRail ?? cacheRail}
+      rail={maintenanceRail ?? cacheRail ?? artworkRail}
       actions={
         <button type="button" onClick={() => router.push('/admin')}>
           Back to settings
@@ -1770,27 +1904,39 @@ export default function SettingsPage({ section }: SettingsPageProps) {
           </div>
         </section>
       ) : null}
-      {settingsSections.length > 0 ? (
+      {renderedSettingsSections.length > 1 ? (
+        <nav className="config-subsection-nav" aria-label={`${SECTION_LABELS[section] ?? 'Settings'} subsections`}>
+          <span>On this page</span>
+          <div>
+            {renderedSettingsSections.map((sectionGroup, index) => (
+              <a key={sectionGroup.key} href={`#config-${sectionGroup.key}`}>
+                <small>{String(index + 1).padStart(2, '0')}</small>
+                {sectionGroup.title}
+              </a>
+            ))}
+          </div>
+        </nav>
+      ) : null}
+      {renderedSettingsSections.length > 0 ? (
       <div className="admin-form admin-zone-stack">
-        {settingsSections
-          .filter(shouldRenderSection)
-          .map((sectionGroup) => (
-          <section key={sectionGroup.key} className="admin-section admin-zone">
+        {renderedSettingsSections.map((sectionGroup, sectionIndex) => (
+          <section id={`config-${sectionGroup.key}`} key={sectionGroup.key} className="admin-section admin-zone config-subsection">
             <div className="section-header">
-              <h2>
-                {sectionGroup.key === 'requests' ? 'Request sync controls' : sectionGroup.title}
-              </h2>
-              {sectionGroup.key === 'sonarr' && (
+              <div className="config-subsection-heading">
+                <span className="section-kicker">Subsection {String(sectionIndex + 1).padStart(2, '0')}</span>
+                <h2>{sectionGroup.title}</h2>
+              </div>
+              {sectionGroup.key === 'sonarr-library' && (
                 <button type="button" onClick={() => loadOptions('sonarr')}>
                   Refresh Sonarr options
                 </button>
               )}
-              {sectionGroup.key === 'radarr' && (
+              {sectionGroup.key === 'radarr-library' && (
                 <button type="button" onClick={() => loadOptions('radarr')}>
                   Refresh Radarr options
                 </button>
               )}
-              {sectionGroup.key === 'jellyfin' && (
+              {sectionGroup.key === 'jellyfin-users' && (
                 <button type="button" onClick={syncJellyfinUsers}>
                   Import Jellyfin users
                 </button>
@@ -1809,7 +1955,7 @@ export default function SettingsPage({ section }: SettingsPageProps) {
                   </button>
                 </div>
               ) : null}
-              {showRequestsExtras && sectionGroup.key === 'requests' && (
+              {showRequestsExtras && sectionGroup.key === 'requests-sync' && (
                 <div className="sync-actions-block">
                   <div className="sync-actions">
                     <button type="button" onClick={syncRequests}>
@@ -1826,25 +1972,24 @@ export default function SettingsPage({ section }: SettingsPageProps) {
                 </div>
               )}
             </div>
-            {(sectionGroup.description || SECTION_DESCRIPTIONS[sectionGroup.key]) &&
-              (!settingsSection || isMagentGroupedSection || isSiteGroupedSection) && (
-                <p className="section-subtitle">
-                  {sectionGroup.description || SECTION_DESCRIPTIONS[sectionGroup.key]}
-                </p>
-              )}
+            {(sectionGroup.description || SECTION_DESCRIPTIONS[sectionGroup.key]) && (
+              <p className="section-subtitle">
+                {sectionGroup.description || SECTION_DESCRIPTIONS[sectionGroup.key]}
+              </p>
+            )}
             {section === 'general' && sectionGroup.key === 'magent-runtime' && (
               <div className="status-banner">
                 Runtime host/port and SSL values are configuration settings. Container/process
                 restarts may still be required before bind/port changes take effect.
               </div>
             )}
-            {sectionGroup.key === 'sonarr' && sonarrError && (
+            {sectionGroup.key === 'sonarr-library' && sonarrError && (
               <div className="error-banner">{sonarrError}</div>
             )}
-            {sectionGroup.key === 'radarr' && radarrError && (
+            {sectionGroup.key === 'radarr-library' && radarrError && (
               <div className="error-banner">{radarrError}</div>
             )}
-            {sectionGroup.key === 'jellyfin' && jellyfinSyncStatus && (
+            {sectionGroup.key === 'jellyfin-users' && jellyfinSyncStatus && (
               <div className="status-banner">{jellyfinSyncStatus}</div>
             )}
             {showArtworkExtras && sectionGroup.key === 'artwork' && artworkPrefetchStatus && (
@@ -1879,10 +2024,10 @@ export default function SettingsPage({ section }: SettingsPageProps) {
                 </div>
               </div>
             )}
-            {showRequestsExtras && sectionGroup.key === 'requests' && requestsSyncStatus && (
+            {showRequestsExtras && sectionGroup.key === 'requests-sync' && requestsSyncStatus && (
               <div className="status-banner">{requestsSyncStatus}</div>
             )}
-            {showRequestsExtras && sectionGroup.key === 'requests' && (
+            {showRequestsExtras && sectionGroup.key === 'requests-sync' && (
               <div className="status-banner">
                 Full refresh checks only decide when to run a full refresh. The delta sync interval
                 polls for new or updated requests.
@@ -1914,7 +2059,7 @@ export default function SettingsPage({ section }: SettingsPageProps) {
                 {artworkPrefetch.message && <div className="meta">{artworkPrefetch.message}</div>}
               </div>
             )}
-            {showRequestsExtras && sectionGroup.key === 'requests' && requestsSync && (
+            {showRequestsExtras && sectionGroup.key === 'requests-sync' && requestsSync && (
               <div className="sync-progress">
                 <div className="sync-meta">
                   <span>Status: {requestsSync.status}</span>
diff --git a/frontend/app/ops-redesign.css b/frontend/app/ops-redesign.css
index e9c722b..31ffd8b 100644
--- a/frontend/app/ops-redesign.css
+++ b/frontend/app/ops-redesign.css
@@ -1126,6 +1126,66 @@ button:disabled,
   gap: 16px;
 }
 
+.config-subsection-nav {
+  display: grid;
+  gap: 11px;
+  padding: 14px 16px;
+  border: 1px solid var(--ops-line);
+  border-radius: var(--ops-radius-lg);
+  background: rgba(255, 255, 255, 0.024);
+}
+
+.config-subsection-nav > span {
+  color: var(--ops-muted);
+  font-size: 0.68rem;
+  font-weight: 800;
+  letter-spacing: 0.09em;
+  text-transform: uppercase;
+}
+
+.config-subsection-nav > div {
+  display: flex;
+  flex-wrap: wrap;
+  gap: 8px;
+}
+
+.config-subsection-nav a {
+  display: inline-flex;
+  align-items: center;
+  gap: 8px;
+  min-height: 36px;
+  padding: 7px 11px;
+  border: 1px solid var(--ops-line-soft);
+  border-radius: var(--ops-radius);
+  background: rgba(255, 255, 255, 0.022);
+  color: var(--ops-text);
+  font-size: 0.76rem;
+  font-weight: 700;
+  text-decoration: none;
+  transition: border-color 0.18s ease, background 0.18s ease, transform 0.18s ease;
+}
+
+.config-subsection-nav a:hover {
+  transform: translateY(-1px);
+  border-color: rgba(126, 215, 255, 0.38);
+  background: rgba(14, 165, 233, 0.09);
+}
+
+.config-subsection-nav a small {
+  color: var(--ops-cyan);
+  font-family: "JetBrains Mono", Consolas, monospace;
+  font-size: 0.64rem;
+}
+
+.config-subsection {
+  scroll-margin-top: 124px;
+}
+
+.config-subsection-heading {
+  display: grid;
+  gap: 4px;
+}
+
 .fleet-status-panel {
   display: grid;
   gap: 16px;
diff --git a/frontend/app/ui/AdminSidebar.tsx b/frontend/app/ui/AdminSidebar.tsx
index b4cdeb0..fc23d6c 100644
--- a/frontend/app/ui/AdminSidebar.tsx
+++ b/frontend/app/ui/AdminSidebar.tsx
@@ -4,18 +4,17 @@ import { usePathname } from 'next/navigation'
 
 const NAV_GROUPS = [
   {
-    title: 'Operations',
+    title: 'Configuration',
     items: [
-      { href: '/admin', label: 'Overview' },
-      { href: '/admin/diagnostics', label: 'System health' },
-      { href: '/new-requests', label: 'New requests' },
-      { href: '/admin/issues', label: 'Issue tracking' },
+      { href: '/admin', label: 'Config overview' },
+      { href: '/admin/general', label: 'Application & proxy' },
+      { href: '/admin/site', label: 'Site & login' },
+      { href: '/admin/notifications', label: 'Notifications' },
     ],
   },
   {
-    title: 'Services',
+    title: 'Media Services',
     items: [
-      { href: '/admin/general', label: 'General' },
       { href: '/admin/seerr', label: 'Seerr' },
       { href: '/admin/jellyfin', label: 'Jellyfin' },
       { href: '/admin/sonarr', label: 'Sonarr' },
@@ -25,24 +24,28 @@ const NAV_GROUPS = [
     ],
   },
   {
-    title: 'Requests',
+    title: 'Request Pipeline',
     items: [
-      { href: '/admin/requests', label: 'Request sync' },
-      { href: '/admin/requests-all', label: 'All requests' },
-      { href: '/admin/cache', label: 'Cache Control' },
+      { href: '/admin/requests', label: 'Sync & retention' },
+      { href: '/admin/cache', label: 'Request cache' },
       { href: '/admin/artwork', label: 'Artwork cache' },
+      { href: '/admin/requests-all', label: 'All requests' },
     ],
   },
   {
-    title: 'Admin',
+    title: 'Users & Access',
     items: [
-      { href: '/admin/notifications', label: 'Notifications' },
-      { href: '/admin/system', label: 'How it works' },
-      { href: '/admin/site', label: 'Site' },
       { href: '/users', label: 'Users' },
       { href: '/admin/invites', label: 'Invite management' },
+    ],
+  },
+  {
+    title: 'System',
+    items: [
+      { href: '/admin/diagnostics', label: 'System health' },
       { href: '/admin/logs', label: 'Activity log' },
       { href: '/admin/maintenance', label: 'Maintenance' },
+      { href: '/admin/system', label: 'How it works' },
     ],
   },
 ]
@@ -59,7 +62,9 @@ export default function AdminSidebar() {
             {group.items.map((item) => {
               const isActive =
                 pathname === item.href ||
-                (item.href !== '/' && pathname.startsWith(item.href))
+                (item.href !== '/' &&
+                  item.href !== '/admin' &&
+                  pathname.startsWith(`${item.href}/`))
               return (
                 <a key={item.href} href={item.href} className={isActive ? 'is-active' : ''}>
                   {item.label}