Merge branch 'main' into bug/v2/improved-cache-busting

# Description of Changes

- **What was changed**
- Added `groovy.json.JsonOutput` and `groovy.json.JsonSlurper` imports
to `build.gradle`.
- Introduced a reusable `writeIfChanged(File targetFile, String
newContent)` helper to avoid unnecessary file writes when content is
unchanged.
  - Added `updateTauriConfigVersion(String version)` to:
    - Parse `frontend/src-tauri/tauri.conf.json`.
    - Set the `version` field from `project.version`.
- Re-write the file as pretty-printed JSON (with a trailing line
separator) only if content actually changed.
- Added `updateSimulationVersion(File fileToUpdate, String version)` to:
- Locate the `appVersion: '<value>'` assignment via regex in simulation
files.
    - Replace the existing version with `project.version`.
- Fail the build with a clear `GradleException` if `appVersion` cannot
be found.
- Registered a new Gradle task `syncAppVersion` (group: `versioning`)
which:
    - Reads `project.version` as the canonical app version.
    - Updates `frontend/src-tauri/tauri.conf.json`.
- Updates `frontend/src/core/testing/serverExperienceSimulations.ts`.
- Updates
`frontend/src/proprietary/testing/serverExperienceSimulations.ts`.
- Updated the main `build` task so it now depends on `syncAppVersion` in
addition to `:stirling-pdf:bootJar` and `buildRestartHelper`.

- **Why the change was made**
- To ensure the desktop Tauri configuration and server experience
simulation configs consistently use the same application version as
defined in `project.version`.
- To remove manual version bumps in multiple files and eliminate the
risk of version mismatches between backend, desktop app, and
simulation/testing tooling.
- To minimize noise in commits and CI by only touching versioned files
when their content actually changes (using `writeIfChanged`).


---

## Checklist

### General

- [ ] I have read the [Contribution
Guidelines](https://github.com/Stirling-Tools/Stirling-PDF/blob/main/CONTRIBUTING.md)
- [ ] I have read the [Stirling-PDF Developer
Guide](https://github.com/Stirling-Tools/Stirling-PDF/blob/main/devGuide/DeveloperGuide.md)
(if applicable)
- [ ] I have read the [How to add new languages to
Stirling-PDF](https://github.com/Stirling-Tools/Stirling-PDF/blob/main/devGuide/HowToAddNewLanguage.md)
(if applicable)
- [ ] I have performed a self-review of my own code
- [ ] My changes generate no new warnings

### Documentation

- [ ] I have updated relevant docs on [Stirling-PDF's doc
repo](https://github.com/Stirling-Tools/Stirling-Tools.github.io/blob/main/docs/)
(if functionality has heavily changed)
- [ ] I have read the section [Add New Translation
Tags](https://github.com/Stirling-Tools/Stirling-PDF/blob/main/devGuide/HowToAddNewLanguage.md#add-new-translation-tags)
(for new translation tags only)

### Translations (if applicable)

- [ ] I ran
[`scripts/counter_translation.py`](https://github.com/Stirling-Tools/Stirling-PDF/blob/main/docs/counter_translation.md)

### UI Changes (if applicable)

- [ ] Screenshots or videos demonstrating the UI changes are attached
(e.g., as comments or direct attachments in the PR)

### Testing (if applicable)

- [ ] I have tested my changes locally. Refer to the [Testing
Guide](https://github.com/Stirling-Tools/Stirling-PDF/blob/main/devGuide/DeveloperGuide.md#6-testing)
for more details.

.github/workflows/build.yml

@@ -262,7 +262,13 @@ jobs:
     strategy:
       fail-fast: false
       matrix:
-        docker-rev: ["docker/embedded/Dockerfile", "docker/embedded/Dockerfile.ultra-lite", "docker/embedded/Dockerfile.fat"]
+        include:
+          - docker-rev: docker/embedded/Dockerfile
+            artifact-suffix: Dockerfile
+          - docker-rev: docker/embedded/Dockerfile.ultra-lite
+            artifact-suffix: Dockerfile.ultra-lite
+          - docker-rev: docker/embedded/Dockerfile.fat
+            artifact-suffix: Dockerfile.fat
     steps:
       - name: Harden Runner
         uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
@@ -272,6 +278,13 @@ jobs:
       - name: Checkout Repository
         uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
 
+      - name: Free disk space on runner
+        run: |
+          echo "Disk space before cleanup:" && df -h
+          sudo rm -rf /usr/share/dotnet /opt/ghc /usr/local/lib/android /usr/local/share/boost
+          docker system prune -af || true
+          echo "Disk space after cleanup:" && df -h
+
       - name: Set up JDK 17
         uses: actions/setup-java@dded0888837ed1f317902acf8a20df0ad188d165 # v5.0.0
         with:
@@ -313,7 +326,7 @@ jobs:
         if: always()
         uses: actions/upload-artifact@ea165f8d65b6e75b540449e92b4886f43607fa02 # v4.6.2
         with:
-          name: reports-docker-${{ matrix.docker-rev }}
+          name: reports-docker-${{ matrix.artifact-suffix }}
           path: |
             build/reports/tests/
             build/test-results/

app/core/src/main/java/stirling/software/SPDF/config/WebMvcConfig.java

@@ -1,10 +1,14 @@
 package stirling.software.SPDF.config;
 
+import java.util.concurrent.TimeUnit;
+
 import org.slf4j.Logger;
 import org.slf4j.LoggerFactory;
 import org.springframework.context.annotation.Configuration;
+import org.springframework.http.CacheControl;
 import org.springframework.web.servlet.config.annotation.CorsRegistry;
 import org.springframework.web.servlet.config.annotation.InterceptorRegistry;
+import org.springframework.web.servlet.config.annotation.ResourceHandlerRegistry;
 import org.springframework.web.servlet.config.annotation.WebMvcConfigurer;
 
 import lombok.RequiredArgsConstructor;
@@ -25,6 +29,20 @@ public class WebMvcConfig implements WebMvcConfigurer {
         registry.addInterceptor(endpointInterceptor);
     }
 
+    @Override
+    public void addResourceHandlers(ResourceHandlerRegistry registry) {
+        // Cache hashed assets (JS/CSS with content hashes) for 1 year
+        // These files have names like index-ChAS4tCC.js that change when content changes
+        registry.addResourceHandler("/assets/**")
+                .addResourceLocations("classpath:/static/assets/")
+                .setCacheControl(CacheControl.maxAge(365, TimeUnit.DAYS).cachePublic());
+
+        // Don't cache index.html - it needs to be fresh to reference latest hashed assets
+        registry.addResourceHandler("/index.html")
+                .addResourceLocations("classpath:/static/")
+                .setCacheControl(CacheControl.noCache().mustRevalidate());
+    }
+
     @Override
     public void addCorsMappings(CorsRegistry registry) {
         // Check if running in Tauri mode

build.gradle

@@ -12,6 +12,8 @@ plugins {
 }
 
 import com.github.jk1.license.render.*
+import groovy.json.JsonOutput
+import groovy.json.JsonSlurper
 
 ext {
     springBootVersion = "3.5.6"
@@ -65,6 +67,51 @@ allprojects {
     }
 }
 
+def writeIfChanged(File targetFile, String newContent) {
+    if (targetFile.getText('UTF-8') != newContent) {
+        targetFile.write(newContent, 'UTF-8')
+    }
+}
+
+def updateTauriConfigVersion(String version) {
+    File tauriConfig = file('frontend/src-tauri/tauri.conf.json')
+    def parsed = new JsonSlurper().parse(tauriConfig)
+    parsed.version = version
+
+    def formatted = JsonOutput.prettyPrint(JsonOutput.toJson(parsed)) + System.lineSeparator()
+    writeIfChanged(tauriConfig, formatted)
+}
+
+def updateSimulationVersion(File fileToUpdate, String version) {
+    def content = fileToUpdate.getText('UTF-8')
+    def matcher = content =~ /(appVersion:\s*')([^']*)(')/
+
+    if (!matcher.find()) {
+        throw new GradleException("Could not locate appVersion in ${fileToUpdate} for synchronization")
+    }
+
+    def updatedContent = matcher.replaceFirst("${matcher.group(1)}${version}${matcher.group(3)}")
+    writeIfChanged(fileToUpdate, updatedContent)
+}
+
+tasks.register('syncAppVersion') {
+    group = 'versioning'
+    description = 'Synchronizes app version across desktop and simulation configs.'
+
+    doLast {
+        def appVersion = project.version.toString()
+        println "Synchronizing application version to ${appVersion}"
+        updateTauriConfigVersion(appVersion)
+
+        [
+            'frontend/src/core/testing/serverExperienceSimulations.ts',
+            'frontend/src/proprietary/testing/serverExperienceSimulations.ts'
+        ].each { path ->
+            updateSimulationVersion(file(path), appVersion)
+        }
+    }
+}
+
 tasks.register('writeVersion', WriteProperties) {
     destinationFile = layout.projectDirectory.file('app/common/src/main/resources/version.properties')
     println "Writing version.properties to ${destinationFile.get().asFile.path}"
@@ -314,7 +361,7 @@ tasks.named('bootRun') {
 tasks.named('build') {
     group = 'build'
     description = 'Delegates to :stirling-pdf:bootJar'
-    dependsOn ':stirling-pdf:bootJar', 'buildRestartHelper'
+    dependsOn ':stirling-pdf:bootJar', 'buildRestartHelper', 'syncAppVersion'
 
     doFirst {
         println "Delegating to :stirling-pdf:bootJar"

frontend/public/locales/en-GB/translation.toml

@@ -5569,6 +5569,28 @@ contactSales = "Contact Sales"
 contactToUpgrade = "Contact us to upgrade or customize your plan"
 maxUsers = "Max Users"
 upTo = "Up to"
+getLicense = "Get Server License"
+upgradeToEnterprise = "Upgrade to Enterprise"
+selectPeriod = "Select Billing Period"
+monthlyBilling = "Monthly Billing"
+yearlyBilling = "Yearly Billing"
+checkoutOpened = "Checkout Opened"
+checkoutInstructions = "Complete your purchase in the Stripe tab. After payment, return here and refresh the page to activate your license. You will also receive an email with your license key."
+activateLicense = "Activate Your License"
+
+[plan.static.licenseActivation]
+checkoutOpened = "Checkout Opened in New Tab"
+instructions = "Complete your purchase in the Stripe tab. Once your payment is complete, you will receive an email with your license key."
+enterKey = "Enter your license key below to activate your plan:"
+keyDescription = "Paste the license key from your email"
+activate = "Activate License"
+doLater = "I'll do this later"
+success = "License Activated!"
+successMessage = "Your license has been successfully activated. You can now close this window."
+
+[plan.static.billingPortal]
+title = "Email Verification Required"
+message = "You will need to verify your email address in the Stripe billing portal. Check your email for a login link."
 
 [plan.period]
 month = "month"

frontend/src/proprietary/components/shared/config/configSections/AdminPlanSection.tsx

@@ -1,5 +1,5 @@
 import React, { useState, useCallback, useEffect, useMemo } from 'react';
-import { Divider, Loader, Alert, Group, Text, Collapse, Button, TextInput, Stack, Paper, SegmentedControl, FileButton } from '@mantine/core';
+import { Divider, Loader, Alert } from '@mantine/core';
 import { useTranslation } from 'react-i18next';
 import { usePlans } from '@app/hooks/usePlans';
 import licenseService, { PlanTierGroup, mapLicenseToTier } from '@app/services/licenseService';
@@ -7,30 +7,25 @@ import { useCheckout } from '@app/contexts/CheckoutContext';
 import { useLicense } from '@app/contexts/LicenseContext';
 import AvailablePlansSection from '@app/components/shared/config/configSections/plan/AvailablePlansSection';
 import StaticPlanSection from '@app/components/shared/config/configSections/plan/StaticPlanSection';
+import LicenseKeySection from '@app/components/shared/config/configSections/plan/LicenseKeySection';
 import { alert } from '@app/components/toast';
-import LocalIcon from '@app/components/shared/LocalIcon';
 import { InfoBanner } from '@app/components/shared/InfoBanner';
 import { useLicenseAlert } from '@app/hooks/useLicenseAlert';
-import { isSupabaseConfigured } from '@app/services/supabaseClient';
 import { getPreferredCurrency, setCachedCurrency } from '@app/utils/currencyDetection';
 import { useLoginRequired } from '@app/hooks/useLoginRequired';
 import LoginRequiredBanner from '@core/components/shared/config/LoginRequiredBanner';
+import { isSupabaseConfigured } from '@app/services/supabaseClient';
 
 const AdminPlanSection: React.FC = () => {
   const { t, i18n } = useTranslation();
   const { loginEnabled, validateLoginEnabled } = useLoginRequired();
   const { openCheckout } = useCheckout();
-  const { licenseInfo, refetchLicense } = useLicense();
+  const { licenseInfo } = useLicense();
   const [currency, setCurrency] = useState<string>(() => {
     // Initialize with auto-detected currency on first render
     return getPreferredCurrency(i18n.language);
   });
   const [useStaticVersion, setUseStaticVersion] = useState(false);
-  const [showLicenseKey, setShowLicenseKey] = useState(false);
-  const [licenseKeyInput, setLicenseKeyInput] = useState<string>('');
-  const [savingLicense, setSavingLicense] = useState(false);
-  const [inputMethod, setInputMethod] = useState<'text' | 'file'>('text');
-  const [licenseFile, setLicenseFile] = useState<File | null>(null);
   const { plans, loading, error, refetch } = usePlans(currency);
   const licenseAlert = useLicenseAlert();
 
@@ -43,69 +38,6 @@ const AdminPlanSection: React.FC = () => {
     }
   }, [error]);
 
-  const handleSaveLicense = async () => {
-    // Block save if login is disabled
-    if (!validateLoginEnabled()) {
-      return;
-    }
-
-    try {
-      setSavingLicense(true);
-
-      let response;
-
-      if (inputMethod === 'file' && licenseFile) {
-        // Upload file
-        response = await licenseService.saveLicenseFile(licenseFile);
-      } else if (inputMethod === 'text' && licenseKeyInput.trim()) {
-        // Save key string (allow empty string to clear/remove license)
-        response = await licenseService.saveLicenseKey(licenseKeyInput.trim());
-      } else {
-        alert({
-          alertType: 'error',
-          title: t('admin.error', 'Error'),
-          body: t('admin.settings.premium.noInput', 'Please provide a license key or file'),
-        });
-        return;
-      }
-
-      if (response.success) {
-        // Refresh license context to update all components
-        await refetchLicense();
-
-        const successMessage = inputMethod === 'file'
-          ? t('admin.settings.premium.file.successMessage', 'License file uploaded and activated successfully')
-          : t('admin.settings.premium.key.successMessage', 'License key activated successfully');
-
-        alert({
-          alertType: 'success',
-          title: t('success', 'Success'),
-          body: successMessage,
-        });
-
-        // Clear inputs
-        setLicenseKeyInput('');
-        setLicenseFile(null);
-        setInputMethod('text'); // Reset to default
-      } else {
-        alert({
-          alertType: 'error',
-          title: t('admin.error', 'Error'),
-          body: response.error || t('admin.settings.saveError', 'Failed to save license'),
-        });
-      }
-    } catch (error) {
-      console.error('Failed to save license:', error);
-      alert({
-        alertType: 'error',
-        title: t('admin.error', 'Error'),
-        body: t('admin.settings.saveError', 'Failed to save license'),
-      });
-    } finally {
-      setSavingLicense(false);
-    }
-  };
-
   const currencyOptions = [
     { value: 'gbp', label: 'British pound (GBP, £)' },
     { value: 'usd', label: 'US dollar (USD, $)' },
@@ -280,169 +212,7 @@ const AdminPlanSection: React.FC = () => {
       <Divider />
 
       {/* License Key Section */}
-      <div>
-        <Button
-          variant="subtle"
-          leftSection={<LocalIcon icon={showLicenseKey ? "expand-less-rounded" : "expand-more-rounded"} width="1.25rem" height="1.25rem" />}
-          onClick={() => setShowLicenseKey(!showLicenseKey)}
-        >
-          {t('admin.settings.premium.licenseKey.toggle', 'Got a license key or certificate file?')}
-        </Button>
-
-        <Collapse in={showLicenseKey} mt="md">
-          <Stack gap="md">
-            <Alert
-              variant="light"
-              color="blue"
-              icon={<LocalIcon icon="info-rounded" width="1rem" height="1rem" />}
-            >
-              <Text size="sm">
-                {t('admin.settings.premium.licenseKey.info', 'If you have a license key or certificate file from a direct purchase, you can enter it here to activate premium or enterprise features.')}
-              </Text>
-            </Alert>
-
-            {/* Severe warning if license already exists */}
-            {licenseInfo?.licenseKey && (
-              <Alert
-                variant="light"
-                color="red"
-                icon={<LocalIcon icon="warning-rounded" width="1rem" height="1rem" />}
-                title={t('admin.settings.premium.key.overwriteWarning.title', '⚠️ Warning: Existing License Detected')}
-              >
-                <Stack gap="xs">
-                  <Text size="sm" fw={600}>
-                    {t('admin.settings.premium.key.overwriteWarning.line1', 'Overwriting your current license key cannot be undone.')}
-                  </Text>
-                  <Text size="sm">
-                    {t('admin.settings.premium.key.overwriteWarning.line2', 'Your previous license will be permanently lost unless you have backed it up elsewhere.')}
-                  </Text>
-                  <Text size="sm" fw={500}>
-                    {t('admin.settings.premium.key.overwriteWarning.line3', 'Important: Keep license keys private and secure. Never share them publicly.')}
-                  </Text>
-                </Stack>
-              </Alert>
-            )}
-
-            {/* Show current license source */}
-            {licenseInfo?.licenseKey && (
-              <Alert
-                variant="light"
-                color="green"
-                icon={<LocalIcon icon="check-circle-rounded" width="1rem" height="1rem" />}
-              >
-                <Stack gap="xs">
-                  <Text size="sm" fw={500}>
-                    {t('admin.settings.premium.currentLicense.title', 'Active License')}
-                  </Text>
-                  <Text size="xs">
-                    {licenseInfo.licenseKey.startsWith('file:')
-                      ? t('admin.settings.premium.currentLicense.file', 'Source: License file ({{path}})', {
-                          path: licenseInfo.licenseKey.substring(5)
-                        })
-                      : t('admin.settings.premium.currentLicense.key', 'Source: License key')}
-                  </Text>
-                  <Text size="xs">
-                    {t('admin.settings.premium.currentLicense.type', 'Type: {{type}}', {
-                      type: licenseInfo.licenseType
-                    })}
-                  </Text>
-                </Stack>
-              </Alert>
-            )}
-
-            {/* Input method selector */}
-            <SegmentedControl
-              value={inputMethod}
-              onChange={(value) => {
-                setInputMethod(value as 'text' | 'file');
-                // Clear opposite input when switching
-                if (value === 'text') setLicenseFile(null);
-                if (value === 'file') setLicenseKeyInput('');
-              }}
-              data={[
-                {
-                  label: t('admin.settings.premium.inputMethod.text', 'License Key'),
-                  value: 'text'
-                },
-                {
-                  label: t('admin.settings.premium.inputMethod.file', 'Certificate File'),
-                  value: 'file'
-                }
-              ]}
-              disabled={!loginEnabled || savingLicense}
-            />
-
-            {/* Input area */}
-            <Paper withBorder p="md" radius="md">
-              <Stack gap="md">
-                {inputMethod === 'text' ? (
-                  /* Existing text input */
-                  <TextInput
-                    label={t('admin.settings.premium.key.label', 'License Key')}
-                    description={t('admin.settings.premium.key.description', 'Enter your premium or enterprise license key. Premium features will be automatically enabled when a key is provided.')}
-                    value={licenseKeyInput}
-                    onChange={(e) => setLicenseKeyInput(e.target.value)}
-                    placeholder={licenseInfo?.licenseKey || '00000000-0000-0000-0000-000000000000'}
-                    type="password"
-                    disabled={!loginEnabled || savingLicense}
-                  />
-                ) : (
-                  /* File upload */
-                  <div>
-                    <Text size="sm" fw={500} mb="xs">
-                      {t('admin.settings.premium.file.label', 'License Certificate File')}
-                    </Text>
-                    <Text size="xs" c="dimmed" mb="md">
-                      {t('admin.settings.premium.file.description', 'Upload your .lic or .cert license file')}
-                    </Text>
-                    <FileButton
-                      onChange={setLicenseFile}
-                      accept=".lic,.cert"
-                      disabled={!loginEnabled || savingLicense}
-                    >
-                      {(props) => (
-                        <Button
-                          {...props}
-                          variant="outline"
-                          leftSection={<LocalIcon icon="upload-file-rounded" width="1rem" height="1rem" />}
-                          disabled={!loginEnabled || savingLicense}
-                        >
-                          {licenseFile
-                            ? licenseFile.name
-                            : t('admin.settings.premium.file.choose', 'Choose License File')}
-                        </Button>
-                      )}
-                    </FileButton>
-                    {licenseFile && (
-                      <Text size="xs" c="dimmed" mt="xs">
-                        {t('admin.settings.premium.file.selected', 'Selected: {{filename}} ({{size}})', {
-                          filename: licenseFile.name,
-                          size: (licenseFile.size / 1024).toFixed(2) + ' KB'
-                        })}
-                      </Text>
-                    )}
-                  </div>
-                )}
-
-                <Group justify="flex-end">
-                  <Button
-                    onClick={handleSaveLicense}
-                    loading={savingLicense}
-                    size="sm"
-                    disabled={
-                      !loginEnabled ||
-                      (inputMethod === 'text' && !licenseKeyInput.trim()) ||
-                      (inputMethod === 'file' && !licenseFile)
-                    }
-                  >
-                    {t('admin.settings.save', 'Save Changes')}
-                  </Button>
-                </Group>
-              </Stack>
-            </Paper>
-          </Stack>
-        </Collapse>
-      </div>
+      <LicenseKeySection currentLicenseInfo={licenseInfo ?? undefined} />
     </div>
   );
 };

frontend/src/proprietary/components/shared/config/configSections/plan/AvailablePlansSection.tsx

@@ -5,6 +5,7 @@ import licenseService, { PlanTier, PlanTierGroup, LicenseInfo, mapLicenseToTier
 import PlanCard from '@app/components/shared/config/configSections/plan/PlanCard';
 import FeatureComparisonTable from '@app/components/shared/config/configSections/plan/FeatureComparisonTable';
 import { Z_INDEX_OVER_CONFIG_MODAL } from '@app/styles/zIndex';
+import { isCurrentTier as checkIsCurrentTier, isDowngrade as checkIsDowngrade } from '@app/utils/planTierUtils';
 
 interface AvailablePlansSectionProps {
   plans: PlanTier[];
@@ -43,28 +44,12 @@ const AvailablePlansSection: React.FC<AvailablePlansSectionProps> = ({
 
   // Determine if the current tier matches (checks both Stripe subscription and license)
   const isCurrentTier = (tierGroup: PlanTierGroup): boolean => {
-    // Check license tier match
-    if (currentTier && tierGroup.tier === currentTier) {
-      return true;
-    }
-    return false;
+    return checkIsCurrentTier(currentTier, tierGroup.tier);
   };
 
   // Determine if selecting this plan would be a downgrade
   const isDowngrade = (tierGroup: PlanTierGroup): boolean => {
-    if (!currentTier) return false;
-
-    // Define tier hierarchy: enterprise > server > free
-    const tierHierarchy: Record<string, number> = {
-      'enterprise': 3,
-      'server': 2,
-      'free': 1
-    };
-
-    const currentLevel = tierHierarchy[currentTier] || 0;
-    const targetLevel = tierHierarchy[tierGroup.tier] || 0;
-
-    return currentLevel > targetLevel;
+    return checkIsDowngrade(currentTier, tierGroup.tier);
   };
 
   return (
@@ -103,7 +88,7 @@ const AvailablePlansSection: React.FC<AvailablePlansSectionProps> = ({
           display: 'grid',
           gridTemplateColumns: 'repeat(3, 1fr)',
           gap: '1rem',
-          marginBottom: '0.5rem',
+          marginBottom: '0.1rem',
         }}
       >
         {groupedPlans.map((group) => (

frontend/src/proprietary/components/shared/config/configSections/plan/LicenseKeySection.tsx

@@ -0,0 +1,273 @@
+import React, { useState } from 'react';
+import { Button, Collapse, Alert, TextInput, Paper, Stack, Group, Text, SegmentedControl, FileButton } from '@mantine/core';
+import { useTranslation } from 'react-i18next';
+import LocalIcon from '@app/components/shared/LocalIcon';
+import { alert } from '@app/components/toast';
+import { LicenseInfo } from '@app/services/licenseService';
+import licenseService from '@app/services/licenseService';
+import { useLicense } from '@app/contexts/LicenseContext';
+import { useLoginRequired } from '@app/hooks/useLoginRequired';
+
+interface LicenseKeySectionProps {
+  currentLicenseInfo?: LicenseInfo;
+}
+
+const LicenseKeySection: React.FC<LicenseKeySectionProps> = ({ currentLicenseInfo }) => {
+  const { t } = useTranslation();
+  const { refetchLicense } = useLicense();
+  const { loginEnabled, validateLoginEnabled } = useLoginRequired();
+  const [showLicenseKey, setShowLicenseKey] = useState(false);
+  const [licenseKeyInput, setLicenseKeyInput] = useState<string>('');
+  const [savingLicense, setSavingLicense] = useState(false);
+  const [inputMethod, setInputMethod] = useState<'text' | 'file'>('text');
+  const [licenseFile, setLicenseFile] = useState<File | null>(null);
+
+  const handleSaveLicense = async () => {
+    // Block save if login is disabled
+    if (!validateLoginEnabled()) {
+      return;
+    }
+
+    try {
+      setSavingLicense(true);
+
+      let response;
+
+      if (inputMethod === 'file' && licenseFile) {
+        // Upload file
+        response = await licenseService.saveLicenseFile(licenseFile);
+      } else if (inputMethod === 'text' && licenseKeyInput.trim()) {
+        // Save key string
+        response = await licenseService.saveLicenseKey(licenseKeyInput.trim());
+      } else {
+        alert({
+          alertType: 'error',
+          title: t('admin.error', 'Error'),
+          body: t('admin.settings.premium.noInput', 'Please provide a license key or file'),
+        });
+        return;
+      }
+
+      if (response.success) {
+        // Refresh license context to update all components
+        await refetchLicense();
+
+        const successMessage =
+          inputMethod === 'file'
+            ? t('admin.settings.premium.file.successMessage', 'License file uploaded and activated successfully')
+            : t('admin.settings.premium.key.successMessage', 'License key activated successfully');
+
+        alert({
+          alertType: 'success',
+          title: t('success', 'Success'),
+          body: successMessage,
+        });
+
+        // Clear inputs
+        setLicenseKeyInput('');
+        setLicenseFile(null);
+        setInputMethod('text'); // Reset to default
+      } else {
+        alert({
+          alertType: 'error',
+          title: t('admin.error', 'Error'),
+          body: response.error || t('admin.settings.saveError', 'Failed to save license'),
+        });
+      }
+    } catch (error) {
+      console.error('Failed to save license:', error);
+      alert({
+        alertType: 'error',
+        title: t('admin.error', 'Error'),
+        body: t('admin.settings.saveError', 'Failed to save license'),
+      });
+    } finally {
+      setSavingLicense(false);
+    }
+  };
+
+  return (
+    <div>
+      <Button
+        variant="subtle"
+        leftSection={
+          <LocalIcon
+            icon={showLicenseKey ? 'expand-less-rounded' : 'expand-more-rounded'}
+            width="1.25rem"
+            height="1.25rem"
+          />
+        }
+        onClick={() => setShowLicenseKey(!showLicenseKey)}
+      >
+        {t('admin.settings.premium.licenseKey.toggle', 'Got a license key or certificate file?')}
+      </Button>
+
+      <Collapse in={showLicenseKey} mt="md">
+        <Stack gap="md">
+          <Alert variant="light" color="blue" icon={<LocalIcon icon="info-rounded" width="1rem" height="1rem" />}>
+            <Text size="sm">
+              {t(
+                'admin.settings.premium.licenseKey.info',
+                'If you have a license key or certificate file from a direct purchase, you can enter it here to activate premium or enterprise features.'
+              )}
+            </Text>
+          </Alert>
+
+          {/* Severe warning if license already exists */}
+          {currentLicenseInfo?.licenseKey && (
+            <Alert
+              variant="light"
+              color="red"
+              icon={<LocalIcon icon="warning-rounded" width="1rem" height="1rem" />}
+              title={t('admin.settings.premium.key.overwriteWarning.title', '⚠️ Warning: Existing License Detected')}
+            >
+              <Stack gap="xs">
+                <Text size="sm" fw={600}>
+                  {t(
+                    'admin.settings.premium.key.overwriteWarning.line1',
+                    'Overwriting your current license key cannot be undone.'
+                  )}
+                </Text>
+                <Text size="sm">
+                  {t(
+                    'admin.settings.premium.key.overwriteWarning.line2',
+                    'Your previous license will be permanently lost unless you have backed it up elsewhere.'
+                  )}
+                </Text>
+                <Text size="sm" fw={500}>
+                  {t(
+                    'admin.settings.premium.key.overwriteWarning.line3',
+                    'Important: Keep license keys private and secure. Never share them publicly.'
+                  )}
+                </Text>
+              </Stack>
+            </Alert>
+          )}
+
+          {/* Show current license source */}
+          {currentLicenseInfo?.licenseKey && (
+            <Alert
+              variant="light"
+              color="green"
+              icon={<LocalIcon icon="check-circle-rounded" width="1rem" height="1rem" />}
+            >
+              <Stack gap="xs">
+                <Text size="sm" fw={500}>
+                  {t('admin.settings.premium.currentLicense.title', 'Active License')}
+                </Text>
+                <Text size="xs">
+                  {currentLicenseInfo.licenseKey.startsWith('file:')
+                    ? t('admin.settings.premium.currentLicense.file', 'Source: License file ({{path}})', {
+                        path: currentLicenseInfo.licenseKey.substring(5),
+                      })
+                    : t('admin.settings.premium.currentLicense.key', 'Source: License key')}
+                </Text>
+                <Text size="xs">
+                  {t('admin.settings.premium.currentLicense.type', 'Type: {{type}}', {
+                    type: currentLicenseInfo.licenseType,
+                  })}
+                </Text>
+              </Stack>
+            </Alert>
+          )}
+
+          {/* Input method selector */}
+          <SegmentedControl
+            value={inputMethod}
+            onChange={(value) => {
+              setInputMethod(value as 'text' | 'file');
+              // Clear opposite input when switching
+              if (value === 'text') setLicenseFile(null);
+              if (value === 'file') setLicenseKeyInput('');
+            }}
+            data={[
+              {
+                label: t('admin.settings.premium.inputMethod.text', 'License Key'),
+                value: 'text',
+              },
+              {
+                label: t('admin.settings.premium.inputMethod.file', 'Certificate File'),
+                value: 'file',
+              },
+            ]}
+            disabled={!loginEnabled || savingLicense}
+          />
+
+          {/* Input area */}
+          <Paper withBorder p="md" radius="md">
+            <Stack gap="md">
+              {inputMethod === 'text' ? (
+                /* Text input */
+                <TextInput
+                  label={t('admin.settings.premium.key.label', 'License Key')}
+                  description={t(
+                    'admin.settings.premium.key.description',
+                    'Enter your premium or enterprise license key. Premium features will be automatically enabled when a key is provided.'
+                  )}
+                  value={licenseKeyInput}
+                  onChange={(e) => setLicenseKeyInput(e.target.value)}
+                  placeholder={currentLicenseInfo?.licenseKey || '00000000-0000-0000-0000-000000000000'}
+                  type="password"
+                  disabled={!loginEnabled || savingLicense}
+                />
+              ) : (
+                /* File upload */
+                <div>
+                  <Text size="sm" fw={500} mb="xs">
+                    {t('admin.settings.premium.file.label', 'License Certificate File')}
+                  </Text>
+                  <Text size="xs" c="dimmed" mb="md">
+                    {t('admin.settings.premium.file.description', 'Upload your .lic or .cert license file')}
+                  </Text>
+                  <FileButton
+                    onChange={setLicenseFile}
+                    accept=".lic,.cert"
+                    disabled={!loginEnabled || savingLicense}
+                  >
+                    {(props) => (
+                      <Button
+                        {...props}
+                        variant="outline"
+                        leftSection={<LocalIcon icon="upload-file-rounded" width="1rem" height="1rem" />}
+                        disabled={!loginEnabled || savingLicense}
+                      >
+                        {licenseFile
+                          ? licenseFile.name
+                          : t('admin.settings.premium.file.choose', 'Choose License File')}
+                      </Button>
+                    )}
+                  </FileButton>
+                  {licenseFile && (
+                    <Text size="xs" c="dimmed" mt="xs">
+                      {t('admin.settings.premium.file.selected', 'Selected: {{filename}} ({{size}})', {
+                        filename: licenseFile.name,
+                        size: (licenseFile.size / 1024).toFixed(2) + ' KB',
+                      })}
+                    </Text>
+                  )}
+                </div>
+              )}
+
+              <Group justify="flex-end">
+                <Button
+                  onClick={handleSaveLicense}
+                  loading={savingLicense}
+                  size="sm"
+                  disabled={
+                    !loginEnabled ||
+                    (inputMethod === 'text' && !licenseKeyInput.trim()) ||
+                    (inputMethod === 'file' && !licenseFile)
+                  }
+                >
+                  {t('admin.settings.save', 'Save Changes')}
+                </Button>
+              </Group>
+            </Stack>
+          </Paper>
+        </Stack>
+      </Collapse>
+    </div>
+  );
+};
+
+export default LicenseKeySection;

frontend/src/proprietary/components/shared/config/configSections/plan/PlanCard.tsx

@@ -6,6 +6,7 @@ import { PricingBadge } from '@app/components/shared/stripeCheckout/components/P
 import { PriceDisplay } from '@app/components/shared/stripeCheckout/components/PriceDisplay';
 import { calculateDisplayPricing } from '@app/components/shared/stripeCheckout/utils/pricingUtils';
 import { getBaseCardStyle } from '@app/components/shared/stripeCheckout/utils/cardStyles';
+import { isEnterpriseBlockedForFree as checkIsEnterpriseBlockedForFree } from '@app/utils/planTierUtils';
 
 interface PlanCardProps {
   planGroup: PlanTierGroup;
@@ -83,7 +84,7 @@ const PlanCard: React.FC<PlanCardProps> = ({ planGroup, isCurrentTier, isDowngra
   const isEnterprise = planGroup.tier === 'enterprise';
 
   // Block enterprise for free tier users (must have server first)
-  const isEnterpriseBlockedForFree = isEnterprise && currentTier === 'free';
+  const isEnterpriseBlockedForFree = checkIsEnterpriseBlockedForFree(currentTier, planGroup.tier);
 
   // Calculate "From" pricing - show yearly price divided by 12 for lowest monthly equivalent
   const { displayPrice, displaySeatPrice, displayCurrency } = calculateDisplayPricing(
@@ -174,7 +175,7 @@ const PlanCard: React.FC<PlanCardProps> = ({ planGroup, isCurrentTier, isDowngra
           withArrow
         >
           <Button
-            variant={isCurrentTier ? 'filled' : isDowngrade ? 'filled' : isEnterpriseBlockedForFree ? 'light' : 'filled'}
+            variant="filled"
             fullWidth
             onClick={() => isCurrentTier && onManageClick ? onManageClick() : onUpgradeClick(planGroup)}
             disabled={!loginEnabled || isDowngrade || isEnterpriseBlockedForFree}

frontend/src/proprietary/components/shared/config/configSections/plan/StaticCheckoutModal.tsx

@@ -0,0 +1,338 @@
+import React, { useState } from 'react';
+import { Modal, Text, Group, ActionIcon, Stack, Paper, Grid, TextInput, Button, Alert } from '@mantine/core';
+import { useTranslation } from 'react-i18next';
+import LocalIcon from '@app/components/shared/LocalIcon';
+import { EmailStage } from '@app/components/shared/stripeCheckout/stages/EmailStage';
+import { validateEmail } from '@app/components/shared/stripeCheckout/utils/checkoutUtils';
+import { getClickablePaperStyle } from '@app/components/shared/stripeCheckout/utils/cardStyles';
+import { STATIC_STRIPE_LINKS, buildStripeUrlWithEmail } from '@app/constants/staticStripeLinks';
+import { alert } from '@app/components/toast';
+import { Z_INDEX_OVER_CONFIG_MODAL } from '@app/styles/zIndex';
+import { useIsMobile } from '@app/hooks/useIsMobile';
+import licenseService from '@app/services/licenseService';
+import { useLicense } from '@app/contexts/LicenseContext';
+
+interface StaticCheckoutModalProps {
+  opened: boolean;
+  onClose: () => void;
+  planName: 'server' | 'enterprise';
+  isUpgrade?: boolean;
+}
+
+type Stage = 'email' | 'period-selection' | 'license-activation';
+
+const StaticCheckoutModal: React.FC<StaticCheckoutModalProps> = ({
+  opened,
+  onClose,
+  planName,
+  isUpgrade = false,
+}) => {
+  const { t } = useTranslation();
+  const isMobile = useIsMobile();
+  const { refetchLicense } = useLicense();
+
+  const [stage, setStage] = useState<Stage>('email');
+  const [email, setEmail] = useState('');
+  const [emailError, setEmailError] = useState('');
+  const [stageHistory, setStageHistory] = useState<Stage[]>([]);
+
+  // License activation state
+  const [licenseKey, setLicenseKey] = useState('');
+  const [savingLicense, setSavingLicense] = useState(false);
+  const [licenseActivated, setLicenseActivated] = useState(false);
+
+  const handleEmailSubmit = () => {
+    const validation = validateEmail(email);
+    if (validation.valid) {
+      setEmailError('');
+      setStageHistory([...stageHistory, 'email']);
+      setStage('period-selection');
+    } else {
+      setEmailError(validation.error);
+    }
+  };
+
+  const handlePeriodSelect = (period: 'monthly' | 'yearly') => {
+    const baseUrl = STATIC_STRIPE_LINKS[planName][period];
+    const urlWithEmail = buildStripeUrlWithEmail(baseUrl, email);
+
+    // Open Stripe checkout in new tab
+    window.open(urlWithEmail, '_blank');
+
+    // Transition to license activation stage
+    setStageHistory([...stageHistory, 'period-selection']);
+    setStage('license-activation');
+  };
+
+  const handleActivateLicense = async () => {
+    if (!licenseKey.trim()) {
+      alert({
+        alertType: 'error',
+        title: t('admin.error', 'Error'),
+        body: t('admin.settings.premium.noInput', 'Please provide a license key'),
+      });
+      return;
+    }
+
+    try {
+      setSavingLicense(true);
+      const response = await licenseService.saveLicenseKey(licenseKey.trim());
+
+      if (response.success) {
+        // Refresh license context to update all components
+        await refetchLicense();
+
+        setLicenseActivated(true);
+
+        alert({
+          alertType: 'success',
+          title: t('success', 'Success'),
+          body: t(
+            'admin.settings.premium.key.successMessage',
+            'License key activated successfully'
+          ),
+        });
+      } else {
+        alert({
+          alertType: 'error',
+          title: t('admin.error', 'Error'),
+          body: response.error || t('admin.settings.saveError', 'Failed to save license'),
+        });
+      }
+    } catch (error) {
+      console.error('Failed to save license:', error);
+      alert({
+        alertType: 'error',
+        title: t('admin.error', 'Error'),
+        body: t('admin.settings.saveError', 'Failed to save license'),
+      });
+    } finally {
+      setSavingLicense(false);
+    }
+  };
+
+  const handleGoBack = () => {
+    if (stageHistory.length > 0) {
+      const newHistory = [...stageHistory];
+      const previousStage = newHistory.pop();
+      setStageHistory(newHistory);
+      if (previousStage) {
+        setStage(previousStage);
+      }
+    }
+  };
+
+  const handleClose = () => {
+    // Reset state when closing
+    setStage('email');
+    setEmail('');
+    setEmailError('');
+    setStageHistory([]);
+    setLicenseKey('');
+    setSavingLicense(false);
+    setLicenseActivated(false);
+    onClose();
+  };
+
+  const getModalTitle = () => {
+    if (stage === 'email') {
+      if (isUpgrade) {
+        return t('plan.static.upgradeToEnterprise', 'Upgrade to Enterprise');
+      }
+      return planName === 'server'
+        ? t('plan.static.getLicense', 'Get Server License')
+        : t('plan.static.upgradeToEnterprise', 'Upgrade to Enterprise');
+    }
+    if (stage === 'period-selection') {
+      return t('plan.static.selectPeriod', 'Select Billing Period');
+    }
+    if (stage === 'license-activation') {
+      return t('plan.static.activateLicense', 'Activate Your License');
+    }
+    return '';
+  };
+
+  const renderContent = () => {
+    switch (stage) {
+      case 'email':
+        return (
+          <EmailStage
+            emailInput={email}
+            setEmailInput={setEmail}
+            emailError={emailError}
+            onSubmit={handleEmailSubmit}
+          />
+        );
+
+      case 'period-selection':
+        return (
+          <Stack gap="lg" style={{ padding: '1rem 2rem' }}>
+            <Grid gutter="xl" style={{ marginTop: '1rem' }}>
+              {/* Monthly Option */}
+              <Grid.Col span={6}>
+                <Paper
+                  withBorder
+                  p="xl"
+                  radius="md"
+                  style={getClickablePaperStyle()}
+                  onClick={() => handlePeriodSelect('monthly')}
+                >
+                  <Stack gap="md" style={{ height: '100%', minHeight: '120px' }} justify="space-between">
+                    <Text size="lg" fw={600}>
+                      {t('payment.monthly', 'Monthly')}
+                    </Text>
+                    <Text size="sm" c="dimmed">
+                      {t('plan.static.monthlyBilling', 'Monthly Billing')}
+                    </Text>
+                  </Stack>
+                </Paper>
+              </Grid.Col>
+
+              {/* Yearly Option */}
+              <Grid.Col span={6}>
+                <Paper
+                  withBorder
+                  p="xl"
+                  radius="md"
+                  style={getClickablePaperStyle()}
+                  onClick={() => handlePeriodSelect('yearly')}
+                >
+                  <Stack gap="md" style={{ height: '100%', minHeight: '120px' }} justify="space-between">
+                    <Text size="lg" fw={600}>
+                      {t('payment.yearly', 'Yearly')}
+                    </Text>
+                    <Text size="sm" c="dimmed">
+                      {t('plan.static.yearlyBilling', 'Yearly Billing')}
+                    </Text>
+                  </Stack>
+                </Paper>
+              </Grid.Col>
+            </Grid>
+          </Stack>
+        );
+
+      case 'license-activation':
+        return (
+          <Stack gap="lg" style={{ padding: '2rem', maxWidth: '600px', margin: '0 auto' }}>
+            <Alert
+              variant="light"
+              color="blue"
+              icon={<LocalIcon icon="info-rounded" width="1rem" height="1rem" />}
+            >
+              <Stack gap="sm">
+                <Text size="sm" fw={600}>
+                  {t('plan.static.licenseActivation.checkoutOpened', 'Checkout Opened in New Tab')}
+                </Text>
+                <Text size="sm">
+                  {t(
+                    'plan.static.licenseActivation.instructions',
+                    'Complete your purchase in the Stripe tab. Once your payment is complete, you will receive an email with your license key.'
+                  )}
+                </Text>
+              </Stack>
+            </Alert>
+
+            {licenseActivated ? (
+              <Alert
+                variant="light"
+                color="green"
+                icon={<LocalIcon icon="check-circle-rounded" width="1rem" height="1rem" />}
+                title={t('plan.static.licenseActivation.success', 'License Activated!')}
+              >
+                <Text size="sm">
+                  {t(
+                    'plan.static.licenseActivation.successMessage',
+                    'Your license has been successfully activated. You can now close this window.'
+                  )}
+                </Text>
+              </Alert>
+            ) : (
+              <Stack gap="md">
+                <Text size="sm" fw={500}>
+                  {t(
+                    'plan.static.licenseActivation.enterKey',
+                    'Enter your license key below to activate your plan:'
+                  )}
+                </Text>
+
+                <TextInput
+                  label={t('admin.settings.premium.key.label', 'License Key')}
+                  description={t(
+                    'plan.static.licenseActivation.keyDescription',
+                    'Paste the license key from your email'
+                  )}
+                  value={licenseKey}
+                  onChange={(e) => setLicenseKey(e.target.value)}
+                  placeholder="00000000-0000-0000-0000-000000000000"
+                  disabled={savingLicense}
+                  type="password"
+                />
+
+                <Group justify="space-between">
+                  <Button variant="subtle" onClick={handleClose} disabled={savingLicense}>
+                    {t('plan.static.licenseActivation.doLater', "I'll do this later")}
+                  </Button>
+                  <Button
+                    onClick={handleActivateLicense}
+                    loading={savingLicense}
+                    disabled={!licenseKey.trim()}
+                  >
+                    {t('plan.static.licenseActivation.activate', 'Activate License')}
+                  </Button>
+                </Group>
+              </Stack>
+            )}
+
+            {licenseActivated && (
+              <Group justify="flex-end">
+                <Button onClick={handleClose}>
+                  {t('common.close', 'Close')}
+                </Button>
+              </Group>
+            )}
+          </Stack>
+        );
+
+      default:
+        return null;
+    }
+  };
+
+  const canGoBack = stageHistory.length > 0 && stage !== 'license-activation';
+
+  return (
+    <Modal
+      opened={opened}
+      onClose={handleClose}
+      title={
+        <Group gap="sm" wrap="nowrap">
+          {canGoBack && (
+            <ActionIcon
+              variant="subtle"
+              size="lg"
+              onClick={handleGoBack}
+              aria-label={t('common.back', 'Back')}
+            >
+              <LocalIcon icon="arrow-back" width={20} height={20} />
+            </ActionIcon>
+          )}
+          <Text fw={600} size="lg">
+            {getModalTitle()}
+          </Text>
+        </Group>
+      }
+      size={isMobile ? '100%' : 600}
+      centered
+      radius="lg"
+      withCloseButton={true}
+      closeOnEscape={true}
+      closeOnClickOutside={false}
+      fullScreen={isMobile}
+      zIndex={Z_INDEX_OVER_CONFIG_MODAL}
+    >
+      {renderContent()}
+    </Modal>
+  );
+};
+
+export default StaticCheckoutModal;

frontend/src/proprietary/components/shared/config/configSections/plan/StaticPlanSection.tsx

@@ -1,20 +1,16 @@
-import React, { useState, useEffect } from 'react';
-import { Card, Text, Group, Stack, Badge, Button, Collapse, Alert, TextInput, Paper, Loader, Divider } from '@mantine/core';
+import React, { useState } from 'react';
+import { Card, Text, Stack, Button, Collapse, Divider, Tooltip } from '@mantine/core';
 import { useTranslation } from 'react-i18next';
-import LocalIcon from '@app/components/shared/LocalIcon';
-import RestartConfirmationModal from '@app/components/shared/config/RestartConfirmationModal';
-import { useRestartServer } from '@app/components/shared/config/useRestartServer';
-import { useAdminSettings } from '@app/hooks/useAdminSettings';
-import PendingBadge from '@app/components/shared/config/PendingBadge';
 import { alert } from '@app/components/toast';
 import { LicenseInfo, mapLicenseToTier } from '@app/services/licenseService';
 import { PLAN_FEATURES, PLAN_HIGHLIGHTS } from '@app/constants/planConstants';
 import FeatureComparisonTable from '@app/components/shared/config/configSections/plan/FeatureComparisonTable';
-
-interface PremiumSettingsData {
-  key?: string;
-  enabled?: boolean;
-}
+import StaticCheckoutModal from '@app/components/shared/config/configSections/plan/StaticCheckoutModal';
+import LicenseKeySection from '@app/components/shared/config/configSections/plan/LicenseKeySection';
+import { STATIC_STRIPE_LINKS } from '@app/constants/staticStripeLinks';
+import { PricingBadge } from '@app/components/shared/stripeCheckout/components/PricingBadge';
+import { getBaseCardStyle } from '@app/components/shared/stripeCheckout/utils/cardStyles';
+import { isCurrentTier as checkIsCurrentTier, isDowngrade as checkIsDowngrade, isEnterpriseBlockedForFree } from '@app/utils/planTierUtils';
 
 interface StaticPlanSectionProps {
   currentLicenseInfo?: LicenseInfo;
@@ -22,38 +18,45 @@ interface StaticPlanSectionProps {
 
 const StaticPlanSection: React.FC<StaticPlanSectionProps> = ({ currentLicenseInfo }) => {
   const { t } = useTranslation();
-  const [showLicenseKey, setShowLicenseKey] = useState(false);
   const [showComparison, setShowComparison] = useState(false);
 
-  // Premium/License key management
-  const { restartModalOpened, showRestartModal, closeRestartModal, restartServer } = useRestartServer();
-  const {
-    settings: premiumSettings,
-    setSettings: setPremiumSettings,
-    loading: premiumLoading,
-    saving: premiumSaving,
-    fetchSettings: fetchPremiumSettings,
-    saveSettings: savePremiumSettings,
-    isFieldPending,
-  } = useAdminSettings<PremiumSettingsData>({
-    sectionName: 'premium',
-  });
+  // Static checkout modal state
+  const [checkoutModalOpened, setCheckoutModalOpened] = useState(false);
+  const [selectedPlan, setSelectedPlan] = useState<'server' | 'enterprise'>('server');
+  const [isUpgrade, setIsUpgrade] = useState(false);
 
-  useEffect(() => {
-    fetchPremiumSettings();
-  }, []);
-
-  const handleSaveLicense = async () => {
-    try {
-      await savePremiumSettings();
-      showRestartModal();
-    } catch (_error) {
+  const handleOpenCheckout = (plan: 'server' | 'enterprise', upgrade: boolean) => {
+    // Prevent Free → Enterprise (must have Server first)
+    const currentTier = mapLicenseToTier(currentLicenseInfo || null);
+    if (currentTier === 'free' && plan === 'enterprise') {
       alert({
-        alertType: 'error',
-        title: t('admin.error', 'Error'),
-        body: t('admin.settings.saveError', 'Failed to save settings'),
+        alertType: 'warning',
+        title: t('plan.enterprise.requiresServer', 'Server Plan Required'),
+        body: t(
+          'plan.enterprise.requiresServerMessage',
+          'Please upgrade to the Server plan first before upgrading to Enterprise.'
+        ),
       });
+      return;
     }
+
+    setSelectedPlan(plan);
+    setIsUpgrade(upgrade);
+    setCheckoutModalOpened(true);
+  };
+
+  const handleManageBilling = () => {
+    // Show warning about email verification
+    alert({
+      alertType: 'warning',
+      title: t('plan.static.billingPortal.title', 'Email Verification Required'),
+      body: t(
+        'plan.static.billingPortal.message',
+        'You will need to verify your email address in the Stripe billing portal. Check your email for a login link.'
+      ),
+    });
+
+    window.open(STATIC_STRIPE_LINKS.billingPortal, '_blank');
   };
 
   const staticPlans = [
@@ -122,7 +125,7 @@ const StaticPlanSection: React.FC<StaticPlanSectionProps> = ({ currentLicenseInf
             display: 'grid',
             gridTemplateColumns: 'repeat(3, 1fr)',
             gap: '1rem',
-            paddingBottom: '1rem',
+            paddingBottom: '0.1rem',
           }}
         >
           {staticPlans.map((plan) => (
@@ -131,53 +134,27 @@ const StaticPlanSection: React.FC<StaticPlanSectionProps> = ({ currentLicenseInf
               padding="lg"
               radius="md"
               withBorder
-              style={{
-                position: 'relative',
-                display: 'flex',
-                flexDirection: 'column',
-                borderColor: plan.id === currentPlan.id ? 'var(--mantine-color-green-6)' : undefined,
-                borderWidth: plan.id === currentPlan.id ? '2px' : undefined,
-              }}
+              style={getBaseCardStyle(plan.id === currentPlan.id)}
+              className="plan-card"
             >
               {plan.id === currentPlan.id && (
-                <Badge
-                  color="green"
-                  variant="filled"
-                  size="sm"
-                  style={{ position: 'absolute', top: '1rem', right: '1rem' }}
-                >
-                  {t('plan.current', 'Current Plan')}
-                </Badge>
+                <PricingBadge
+                  type="current"
+                  label={t('plan.current', 'Current Plan')}
+                />
               )}
               {plan.popular && plan.id !== currentPlan.id && (
-                <Badge
-                  variant="filled"
-                  size="xs"
-                  style={{ position: 'absolute', top: '0.5rem', right: '0.5rem' }}
-                >
-                  {t('plan.popular', 'Popular')}
-                </Badge>
+                <PricingBadge
+                  type="popular"
+                  label={t('plan.popular', 'Popular')}
+                />
               )}
 
               <Stack gap="md" style={{ height: '100%' }}>
                 <div>
-                  <Text size="lg" fw={600}>
+                  <Text size="xl" fw={700} style={{ fontSize: '2rem' }}>
                     {plan.name}
                   </Text>
-                  <Group gap="xs" style={{ alignItems: 'baseline' }}>
-                    <Text size="xl" fw={700} style={{ fontSize: '2rem' }}>
-                      {plan.price === 0 && plan.id !== 'free'
-                        ? t('plan.customPricing', 'Custom')
-                        : plan.price === 0
-                          ? t('plan.free.name', 'Free')
-                          : `${plan.currency}${plan.price}`}
-                    </Text>
-                    {plan.period && (
-                      <Text size="sm" c="dimmed">
-                        {plan.period}
-                      </Text>
-                    )}
-                  </Group>
                   <Text size="xs" c="dimmed" mt="xs">
                     {typeof plan.maxUsers === 'string'
                       ? plan.maxUsers
@@ -195,18 +172,123 @@ const StaticPlanSection: React.FC<StaticPlanSectionProps> = ({ currentLicenseInf
 
                 <div style={{ flexGrow: 1 }} />
 
-                <Button
-                  variant={plan.id === currentPlan.id ? 'light' : 'filled'}
-                  disabled={plan.id === currentPlan.id}
-                  fullWidth
-                  onClick={() =>
-                    window.open('https://www.stirling.com/contact', '_blank')
+                {/* Tier-based button logic */}
+                {(() => {
+                  const currentTier = mapLicenseToTier(currentLicenseInfo || null);
+                  const isCurrent = checkIsCurrentTier(currentTier, plan.id);
+                  const isDowngradePlan = checkIsDowngrade(currentTier, plan.id);
+
+                  // Free Plan
+                  if (plan.id === 'free') {
+                    return (
+                      <Button
+                        variant="filled"
+                        disabled
+                        fullWidth
+                        className="plan-button"
+                      >
+                        {isCurrent
+                          ? t('plan.current', 'Current Plan')
+                          : t('plan.free.included', 'Included')}
+                      </Button>
+                    );
                   }
-                >
-                  {plan.id === currentPlan.id
-                    ? t('plan.current', 'Current Plan')
-                    : t('plan.contact', 'Contact Us')}
-                </Button>
+
+                  // Server Plan
+                  if (plan.id === 'server') {
+                    if (currentTier === 'free') {
+                      return (
+                        <Button
+                          variant="filled"
+                          fullWidth
+                          onClick={() => handleOpenCheckout('server', false)}
+                          className="plan-button"
+                        >
+                          {t('plan.upgrade', 'Upgrade')}
+                        </Button>
+                      );
+                    }
+                    if (isCurrent) {
+                      return (
+                        <Button
+                          variant="filled"
+                          fullWidth
+                          onClick={handleManageBilling}
+                          className="plan-button"
+                        >
+                          {t('plan.manage', 'Manage')}
+                        </Button>
+                      );
+                    }
+                    if (isDowngradePlan) {
+                      return (
+                        <Button
+                          variant="filled"
+                          disabled
+                          fullWidth
+                          className="plan-button"
+                        >
+                          {t('plan.free.included', 'Included')}
+                        </Button>
+                      );
+                    }
+                  }
+
+                  // Enterprise Plan
+                  if (plan.id === 'enterprise') {
+                    if (isEnterpriseBlockedForFree(currentTier, plan.id)) {
+                      return (
+                        <Tooltip label={t('plan.enterprise.requiresServer', 'Requires Server plan')} position="top" withArrow>
+                          <Button
+                            variant="filled"
+                            disabled
+                            fullWidth
+                            className="plan-button"
+                          >
+                            {t('plan.enterprise.requiresServer', 'Requires Server')}
+                          </Button>
+                        </Tooltip>
+                      );
+                    }
+                    if (currentTier === 'server') {
+                      // TODO: Re-enable checkout flow when account syncing is ready
+                      // return (
+                      //   <Button
+                      //     variant="filled"
+                      //     fullWidth
+                      //     onClick={() => handleOpenCheckout('enterprise', true)}
+                      //     className="plan-button"
+                      //   >
+                      //     {t('plan.selectPlan', 'Select Plan')}
+                      //   </Button>
+                      // );
+                      return (
+                        <Button
+                          variant="filled"
+                          fullWidth
+                          disabled
+                          className="plan-button"
+                        >
+                          {t('plan.contact', 'Contact Us')}
+                        </Button>
+                      );
+                    }
+                    if (isCurrent) {
+                      return (
+                        <Button
+                          variant="filled"
+                          fullWidth
+                          onClick={handleManageBilling}
+                          className="plan-button"
+                        >
+                          {t('plan.manage', 'Manage')}
+                        </Button>
+                      );
+                    }
+                  }
+
+                  return null;
+                })()}
               </Stack>
             </Card>
           ))}
@@ -230,66 +312,14 @@ const StaticPlanSection: React.FC<StaticPlanSectionProps> = ({ currentLicenseInf
       <Divider />
 
       {/* License Key Section */}
-      <div>
-        <Button
-          variant="subtle"
-          leftSection={<LocalIcon icon={showLicenseKey ? "expand-less-rounded" : "expand-more-rounded"} width="1.25rem" height="1.25rem" />}
-          onClick={() => setShowLicenseKey(!showLicenseKey)}
-        >
-          {t('admin.settings.premium.licenseKey.toggle', 'Got a license key or certificate file?')}
-        </Button>
+      <LicenseKeySection currentLicenseInfo={currentLicenseInfo} />
 
-        <Collapse in={showLicenseKey} mt="md">
-          <Stack gap="md">
-            <Alert
-              variant="light"
-              color="blue"
-              icon={<LocalIcon icon="info-rounded" width="1rem" height="1rem" />}
-            >
-              <Text size="sm">
-                {t('admin.settings.premium.licenseKey.info', 'If you have a license key or certificate file from a direct purchase, you can enter it here to activate premium or enterprise features.')}
-              </Text>
-            </Alert>
-
-            {premiumLoading ? (
-              <Stack align="center" justify="center" h={100}>
-                <Loader size="md" />
-              </Stack>
-            ) : (
-              <Paper withBorder p="md" radius="md">
-                <Stack gap="md">
-                  <div>
-                    <TextInput
-                      label={
-                        <Group gap="xs">
-                          <span>{t('admin.settings.premium.key.label', 'License Key')}</span>
-                          <PendingBadge show={isFieldPending('key')} />
-                        </Group>
-                      }
-                      description={t('admin.settings.premium.key.description', 'Enter your premium or enterprise license key. Premium features will be automatically enabled when a key is provided.')}
-                      value={premiumSettings.key || ''}
-                      onChange={(e) => setPremiumSettings({ ...premiumSettings, key: e.target.value })}
-                      placeholder="00000000-0000-0000-0000-000000000000"
-                    />
-                  </div>
-
-                  <Group justify="flex-end">
-                    <Button onClick={handleSaveLicense} loading={premiumSaving} size="sm">
-                      {t('admin.settings.save', 'Save Changes')}
-                    </Button>
-                  </Group>
-                </Stack>
-              </Paper>
-            )}
-          </Stack>
-        </Collapse>
-      </div>
-
-      {/* Restart Confirmation Modal */}
-      <RestartConfirmationModal
-        opened={restartModalOpened}
-        onClose={closeRestartModal}
-        onRestart={restartServer}
+      {/* Static Checkout Modal */}
+      <StaticCheckoutModal
+        opened={checkoutModalOpened}
+        onClose={() => setCheckoutModalOpened(false)}
+        planName={selectedPlan}
+        isUpgrade={isUpgrade}
       />
     </div>
   );

frontend/src/proprietary/constants/staticStripeLinks.ts

@@ -0,0 +1,56 @@
+/**
+ * Static Stripe payment links for offline/self-hosted environments
+ *
+ * These links are used when Supabase is not configured, allowing users to
+ * purchase licenses directly through Stripe hosted checkout pages.
+ *
+ * NOTE: These are test environment URLs. Replace with production URLs before release.
+ */
+
+export interface StaticStripeLinks {
+  server: {
+    monthly: string;
+    yearly: string;
+  };
+  enterprise: {
+    monthly: string;
+    yearly: string;
+  };
+  billingPortal: string;
+}
+// PRODCUTION LINKS FOR LIVE SERVER
+export const STATIC_STRIPE_LINKS: StaticStripeLinks = {
+  server: {
+    monthly: 'https://buy.stripe.com/fZu4gB8Nv6ysfAj0ts8Zq03',
+    yearly: 'https://buy.stripe.com/9B68wR6Fn0a40Fpcca8Zq02',
+  },
+  enterprise: {
+    monthly: '',
+    yearly: '',
+  },
+  billingPortal: 'https://billing.stripe.com/p/login/test_aFa5kv1Mz2s10Fr3Cp83C00',
+};
+
+// LINKS FOR TEST SERVER: 
+// export const STATIC_STRIPE_LINKS: StaticStripeLinks = {
+//   server: {
+//     monthly: 'https://buy.stripe.com/test_8x27sD4YL9Ut0Fr3Cp83C02',
+//     yearly: 'https://buy.stripe.com/test_4gMdR11Mz4A9ag17SF83C03',
+//   },
+//   enterprise: {
+//     monthly: 'https://buy.stripe.com/test_8x2cMX9f18Qp9bX0qd83C04',
+//     yearly: 'https://buy.stripe.com/test_6oU00b2QD2s173P6OB83C05',
+//   },
+//   billingPortal: 'https://billing.stripe.com/p/login/test_aFa5kv1Mz2s10Fr3Cp83C00',
+// };
+
+/**
+ * Builds a Stripe URL with a prefilled email parameter
+ * @param baseUrl - The base Stripe checkout URL
+ * @param email - The email address to prefill
+ * @returns The complete URL with encoded email parameter
+ */
+export function buildStripeUrlWithEmail(baseUrl: string, email: string): string {
+  const encodedEmail = encodeURIComponent(email);
+  return `${baseUrl}?locked_prefilled_email=${encodedEmail}`;
+}

frontend/src/proprietary/utils/planTierUtils.ts

@@ -0,0 +1,40 @@
+/**
+ * Shared utilities for plan tier comparisons and button logic
+ */
+
+export type PlanTier = 'free' | 'server' | 'enterprise';
+
+const TIER_HIERARCHY: Record<PlanTier, number> = {
+  'free': 1,
+  'server': 2,
+  'enterprise': 3,
+};
+
+/**
+ * Get numeric level for a tier
+ */
+export function getTierLevel(tier: PlanTier | string | null | undefined): number {
+  if (!tier) return 1;
+  return TIER_HIERARCHY[tier as PlanTier] || 1;
+}
+
+/**
+ * Check if target tier is the current tier
+ */
+export function isCurrentTier(currentTier: PlanTier | string | null | undefined, targetTier: PlanTier | string): boolean {
+  return getTierLevel(currentTier) === getTierLevel(targetTier);
+}
+
+/**
+ * Check if target tier is a downgrade from current tier
+ */
+export function isDowngrade(currentTier: PlanTier | string | null | undefined, targetTier: PlanTier | string): boolean {
+  return getTierLevel(currentTier) > getTierLevel(targetTier);
+}
+
+/**
+ * Check if enterprise is blocked for free tier users
+ */
+export function isEnterpriseBlockedForFree(currentTier: PlanTier | string | null | undefined, targetTier: PlanTier | string): boolean {
+  return currentTier === 'free' && targetTier === 'enterprise';
+}