diff --git a/packages/upgrade/scripts/generate-guide.js b/packages/upgrade/scripts/generate-guide.js
index b434fcdada9..efbd1d0a02f 100644
--- a/packages/upgrade/scripts/generate-guide.js
+++ b/packages/upgrade/scripts/generate-guide.js
@@ -9,25 +9,44 @@ import meow from 'meow';
 const __dirname = path.dirname(fileURLToPath(import.meta.url));
 const VERSIONS_DIR = path.join(__dirname, '../src/versions');
 
+const SDK_DISPLAY_NAMES = {
+  astro: 'Astro',
+  'chrome-extension': 'Chrome Extension',
+  expo: 'Expo',
+  express: 'Express',
+  fastify: 'Fastify',
+  nextjs: 'Next.js',
+  nuxt: 'Nuxt',
+  react: 'React',
+  'react-router': 'React Router',
+  'tanstack-react-start': 'TanStack Start',
+  vue: 'Vue',
+};
+
 const cli = meow(
   `
     Usage
-      $ pnpm run generate-guide --version=<version> --sdk=<sdk>
+      $ pnpm run generate-guide --version=<version> [--sdk=<sdk>] [--output-dir=<dir>]
 
     Options
-      --version    Version directory to use (e.g., core-3)
-      --sdk        SDK to generate guide for (e.g., nextjs, react, expo)
+      --version      Version directory to use (e.g., core-3)
+      --sdk          SDK to generate guide for (e.g., nextjs, react, expo)
+                     If omitted, generates guides for all SDKs
+      --output-dir   Directory to write generated files to
+                     If omitted, outputs to stdout (single SDK only)
 
     Examples
       $ pnpm run generate-guide --version=core-3 --sdk=nextjs
       $ pnpm run generate-guide --version=core-3 --sdk=react > react-guide.md
+      $ pnpm run generate-guide --version=core-3 --output-dir=./guides
 `,
   {
-    importMeta: import.meta,
     flags: {
-      version: { type: 'string', isRequired: true },
-      sdk: { type: 'string', isRequired: true },
+      outputDir: { type: 'string' },
+      sdk: { type: 'string' },
+      version: { isRequired: true, type: 'string' },
     },
+    importMeta: import.meta,
   },
 );
 
@@ -50,7 +69,10 @@ function loadChanges(version, sdk) {
     return [];
   }
 
-  const files = fs.readdirSync(changesDir).filter(f => f.endsWith('.md'));
+  const files = fs
+    .readdirSync(changesDir)
+    .filter(f => f.endsWith('.md'))
+    .sort();
   const changes = [];
 
   for (const file of files) {
@@ -94,27 +116,74 @@ function groupByCategory(changes) {
 
 function getCategoryHeading(category) {
   const headings = {
+    'behavior-change': 'Behavior Change',
     breaking: 'Breaking Changes',
+    deprecation: 'Deprecations',
     'deprecation-removal': 'Deprecation Removals',
+    version: 'Version',
     warning: 'Warnings',
   };
-  return headings[category] || category;
+  if (headings[category]) {
+    return headings[category];
+  }
+
+  return category.replace(/[-_]+/g, ' ').replace(/\b\w/g, char => char.toUpperCase());
+}
+
+function normalizeSdk(sdk) {
+  return sdk.replace(/^@clerk\//, '');
+}
+
+function getSdkDisplayName(sdk) {
+  return SDK_DISPLAY_NAMES[sdk] || sdk;
+}
+
+function indent(text, spaces) {
+  const padding = ' '.repeat(spaces);
+  return text
+    .split('\n')
+    .map(line => (line.trim() ? padding + line : line))
+    .join('\n');
+}
+
+function generateFrontmatter(sdk, versionName) {
+  const displayName = getSdkDisplayName(sdk);
+  return `---
+title: "Upgrading ${displayName} to ${versionName}"
+description: "Learn how to upgrade Clerk's ${displayName} SDK to the latest version."
+---
+
+{/* WARNING: This is a generated file and should not be edited directly. To update its contents, see the "upgrade" package in the clerk/javascript repo. */}`;
+}
+
+function renderAccordionCategory(lines, category, categoryChanges) {
+  const sortedChanges = [...categoryChanges].sort((a, b) => a.title.localeCompare(b.title));
+  const titles = sortedChanges.map(change => JSON.stringify(change.title));
+
+  lines.push(`## ${getCategoryHeading(category)}`);
+  lines.push('');
+  lines.push(`<Accordion titles={[${titles.join(', ')}]}>`);
+
+  for (const change of sortedChanges) {
+    lines.push('  <AccordionPanel>');
+    lines.push(indent(change.content, 4));
+    lines.push('  </AccordionPanel>');
+  }
+
+  lines.push('</Accordion>');
+  lines.push('');
 }
 
 function generateMarkdown(sdk, versionConfig, changes) {
   const lines = [];
   const versionName = versionConfig.name || versionConfig.id;
 
-  lines.push(`# Upgrading @clerk/${sdk} to ${versionName}`);
+  lines.push(generateFrontmatter(sdk, versionName));
   lines.push('');
 
-  if (versionConfig.docsUrl) {
-    lines.push(`For the full migration guide, see: ${versionConfig.docsUrl}`);
-    lines.push('');
-  }
-
   const grouped = groupByCategory(changes);
-  const categoryOrder = ['breaking', 'deprecation-removal', 'warning'];
+  const categoryOrder = ['breaking', 'deprecation-removal', 'deprecation', 'warning', 'version', 'behavior-change'];
+  const seenCategories = new Set();
 
   for (const category of categoryOrder) {
     const categoryChanges = grouped[category];
@@ -122,10 +191,16 @@ function generateMarkdown(sdk, versionConfig, changes) {
       continue;
     }
 
+    seenCategories.add(category);
+    if (category === 'breaking') {
+      renderAccordionCategory(lines, category, categoryChanges);
+      continue;
+    }
+
     lines.push(`## ${getCategoryHeading(category)}`);
     lines.push('');
 
-    for (const change of categoryChanges) {
+    for (const change of [...categoryChanges].sort((a, b) => a.title.localeCompare(b.title))) {
       lines.push(`### ${change.title}`);
       lines.push('');
       lines.push(change.content);
@@ -134,15 +209,20 @@ function generateMarkdown(sdk, versionConfig, changes) {
   }
 
   // Handle any categories not in the predefined order
-  for (const [category, categoryChanges] of Object.entries(grouped)) {
-    if (categoryOrder.includes(category)) {
+  for (const [category, categoryChanges] of Object.entries(grouped).sort(([a], [b]) => a.localeCompare(b))) {
+    if (seenCategories.has(category)) {
+      continue;
+    }
+
+    if (category === 'breaking') {
+      renderAccordionCategory(lines, category, categoryChanges);
       continue;
     }
 
     lines.push(`## ${getCategoryHeading(category)}`);
     lines.push('');
 
-    for (const change of categoryChanges) {
+    for (const change of [...categoryChanges].sort((a, b) => a.title.localeCompare(b.title))) {
       lines.push(`### ${change.title}`);
       lines.push('');
       lines.push(change.content);
@@ -153,19 +233,72 @@ function generateMarkdown(sdk, versionConfig, changes) {
   return lines.join('\n');
 }
 
+function generateGuideForSdk(sdk, version, versionConfig) {
+  const changes = loadChanges(version, sdk);
+
+  if (changes.length === 0) {
+    return null;
+  }
+
+  return generateMarkdown(sdk, versionConfig, changes);
+}
+
+function writeGuideToFile(outputDir, sdk, content) {
+  if (!fs.existsSync(outputDir)) {
+    fs.mkdirSync(outputDir, { recursive: true });
+  }
+
+  const filePath = path.join(outputDir, `${sdk}.mdx`);
+  fs.writeFileSync(filePath, content);
+  return filePath;
+}
+
 async function main() {
-  const { version, sdk } = cli.flags;
+  const { outputDir, sdk, version } = cli.flags;
 
   const versionConfig = await loadVersionConfig(version);
-  const changes = loadChanges(version, sdk);
 
-  if (changes.length === 0) {
-    console.error(`No changes found for ${sdk} in ${version}`);
+  // Determine which SDKs to generate
+  const sdksToGenerate = sdk ? [normalizeSdk(sdk)] : Object.keys(versionConfig.sdkVersions || {});
+
+  if (sdksToGenerate.length === 0) {
+    console.error(`No SDKs found in version config for ${version}`);
+    process.exit(1);
+  }
+
+  // If multiple SDKs and no output dir, require output dir
+  if (sdksToGenerate.length > 1 && !outputDir) {
+    console.error('--output-dir is required when generating multiple SDK guides');
+    console.error(`SDKs to generate: ${sdksToGenerate.join(', ')}`);
     process.exit(1);
   }
 
-  const markdown = generateMarkdown(sdk, versionConfig, changes);
-  console.log(markdown);
+  const results = [];
+
+  for (const currentSdk of sdksToGenerate) {
+    const markdown = generateGuideForSdk(currentSdk, version, versionConfig);
+
+    if (!markdown) {
+      console.error(`No changes found for ${currentSdk} in ${version}, skipping...`);
+      continue;
+    }
+
+    if (outputDir) {
+      const filePath = writeGuideToFile(outputDir, currentSdk, markdown);
+      results.push({ sdk: currentSdk, filePath });
+    } else {
+      // Single SDK, output to stdout
+      console.log(markdown);
+    }
+  }
+
+  if (outputDir && results.length > 0) {
+    console.log(`\nGenerated ${results.length} guide(s):`);
+    for (const { sdk: generatedSdk, filePath } of results) {
+      const displayName = getSdkDisplayName(generatedSdk);
+      console.log(`  ${displayName}: ${filePath}`);
+    }
+  }
 }
 
 main().catch(error => {