diff --git a/package.json b/package.json
index 81de7a9faa..75239089b0 100644
--- a/package.json
+++ b/package.json
@@ -16,6 +16,7 @@
   },
   "exports": "./src/frame/server.ts",
   "scripts": {
+    "add-content-type": "tsx src/content-render/scripts/add-content-type.ts",
     "ai-edit": "tsx src/ai-editors/scripts/ai-edit.ts",
     "all-documents": "tsx src/content-render/scripts/all-documents/cli.ts",
     "analyze-text": "tsx src/search/scripts/analyze-text.ts",
diff --git a/src/content-render/scripts/add-content-type.ts b/src/content-render/scripts/add-content-type.ts
new file mode 100644
index 0000000000..f74d5e2177
--- /dev/null
+++ b/src/content-render/scripts/add-content-type.ts
@@ -0,0 +1,186 @@
+// This script auto-populates the `contentType` frontmatter property based on
+// the directory location of the content file.
+// Run with:
+// npm run-script -- add-content-type --help
+
+import fs from 'fs'
+import path from 'path'
+import { program } from 'commander'
+import frontmatter from '@/frame/lib/read-frontmatter'
+import walkFiles from '@/workflows/walk-files'
+import { contentTypesEnum } from '#src/frame/lib/frontmatter.js'
+import type { MarkdownFrontmatter } from '@/types'
+
+const RESPONSIBLE_USE_STRING = 'responsible-use'
+const LANDING_TYPE = 'landing'
+const RAI_TYPE = 'rai'
+const OTHER_TYPE = 'other'
+
+interface ScriptOptions {
+  dryRun?: boolean
+  paths?: string[]
+  removeType?: boolean
+  verbose?: boolean
+}
+
+program
+  .description('Auto-populate the contentType frontmatter property based on file location')
+  .option(
+    '-p, --paths [paths...]',
+    'One or more specific paths to process (e.g., copilot or content/copilot/how-tos/file.md)',
+  )
+  .option('-r, --remove-type', `Remove the legacy 'type' frontmatter property if present`)
+  .option('-d, --dry-run', 'Preview changes without modifying files')
+  .option('-v, --verbose', 'Show detailed output of changes made')
+  .addHelpText(
+    'after',
+    `
+Possible contentType values:
+  ${contentTypesEnum.join(', ')}
+
+Examples:
+  npm run-script -- add-content-type // runs on all content files, does not remove legacy 'type' prop
+  npm run-script -- add-content-type --paths copilot actions --remove-type --dry-run
+  npm run-script -- add-content-type --paths content/copilot/how-tos
+  npm run-script -- add-content-type --verbose`,
+  )
+  .parse(process.argv)
+
+const options: ScriptOptions = program.opts()
+
+const contentDir = path.join(process.cwd(), 'content')
+
+async function main() {
+  const filesToProcess: string[] = walkFiles(contentDir, ['.md']).filter((file: string) => {
+    if (file.endsWith('README.md')) return false
+    if (file.includes('early-access')) return false
+    if (!options.paths) return true
+    return options.paths.some((p: string) => {
+      // Allow either a full content path like "content/foo/bar.md"
+      // or a top-level directory name like "copilot"
+      if (!p.startsWith('content')) {
+        p = path.join('content', p)
+      }
+      if (!fs.existsSync(p)) {
+        console.error(`${p} not found`)
+        process.exit(1)
+      }
+      if (path.relative(process.cwd(), file).startsWith(p)) return true
+    })
+  })
+
+  let processedCount = 0
+  let updatedCount = 0
+
+  for (const filePath of filesToProcess) {
+    try {
+      const result = processFile(filePath, options)
+      if (result.processed) processedCount++
+      if (result.updated) updatedCount++
+    } catch (error) {
+      console.error(
+        `Error processing ${filePath}:`,
+        error instanceof Error ? error.message : String(error),
+      )
+    }
+  }
+
+  console.log(`\nUpdated ${updatedCount} files out of ${processedCount}`)
+}
+
+function processFile(filePath: string, options: ScriptOptions) {
+  const fileContent = fs.readFileSync(filePath, 'utf8')
+  const relativePath = path.relative(contentDir, filePath)
+
+  const { data, content } = frontmatter(fileContent) as unknown as {
+    data: MarkdownFrontmatter & { contentType?: string }
+    content: string
+  }
+
+  if (!data) return { processed: false, updated: false }
+
+  // Remove the legacy type property if option is passed
+  const removeLegacyType = Boolean(options.removeType && data.type)
+
+  // Skip if contentType already exists and we're not removing legacy type
+  if (data.contentType && !removeLegacyType) {
+    console.log(`contentType already set on ${relativePath}`)
+    return { processed: true, updated: false }
+  }
+
+  const newContentType = data.contentType || determineContentType(relativePath, data.type || '')
+
+  if (options.dryRun) {
+    console.log(`\n${relativePath}`)
+    if (!data.contentType) {
+      console.log(`   ✅  Would set contentType: "${newContentType}"`)
+    }
+    if (removeLegacyType) {
+      console.log(`   ✂️  Would remove legacy type: "${data.type}"`)
+    }
+    return { processed: true, updated: false }
+  }
+
+  // Set the contentType property if it doesn't exist
+  if (!data.contentType) {
+    data.contentType = newContentType
+  }
+
+  let legacyTypeValue
+  if (removeLegacyType) {
+    legacyTypeValue = data.type
+    delete data.type
+  }
+
+  // Write the file back
+  fs.writeFileSync(filePath, frontmatter.stringify(content, data, { lineWidth: -1 } as any))
+
+  if (options.verbose) {
+    console.log(`\n${relativePath}`)
+    console.log(`   ✅  Set contentType: "${newContentType}"`)
+    if (removeLegacyType) {
+      console.log(`   ✂️  Removed legacy type: "${legacyTypeValue}"`)
+    }
+  }
+
+  return { processed: true, updated: true }
+}
+
+function determineContentType(relativePath: string, legacyType: string): string {
+  // The split path array will be structured like:
+  // [ 'copilot', 'how-tos', 'troubleshoot', 'index.md' ]
+  // where the content type we want is in slot 1.
+  const pathSegments = relativePath.split(path.sep)
+
+  const topLevelDirectory = pathSegments[0]
+  const derivedContentType = pathSegments[1]
+
+  // There is only one content/index.md, and it's the homepage.
+  if (topLevelDirectory === 'index.md') return 'homepage'
+
+  // SPECIAL HANDLING FOR RAI
+  // If a legacy type includes 'rai', use it for the contentType.
+  // If a directory name includes a responsible-use string, assume the 'rai' type.
+  if (legacyType === 'rai' || derivedContentType.includes(RESPONSIBLE_USE_STRING)) {
+    return RAI_TYPE
+  }
+
+  // When the content directory matches any of the allowed
+  // content type values (such as 'get-started',
+  // 'concepts', 'how-tos', 'reference', and 'tutorials'),
+  // immediately return it. We're satisfied.
+  if (contentTypesEnum.includes(derivedContentType)) {
+    return derivedContentType
+  }
+
+  // There is only one content/<product>/index.md file per doc set.
+  // This index.md is always a landing page.
+  if (derivedContentType === 'index.md') {
+    return LANDING_TYPE
+  }
+
+  // Classify anything else as 'other'.
+  return OTHER_TYPE
+}
+
+main().catch(console.error)
diff --git a/src/frame/lib/frontmatter.js b/src/frame/lib/frontmatter.js
index 9d12b70497..097e09fe3a 100644
--- a/src/frame/lib/frontmatter.js
+++ b/src/frame/lib/frontmatter.js
@@ -17,8 +17,24 @@ const layoutNames = [
   false,
 ]
 
+// DEPRECATED: Use 'contentType' instead of 'type' for new content.
+// 'type' exists on ~40% of files but is used only for internal analytics.
+// Migration tool: src/content-render/scripts/add-content-type.ts
 const guideTypes = ['overview', 'quick_start', 'tutorial', 'how_to', 'reference', 'rai']
 
+// As of July 2025, use 'contentType' rather than 'type'.
+export const contentTypesEnum = [
+  'get-started',
+  'concepts',
+  'how-tos',
+  'reference',
+  'tutorials',
+  'homepage', // Only applies to the sole 'content/index.md' file (the homepage).
+  'landing', // Only applies to 'content/<product>/index.md' files (product landings).
+  'rai', // Only applies to files that live in directories with 'responsible-use' in the name.
+  'other', // Everything else.
+]
+
 export const schema = {
   type: 'object',
   required: ['title', 'versions'],
@@ -150,10 +166,18 @@ export const schema = {
         prefix: { type: 'string' },
       },
     },
+    // DEPRECATED: Use 'contentType' instead of 'type' for new content.
+    // 'type' exists on ~40% of files but is used only for internal analytics.
+    // Migration tool: src/content-render/scripts/add-content-type.ts
     type: {
       type: 'string',
       enum: guideTypes,
     },
+    // As of July 2025, use 'contentType' rather than 'type'.
+    contentType: {
+      type: 'string',
+      enum: contentTypesEnum,
+    },
     topics: {
       type: 'array',
     },
diff --git a/src/frame/lib/page.ts b/src/frame/lib/page.ts
index 4530297786..5da0d76918 100644
--- a/src/frame/lib/page.ts
+++ b/src/frame/lib/page.ts
@@ -187,8 +187,12 @@ class Page {
 
   constructor(opts: PageReadResult) {
     if (opts.frontmatterErrors && opts.frontmatterErrors.length) {
+      console.error(
+        `${opts.frontmatterErrors.length} frontmatter errors trying to load ${opts.fullPath}:`,
+      )
+      console.error(opts.frontmatterErrors)
       throw new FrontmatterErrorsError(
-        `${opts.frontmatterErrors.length} frontmatter errors trying to load ${opts.fullPath}`,
+        `${opts.frontmatterErrors.length} frontmatter errors in ${opts.fullPath}`,
         opts.frontmatterErrors,
       )
     }
diff --git a/src/types.ts b/src/types.ts
index 1f78aa94c7..d624ab9ea5 100644
--- a/src/types.ts
+++ b/src/types.ts
@@ -471,4 +471,6 @@ export type MarkdownFrontmatter = {
   versions: FrontmatterVersions
   subcategory?: boolean
   hidden?: boolean
+  type?: string
+  contentType?: string
 }
diff --git a/src/workflows/fm-utils.ts b/src/workflows/fm-utils.ts
index 7a1d6c8fb9..b6d39e53ce 100644
--- a/src/workflows/fm-utils.ts
+++ b/src/workflows/fm-utils.ts
@@ -8,7 +8,7 @@ export function checkContentType(filePaths: string[], type: string) {
   const unallowedChangedFiles = []
   for (const filePath of filePaths) {
     const { data } = matter(readFileSync(filePath, 'utf8'))
-    if (data.type === type) {
+    if (data.type === type || data.contentType === type) {
       unallowedChangedFiles.push(filePath)
     }
   }
diff --git a/src/workflows/unallowed-contributions.ts b/src/workflows/unallowed-contributions.ts
index 39a8654052..526774aa0d 100755
--- a/src/workflows/unallowed-contributions.ts
+++ b/src/workflows/unallowed-contributions.ts
@@ -46,7 +46,7 @@ async function main() {
   const listUnallowedChangedFiles = unallowedChangedFiles.map((file) => `\n - ${file}`).join('')
   const listUnallowedFiles = filters.notAllowed.map((file: string) => `\n - ${file}`).join('')
 
-  const reviewMessage = `👋 Hey there spelunker. It looks like you've modified some files that we can't accept as contributions:${listUnallowedChangedFiles}\n\nYou'll need to revert all of the files you changed that match that list using [GitHub Desktop](https://docs.github.com/en/free-pro-team@latest/desktop/contributing-and-collaborating-using-github-desktop/managing-commits/reverting-a-commit-in-github-desktop) or \`git checkout origin/main <file name>\`. Once you get those files reverted, we can continue with the review process. :octocat:\n\nThe complete list of files we can't accept are:${listUnallowedFiles}\n\nWe also can't accept contributions to files in the content directory with frontmatter \`type: rai\`.`
+  const reviewMessage = `👋 Hey there spelunker. It looks like you've modified some files that we can't accept as contributions:${listUnallowedChangedFiles}\n\nYou'll need to revert all of the files you changed that match that list using [GitHub Desktop](https://docs.github.com/en/free-pro-team@latest/desktop/contributing-and-collaborating-using-github-desktop/managing-commits/reverting-a-commit-in-github-desktop) or \`git checkout origin/main <file name>\`. Once you get those files reverted, we can continue with the review process. :octocat:\n\nThe complete list of files we can't accept are:${listUnallowedFiles}\n\nWe also can't accept contributions to files in the content directory with frontmatter \`type: rai\` or \`contentType: rai\`.`
 
   let workflowFailMessage =
     "It looks like you've modified some files that we can't accept as contributions."