diff --git a/src/automated-pipelines/lib/update-markdown.js b/src/automated-pipelines/lib/update-markdown.js
index 84ed7a35a7..b10c6cf449 100644
--- a/src/automated-pipelines/lib/update-markdown.js
+++ b/src/automated-pipelines/lib/update-markdown.js
@@ -16,12 +16,12 @@ export const MARKDOWN_COMMENT =
 
 // Main entrypoint into this module. This function adds, removes, and updates
 // versions frontmatter in all directories under the targetDirectory.
-export async function updateContentDirectory(
+export async function updateContentDirectory({
   targetDirectory,
   sourceContent,
   frontmatter,
-  indexOrder
-) {
+  indexOrder,
+}) {
   const sourceFiles = Object.keys(sourceContent)
   await createDirectory(targetDirectory)
   await removeMarkdownFiles(targetDirectory, sourceFiles, frontmatter.autogenerated)
diff --git a/src/automated-pipelines/tests/update-content-directory.js b/src/automated-pipelines/tests/update-content-directory.js
index 05b1b6f768..16859a1fd3 100644
--- a/src/automated-pipelines/tests/update-content-directory.js
+++ b/src/automated-pipelines/tests/update-content-directory.js
@@ -73,18 +73,19 @@ describe('automated content directory updates', () => {
 
     // Rewrites the content directory in the operating system's
     // temp directory.
-    await updateContentDirectory(
+    await updateContentDirectory({
       targetDirectory,
-      contentDataFullPath,
-      {
+      sourceContent: contentDataFullPath,
+      frontmatter: {
         autogenerated: 'rest',
       },
-      indexOrder
-    )
+      indexOrder,
+    })
   })
 
   afterAll(async () => {
     await rm(tempDirectory, { recursive: true, force: true })
+    delete process.env.TEST_OS_ROOT_DIR
   })
 
   test('expected files and directories are removed', async () => {
diff --git a/src/codeql-cli/scripts/sync.js b/src/codeql-cli/scripts/sync.js
index cb9779a605..6528ec1dfd 100755
--- a/src/codeql-cli/scripts/sync.js
+++ b/src/codeql-cli/scripts/sync.js
@@ -43,7 +43,11 @@ async function main() {
     cliMarkdownContents[targetFilename] = { data: sourceData, content: finalSourceContent }
   }
   // Begin updating Markdown files in the content directory
-  await updateContentDirectory(targetDirectory, cliMarkdownContents, frontmatterDefaults)
+  await updateContentDirectory({
+    targetDirectory,
+    sourceContent: cliMarkdownContents,
+    frontmatter: frontmatterDefaults,
+  })
 }
 
 // Separates out steps that need to be done before the sync can begin
diff --git a/src/rest/scripts/utils/update-markdown.js b/src/rest/scripts/utils/update-markdown.js
index 9e456f6219..923d48e1b8 100644
--- a/src/rest/scripts/utils/update-markdown.js
+++ b/src/rest/scripts/utils/update-markdown.js
@@ -17,7 +17,11 @@ const { frontmatterDefaults, targetDirectory } = JSON.parse(
 export async function updateRestFiles() {
   const restVersions = await getDataFrontmatter(REST_DATA_DIR, REST_SCHEMA_FILENAME)
   const restMarkdownContent = await getMarkdownContent(restVersions)
-  await updateContentDirectory(targetDirectory, restMarkdownContent, frontmatterDefaults)
+  await updateContentDirectory({
+    targetDirectory,
+    sourceContent: restMarkdownContent,
+    frontmatter: frontmatterDefaults,
+  })
 }
 
 // Reads data files from the directory provided and returns a
@@ -80,10 +84,12 @@ async function getMarkdownContent(versions) {
 
   for (const category of Object.keys(versions)) {
     const subcategories = Object.keys(versions[category])
-    // When there is only a single subcategory, the Markdown file
-    // will be at the root of the content/rest directory. The
-    // file path will be content/rest/<category>.md
-    if (subcategories.length === 1) {
+    // When there is only a single subcategory and the name
+    // matches the category, this is an override due to a
+    // subcategory not being defined. In this case,
+    // the markdown file will be in the content/rest directory.
+    // The file path will be content/rest/<category>.md
+    if (subcategories.length === 1 && category === subcategories[0]) {
       // this will be a file in the root of the rest directory
       const filepath = path.join('content/rest', `${category}.md`)
       markdownUpdates[filepath] = {