diff --git a/src/ghes-releases/scripts/deprecate/update-content.ts b/src/ghes-releases/scripts/deprecate/update-content.ts
index aa5f04794896..95afdaf1f0d1 100644
--- a/src/ghes-releases/scripts/deprecate/update-content.ts
+++ b/src/ghes-releases/scripts/deprecate/update-content.ts
@@ -89,27 +89,68 @@ export function updateContentFiles() {
 
     if (appliesToNoSupportedGhesReleases) {
       if (Object.keys(data.versions).length === 1) {
-        console.log('Removing file: ', file)
-        fs.unlinkSync(file)
-        const indexFile = file.replace(path.basename(file), 'index.md')
-        const indexFileContent = fs.readFileSync(indexFile, 'utf8')
-        const { content, data } = frontmatter(indexFileContent) as {
-          content: string | undefined
-          data: { children: string[] } | undefined
-        }
-        if (!data) continue
-        data.children = data.children.filter((child) => child !== '/' + path.basename(file, '.md'))
-        console.log('..Updating children in: ', indexFile)
-        fs.writeFileSync(
-          indexFile,
-          frontmatter.stringify(content || '', data, { lineWidth: -1 } as any),
-        )
-        continue
+        removeFileUpdateParent(file)
+      } else {
+        // Remove the ghes property from versions Fm and return
+        delete data.versions.ghes
+        console.log('Removing GHES version from: ', file)
+        fs.writeFileSync(file, frontmatter.stringify(content, data, { lineWidth: -1 } as any))
       }
-      // Remove the ghes property from versions Fm and return
-      delete data.versions.ghes
-      console.log('Removing GHES version from: ', file)
-      fs.writeFileSync(file, frontmatter.stringify(content, data, { lineWidth: -1 } as any))
     }
   }
 }
+
+function removeFileUpdateParent(filePath: string) {
+  console.log('Removing file: ', filePath)
+  fs.unlinkSync(filePath)
+  const filePathDirectory = path.dirname(filePath)
+  if (fs.readdirSync(filePathDirectory).length === 0) {
+    fs.rmdirSync(filePathDirectory)
+  }
+  const parentFilePath = getParentFilePath(filePath)
+  if (!parentFilePath) return
+  const indexFileContent = fs.readFileSync(parentFilePath, 'utf8')
+  const { content, data } = frontmatter(indexFileContent) as {
+    content: string | undefined
+    data: { children: string[] } | undefined
+  }
+  if (!data) return
+  // Children paths are relative to the index.md file's directory
+  const childPath = filePath.endsWith('index.md')
+    ? '/' + path.basename(path.dirname(filePath))
+    : '/' + path.basename(filePath, '.md')
+
+  // Remove the childPath from the parent index.md file's children frontmatter
+  data.children = data.children.filter((child) => child !== childPath)
+
+  // If removing the childPath leaves the parent index.md file empty, remove it
+  if (data.children.length === 0) {
+    removeFileUpdateParent(parentFilePath)
+  } else {
+    console.log('..Updating children in: ', parentFilePath)
+    fs.writeFileSync(
+      parentFilePath,
+      frontmatter.stringify(content || '', data, { lineWidth: -1 } as any),
+    )
+  }
+}
+
+// Gets the next parent file path.
+// If the filePath is an article (e.g., doesn't end with index.md),
+// then the parent file is the index.md file in the same directory.
+// If the filePath is a category or subcategory (e.g., ends with index.md),
+// the parent is the index.md file in the next directory up.
+function getParentFilePath(filePath: string) {
+  // This is the root index.md file, it has no parent
+  if (!filePath || filePath === 'content/index.md') return null
+  // Handle index.md files with index.md parent in directory above
+  if (filePath.endsWith('index.md')) {
+    const pathParts = filePath.split('/')
+    pathParts.pop()
+    pathParts.pop()
+    pathParts.push('index.md')
+    return pathParts.join('/')
+  }
+  // Handle articles with a parent index.md file
+  return filePath.replace(path.basename(filePath), 'index.md')
+}