diff --git a/content/repositories/viewing-activity-and-data-for-your-repository/viewing-a-projects-contributors.md b/content/repositories/viewing-activity-and-data-for-your-repository/viewing-a-projects-contributors.md
index 5511e1e9ca75..41e5b0330dde 100644
--- a/content/repositories/viewing-activity-and-data-for-your-repository/viewing-a-projects-contributors.md
+++ b/content/repositories/viewing-activity-and-data-for-your-repository/viewing-a-projects-contributors.md
@@ -23,7 +23,7 @@ category:
 You can view the top 100 contributors to a repository{% ifversion ghes %}, including commit co-authors,{% endif %} in the contributors graph. Merge commits and empty commits aren't counted as contributions for this graph.
 
 {% ifversion fpt or ghec %}
-You can also see a list of people who have contributed to the project's Python dependencies. To access this list of community contributors, visit `https://github.com/REPO-OWNER/REPO-NAME/graphs/contributors`.
+To access the list of community contributors, visit `https://github.com/REPO-OWNER/REPO-NAME/graphs/contributors`.
 {% endif %}
 
 ## Accessing the contributors graph
diff --git a/src/assets/middleware/dynamic-assets.ts b/src/assets/middleware/dynamic-assets.ts
index b59d558097e1..4cd1cca5ce80 100644
--- a/src/assets/middleware/dynamic-assets.ts
+++ b/src/assets/middleware/dynamic-assets.ts
@@ -6,6 +6,9 @@ import sharp from 'sharp'
 import type { ExtendedRequest } from '@/types'
 import { assetCacheControl, defaultCacheControl } from '@/frame/middleware/cache-control'
 import { setFastlySurrogateKey, SURROGATE_ENUMS } from '@/frame/middleware/set-fastly-surrogate-key'
+import { createLogger } from '@/observability/logger'
+
+const logger = createLogger(import.meta.url)
 
 /**
  * This is the indicator that is a virtual part of the URL.
@@ -83,6 +86,7 @@ export default async function dynamicAssets(
   if (req.path.endsWith('.webp')) {
     const { url, maxWidth, error } = deconstructImageURL(req.path)
     if (error) {
+      logger.warn('Invalid dynamic asset URL', { path: req.path, error })
       return res.status(400).type('text/plain').send(error.toString())
     }
     try {
@@ -149,6 +153,7 @@ export default async function dynamicAssets(
         'code' in catchError &&
         (catchError as NodeJS.ErrnoException).code !== 'ENOENT'
       ) {
+        logger.error('Failed to process dynamic asset', { path: req.path, error: catchError })
         throw catchError
       }
     }
diff --git a/src/automated-pipelines/lib/update-markdown.ts b/src/automated-pipelines/lib/update-markdown.ts
index 6ca36f482b71..49addfc6ee14 100644
--- a/src/automated-pipelines/lib/update-markdown.ts
+++ b/src/automated-pipelines/lib/update-markdown.ts
@@ -9,8 +9,11 @@ import { difference, isEqual } from 'lodash-es'
 
 import { allVersions } from '@/versions/lib/all-versions'
 import getApplicableVersions from '@/versions/lib/get-applicable-versions'
+import { createLogger } from '@/observability/logger'
 import type { MarkdownFrontmatter } from '@/types'
 
+const logger = createLogger(import.meta.url)
+
 // Type definitions - extending existing type to add missing fields and make most fields optional
 type FrontmatterData = Partial<MarkdownFrontmatter> & {
   autogenerated?: string
@@ -89,6 +92,12 @@ async function removeMarkdownFiles(
   // If the first array contains items that the second array does not,
   // it means that a Markdown page was deleted from the OpenAPI schema
   const filesToRemove = difference(autogeneratedFiles, sourceFiles)
+  if (filesToRemove.length > 0) {
+    logger.info('Removing stale markdown files', {
+      targetDirectory,
+      count: filesToRemove.length,
+    })
+  }
   // Markdown files that need to be deleted
   for (const file of filesToRemove) {
     unlinkSync(file)
@@ -159,6 +168,7 @@ async function updateMarkdownFile(
     const matcher = new RegExp(commentDelimiter, 'g')
     const matches = content.match(matcher)
     if (matches && matches.length > 1) {
+      logger.error('File has multiple comment delimiters', { file })
       throw new Error(`Error: ${file} has multiple comment delimiters`)
     }
 
@@ -171,9 +181,17 @@ async function updateMarkdownFile(
     const isVersionsSame = isEqual(sourceData.versions, data.versions)
     // Only proceed if the content or versions have changed
     if (isContentSame && isVersionsSame && !isDelimiterMissing) {
+      logger.debug('Markdown file unchanged, skipping', { file })
       return
     }
 
+    logger.debug('Updating existing markdown file', {
+      file,
+      contentChanged: !isContentSame,
+      versionsChanged: !isVersionsSame,
+      delimiterMissing: isDelimiterMissing,
+    })
+
     // Create a new object so that we don't mutate the original data
     const newData = { ...data }
     // Only modify the versions property when a file already exists
@@ -182,6 +200,7 @@ async function updateMarkdownFile(
     const newFileContent = appendVersionComment(matter.stringify(targetContent, newData))
     await writeFile(file, newFileContent)
   } else {
+    logger.info('Creating new markdown file', { file })
     await createDirectory(path.dirname(file))
     const newFileContent = appendVersionComment(
       matter.stringify(commentDelimiter + sourceContent, sourceData),
@@ -202,6 +221,7 @@ async function updateDirectory(
   const initialDirectoryListing = await getDirectoryInfo(directory)
   // If there are no children on disk, remove the directory
   if (initialDirectoryListing.directoryContents.length === 0 && !rootDirectoryOnly) {
+    logger.info('Removing empty directory', { directory })
     await rimraf(directory)
     return
   }
@@ -231,6 +251,7 @@ async function updateDirectory(
   const itemsToAdd = difference(childrenOnDisk, indexChildren)
   const itemsToRemove = difference(indexChildren, childrenOnDisk)
   if (itemsToRemove.length === 0 && itemsToAdd.length === 0) {
+    logger.debug('Index children unchanged, skipping', { indexFile })
     return
   }
 
@@ -268,6 +289,7 @@ function getChildrenToCompare(
   fmChildren: string[] | undefined,
 ): ChildrenComparison {
   if (!fmChildren) {
+    logger.error('No children property found in index file', { indexFile })
     throw new Error(`No children property found in ${indexFile}`)
   }
 
@@ -386,6 +408,7 @@ async function getIndexFileVersions(
     files.map(async (file) => {
       const filepath = path.join(directory, file)
       if (!existsSync(filepath)) {
+        logger.error('File does not exist while assembling index versions', { filepath })
         throw new Error(
           `File ${filepath} does not exist while assembling directory index.md files to create parent version.`,
         )
@@ -396,6 +419,7 @@ async function getIndexFileVersions(
       }
       const { data } = matter(await readFile(filepath, 'utf-8'))
       if (!data || !data.versions) {
+        logger.error('Frontmatter missing versions', { filepath })
         throw new Error(`Frontmatter in ${filepath} does not contain versions.`)
       }
       const fmVersions = getApplicableVersions(data.versions)
@@ -526,6 +550,7 @@ async function createDirectory(targetDirectory: string): Promise<void> {
 
 async function getDirectoryInfo(directory: string): Promise<DirectoryInfo> {
   if (!existsSync(directory)) {
+    logger.error('Directory does not exist', { directory })
     throw new Error(`Directory ${directory} did not exist when attempting to get directory info.`)
   }
   const directoryContents = (await readdir(directory)).filter(