diff --git a/src/content-render/scripts/add-content-type.ts b/src/content-render/scripts/add-content-type.ts
index f74d5e2177c3..88fc414a0a1f 100644
--- a/src/content-render/scripts/add-content-type.ts
+++ b/src/content-render/scripts/add-content-type.ts
@@ -102,13 +102,7 @@ function processFile(filePath: string, options: ScriptOptions) {
   // 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 || '')
+  const newContentType = determineContentType(relativePath, data.type || '')
 
   if (options.dryRun) {
     console.log(`\n${relativePath}`)
@@ -121,9 +115,24 @@ function processFile(filePath: string, options: ScriptOptions) {
     return { processed: true, updated: false }
   }
 
-  // Set the contentType property if it doesn't exist
-  if (!data.contentType) {
+  // Check if we're actually changing an existing contentType
+  const isChangingContentType = data.contentType && data.contentType !== newContentType
+  const isAddingContentType = !data.contentType
+
+  if (isChangingContentType) {
+    console.log(
+      `Changing contentType from '${data.contentType}' to '${newContentType}' on ${relativePath}`,
+    )
+  } else if (isAddingContentType) {
+    console.log(`Adding contentType '${newContentType}' on ${relativePath}`)
+  }
+
+  // Only update if there's actually a change needed
+  if (isChangingContentType || isAddingContentType) {
     data.contentType = newContentType
+  } else {
+    console.log(`contentType is already set to '${data.contentType}' on ${relativePath}`)
+    return { processed: true, updated: false }
   }
 
   let legacyTypeValue
diff --git a/src/events/lib/hydro.ts b/src/events/lib/hydro.ts
index 7a061ab2c4e5..34242d41c8e8 100644
--- a/src/events/lib/hydro.ts
+++ b/src/events/lib/hydro.ts
@@ -5,6 +5,9 @@ import { isNil } from 'lodash-es'
 import statsd from '@/observability/lib/statsd'
 import { report } from '@/observability/lib/failbot'
 import { MAX_REQUEST_TIMEOUT } from '@/frame/lib/constants'
+import { createLogger } from '@/observability/logger'
+
+const logger = createLogger(import.meta.url)
 
 const TIME_OUT_TEXT = 'ms has passed since batch creation'
 const SERVER_DISCONNECT_TEXT = 'The server disconnected before a response was received'
@@ -70,6 +73,13 @@ async function _publish(
   ) {
     const error = new Error(`Failed to send event to Hydro (${statusCode})`)
     if (inProd) {
+      logger.error('Failed to send event to Hydro', {
+        error,
+        statusCode,
+        body,
+        requestBody,
+      })
+      // Report the error to Failbot
       report(error, { statusCode, body, requestBody })
     } else {
       throw error
diff --git a/src/search/lib/helpers/external-search-analytics.ts b/src/search/lib/helpers/external-search-analytics.ts
index e2ba35b5241f..127304709c74 100644
--- a/src/search/lib/helpers/external-search-analytics.ts
+++ b/src/search/lib/helpers/external-search-analytics.ts
@@ -1,3 +1,4 @@
+import { ExtendedRequest } from '@/types'
 import { publish } from '@/events/lib/hydro'
 import { hydroNames } from '@/events/lib/schema'
 import { createLogger } from '@/observability/logger'
@@ -9,7 +10,7 @@ const logger = createLogger(import.meta.url)
  * Returns null if the request should continue, or an error response object if validation failed
  */
 export async function handleExternalSearchAnalytics(
-  req: any,
+  req: ExtendedRequest,
   searchContext: string,
 ): Promise<{ error: string; status: number } | null> {
   const host = req.headers['x-host'] || req.headers.host
@@ -73,12 +74,12 @@ export async function handleExternalSearchAnalytics(
           version: '1.0.0',
           created: new Date().toISOString(),
           hostname: normalizedHost,
-          path: '',
-          search: '',
+          path: req?.context?.path || '',
+          search: 'REDACTED',
           hash: '',
-          path_language: 'en',
-          path_version: '',
-          path_product: '',
+          path_language: req?.context?.language || 'en',
+          path_version: req?.context?.version || '',
+          path_product: req?.context?.product || '',
           path_article: '',
         },
         search_query: 'REDACTED',
@@ -90,7 +91,7 @@ export async function handleExternalSearchAnalytics(
     await publish(analyticsPayload)
   } catch (error) {
     // Don't fail the request if analytics fails
-    console.error('Failed to send search analytics:', error)
+    logger.error('Failed to send search analytics:', { error })
   }
 
   return null
@@ -146,16 +147,12 @@ function stripPort(host: string): string {
   return hostname
 }
 
-interface ExternalAPIRequestLike {
-  headers: Record<string, string | undefined>
-}
-
 /**
  * Determines if a request is likely from an external API client rather than a browser
  * Uses multiple heuristics to detect programmatic vs browser requests
  */
 const userAgentRegex = /^(curl|wget|python-requests|axios|node-fetch|Go-http-client|okhttp)/i
-function isExternalAPIRequest(req: ExternalAPIRequestLike): boolean {
+function isExternalAPIRequest(req: ExtendedRequest): boolean {
   const headers = req.headers
 
   // Browser security headers that APIs typically don't send