diff --git a/apps/docs/app/guides/ai-tools/ai-prompts/[slug]/page.tsx b/apps/docs/app/guides/ai-tools/ai-prompts/[slug]/page.tsx
index 7eaf8f3ceae..df39f6ee8eb 100644
--- a/apps/docs/app/guides/ai-tools/ai-prompts/[slug]/page.tsx
+++ b/apps/docs/app/guides/ai-tools/ai-prompts/[slug]/page.tsx
@@ -6,8 +6,8 @@ import {
   wrapInMarkdownCodeBlock,
 } from '~/app/guides/getting-started/ai-prompts/[slug]/AiPrompts.utils'
 import { GuideTemplate, newEditLink } from '~/features/docs/GuidesMdx.template'
+import { notFoundWithPathname } from '~/features/docs/notFound.utils'
 import { source } from 'common-tags'
-import { notFound } from 'next/navigation'
 
 export const dynamicParams = false
 
@@ -18,7 +18,7 @@ export default async function AiPromptsPage(props: { params: Promise<{ slug: str
 
   const prompt = await getAiPrompt(slug)
   if (!prompt) {
-    notFound()
+    notFoundWithPathname(`/guides/ai-tools/ai-prompts/${slug}`)
   }
 
   let { heading, content } = prompt
diff --git a/apps/docs/app/guides/ai/python/[slug]/page.tsx b/apps/docs/app/guides/ai/python/[slug]/page.tsx
index e31bc6b1595..e64133a1c39 100644
--- a/apps/docs/app/guides/ai/python/[slug]/page.tsx
+++ b/apps/docs/app/guides/ai/python/[slug]/page.tsx
@@ -1,14 +1,13 @@
-import { notFound } from 'next/navigation'
 import { relative } from 'path'
-import rehypeSlug from 'rehype-slug'
-
 import { GuideTemplate, newEditLink } from '~/features/docs/GuidesMdx.template'
 import { genGuideMeta, removeRedundantH1 } from '~/features/docs/GuidesMdx.utils'
-import { getGitHubFileContents } from '~/lib/octokit'
-import { UrlTransformFunction, linkTransform } from '~/lib/mdx/plugins/rehypeLinkTransform'
+import { notFoundWithPathname } from '~/features/docs/notFound.utils'
+import { linkTransform, UrlTransformFunction } from '~/lib/mdx/plugins/rehypeLinkTransform'
 import remarkMkDocsAdmonition from '~/lib/mdx/plugins/remarkAdmonition'
 import { removeTitle } from '~/lib/mdx/plugins/remarkRemoveTitle'
+import { getGitHubFileContents } from '~/lib/octokit'
 import { SerializeOptions } from '~/types/next-mdx-remote-serialize'
+import rehypeSlug from 'rehype-slug'
 
 export const dynamicParams = false
 
@@ -76,7 +75,7 @@ const getContent = async ({ slug }: Params) => {
   const page = pageMap.find(({ slug: validSlug }) => validSlug && validSlug === slug)
 
   if (!page) {
-    notFound()
+    notFoundWithPathname(`/guides/ai/python/${slug}`)
   }
 
   const { remoteFile, meta } = page
diff --git a/apps/docs/app/guides/database/extensions/wrappers/[[...slug]]/page.tsx b/apps/docs/app/guides/database/extensions/wrappers/[[...slug]]/page.tsx
index ebafbd690b7..f85355e895a 100644
--- a/apps/docs/app/guides/database/extensions/wrappers/[[...slug]]/page.tsx
+++ b/apps/docs/app/guides/database/extensions/wrappers/[[...slug]]/page.tsx
@@ -5,6 +5,7 @@ import {
   genGuidesStaticParams,
   removeRedundantH1,
 } from '~/features/docs/GuidesMdx.utils'
+import { notFoundWithPathname } from '~/features/docs/notFound.utils'
 import { newEditLink } from '~/features/helpers.edit-link'
 import { Guide, GuideArticle, GuideFooter, GuideHeader, GuideMdxContent } from '~/features/ui/guide'
 // End of third-party imports
@@ -20,7 +21,6 @@ import type { SerializeOptions } from '~/types/next-mdx-remote-serialize'
 import { isFeatureEnabled } from 'common'
 import matter from 'gray-matter'
 import Link from 'next/link'
-import { notFound } from 'next/navigation'
 import rehypeSlug from 'rehype-slug'
 import emoji from 'remark-emoji'
 import { Button } from 'ui'
@@ -334,11 +334,14 @@ interface Params {
 }
 
 const WrappersDocs = async (props: { params: Promise<Params> }) => {
+  const params = await props.params
+
   if (!isFeatureEnabled('docs:fdw')) {
-    notFound()
+    notFoundWithPathname(
+      `/guides/database/extensions/wrappers${params.slug?.length ? `/${params.slug.join('/')}` : ''}`
+    )
   }
 
-  const params = await props.params
   const { isExternal, meta, assetsBaseUrl, ...data } = await getContent(params)
 
   // Create a combined URL transformer that handles both regular URLs and asset URLs
diff --git a/apps/docs/app/guides/deployment/ci/[slug]/page.tsx b/apps/docs/app/guides/deployment/ci/[slug]/page.tsx
index 4053787f65e..2a2cf31e917 100644
--- a/apps/docs/app/guides/deployment/ci/[slug]/page.tsx
+++ b/apps/docs/app/guides/deployment/ci/[slug]/page.tsx
@@ -1,15 +1,14 @@
-import { notFound } from 'next/navigation'
 import { relative } from 'node:path'
-import rehypeSlug from 'rehype-slug'
-
 import { GuideTemplate, newEditLink } from '~/features/docs/GuidesMdx.template'
 import { genGuideMeta, removeRedundantH1 } from '~/features/docs/GuidesMdx.utils'
-import { getGitHubFileContents } from '~/lib/octokit'
-import { UrlTransformFunction, linkTransform } from '~/lib/mdx/plugins/rehypeLinkTransform'
+import { notFoundWithPathname } from '~/features/docs/notFound.utils'
+import { linkTransform, UrlTransformFunction } from '~/lib/mdx/plugins/rehypeLinkTransform'
 import remarkMkDocsAdmonition from '~/lib/mdx/plugins/remarkAdmonition'
 import { removeTitle } from '~/lib/mdx/plugins/remarkRemoveTitle'
 import remarkPyMdownTabs from '~/lib/mdx/plugins/remarkTabs'
+import { getGitHubFileContents } from '~/lib/octokit'
 import { SerializeOptions } from '~/types/next-mdx-remote-serialize'
+import rehypeSlug from 'rehype-slug'
 
 export const dynamicParams = false
 
@@ -75,7 +74,7 @@ const getContent = async ({ slug }: Params) => {
   const page = pageMap.find(({ slug: validSlug }) => validSlug && validSlug === slug)
 
   if (!page) {
-    notFound()
+    notFoundWithPathname(`/guides/deployment/ci/${slug}`)
   }
 
   const { remoteFile, meta } = page
diff --git a/apps/docs/app/guides/deployment/terraform/[[...slug]]/page.tsx b/apps/docs/app/guides/deployment/terraform/[[...slug]]/page.tsx
index 153c814eff3..2fafd8ea780 100644
--- a/apps/docs/app/guides/deployment/terraform/[[...slug]]/page.tsx
+++ b/apps/docs/app/guides/deployment/terraform/[[...slug]]/page.tsx
@@ -1,5 +1,6 @@
 import { GuideTemplate, newEditLink } from '~/features/docs/GuidesMdx.template'
 import { genGuideMeta, removeRedundantH1 } from '~/features/docs/GuidesMdx.utils'
+import { notFoundWithPathname } from '~/features/docs/notFound.utils'
 import { getEmptyArray } from '~/features/helpers.fn'
 import { IS_DEV } from '~/lib/constants'
 import { isValidGuideFrontmatter } from '~/lib/docs'
@@ -10,7 +11,6 @@ import remarkPyMdownTabs from '~/lib/mdx/plugins/remarkTabs'
 import { getGitHubFileContents } from '~/lib/octokit'
 import { SerializeOptions } from '~/types/next-mdx-remote-serialize'
 import matter from 'gray-matter'
-import { notFound } from 'next/navigation'
 import rehypeSlug from 'rehype-slug'
 
 import {
@@ -106,7 +106,7 @@ const getContent = async ({ slug }: Params) => {
   const page = pageMap.find((page) => page.slug === requestedSlug)
 
   if (!page) {
-    notFound()
+    notFoundWithPathname(`/guides/deployment/terraform${slug?.length ? `/${slug.join('/')}` : ''}`)
   }
 
   const { meta, remoteFile, useRoot } = page
diff --git a/apps/docs/app/guides/graphql/[[...slug]]/page.tsx b/apps/docs/app/guides/graphql/[[...slug]]/page.tsx
index eb0c01b48f5..dda40f712a9 100644
--- a/apps/docs/app/guides/graphql/[[...slug]]/page.tsx
+++ b/apps/docs/app/guides/graphql/[[...slug]]/page.tsx
@@ -1,6 +1,7 @@
 import { isAbsolute, relative } from 'path'
 import { GuideTemplate, newEditLink } from '~/features/docs/GuidesMdx.template'
 import { genGuideMeta } from '~/features/docs/GuidesMdx.utils'
+import { notFoundWithPathname } from '~/features/docs/notFound.utils'
 import { getEmptyArray } from '~/features/helpers.fn'
 import { IS_DEV } from '~/lib/constants'
 import { linkTransform, UrlTransformFunction } from '~/lib/mdx/plugins/rehypeLinkTransform'
@@ -9,7 +10,6 @@ import { removeTitle } from '~/lib/mdx/plugins/remarkRemoveTitle'
 import remarkPyMdownTabs from '~/lib/mdx/plugins/remarkTabs'
 import { getGitHubFileContents } from '~/lib/octokit'
 import { SerializeOptions } from '~/types/next-mdx-remote-serialize'
-import { notFound } from 'next/navigation'
 import rehypeSlug from 'rehype-slug'
 
 // We fetch these docs at build time from an external repo
@@ -128,7 +128,7 @@ const getContent = async ({ slug }: Params) => {
   const page = pageMap.find((page) => page.slug === slug?.at(0))
 
   if (!page) {
-    notFound()
+    notFoundWithPathname(`/guides/graphql${slug?.length ? `/${slug.join('/')}` : ''}`)
   }
 
   const { remoteFile, meta } = page
diff --git a/apps/docs/app/guides/troubleshooting/[slug]/page.tsx b/apps/docs/app/guides/troubleshooting/[slug]/page.tsx
index 9f15cac7d53..f0868e8c167 100644
--- a/apps/docs/app/guides/troubleshooting/[slug]/page.tsx
+++ b/apps/docs/app/guides/troubleshooting/[slug]/page.tsx
@@ -1,5 +1,4 @@
-import { notFound } from 'next/navigation'
-
+import { notFoundWithPathname } from '~/features/docs/notFound.utils'
 import TroubleshootingPage from '~/features/docs/Troubleshooting.page'
 import { getAllTroubleshootingEntries, getArticleSlug } from '~/features/docs/Troubleshooting.utils'
 import { PROD_URL } from '~/lib/constants'
@@ -20,7 +19,7 @@ export default async function TroubleshootingEntryPage(props: {
   const entry = allTroubleshootingEntries.find((entry) => getArticleSlug(entry) === slug)
 
   if (!entry) {
-    notFound()
+    notFoundWithPathname(`/guides/troubleshooting/${slug}`)
   }
 
   return <TroubleshootingPage entry={entry} />
diff --git a/apps/docs/app/reference/[...slug]/page.tsx b/apps/docs/app/reference/[...slug]/page.tsx
index 0ed5497704c..d224a81cb7e 100644
--- a/apps/docs/app/reference/[...slug]/page.tsx
+++ b/apps/docs/app/reference/[...slug]/page.tsx
@@ -1,6 +1,5 @@
-import { notFound } from 'next/navigation'
-
 import { REFERENCES } from '~/content/navigation.references'
+import { notFoundWithPathname } from '~/features/docs/notFound.utils'
 import { ApiReferencePage } from '~/features/docs/Reference.apiPage'
 import { CliReferencePage } from '~/features/docs/Reference.cliPage'
 import { ClientSdkReferencePage } from '~/features/docs/Reference.sdkPage'
@@ -18,9 +17,10 @@ export default async function ReferencePage(props: { params: Promise<{ slug: Arr
   const params = await props.params
 
   const { slug } = params
+  const referencePath = `/reference/${slug.join('/')}`
 
   if (!Object.keys(REFERENCES).includes(slug[0].replaceAll('-', '_'))) {
-    notFound()
+    notFoundWithPathname(referencePath)
   }
 
   const parsedPath = parseReferencePath(slug)
@@ -34,7 +34,7 @@ export default async function ReferencePage(props: { params: Promise<{ slug: Arr
 
     const sdkData = REFERENCES[sdkId]
     if (sdkData.enabled === false) {
-      notFound()
+      notFoundWithPathname(referencePath)
     }
 
     const latestVersion = sdkData.versions[0]
@@ -52,7 +52,7 @@ export default async function ReferencePage(props: { params: Promise<{ slug: Arr
       <SelfHostingReferencePage service={parsedPath.service} servicePath={parsedPath.servicePath} />
     )
   } else {
-    notFound()
+    notFoundWithPathname(referencePath)
   }
 }
 
diff --git a/apps/docs/features/docs/GuidesMdx.utils.tsx b/apps/docs/features/docs/GuidesMdx.utils.tsx
index 1cd8e04a9eb..e719d2caa9f 100644
--- a/apps/docs/features/docs/GuidesMdx.utils.tsx
+++ b/apps/docs/features/docs/GuidesMdx.utils.tsx
@@ -14,10 +14,10 @@ import { fromMarkdown } from 'mdast-util-from-markdown'
 import { gfmFromMarkdown } from 'mdast-util-gfm'
 import { gfm } from 'micromark-extension-gfm'
 import { type Metadata, type ResolvingMetadata } from 'next'
-import { notFound } from 'next/navigation'
 
 import { newEditLink } from './GuidesMdx.template'
 import { checkGuidePageEnabled } from './NavigationPageStatus.utils'
+import { notFoundWithPathname } from './notFound.utils'
 
 const { metadataTitle } = getCustomContent(['metadata:title'])
 
@@ -56,7 +56,7 @@ const getGuidesMarkdownInternal = async (slug: string[]) => {
     !fullPath.startsWith(GUIDES_DIRECTORY) ||
     !PUBLISHED_SECTIONS.some((section) => relPath.startsWith(section))
   ) {
-    notFound()
+    notFoundWithPathname(guidesPath)
   }
 
   /**
@@ -65,7 +65,7 @@ const getGuidesMarkdownInternal = async (slug: string[]) => {
    */
   if (!checkGuidePageEnabled(guidesPath)) {
     console.log('Page is disabled: %s', guidesPath)
-    notFound()
+    notFoundWithPathname(guidesPath)
   }
 
   try {
@@ -100,7 +100,7 @@ const getGuidesMarkdownInternal = async (slug: string[]) => {
       )
       Sentry.captureException(error)
     }
-    notFound()
+    notFoundWithPathname(guidesPath)
   }
 }
 
diff --git a/apps/docs/features/docs/notFound.utils.ts b/apps/docs/features/docs/notFound.utils.ts
new file mode 100644
index 00000000000..cd090a1e546
--- /dev/null
+++ b/apps/docs/features/docs/notFound.utils.ts
@@ -0,0 +1,19 @@
+import * as Sentry from '@sentry/nextjs'
+import { notFound } from 'next/navigation'
+
+/**
+ * Triggers a Next.js 404 while recording the requested path as a Sentry tag.
+ *
+ * `notFound()` itself does not create a Sentry event, but tagging the active
+ * scope means any error captured during the same request (and any event the
+ * Sentry SDK records for the render) carries the exact path under
+ * `404.pathname`. That makes 404s filterable and groupable in Sentry/Discover
+ * instead of only being inferable from the route's transaction name.
+ *
+ * @param pathname - The user-facing path that was not found, e.g.
+ * `/guides/functions/runtimes/node-22`.
+ */
+export function notFoundWithPathname(pathname: string): never {
+  Sentry.setTag('404.pathname', pathname)
+  notFound()
+}
diff --git a/apps/docs/resources/guide/guideModelLoader.ts b/apps/docs/resources/guide/guideModelLoader.ts
index 551bd98abfe..1fa7858336a 100644
--- a/apps/docs/resources/guide/guideModelLoader.ts
+++ b/apps/docs/resources/guide/guideModelLoader.ts
@@ -1,13 +1,13 @@
-import matter from 'gray-matter'
 import { promises as fs } from 'node:fs'
 import { join, relative, resolve } from 'node:path'
-
 import { extractMessageFromAnyError, FileNotFoundError, MultiError } from '~/app/api/utils'
 import { preprocessMdxWithDefaults } from '~/features/directives/utils'
 import { checkGuidePageEnabled } from '~/features/docs/NavigationPageStatus.utils'
 import { Both, Result } from '~/features/helpers.fn'
 import { GUIDES_DIRECTORY } from '~/lib/docs'
 import { processMdx } from '~/scripts/helpers.mdx'
+import matter from 'gray-matter'
+
 import { GuideModel } from './guideModel'
 
 /**
@@ -140,7 +140,7 @@ export class GuideModelLoader {
       },
       (error) => {
         if (error instanceof Error && 'code' in error && error.code === 'ENOENT') {
-          throw new FileNotFoundError('', error)
+          throw new FileNotFoundError(join(GUIDES_DIRECTORY, relPath), error)
         }
         throw new Error(
           `Failed to load guide from ${relPath}: ${extractMessageFromAnyError(error)}`,