diff --git a/app/[[...path]]/page.tsx b/app/[[...path]]/page.tsx
index 6755f52b5acb66..3a980e1a43f16c 100644
--- a/app/[[...path]]/page.tsx
+++ b/app/[[...path]]/page.tsx
@@ -3,6 +3,7 @@ import {Metadata} from 'next';
 import {notFound} from 'next/navigation';
 import {Fragment, useMemo} from 'react';
 import {apiCategories} from 'sentry-docs/build/resolveOpenAPI';
+import {canonicalPath} from 'sentry-docs/canonical';
 import {ApiCategoryPage} from 'sentry-docs/components/apiCategoryPage';
 import {ApiPage} from 'sentry-docs/components/apiPage';
 import {DocPage} from 'sentry-docs/components/docPage';
@@ -289,17 +290,6 @@ type MetadataProps = {
   }>;
 };
 
-// Helper function to clean up canonical tags missing leading or trailing slash
-function formatCanonicalTag(tag: string) {
-  if (tag.charAt(0) !== '/') {
-    tag = '/' + tag;
-  }
-  if (tag.charAt(tag.length - 1) !== '/') {
-    tag += '/';
-  }
-  return tag;
-}
-
 // Helper function to resolve OG image URLs
 function resolveOgImageUrl(
   imageUrl: string | undefined,
@@ -369,7 +359,7 @@ export async function generateMetadata(props: MetadataProps): Promise<Metadata>
       description = pageNode.frontmatter.description ?? '';
 
       if (pageNode.frontmatter.customCanonicalTag) {
-        customCanonicalTag = formatCanonicalTag(pageNode.frontmatter.customCanonicalTag);
+        customCanonicalTag = pageNode.frontmatter.customCanonicalTag;
       }
 
       noindex = pageNode.frontmatter.noindex;
@@ -399,11 +389,9 @@ export async function generateMetadata(props: MetadataProps): Promise<Metadata>
 
   const images = [{url: ogImageUrl, width: 1200, height: 630}];
 
-  const canonical = customCanonicalTag
-    ? domain + customCanonicalTag
-    : params.path
-      ? `${domain}/${params.path.join('/')}/`
-      : domain;
+  const canonical = `${domain}${canonicalPath(
+    customCanonicalTag || params.path?.join('/') || ''
+  )}`;
 
   return {
     title,
diff --git a/app/sitemap.ts b/app/sitemap.ts
index 7ba3a6c6ba4609..85ffb16a5fdf80 100644
--- a/app/sitemap.ts
+++ b/app/sitemap.ts
@@ -1,4 +1,5 @@
 import type {MetadataRoute} from 'next';
+import {canonicalPath} from 'sentry-docs/canonical';
 import {DEVELOP_DOCS_INDEXABLE_ROOTS} from 'sentry-docs/developDocsConfig';
 import {type DocNode, getDocsRootNode} from 'sentry-docs/docTree';
 import {isDeveloperDocs} from 'sentry-docs/isDeveloperDocs';
@@ -50,13 +51,7 @@ export default async function sitemap(): Promise<MetadataRoute.Sitemap> {
 }
 
 function docsToSitemap(paths: string[], baseUrl: string): MetadataRoute.Sitemap {
-  const appendSlash = (path: string) => {
-    if (path === '' || path.endsWith('/')) {
-      return path;
-    }
-    return path + '/';
-  };
-  const toFullUrl = (path: string) => `${appendSlash(baseUrl)}${appendSlash(path)}`;
+  const toFullUrl = (path: string) => `${baseUrl}${canonicalPath(path)}`;
   const toSitemapEntry = (path: string) => ({url: toFullUrl(path)});
   return ['', ...paths].map(toSitemapEntry);
 }
diff --git a/middleware.test.ts b/middleware.test.ts
index 6e8f6e7763517f..e36db091965ed1 100644
--- a/middleware.test.ts
+++ b/middleware.test.ts
@@ -199,6 +199,17 @@ describe('canonical Link header on .md responses', () => {
     );
   });
 
+  it.each([
+    '/platforms/java/migration/7.x-to-8.0',
+    '/platforms/python/migration/1.x-to-2.x',
+  ])('does not add a trailing slash to a dotted document path: %s', async path => {
+    const {middleware} = await importMiddleware({});
+    const res = middleware(makeRequest(`${path}.md`));
+    expect(res.headers.get('Link')).toBe(
+      `<https://docs.sentry.io${path}>; rel="canonical"`
+    );
+  });
+
   it('maps /index.md to the root canonical URL', async () => {
     const {middleware} = await importMiddleware({});
     const res = middleware(makeRequest('/index.md'));
diff --git a/middleware.ts b/middleware.ts
index 59b1b8cec656b4..713904c16bea64 100644
--- a/middleware.ts
+++ b/middleware.ts
@@ -1,6 +1,7 @@
 import * as Sentry from '@sentry/nextjs';
 import type {NextRequest} from 'next/server';
 import {NextResponse, userAgent} from 'next/server';
+import {canonicalPath} from 'sentry-docs/canonical';
 import {
   AI_AGENT_PATTERN,
   matchPattern,
@@ -21,7 +22,11 @@ const CANONICAL_HOST = new URL(BASE_URL).hostname;
 // Production domains whose content should be indexable by search engines.
 // All other hostnames (Vercel preview/deployment URLs, old production deployments)
 // get X-Robots-Tag: noindex to prevent search engines from indexing stale content.
-const INDEXABLE_HOSTNAMES = new Set(['docs.sentry.io', 'develop.sentry.dev', 'localhost']);
+const INDEXABLE_HOSTNAMES = new Set([
+  'docs.sentry.io',
+  'develop.sentry.dev',
+  'localhost',
+]);
 
 export const config = {
   // learn more: https://nextjs.org/docs/pages/building-your-application/routing/middleware#matcher
@@ -309,7 +314,7 @@ function rewriteWithClassification(
 function mdToCanonicalPath(mdPathname: string): string {
   const withoutExt = mdPathname.replace(/\.md$/, '');
   if (withoutExt === '/index') return '/';
-  return withoutExt.endsWith('/') ? withoutExt : `${withoutExt}/`;
+  return canonicalPath(withoutExt);
 }
 
 /**
diff --git a/src/canonical.spec.ts b/src/canonical.spec.ts
new file mode 100644
index 00000000000000..7783406db54ff1
--- /dev/null
+++ b/src/canonical.spec.ts
@@ -0,0 +1,16 @@
+import {describe, expect, it} from 'vitest';
+
+import {canonicalPath} from './canonical';
+
+describe('canonicalPath', () => {
+  it.each([
+    ['', '/'],
+    ['/', '/'],
+    ['platforms/java/configuration/options', '/platforms/java/configuration/options/'],
+    ['/platforms/java/configuration/options/', '/platforms/java/configuration/options/'],
+    ['platforms/java/migration/7.x-to-8.0', '/platforms/java/migration/7.x-to-8.0'],
+    ['/platforms/python/migration/1.x-to-2.x/', '/platforms/python/migration/1.x-to-2.x'],
+  ])('formats %j as %j', (pathname, expected) => {
+    expect(canonicalPath(pathname)).toBe(expected);
+  });
+});
diff --git a/src/canonical.ts b/src/canonical.ts
new file mode 100644
index 00000000000000..bb13aa5e71a586
--- /dev/null
+++ b/src/canonical.ts
@@ -0,0 +1,18 @@
+/**
+ * Formats a documentation pathname to match Next.js's `trailingSlash: true`
+ * redirects. Next.js treats a final segment ending in `.<word characters>` as
+ * file-like and removes its trailing slash.
+ */
+export function canonicalPath(pathname: string): string {
+  const withLeadingSlash = pathname.startsWith('/') ? pathname : `/${pathname}`;
+  const withoutTrailingSlash = withLeadingSlash.replace(/\/+$/, '');
+
+  if (!withoutTrailingSlash) {
+    return '/';
+  }
+
+  const finalSegment = withoutTrailingSlash.slice(
+    withoutTrailingSlash.lastIndexOf('/') + 1
+  );
+  return /\.\w+$/.test(finalSegment) ? withoutTrailingSlash : `${withoutTrailingSlash}/`;
+}