diff --git a/layouts/DocsPage/Navigation.stories.tsx b/layouts/DocsPage/Navigation.stories.tsx
index cd3e40fc91..441e3d3194 100644
--- a/layouts/DocsPage/Navigation.stories.tsx
+++ b/layouts/DocsPage/Navigation.stories.tsx
@@ -22,6 +22,10 @@ export const NavigationFourLevels = () => {
                   title: "Deploy Machine ID on AWS",
                   slug: "/enroll-resources/machine-id/deployment/aws/",
                 },
+                {
+                  title: "General Deployment Tips",
+                  slug: "/enroll-resources/machine-id/deployment/deployment/",
+                },
               ],
             },
           ],
diff --git a/layouts/DocsPage/Navigation.tsx b/layouts/DocsPage/Navigation.tsx
index 4de84d9678..b753628e54 100644
--- a/layouts/DocsPage/Navigation.tsx
+++ b/layouts/DocsPage/Navigation.tsx
@@ -12,6 +12,7 @@ import {
 } from "./types";
 import styles from "./Navigation.module.css";
 import { useVersionAgnosticPages } from "utils/useVersionAgnosticPages";
+import { dirname } from "path";
 
 const SCOPELESS_HREF_REGEX = /\?|\#/;
 
@@ -45,10 +46,13 @@ const DocsNavigationItems = ({
     <>
       {!!entries.length &&
         entries.map((entry) => {
+          // Determine whether to highlight the entry in the navigation sidebar.
+          // We highlight an entry if:
+          // - It is the currently selected entry.
+          // - One of its entries is either the currently selected entry or the
+          //   parent of the currently selected entry.
           const selected = entry.slug === docPath;
-          const active =
-            selected ||
-            entry.entries?.some((entry) => docPath.startsWith(entry.slug));
+          const active = hasChildEntry(entry, docPath);
 
           return (
             <li key={entry.slug}>
@@ -84,6 +88,24 @@ const DocsNavigationItems = ({
   );
 };
 
+// hasChildEntry recursively descends through entry to determine if it or one of
+// its children has the provided slug.
+function hasChildEntry(
+  entry: NavigationCategory | NavigationItem,
+  slug: string
+) {
+  const item = entry as NavigationItem;
+  if (item.slug && item.slug === slug) {
+    return true;
+  }
+  if (!entry.entries) {
+    return false;
+  }
+  return entry.entries.some((e) => {
+    return hasChildEntry(e, slug);
+  });
+}
+
 interface DocNavigationCategoryProps extends NavigationCategory {
   id: number;
   opened: boolean;
diff --git a/server/pages-helpers.ts b/server/pages-helpers.ts
index 88f68f6f6e..d982716981 100644
--- a/server/pages-helpers.ts
+++ b/server/pages-helpers.ts
@@ -98,11 +98,18 @@ const categoryPagePathForDir = (fs, dirPath) => {
 
   const outerCategoryPage = join(dirname(dirPath), name + ".mdx");
   const innerCategoryPage = join(dirPath, name + ".mdx");
+  const outerExists = fs.existsSync(outerCategoryPage);
+  const innerExists = fs.existsSync(innerCategoryPage);
 
-  if (fs.existsSync(outerCategoryPage)) {
+  if (outerExists && innerExists) {
+    throw new Error(
+      `cannot generate the docs navigation sidebar due to an ambiguous category page: must have a page named ${outerCategoryPage} or ${innerCategoryPage}, not not both`
+    );
+  }
+  if (outerExists) {
     return outerCategoryPage;
   }
-  if (fs.existsSync(innerCategoryPage)) {
+  if (innerExists) {
     return innerCategoryPage;
   }
   throw new Error(
diff --git a/uvu-tests/config-docs.test.ts b/uvu-tests/config-docs.test.ts
index b7272875d6..54524d8b5b 100644
--- a/uvu-tests/config-docs.test.ts
+++ b/uvu-tests/config-docs.test.ts
@@ -434,4 +434,29 @@ title: Database Access Deployment Guides
   assert.equal(actual, expected);
 });
 
+Suite("page named after directory at two possible dir levels", () => {
+  const files = {
+    "/docs/pages/database-access/deployment/deployment.mdx": `---
+title: Database Access Deployment Guides
+---`,
+    "/docs/pages/database-access/deployment.mdx": `---
+title: Deploying the Database Service
+---`,
+    "/docs/pages/database-access/deployment/kubernetex.mdx": `---
+title: Deploying the Database Service on Kubernetes
+---`,
+  };
+
+  const vol = Volume.fromJSON(files);
+  const fs = createFsFromVolume(vol);
+  assert.throws(
+    () => {
+      const actual = generateNavPaths(fs, "/docs/pages/database-access");
+      console.log(actual);
+    },
+    "database-access/deployment/deployment.mdx",
+    "database-access/deployment.mdx"
+  );
+});
+
 Suite.run();