diff --git a/Source/SuperOffice.DocsNext/ClientApp/astro.config.mjs b/Source/SuperOffice.DocsNext/ClientApp/astro.config.mjs
index a28417b5..c2266a64 100644
--- a/Source/SuperOffice.DocsNext/ClientApp/astro.config.mjs
+++ b/Source/SuperOffice.DocsNext/ClientApp/astro.config.mjs
@@ -10,6 +10,7 @@ import { rehypeHeadingIds } from "@astrojs/markdown-remark";
 import rehypeAutolinkHeadings from "rehype-autolink-headings";
 import remarkIncludeDirective from "./src/plugins/AddIncludesToMarkdown.js";
 import remarkRestyleDirective from "./src/plugins/RestyleDirectives.js";
+import remarkFixRelativeLinks from "./src/plugins/FixMarkdownLinks.js"
 import react from "@astrojs/react";
 import yaml from '@rollup/plugin-yaml';
 import redirectFrom from "astro-redirect-from";
@@ -22,7 +23,8 @@ export default defineConfig({
   ],
 
   markdown: {
-    remarkPlugins: [remarkDirective, codeImport, remarkIncludeDirective, remarkRestyleDirective],
+    remarkPlugins: [remarkDirective, codeImport, remarkIncludeDirective, remarkRestyleDirective, remarkFixRelativeLinks
+    ],
     rehypePlugins: [
       rehypeHeadingIds,
       [
@@ -123,5 +125,5 @@ export default defineConfig({
   logLevel: process.env.CI ? 'error' : 'info',
   site: "https://app-superoffice-docs-dev.azurewebsites.net/",
   // base: "/",
-  // trailingSlash: "never",
+  // trailingSlash: "ignore",
 });
diff --git a/Source/SuperOffice.DocsNext/ClientApp/src/components/CategoryLandingAdditionalContentCard.astro b/Source/SuperOffice.DocsNext/ClientApp/src/components/CategoryLandingAdditionalContentCard.astro
index 211e0a4e..d6464e0a 100644
--- a/Source/SuperOffice.DocsNext/ClientApp/src/components/CategoryLandingAdditionalContentCard.astro
+++ b/Source/SuperOffice.DocsNext/ClientApp/src/components/CategoryLandingAdditionalContentCard.astro
@@ -17,14 +17,14 @@ interface Props {
     class={`bg-white px-3 py-5 lg:m-0 duration-300 ease-in-out transition-shadow hover:shadow-[0_0px_8px_rgba(0,0,0,0.70)] min-h-full`}
   >
     <div class="grid grid-cols-1 gap-2 h-fit">
-      <a href={item.url && resolveRelativeFilePath(currentPath,item.url)} class="font-bold text-[17px]">{item.title}</a>
+      <a href={item.url && resolveRelativeFilePath(currentPath, item.url)} class="font-bold text-[17px]">{item.title}</a>
       {
         item.links?.map((subitem) => {
           return (
             <div class="flex flex-col items-center pb-1">
               <a
                 class="w-full hover:underline text-superOfficeGreen"
-                href={subitem.url}
+                href={resolveRelativeFilePath(currentPath, subitem.url)}
               >
                 {subitem.text}
               </a>
diff --git a/Source/SuperOffice.DocsNext/ClientApp/src/components/TableOfContentList.tsx b/Source/SuperOffice.DocsNext/ClientApp/src/components/TableOfContentList.tsx
index ca5bfa3c..887fff4b 100644
--- a/Source/SuperOffice.DocsNext/ClientApp/src/components/TableOfContentList.tsx
+++ b/Source/SuperOffice.DocsNext/ClientApp/src/components/TableOfContentList.tsx
@@ -104,7 +104,7 @@ export default function TableOfContentList({
       // console.warn(`[generatePath] Missing href/topicHref for TOC item:`, item);
       return "#";
     }
-    const formattedURL = `${slug}/${trimFileExtension(rawPath)}`.replace("/index", "")
+    const formattedURL = `${slug}/${trimFileExtension(rawPath)}`.replace("/index", "/")
     const resolvedPath = new URL(formattedURL, "http://docs.superoffice.com").pathname;
     return resolvedPath;
   };
diff --git a/Source/SuperOffice.DocsNext/ClientApp/src/plugins/FixMarkdownLinks.js b/Source/SuperOffice.DocsNext/ClientApp/src/plugins/FixMarkdownLinks.js
new file mode 100644
index 00000000..326e069d
--- /dev/null
+++ b/Source/SuperOffice.DocsNext/ClientApp/src/plugins/FixMarkdownLinks.js
@@ -0,0 +1,26 @@
+import { visit } from 'unist-util-visit';
+
+/**
+ * Fix Markdown links and definitions that end with `.md` or `/index.md`
+ */
+export default function remarkFixMarkdownLinks() {
+  return (tree) => {
+    // Handle both inline links and reference definitions
+    visit(tree, ['link', 'definition'], (node) => {
+      if (!node.url || typeof node.url !== 'string') return;
+
+      let url = node.url.trim();
+
+      // Skip external and anchor links
+      if (url.startsWith('http') || url.startsWith('#')) return;
+
+      // Remove trailing /index.md
+      url = url.replace(/\/index\.md(?=$|[?#])/i, '/');
+
+      // Remove trailing .md
+      url = url.replace(/\.md$/i, '');
+
+      node.url = url;
+    });
+  };
+}
diff --git a/Source/SuperOffice.DocsNext/ClientApp/src/plugins/RestyleDirectives.js b/Source/SuperOffice.DocsNext/ClientApp/src/plugins/RestyleDirectives.js
index a52007a4..2ed8d653 100644
--- a/Source/SuperOffice.DocsNext/ClientApp/src/plugins/RestyleDirectives.js
+++ b/Source/SuperOffice.DocsNext/ClientApp/src/plugins/RestyleDirectives.js
@@ -46,9 +46,10 @@ export default function remarkRestyleDirective() {
       
       if (remainingText) {
         textNode.value = remainingText;
-        contentChildren = para.children;
+        contentChildren = node.children;
       } else {
-        contentChildren = para.children.slice(1);
+        // Remove first paragraph if it only contained the directive
+        contentChildren = node.children.slice(1);
       }
 
       node.type = 'parent';
diff --git a/Source/SuperOffice.DocsNext/ClientApp/src/utils/slugUtils.ts b/Source/SuperOffice.DocsNext/ClientApp/src/utils/slugUtils.ts
index a4b8ce5e..03247637 100644
--- a/Source/SuperOffice.DocsNext/ClientApp/src/utils/slugUtils.ts
+++ b/Source/SuperOffice.DocsNext/ClientApp/src/utils/slugUtils.ts
@@ -9,7 +9,7 @@ const contentRepo = "superoffice-docs"; // primary content repository
  */
 export function stripFilePathAndExtension(filePath: string, collection: string): string {
   const base = `${contentDir}/`
-  return filePath.replace(base, "").replace(`${collection}/`, "").replace(/\/index/g, "").replace(/\.(md|yml|yaml)$/g, "");;
+  return filePath.replace(base, "").replace(`${collection}/`, "").replace(/\/index/g, "/").replace(/\.(md|yml|yaml)$/g, "");;
 }
 
 /**
@@ -154,6 +154,6 @@ export function resolveRelativeFilePath(currentPath: string, filepath: string):
     return filepath
   }
 
-  return `${currentPath.split("/").pop()?.replace(/\.html$/, "")}/${trimFileExtension(filepath).replace(/\/index$/, "")}`
+  return `${currentPath.split("/").filter(Boolean).pop()?.replace(/\.html$/, "")}/${trimFileExtension(filepath).replace(/\/index$/, "/")}`
 
 }
\ No newline at end of file
diff --git a/Source/SuperOffice.DocsNext/Program.cs b/Source/SuperOffice.DocsNext/Program.cs
index 5b7a74b2..7073ff34 100644
--- a/Source/SuperOffice.DocsNext/Program.cs
+++ b/Source/SuperOffice.DocsNext/Program.cs
@@ -108,6 +108,7 @@
         // Redirect /something.html -> /something (permanent redirect)
         .AddRedirect(@"^(.*)\.html$", "$1", statusCode: 301)
         .AddRewrite(@"^$", "index.html", skipRemainingRules: true)
+        .AddRewrite(@"^(.*)/$", "$1.html", skipRemainingRules: true)
         // Rewrite /something -> /something.html (internal rewrite)
         // But avoids rewriting known static file types
         .AddRewrite(@"^(?!.*\.(?:js|css|png|jpg|jpeg|gif|svg|ico|json|txt|xml|map)$)(.*)$", "$1.html", skipRemainingRules: true);