diff --git a/package-lock.json b/package-lock.json
index 72efcda..a449986 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -1175,9 +1175,9 @@
       }
     },
     "node_modules/@fastify/static": {
-      "version": "9.1.0",
-      "resolved": "https://registry.npmjs.org/@fastify/static/-/static-9.1.0.tgz",
-      "integrity": "sha512-EPRNQYqEYEYTK8yyGbcM0iHpyJaupb94bey5O6iCQfLTADr02kaZU+qeHSdd9H9TiMwTBVkrMa59V8CMbn3avQ==",
+      "version": "9.1.3",
+      "resolved": "https://registry.npmjs.org/@fastify/static/-/static-9.1.3.tgz",
+      "integrity": "sha512-aXrYtsiryLhRxRNaxNqsn7FUISeb7rB9q4eHUPIot5aeQBLNahnz1m6thzm7JWC1poSGXS9XrX8DvuMivp2hkQ==",
       "funding": [
         {
           "type": "github",
@@ -4052,9 +4052,9 @@
       "license": "BSD-3-Clause"
     },
     "node_modules/fastify": {
-      "version": "5.8.4",
-      "resolved": "https://registry.npmjs.org/fastify/-/fastify-5.8.4.tgz",
-      "integrity": "sha512-sa42J1xylbBAYUWALSBoyXKPDUvM3OoNOibIefA+Oha57FryXKKCZarA1iDntOCWp3O35voZLuDg2mdODXtPzQ==",
+      "version": "5.8.5",
+      "resolved": "https://registry.npmjs.org/fastify/-/fastify-5.8.5.tgz",
+      "integrity": "sha512-Yqptv59pQzPgQUSIm87hMqHJmdkb1+GPxdE6vW6FRyVE9G86mt7rOghitiU4JHRaTyDUk9pfeKmDeu70lAwM4Q==",
       "funding": [
         {
           "type": "github",
@@ -7294,9 +7294,9 @@
       }
     },
     "node_modules/postcss": {
-      "version": "8.5.8",
-      "resolved": "https://registry.npmjs.org/postcss/-/postcss-8.5.8.tgz",
-      "integrity": "sha512-OW/rX8O/jXnm82Ey1k44pObPtdblfiuWnrd8X7GJ7emImCOstunGbXUpp7HdBrFQX6rJzn3sPT397Wp5aCwCHg==",
+      "version": "8.5.13",
+      "resolved": "https://registry.npmjs.org/postcss/-/postcss-8.5.13.tgz",
+      "integrity": "sha512-qif0+jGGZoLWdHey3UFHHWP0H7Gbmsk8T5VEqyYFbWqPr1XqvLGBbk/sl8V5exGmcYJklJOhOQq1pV9IcsiFag==",
       "dev": true,
       "funding": [
         {
diff --git a/src/client/routes/wiki-route.tsx b/src/client/routes/wiki-route.tsx
index afc7d31..6a12ea2 100644
--- a/src/client/routes/wiki-route.tsx
+++ b/src/client/routes/wiki-route.tsx
@@ -15,17 +15,56 @@ import { useWikiConfig } from "@/client/wiki-config";
 import { getTopicColor, type TopicAliasConfig } from "@/lib/wiki-config";
 import type { WikiHeading, WikiNeighbor, WikiPageData } from "@/lib/wiki-shared";
 import { usePersonImage } from "@/client/use-person-image";
+import { createHeadingId } from "@/lib/markdown";
 
 import { fetchJson, isSetupRequiredResponse } from "../api";
 import { RouteErrorBoundary } from "../route-error-boundary";
 
 const remarkPlugins = [remarkGfm];
 const rehypePlugins = [rehypeHighlight];
+
+/** Extracts plain text from React children to use for ID generation */
+function getTextContent(children: React.ReactNode): string {
+  if (typeof children === "string") return children;
+  if (Array.isArray(children)) return children.map(getTextContent).join("");
+  // @ts-ignore - children might be a ReactElement with props
+  if (children?.props?.children) return getTextContent(children.props.children);
+  return "";
+}
+
 const markdownComponents = {
-  h1: ({ ...props }) => <h1 className="mb-4 text-3xl scroll-mt-20" {...props} />,
-  h2: ({ ...props }) => <h2 className="font-display mb-3 mt-10 text-xl font-light scroll-mt-20" {...props} />,
-  h3: ({ ...props }) => <h3 className="font-display mb-2 mt-7 text-lg font-light scroll-mt-20" {...props} />,
-  h4: ({ ...props }) => <h4 className="mb-2 mt-5 text-base font-medium scroll-mt-20" {...props} />,
+  h1: ({ children, ...props }: any) => {
+    const id = createHeadingId(getTextContent(children));
+    return (
+      <h1 id={id} className="mb-4 text-3xl scroll-mt-20" {...props}>
+        {children}
+      </h1>
+    );
+  },
+  h2: ({ children, ...props }: any) => {
+    const id = createHeadingId(getTextContent(children));
+    return (
+      <h2 id={id} className="font-display mb-3 mt-10 text-xl font-light scroll-mt-20" {...props}>
+        {children}
+      </h2>
+    );
+  },
+  h3: ({ children, ...props }: any) => {
+    const id = createHeadingId(getTextContent(children));
+    return (
+      <h3 id={id} className="font-display mb-2 mt-7 text-lg font-light scroll-mt-20" {...props}>
+        {children}
+      </h3>
+    );
+  },
+  h4: ({ children, ...props }: any) => {
+    const id = createHeadingId(getTextContent(children));
+    return (
+      <h4 id={id} className="mb-2 mt-5 text-base font-medium scroll-mt-20" {...props}>
+        {children}
+      </h4>
+    );
+  },
   p: ({ ...props }) => <p className="mb-4 leading-[1.8]" {...props} />,
   ul: ({ ...props }) => <ul className="mb-4 list-disc pl-6 leading-[1.8]" {...props} />,
   ol: ({ ...props }) => <ol className="mb-4 list-decimal pl-6 leading-[1.8]" {...props} />,
@@ -669,7 +708,7 @@ export function Component() {
           )}
 
           {/* Desktop sidebar — TOC + mini graph */}
-          <aside className="hidden xl:block absolute -right-60 top-0 w-52">
+          <aside className="hidden xl:block absolute -right-60 top-0 bottom-0 w-52">
             <div className="sticky top-8">
               {filteredHeadings.length > 0 && (
                 <TableOfContents headings={filteredHeadings} activeId={activeId} />
diff --git a/src/lib/markdown.ts b/src/lib/markdown.ts
index ce2f37e..48011bc 100644
--- a/src/lib/markdown.ts
+++ b/src/lib/markdown.ts
@@ -133,7 +133,12 @@ export function stripLeadingMarkdownTitle(markdown: string) {
 }
 
 export function createHeadingId(text: string) {
-  return text.toLowerCase().replace(/[^\w\s-]/g, "").replace(/\s+/g, "-");
+  return text
+    .toLowerCase()
+    .replace(/[^\w\s-]/g, "")
+    .replace(/_/g, "")
+    .trim()
+    .replace(/\s+/g, "-");
 }
 
 export function extractMarkdownHeadings(markdown: string): WikiHeading[] {