diff --git a/site/gatsby-site/playwright/e2e/navigation.spec.ts b/site/gatsby-site/playwright/e2e/navigation.spec.ts
index eb5578903f..b27595873a 100644
--- a/site/gatsby-site/playwright/e2e/navigation.spec.ts
+++ b/site/gatsby-site/playwright/e2e/navigation.spec.ts
@@ -36,4 +36,48 @@ test.describe('Navigation', () => {
     await page.getByTestId('sidebar-desktop').locator('#sidebar > [data-testid="sidebar-tree"] > [data-testid="sidebar-welcome"] > [data-testid="sidebar-link"]').click();
     await expect(page.locator('.rightSideTitle')).not.toBeVisible();
   });
+
+  test('Check right sidebar "Contents" scroll-to section on click on docs', async ({ page }) => {
+    await page.setViewportSize({ width: 1280, height: 800 });
+
+    await page.goto('/');
+
+    const aboutLink = await page.locator('#main-footer .tw-footer-link').filter({ hasText: /^About$/ });
+    if (await aboutLink.count() > 0) {
+      await aboutLink.click();
+      
+      await page.locator('.rightSideTitle:has-text("CONTENTS")').waitFor({ state: 'visible' });
+      const listItems = await page.locator('.rightSideBarUL li');
+      expect(await listItems.count()).toBeGreaterThanOrEqual(1);
+
+      await listItems.nth(1).click();
+      await page.waitForTimeout(700);
+
+      const subject = await page.locator('h2:has-text(\'Why "AI Incidents"?\')');
+      const boundingBox = await subject.boundingBox();
+      expect(boundingBox?.y).toBeCloseTo(0, 30);
+    }
+  });
+
+  test('Check right sidebar "Contents" scroll-to section on click on prismic blog post', async ({ page }) => {
+    await page.setViewportSize({ width: 1280, height: 800 });
+
+    await page.goto('/blog');
+
+    const postLink = await page.locator('h5:has-text("AI Incident Roundup – January ‘24")');
+    if (await postLink.count() > 0) {
+      await postLink.click();
+
+      await page.locator('.rightSideTitle:has-text("CONTENTS")').waitFor({ state: 'visible' });
+      const listItems = await page.locator('.rightSideBarUL li');
+      expect(await listItems.count()).toBeGreaterThanOrEqual(1);
+
+      await listItems.nth(1).click();
+      await page.waitForTimeout(700);
+
+      const subject = await page.locator('h2:has-text("🗄 Trending in the AIID")');
+      const boundingBox = await subject.boundingBox();
+      expect(boundingBox?.y).toBeCloseTo(0, 30);
+    }
+  });
 });
diff --git a/site/gatsby-site/src/components/CustomHeaders.js b/site/gatsby-site/src/components/CustomHeaders.js
new file mode 100644
index 0000000000..7d3f6d3ff9
--- /dev/null
+++ b/site/gatsby-site/src/components/CustomHeaders.js
@@ -0,0 +1,33 @@
+import React from 'react';
+import slugify from 'slugify';
+
+const getText = (children) => {
+  // Recursively find all text nodes in the children
+  let text = '';
+
+  React.Children.forEach(children, (child) => {
+    if (typeof child === 'string') {
+      text += child;
+    } else if (child.props && child.props.children) {
+      text += getText(child.props.children);
+    }
+  });
+  return text;
+};
+
+const Heading = ({ level, children }) => {
+  const text = getText(children);
+
+  const id = slugify(text, { lower: true });
+
+  const HeadingComponent = `h${level}`;
+
+  return <HeadingComponent id={id}>{children}</HeadingComponent>;
+};
+
+export const Heading1 = ({ children }) => <Heading level={1}>{children}</Heading>;
+export const Heading2 = ({ children }) => <Heading level={2}>{children}</Heading>;
+export const Heading3 = ({ children }) => <Heading level={3}>{children}</Heading>;
+export const Heading4 = ({ children }) => <Heading level={4}>{children}</Heading>;
+export const Heading5 = ({ children }) => <Heading level={5}>{children}</Heading>;
+export const Heading6 = ({ children }) => <Heading level={6}>{children}</Heading>;
diff --git a/site/gatsby-site/src/components/PrismicOutline.js b/site/gatsby-site/src/components/PrismicOutline.js
new file mode 100644
index 0000000000..6625f3f1fe
--- /dev/null
+++ b/site/gatsby-site/src/components/PrismicOutline.js
@@ -0,0 +1,35 @@
+import React from 'react';
+
+const PrismicSidebarLayout = ({ tableOfContents }) => {
+  let navItems;
+
+  if (tableOfContents.length > 0) {
+    navItems = tableOfContents.map((item) => {
+      return (
+        <li key={item.id} className="list-none">
+          <a
+            href={`#${item.id}`}
+            className="text-[#5c6975] no-underline font-normal py-2 pr-0 block relative hover:text-blue-500"
+          >
+            {item.title}
+          </a>
+        </li>
+      );
+    });
+  }
+
+  return (
+    <aside className="sidebar right">
+      <ul data-cy="outline" className="rightSideBarUL list-revert pl-8">
+        {navItems?.length > 0 && (
+          <>
+            <li className="rightSideTitle">CONTENTS</li>
+            {navItems}
+          </>
+        )}
+      </ul>
+    </aside>
+  );
+};
+
+export default PrismicSidebarLayout;
diff --git a/site/gatsby-site/src/components/blog/PrismicBlogPost.js b/site/gatsby-site/src/components/blog/PrismicBlogPost.js
index 021585d462..6f50575f45 100644
--- a/site/gatsby-site/src/components/blog/PrismicBlogPost.js
+++ b/site/gatsby-site/src/components/blog/PrismicBlogPost.js
@@ -8,9 +8,23 @@ import React, { useEffect } from 'react';
 import { Trans } from 'react-i18next';
 import config from '../../../config';
 import { useLayoutContext } from 'contexts/LayoutContext';
-import Outline from 'components/Outline';
+import PrismicOutline from 'components/PrismicOutline';
+import { extractHeaders } from 'utils/extractHeaders';
+import { Heading1, Heading2 } from 'components/CustomHeaders';
 
 const PrismicBlogPost = ({ post, location }) => {
+  let headers = [];
+
+  const extractedHeaders = extractHeaders(post.data.content);
+
+  headers = extractedHeaders;
+
+  // Define custom components for Prismic Rich Text
+  const components = {
+    heading1: ({ children }) => <Heading1>{children}</Heading1>,
+    heading2: ({ children }) => <Heading2>{children}</Heading2>,
+  };
+
   const metaTitle = post.data.metatitle;
 
   const canonicalUrl = config.gatsby.siteUrl + location.pathname;
@@ -19,7 +33,7 @@ const PrismicBlogPost = ({ post, location }) => {
 
   const rightSidebar = (
     <>
-      <Outline location={loc} />
+      <PrismicOutline location={loc} tableOfContents={headers} />
     </>
   );
 
@@ -61,7 +75,7 @@ const PrismicBlogPost = ({ post, location }) => {
         </span>
       </div>
       <div className="prose">
-        <PrismicRichText field={post.data.content.richText} />
+        <PrismicRichText field={post.data.content.richText} components={components} />
       </div>
     </>
   );
diff --git a/site/gatsby-site/src/components/doc/PrismicDocPost.js b/site/gatsby-site/src/components/doc/PrismicDocPost.js
index f2475bf791..3387968f99 100644
--- a/site/gatsby-site/src/components/doc/PrismicDocPost.js
+++ b/site/gatsby-site/src/components/doc/PrismicDocPost.js
@@ -1,19 +1,27 @@
+import React, { useEffect } from 'react';
 import { PrismicRichText } from '@prismicio/react';
-import TranslationBadge from 'components/i18n/TranslationBadge';
 import { Link } from 'gatsby';
-import React, { useEffect } from 'react';
 import { Trans } from 'react-i18next';
 import config from '../../../config';
 import { useLayoutContext } from 'contexts/LayoutContext';
-import Outline from 'components/Outline';
+import PrismicOutline from 'components/PrismicOutline';
 import Leaderboards from 'components/landing/Leaderboards';
 import Sponsors from 'components/landing/Sponsors';
-import { RichText } from 'prismic-reactjs';
-import ReactMarkdown from 'react-markdown';
-import remarkGfm from 'remark-gfm';
+import TranslationBadge from 'components/i18n/TranslationBadge';
+import { extractHeaders } from 'utils/extractHeaders';
+import { Heading1, Heading2 } from 'components/CustomHeaders';
 
 const PrismicDocPost = ({ doc, location }) => {
+  let headers = [];
+
+  const extractedHeaders = extractHeaders(doc.data.content);
+
+  headers = extractedHeaders;
+
+  // Define custom components for Prismic Rich Text
   const components = {
+    heading1: ({ children }) => <Heading1>{children}</Heading1>,
+    heading2: ({ children }) => <Heading2>{children}</Heading2>,
     Leaderboards: <Leaderboards />,
     Sponsors: <Sponsors />,
   };
@@ -24,7 +32,7 @@ const PrismicDocPost = ({ doc, location }) => {
 
   const rightSidebar = (
     <>
-      <Outline location={loc} />
+      <PrismicOutline location={loc} tableOfContents={headers} />
     </>
   );
 
@@ -36,7 +44,7 @@ const PrismicDocPost = ({ doc, location }) => {
 
   return (
     <>
-      <div className={'titleWrapper'}>
+      <div className="titleWrapper">
         <h1>{doc.data.title}</h1>
       </div>
       <div className="flex items-center mb-6 -mt-1 flex-wrap">
@@ -49,27 +57,16 @@ const PrismicDocPost = ({ doc, location }) => {
           </>
         )}
       </div>
-      {doc.data.content.map((content, index) => {
-        return (
-          <>
-            {content.markdown && (
-              <div className="prose">
-                {(() => {
-                  const rawMarkdown = RichText.asText(content.markdown.richText);
-
-                  return <ReactMarkdown remarkPlugins={[remarkGfm]}>{rawMarkdown}</ReactMarkdown>;
-                })()}
-              </div>
-            )}
-            {content.text && (
-              <div className="prose">
-                <PrismicRichText key={index} field={content.text.richText} />
-              </div>
-            )}
-            {content.component && <div className=" mt-4">{components[content.component]}</div>}
-          </>
-        );
-      })}
+      {doc.data.content.map((content, index) => (
+        <>
+          {content.text && (
+            <div className="prose">
+              <PrismicRichText key={index} field={content.text.richText} components={components} />
+            </div>
+          )}
+          {content.component && <div className="mt-4">{components[content.component]}</div>}
+        </>
+      ))}
     </>
   );
 };
diff --git a/site/gatsby-site/src/utils/extractHeaders.js b/site/gatsby-site/src/utils/extractHeaders.js
new file mode 100644
index 0000000000..3d8fc4217a
--- /dev/null
+++ b/site/gatsby-site/src/utils/extractHeaders.js
@@ -0,0 +1,36 @@
+import slugify from 'slugify';
+
+// Extract headers from a content object
+export const extractHeaders = (content) => {
+  const headers = [];
+
+  let richText;
+
+  if (content.length > 0) {
+    content.forEach((block) => {
+      richText = block.text.richText;
+      headers.push(...extractHeadersFromRichText(richText));
+    });
+  } else {
+    richText = content.richText;
+    headers.push(...extractHeadersFromRichText(richText));
+  }
+
+  return headers;
+};
+
+// Extract headers from a rich text object and return an array of headers with id and title
+const extractHeadersFromRichText = (richText) => {
+  const headers = [];
+
+  richText.forEach((block) => {
+    if (block.type === 'heading1' || block.type === 'heading2') {
+      headers.push({
+        id: slugify(block.text, { lower: true }),
+        title: block.text,
+      });
+    }
+  });
+
+  return headers;
+};