diff --git a/CHANGELOG.md b/CHANGELOG.md
index 063734640..ef38d64be 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -2,31 +2,31 @@
 
 ## 0.25.0
 
-## Automated Changelog Generation
+### Automated Changelog Generation
 
 We now automatically generate changelog entries for the `auto` changelog policy where none provided, instead of saying "No documented changes". The commits/PRs are grouped by their associated GitHub milestones and the milestone title and description are used in the changelog along with a list of related commits/PRs. Any unaccounted changes are grouped under the "Various improvements and fixes" section.
 
 PRs: #291, #290, #289, #287, #285
 
-## Added Maven Target (ongoing)
+### Added Maven Target (ongoing)
 
 Added the long-awaited Maven target, full with Android support.
 
 PRs: #271, #275, #276, #270, #258
 
-## Added symbol-collector Target
+### Added symbol-collector Target
 
 Added target for our very own [symbol-collector](https://github.com/getsentry/symbol-collector/) to collect and upload all native system symbols with Craft.
 
 PRs: #284, #277, #269, #268, #267, #266
 
-## Fixed Cocoapods Support
+### Fixed Cocoapods Support
 
-Turns out our Cocoapods target was a bit outdated and broken. We have fixed it in this release! 🥳 
+Turns out our Cocoapods target was a bit outdated and broken. We have fixed it in this release! 🥳
 
 PRs: #281, #282
 
-## Various fixes & improvements
+### Various fixes & improvements
 
 - build: Drop Node 12 support, target Node 14 (#293)
 - build(deps): Bump tmpl from 1.0.4 to 1.0.5 (#292)
@@ -37,7 +37,7 @@ PRs: #281, #282
 - build(deps): Bump path-parse from 1.0.6 to 1.0.7 (#274)
 - build(deps-dev): Bump tar from 4.4.8 to 4.4.15 (#273)
 - docs: Consistent code samples for shell (e84f693f)
-- docs: Mention release/** branches on README (#263)
+- docs: Mention release/\*\* branches on README (#263)
 
 ## 0.24.4
 
diff --git a/src/utils/__tests__/changelog.test.ts b/src/utils/__tests__/changelog.test.ts
index 71eb8c1ee..e2d2a835b 100644
--- a/src/utils/__tests__/changelog.test.ts
+++ b/src/utils/__tests__/changelog.test.ts
@@ -318,7 +318,7 @@ describe('generateChangesetFromGit', () => {
       makeCommitResponse([]);
       const changes = await generateChangesetFromGit(dummyGit, '1.0.0');
       expect(changes).toMatchInlineSnapshot(`
-        "## Various fixes & improvements
+        "### Various fixes & improvements
 
         - Upgraded the kernel (abcdef12)"
       `);
@@ -336,7 +336,7 @@ describe('generateChangesetFromGit', () => {
       makeCommitResponse([{ hash: 'abcdef1234567890' }]);
       const changes = await generateChangesetFromGit(dummyGit, '1.0.0');
       expect(changes).toMatchInlineSnapshot(`
-        "## Various fixes & improvements
+        "### Various fixes & improvements
 
         - Upgraded the kernel (abcdef12)"
       `);
@@ -357,7 +357,7 @@ describe('generateChangesetFromGit', () => {
       ]);
       const changes = await generateChangesetFromGit(dummyGit, '1.0.0');
       expect(changes).toMatchInlineSnapshot(`
-        "## Various fixes & improvements
+        "### Various fixes & improvements
 
         - Upgraded the kernel (#123)"
       `);
@@ -374,7 +374,7 @@ describe('generateChangesetFromGit', () => {
       makeCommitResponse([{ hash: 'abcdef1234567890', pr: '123' }]);
       const changes = await generateChangesetFromGit(dummyGit, '1.0.0');
       expect(changes).toMatchInlineSnapshot(`
-        "## Various fixes & improvements
+        "### Various fixes & improvements
 
         - Upgraded the kernel (#123)"
       `);
@@ -410,7 +410,7 @@ describe('generateChangesetFromGit', () => {
       ]);
       const changes = await generateChangesetFromGit(dummyGit, '1.0.0');
       expect(changes).toMatchInlineSnapshot(`
-        "## Various fixes & improvements
+        "### Various fixes & improvements
 
         - Upgraded the kernel (abcdef12)
         - Upgraded the manifold (#123)
@@ -495,19 +495,19 @@ describe('generateChangesetFromGit', () => {
     });
     const changes = await generateChangesetFromGit(dummyGit, '1.0.0');
     expect(changes).toMatchInlineSnapshot(`
-      "## Better drivetrain
+      "### Better drivetrain
 
       We have upgraded the drivetrain for a smoother and more performant driving experience. Enjoy!
 
       PRs: #123, #456
 
-      ## Better driver experience (ongoing)
+      ### Better driver experience (ongoing)
 
       We are working on making your driving experience more pleasant and safer.
 
       PRs: #789, #900
 
-      ## Various fixes & improvements
+      ### Various fixes & improvements
 
       - Upgraded the kernel (abcdef12)
       - Fix the clacking sound on gear changes (#950)"
diff --git a/src/utils/changelog.ts b/src/utils/changelog.ts
index ee73a5a53..629e73571 100644
--- a/src/utils/changelog.ts
+++ b/src/utils/changelog.ts
@@ -12,7 +12,14 @@ import { getVersion } from './version';
 export const DEFAULT_CHANGELOG_PATH = 'CHANGELOG.md';
 export const DEFAULT_UNRELEASED_TITLE = 'Unreleased';
 const DEFAULT_CHANGESET_BODY = '- No documented changes.';
+const VERSION_HEADER_LEVEL = 2;
+const SUBSECTION_HEADER_LEVEL = VERSION_HEADER_LEVEL + 1;
 
+// Ensure subsections are nested under version headers otherwise we won't be
+// able to find them and put on GitHub releases.
+if (SUBSECTION_HEADER_LEVEL <= VERSION_HEADER_LEVEL) {
+  throw new Error('Subsection headers should nest under version headers!');
+}
 /**
  * A single changeset with name and description
  */
@@ -32,6 +39,11 @@ export interface ChangesetLoc {
   padding: string;
 }
 
+function markdownHeader(level: number, text: string): string {
+  const prefix = new Array(level + 1).join('#');
+  return `${prefix} ${text}`;
+}
+
 /**
  * Extracts a specific changeset from a markdown document
  *
@@ -70,7 +82,10 @@ function locateChangeset(
   markdown: string,
   predicate: (match: string) => boolean
 ): ChangesetLoc | null {
-  const HEADER_REGEX = /^( *)(?:## +([^\n]+?) *(?:##)?|([^\n]+)\n *(?:-){2,}) *(?:\n+|$)/gm;
+  const HEADER_REGEX = new RegExp(
+    `^( *)(?:#{${VERSION_HEADER_LEVEL}} +([^\\n]+?) *(?:#{${VERSION_HEADER_LEVEL}})?|([^\\n]+)\\n *(?:-){2,}) *(?:\\n+|$)`,
+    'gm'
+  );
 
   for (
     let match = HEADER_REGEX.exec(markdown);
@@ -171,7 +186,7 @@ export function prependChangeset(
     const underline = new Array(changeset.name.length + 1).join('-');
     header = `${changeset.name}\n${underline}`;
   } else {
-    header = `## ${changeset.name}`;
+    header = markdownHeader(VERSION_HEADER_LEVEL, changeset.name);
   }
   const newSection = `${padding}${header}\n\n${body.replace(
     /^/gm,
@@ -269,7 +284,10 @@ export async function generateChangesetFromGit(
     }
 
     changelogSections.push(
-      `## ${milestone.title}${milestone.state === 'OPEN' ? ' (ongoing)' : ''}`
+      markdownHeader(
+        SUBSECTION_HEADER_LEVEL,
+        `${milestone.title}${milestone.state === 'OPEN' ? ' (ongoing)' : ''}`
+      )
     );
     changelogSections.push(milestone.description);
     changelogSections.push(
@@ -278,7 +296,9 @@ export async function generateChangesetFromGit(
   }
 
   if (leftovers.length > 0) {
-    changelogSections.push(`## Various fixes & improvements`);
+    changelogSections.push(
+      markdownHeader(SUBSECTION_HEADER_LEVEL, 'Various fixes & improvements')
+    );
     changelogSections.push(leftovers.map(formatCommit).join('\n'));
   }