diff --git a/redirects.ts b/redirects.ts
index 8c311736..14762816 100644
--- a/redirects.ts
+++ b/redirects.ts
@@ -194,13 +194,36 @@ export function createRedirects(existingPath: string, basePath: string = ''): st
 		// Extract the path after /release-notes/
 		const subpath = existingPath.replace('/release-notes/', '');
 
+		// Handle old version naming (4.tucker -> v4-tucker, etc.)
+		let oldSubpath = subpath;
+		const versionMap: Record<string, string> = {
+			'v1-alby': '1.alby',
+			'v2-penny': '2.penny',
+			'v3-monkey': '3.monkey',
+			'v4-tucker': '4.tucker',
+		};
+
+		// Check if the path starts with a new version name and convert to old format
+		for (const [newName, oldName] of Object.entries(versionMap)) {
+			if (subpath.startsWith(`${newName}/`) || subpath === newName) {
+				oldSubpath = subpath.replace(newName, oldName);
+				break;
+			}
+		}
+
 		// Add redirects from current version docs (4.6 is served at /docs/)
 		redirects.push(`/docs/technical-details/release-notes/${subpath}`);
+		if (oldSubpath !== subpath) {
+			redirects.push(`/docs/technical-details/release-notes/${oldSubpath}`);
+		}
 
 		// Also redirect from all versioned docs paths
 		const versions = ['4.1', '4.2', '4.3', '4.4', '4.5', '4.6'];
 		for (const version of versions) {
 			redirects.push(`/docs/${version}/technical-details/release-notes/${subpath}`);
+			if (oldSubpath !== subpath) {
+				redirects.push(`/docs/${version}/technical-details/release-notes/${oldSubpath}`);
+			}
 		}
 	}
 
diff --git a/scripts/postbuild.js b/scripts/postbuild.js
index bdf67acd..c1c35ef0 100644
--- a/scripts/postbuild.js
+++ b/scripts/postbuild.js
@@ -54,6 +54,65 @@ async function generateIndexHtmlFiles(outDir) {
 	}
 }
 
+// Copy redirect index.html files to .html ONLY for old release notes paths
+// This ensures redirects work with simple HTTP servers like `npm run serve`
+// Example: docs/technical-details/release-notes/4.tucker/4.4.0/index.html
+//       -> docs/technical-details/release-notes/4.tucker/4.4.0.html
+async function generateReleaseNotesRedirectHtmlFiles(outDir) {
+	console.log('Post-build: Creating .html redirect files for old release notes paths...');
+
+	const redirectBase = path.join(outDir, 'docs', 'technical-details', 'release-notes');
+
+	try {
+		await fs.stat(redirectBase);
+	} catch {
+		console.log('Post-build: No release notes redirects found, skipping');
+		return;
+	}
+
+	// Walk through all directories recursively
+	async function* walkDirs(dir) {
+		const dirents = await fs.readdir(dir, { withFileTypes: true });
+		for (const dirent of dirents) {
+			if (dirent.isDirectory()) {
+				const res = path.resolve(dir, dirent.name);
+				yield res;
+				yield* walkDirs(res);
+			}
+		}
+	}
+
+	const processedFiles = [];
+
+	for await (const dirPath of walkDirs(redirectBase)) {
+		// Check if this directory has an index.html redirect file
+		const indexPath = path.join(dirPath, 'index.html');
+		try {
+			const content = await fs.readFile(indexPath, 'utf8');
+			// Check if it's a redirect file (contains meta refresh)
+			if (content.includes('meta http-equiv="refresh"')) {
+				// Create a sibling .html file with the same content
+				const dirName = path.basename(dirPath);
+				const siblingHtmlPath = path.join(path.dirname(dirPath), `${dirName}.html`);
+				await fs.copyFile(indexPath, siblingHtmlPath);
+				processedFiles.push(`${dirName}/index.html → ${dirName}.html`);
+			}
+		} catch {
+			// No index.html or other error, skip
+		}
+	}
+
+	if (processedFiles.length > 0) {
+		console.log(`Post-build: Created ${processedFiles.length} .html redirect files`);
+		// Uncomment to see details:
+		// processedFiles.forEach(f => console.log(`  - ${f}`));
+	} else {
+		console.log('Post-build: No .html redirect files needed');
+	}
+}
+
 // Run the post-processing
 const buildDir = path.join(__dirname, '..', 'build');
-generateIndexHtmlFiles(buildDir).catch(console.error);
+generateIndexHtmlFiles(buildDir)
+	.then(() => generateReleaseNotesRedirectHtmlFiles(buildDir))
+	.catch(console.error);