Rethinking my blog's URL structure

Today’s goal was simple: redirect outdated URLs to their current versions (like /what-11-hours-layover-in-suvarnabhumi-airport-bkk-bangkok-was-like to /11-hours-layover-in-suvarnabhumi-airport). The implementation, however, raised some interesting architectural challenges.

My initial approach involved fuzzy matching old URLs to current ones using a keyword-based similarity algorithm:

const findClosestSlug = (requestedSlug: string, currentSlugs: string[]): string | null => {
 const requestedKeywords = extractKeywords(requestedSlug);
 let bestMatch = {
   slug: '',
   score: 0,
   matchedKeywords: 0
 };

 for (const slug of currentSlugs) {
   const slugKeywords = extractKeywords(slug);
   const matchResult = evaluateMatch(requestedKeywords, slugKeywords);

   if (matchResult.score > bestMatch.score) {
     bestMatch = {
       slug,
       score: matchResult.score,
       matchedKeywords: matchResult.matches
     };
   }
 }

 return bestMatch.score >= 0.4 ? bestMatch.slug : null;
};

While this worked, it led to a bigger challenge: my domain uses a combination of Cloudflare Workers (for specific paths) and Vercel (for everything else). Workers need predefined route patterns, which means I’ll need to handle route handling at fetch time:

async fetch(request: Request, env: Env, ctx: ExecutionContext): Promise<Response> {
  const url = new URL(request.url);
  const path = url.pathname;

  // Only process non-existent paths
  if (!url.pathname.startsWith('/assets/') && 
      !url.pathname.startsWith('/api/') && 
      !url.pathname.startsWith('/webhooks/')) {
    const slug = path.replace(/^\//, '');
    const redirectSlug = findClosestSlug(slug, currentSlugs);
    if (redirectSlug) {
      return Response.redirect(`${url.origin}/${redirectSlug}`, 301);
    }
  }
}

I am not keen on that, so I thinking of moving back to /blog prefix for the routes configuration on the Workers script to be simplified:

1. Clear separation between blog and non-blog content
2. Simple Worker route configuration ({ pattern = "*.arun.blog/blog/*", zone_name = "arun.blog" })
3. Predictable URL structure for redirects

I’m still on the fence about this change - while the /blog/ prefix offers simplicity and better routing control, part of me wants to keep URLs as clean as possible. Guess I’ll need to make a call on this soon, as having inconsistent URLs isn’t helping anyone. For now, I’m leaning towards bringing back the /blog/ prefix, but we’ll see where I land.