AWS S3 + CloudFront Subdirectory Hosting: Architecture & Edge Cases

Overview

While deploying a static documentation site using AWS S3, CloudFront, and Cloudflare, I came across several edge cases that weren't immediately obvious from the documentation. This post summarizes the issues, their root causes, and the solutions that worked. I'm documenting these as technical notes for future reference, and hopefully they'll be useful to others facing similar problems.

Lesson 1: Local Redirect Caching

Issue

HTTPS configuration and redirect changes worked correctly in Incognito mode, but normal browser sessions continued to show outdated redirects or "Not Secure" warnings.

AWS S3 + CloudFront Subdirectory Hosting: Architecture & Edge Cases

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