How to Fix Infinite HTTP to HTTPS Redirect Loops (ERR_TOO_MANY_REDIRECTS)

Step-by-Step Solution

Step 1: Set Cloudflare Encryption to Full (Strict)

If Cloudflare is set to Flexible, it queries your backend over unencrypted HTTP (port 80). If your origin server enforces HTTPS, an infinite redirect loop forms:

1. 1

   Step 1

   Log into your Cloudflare Dashboard.
2. 2

   Step 2

   Navigate to SSL/TLS > Overview.
3. 3

   Step 3

   Change encryption setting from Flexible to Full or Full (Strict).

Step 2: Configure Proxy Header Recognition in WordPress

Instruct WordPress to recognize secure edge connections forwarded by proxies:

// Add at top of wp-config.php before require_once wp-settings.php:
if (isset($_SERVER['HTTP_X_FORWARDED_PROTO']) && $_SERVER['HTTP_X_FORWARDED_PROTO'] === 'https') {
    $_SERVER['HTTPS'] = 'on';
}

Step 3: Establish Clean Server Directives in Nginx

Ensure port 80 redirects cleanly without triggering self-referential loops on port 443:

# HTTP server block (Port 80) -> Redirect to HTTPS
server {
    listen 80;
    server_name mysite.com www.mysite.com;
    return 301 https://$host$request_uri;
}

# HTTPS server block (Port 443) -> Serve application
server {
    listen 443 ssl http2;
    server_name mysite.com www.mysite.com;

    ssl_certificate /etc/letsencrypt/live/mysite.com/fullchain.pem;
    ssl_certificate_key /etc/letsencrypt/live/mysite.com/privkey.pem;

    location / {
        proxy_set_header X-Forwarded-Proto https;
        proxy_pass http://localhost:3000;
    }
}

Step 4: Clear Cached 301 Redirects in Browser

HTTP 301 Permanent Redirects are aggressively cached by client browsers:

1. Verify behavior inside a Private / Incognito window.
2. Purge browser cached images and files.

❓ Frequently Asked Questions (FAQ)

Why does Cloudflare Flexible SSL create loops?

Visitors request HTTPS from Cloudflare, Cloudflare requests HTTP from the origin, the origin issues a 301 to HTTPS, and Cloudflare restarts the identical cycle indefinitely.

How do I trace redirection hops from the terminal?

Run curl -IL https://mysite.com to inspect every HTTP response status header across the connection chain.