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If you’re pointing the blog cname to tumblr it has nothing to do with your server. You probably need to register your domain somehow with tumblr.
So the problem is that I’d set the HSTS to include subdomains, this line here being the culprit:
# Add HSTS
add_header Strict-Transport-Security "max-age=31536000; includeSubdomains";
Taking out includeSubdomains means browsers don’t automatically switch to HTTPS.
If you’ve done the same and are using Chrome and want to clear your HSTS ‘cache’, type this into the url bar:
chrome://net-internals/#hsts