Can't update SSL cert: remote error: tls: handshake failure. (disable cloudflare)

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1

Please fill out the fields below so we can help you better. Note: you must provide your domain name to get help. Domain names for issued certificates are all made public in Certificate Transparency logs (e.g. https://crt.sh/?q=example.com), so withholding your domain name here does not increase secrecy, but only makes it harder for us to provide help.

My domain is: simon.fearby.com

I ran this command: sudo certbot renew

It produced this output:

sudo certbot renew
Saving debug log to /var/log/letsencrypt/letsencrypt.log

Processing /etc/letsencrypt/renewal/simon.fearby.com.conf

Cert is due for renewal, auto-renewing…
Plugins selected: Authenticator nginx, Installer nginx
Renewing an existing certificate
Performing the following challenges:
tls-sni-01 challenge for simon.fearby.com
Waiting for verification…
Cleaning up challenges
Attempting to renew cert (simon.fearby.com) from /etc/letsencrypt/renewal/simon.fearby.com.conf produced an unexpected error: Failed authorization procedure. simon.fearby.com (tls-sni-01): urn:acme:error:tls :: The server experienced a TLS error during domain verification :: remote error: tls: handshake failure. Skipping.
All renewal attempts failed. The following certs could not be renewed:
/etc/letsencrypt/live/simon.fearby.com/fullchain.pem (failure)

All renewal attempts failed. The following certs could not be renewed:
/etc/letsencrypt/live/simon.fearby.com/fullchain.pem (failure)

1 renew failure(s), 0 parse failure(s)

IMPORTANT NOTES:

  • The following errors were reported by the server:

    Domain: simon.fearby.com
    Type: tls
    Detail: remote error: tls: handshake failure

    To fix these errors, please make sure that your domain name was
    entered correctly and the DNS A/AAAA record(s) for that domain
    contain(s) the right IP address. Additionally, please check that
    you have an up-to-date TLS configuration that allows the server to
    communicate with the Certbot client.

My web server is (include version): nginx/1.13.12

The operating system my web server runs on is (include version): Ubuntu 16.04

My hosting provider, if applicable, is: Vultr

I can login to a root shell on my machine (yes or no, or I don’t know): Yes / SSH

I’m using a control panel to manage my site (no, or provide the name and version of the control panel): No Raw SSH

2

Since you’re using Cloudflare, you cannot use the TLS-SNI challenge.

Try

sudo certbot renew --preferred-challenges http

Also check that you are on a recent version of Certbot.

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