LetsEncrypt IP Addresses... It's Actually pretty important

The entire DNS-01 provisioning lifecycle - from running a client, configuring and responding to challenges, and obtaining the certificate - can happen outside of the fragile server.

The only benefit to a paid certificate is only having to install it once a year.

If I were in the OP's situation, I would probably opt for a paid certificate for this reason. Scheduling a manual certificate installation every 2 months is silly, when you can spend under $10 to get a paid 1 year certificate. However... if there were more than 1 certificate/server needed, I would probably write something using Fabric or Invoke to run the DNS-01 challenge locally and then deploy the certificates onto the servers.

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@rmbolger @jvanasco

I agree that if one would move the issuance of the certificate away from the ancient, security hazard system, it would cost less time to move away from Let’s Encrypt.

Luckily, Buypass offers free certificates through ACME with a lifetime of max. 180 days!

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