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> With On-Demand TLS, only Caddy obtains, renews, and maintains certificates on-the-fly during TLS handshakes. Perfect for customer-owned domains.

Does it allow to plug-in into this system so that post-renewal actions are possible, like distributing those certificates to other machines through Python scripts?

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Yes, it has events on cert issuance/renewal you can hook into with Go plugins (which can trigger your python script). But generally you want all Caddy instances to share storage via storage modules (e.g. Redis or Consul or a DB, or synced filesystem) and Caddy manages locks through the storage so they don't step on eachother's toes.

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