Apple drops a bomb on long-life HTTPS certificates

Oh joy, more regular SSL certificate maintenance. Thanks Apple.

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Maybe it will provide some impetus for Claris to support automation when it comes to certificate management?

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Likely this will come from the community. GitHub - dansmith65/FileMaker-LetsEncrypt-Win: A PowerShell script for fetching and renewing Let's Encrypt SSL certificates for FileMaker Server running on Windows Server.

I have thoughts and feelings about some methods I've seen, but it is getting better.

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sounds very good - this one about let's encrypt. L'e has to be renewed much more often than other certs

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FWIW, the script that @jormond linked can be configured to renew automatically with Windows task scheduler. I use this script on 3 production servers. PS, you may need to use the version on Dan's dev branch rather than the master for new deployments.