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In this video, the speaker discusses a challenge they faced when setting up a server with HTTPS using Let's Encrypt certificates. While Let's Encrypt is a free option, it provides certificates in .pem format, which was not compatible with the server they were using. The server required a pfx or PKCS#12 formatted file that combines the private key and certificate into a single file. The speaker acknowledges that converting the .pem files to the required format is straightforward using OpenSSL, and they plan to outline their solution for the conversion process.