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I think the headers are there so they can see if commercial sites are using the personal version and get them to pony up.

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commercial sites have the easy ability to go to https://github.com/mholt/caddy; download the source; remove the header from header.go and server.go; compile; run

i'd venture to guess many build the binary themselves already. so they can add their own tweaks.

how would anyone be able to prove a website is being ran by caddy if the server doesn't announce that it is caddy?

If you do build it yourself, you don't fall under the commercial license, so it's correct if those are not detected.

Wouldn't they already know who their customers are?

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