I have found that using the both the built in Apache webserver and the Homebrew variant does not work with the ssl related modules enabled, I have not narrowed down which module specifically crashes httpd, but I believe I have narrowed it down to be one of the ones that are required to use ssl. It exits with zsh: abort sudo httpd -k start while printing dyld[31928]: Assertion failed: (this->magic == kMagic), function isDelayInit, file Loader.cpp, line 464. to the error_log. I can provide more details, right now I feel like I'm forgetting to add something but I can't think of what it is.