How to override core is_ssl() function?

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If you look at the source of the is_ssl() function you’ll see it checks various $_SERVER variables. Therefore, you could try adding this to a plugin:

if ( isset( $_SERVER['HTTP_MY_CUSTOM_HEADER'] ) )
  $_SERVER['HTTPS'] = 'on';

You’d need to call that code as early as possible, ie. directly in the plugin body rather than on a hook.

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