The windows version of Alpine can be compiled with LibreSSL. The build 
script will compile using LibreSSL if there is a libressl folder in the 
main Alpine source code directory. If you rename or remove this folder, 
Alpine will be compiled using the default SSL libraries in your computer.

There are pros and cons to every decision. Here are the pros and cons to
building using LibreSSL.

Pros:

  * LibreSSL can be updated at any time. This will make it possible to
    build Alpine with the latest features of LibreSSL. If you decide to
    not use LibreSSL, your SSL libraries will eventually not be updated.

  * Certificates can be updated at any time, and so you can run your
    favorite version of Alpine for many years, even after your Windows
    version is not supported anymore.

  * You get S/MIME support in Windows for free.

Cons:

  * LibreSSL will check certificates not using the certificates installed 
    in your Windows computer, but it will do so in a different location. 
    This means that it is the responsibility of the user to update the 
    certificates. No matter what choice is made, if certificates are not
    updated, validation will always eventually fail. 

Default Certificates Location:

  * When Alpine is compiled with LibreSSL support, certificates must be
    placed in the C:\\libressl\ssl\certs directory. You can find a copy
    of certificates in the git repository in the libressl/certs directory.
    All you have to do is to copy the certificates in that directory to 
    the C:\\libressl\ssl\certs directory.

  * In order to make it easy to distribute certificates, each certificate
    is distributed twice. Once with a long name, and another with the 
    short name. The short name is called the "subject hash". A unix script 
    called "doit.sh" can be used to create the short name. You can run 
    such script, from this directory by using the command

     ./doit.sh

    and copy the resulting files with short names, to the 
    C:\\libressl\ssl\certs folder. You only need the files with the short 
    names, but both are distributed.