My original error was this:

$ port outdated
The following installed ports are outdated:
rsync                          3.1.3_0 < 3.2.1_1         
yubico-piv-tool                1.7.0_1 < 2.0.0_0         
$ sudo port upgrade outdated and not yubico-piv-tool
--->  Computing dependencies for openssl
Error: Can't install openssl because conflicting ports are active: libressl
Error: Problem while installing openssl
Error: Follow https://guide.macports.org/#project.tickets to report a bug.


Just for kicks, I replaced line 31 in rsync port file

  port:openssl

with

  port:libressl

and was able to build rsync 3.2.1_1 successfully after that.

$ otool -L /opt/local/bin/rsync
/opt/local/bin/rsync:
        /opt/local/lib/libpopt.0.dylib (compatibility version 1.0.0, current 
version 1.0.0)
        /opt/local/lib/libiconv.2.dylib (compatibility version 9.0.0, current 
version 9.1.0)
        /opt/local/lib/liblz4.1.dylib (compatibility version 1.0.0, current 
version 1.9.2)
        /opt/local/lib/libzstd.1.dylib (compatibility version 1.0.0, current 
version 1.4.5)
        /opt/local/lib/libxxhash.0.dylib (compatibility version 0.0.0, current 
version 0.7.4)
        /opt/local/lib/libcrypto.44.dylib (compatibility version 45.0.0, 
current version 45.1.0)
        /usr/lib/libSystem.B.dylib (compatibility version 1.0.0, current 
version 1252.50.4)


$ port provides /opt/local/lib/libcrypto.44.dylib
/opt/local/lib/libcrypto.44.dylib is provided by: libressl

$ /opt/local/bin/rsync --version
rsync  version 3.2.1  protocol version 31
Copyright (C) 1996-2020 by Andrew Tridgell, Wayne Davison, and others.
Web site: https://rsync.samba.org/
Capabilities:
    64-bit files, 64-bit inums, 64-bit timestamps, 64-bit long ints,
    socketpairs, hardlinks, symlinks, IPv6, no atimes, batchfiles, inplace,
    append, ACLs, xattrs, optional protect-args, iconv, symtimes,
    no prealloc, file-flags, crtimes
Checksum list:
    xxh64 (xxhash) md5 md4 none
Compress list:
    zstd lz4 zlibx zlib none

rsync comes with ABSOLUTELY NO WARRANTY.  This is free software, and you
are welcome to redistribute it under certain conditions.  See the GNU
General Public Licence for details.

So rsync 3.2.1 can be built with libressl. 

I wonder what is the proper way to make rsync port automatically use libressl 
if it is installed already.

Thanks,

Kastus 


> On Jun 28, 2020, at 2:54 PM, Kastus Shchuka <[email protected]> wrote:
> 
> In version 3.2.0 (June 19 2020) rsync introduced new binary rsync-ssl. Port 
> file of rsync now has a new dependency, openssl. Macports does not allow to 
> have both libressl and openssl ports installed at the same time. Does it mean 
> that I cannot upgrade rsync beyond version 3.1.3 if I am using libressl?
> 
> Thanks,
> 
> Kastus

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