LibreSSL and OpenSSH on Mac OS X 10.5 Leopard?

Vogone

New Tinkerer
Nov 21, 2025
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Hello everyone,

I recently got a good deal on a used copy of Amit Singh's “Max OS X Internals” and am considering buying a PowerBook G4 to learn about the PowerPC architecture.

One criterion for me would be data exchange with another system via SSH. Since LibreSSL has almost no dependencies and OpenSSH mainly uses LibreSSL (and the build worked wonderfully under macOS 10.13 High Sierra), I wanted to ask if anyone has any experience with this.

Are the dependencies for the LibreSSL build covered with Xcode 3.1.4 and the Command Line Tools?

Many thanks in advance!

Best regards
 

eric

Administrator
Staff member
Sep 2, 2021
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bluescsi.com
Few links that might interest you. I've not dived into this but a lot of people around here have.

https://github.com/classilla/cryanc


 

ClassicHasClass

Tinkerer
Aug 30, 2022
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www.floodgap.com
Unfortunately (speaking as the maintainer of Crypto Ancienne) it does not currently support SSH, just generic TLS which it uses for HTTPS.

I'd use Dropbear for SSH; it works with pretty much anything I've ever thrown it at, even very old systems. It should certainly work with 10.5. Also, Australia.