Compile OpenSSH Portable on OSX / MacOS

macos-openssh-portable.sh

#!/usr/bin/env bash

brew install openssl

git clone git://anongit.mindrot.org/openssh.git
cd openssh

# The './configure' script does not exist, so we have to build it
autoreconf

mkdir dist

# Get the dir of the openssl install...
BREW_OPENSSL_DIR="$(brew --prefix openssl)"
# If you can't get the command above to work... try one of these:
# BREW_OPENSSL_DIR=/opt/homebrew/opt/openssl
# BREW_OPENSSL_DIR=/usr/local/opt/openssl

./configure \
  --prefix="$(pwd)/dist" \
  LDFLAGS="-L${BREW_OPENSSL_DIR}/lib" \
  CPPFLAGS="-I${BREW_OPENSSL_DIR}/include"

make

HOLY SMOKES! THIS WORKED WITHOUT A SINGLE HITCH (on my old macbook w/catalina). After hours of crazy complicated and bad instructions. Thanks!

I don't remember why I made this gist 7 years ago, but hey I'm glad I could help!! haha

Worked like a charm for me as well. Thank you @surjikal!

Cool! Why do you guys need this? I don't remember why I needed this!

@surjikal, im my case, I'm currently testing macOS Monterey beta. It ships a newer version of OpenSSH, 8.6. OpenSSH supports comments at the end of config lines since version 8.5, but this broke the parsing of ProxyCommand. Fortunately, this was reported (https://bugzilla.mindrot.org/show_bug.cgi?id=3288) and fixed. Recompiling OpenSSH from latest source code is my workaround, until version 8.7 of OpenSSH is released - at that point I'll simply be able to install it via Brew.

I needed a fresh install and brew was not working, nor manual normal building.

This is great, thanks!

FYI for people on M1 Macs, homebrew installs in /opt/homebrew, so the configure command is slightly different:

./configure \
  --prefix="$(pwd)/dist" \
  LDFLAGS="-L/opt/homebrew/opt/openssl/lib" \
  CPPFLAGS="-I/opt/homebrew/opt/openssl/include"

@oxtoacart cool! Your comment gave me an idea... thank you!

gist updated to get the install location from brew, instead of hardcoding the path.