repro.sh

#!/bin/bash

# Install homebrew
export HOMEBREW_NO_EMOJI=true
export HOMEBREW_NO_ANALYTICS=1
sudo dscl . -create /Users/test
sudo dscl . -create /Users/test UserShell /bin/bash
sudo dscl . -create /Users/test UniqueID 1001
sudo dscl . -create /Users/test PrimaryGroupID 1000
sudo dscl . -create /Users/test NFSHomeDirectory /Users/test
sudo dscl . -passwd /Users/test password
sudo dscl . -merge /Groups/admin GroupMembership test
echo "test ALL=(ALL:ALL) NOPASSWD: ALL" > /etc/sudoers.d/username
mkdir -p /etc/homebrew
cd /etc/homebrew
createhomedir -c -u test
su test -c 'echo | /bin/bash -c "$(curl -fsSL https://raw.githubusercontent.com/Homebrew/install/HEAD/install.sh)"'

# REMIND: /opt/homebrew vs /usr/local
echo >> /Users/test/.bash_profile
echo 'eval "$(/opt/homebrew/bin/brew shellenv)"' >> /Users/test/.bash_profile
eval "$(/opt/homebrew/bin/brew shellenv)"

# Install openssl@3, which installs 3.3.0
su test -c 'brew install openssl@3'

# Unlink openssl so it's not visible to our build
su test -c 'brew unlink openssl'

# Build and install openssl 3.0.13 to /opt/foobar
mkdir /var/tmp/foobar
cd /var/tmp/foobar
curl -LO https://github.com/openssl/openssl/releases/download/openssl-3.0.13/openssl-3.0.13.tar.gz
tar xf openssl-3.0.13.tar.gz
cd openssl-3.0.13
./Configure --prefix=/opt/foobar --libdir=lib --openssldir=/opt/foobar/ssl shared darwin64-x86_64
make
make install

# Build and install curl 8.7.1 using openssl 3.0.13
cd /var/tmp/foobar
curl -LO https://github.com/curl/curl/releases/download/curl-8_7_1/curl-8.7.1.tar.gz
tar xf curl-8.7.1.tar.gz
cd curl-8.7.1
export CFLAGS='-mmacosx-version-min=12.0'
export CPPFLAGS='-I/opt/foobar/include'
export LDFLAGS='-L/opt/foobar/lib'
./configure --prefix=/opt/foobar --with-ssl=/opt/foobar --host x86_64-apple-darwin --build x86_64-apple-darwin
make
make install

# Curl imports this symbol which is only present in openssl 3.2.0 and up
nm -m /opt/foobar/lib/libcurl.dylib | grep SSL_get0_group_name

# Our openssl doesn't export this symbol
nm -gU /opt/foobar/lib/libssl.dylib | grep SSL_get0_group_name

/bin/bash -xc "$(curl -fsSL https://gist.githubusercontent.com/joshcooper/2e2bfbe75081621f7530b7f14ef6816e/raw/775d04ca10dfc138f0b98d294c56743a0f509a60/repro.sh)"

https://gist.githubusercontent.com/joshcooper/2e2bfbe75081621f7530b7f14ef6816e/raw/dd7d0398f53f2e649ad7c16b36e2fe830b28b6e2/repro.sh