Open SSL 1.0 was removed because it reached EOL. Had it been for any other reason I’d be open to discussing readding it, but using EOL cryptography software sounds outright dangerous and I doubt we want to participate in that, even if the broken software is (insanely) popular.

powershell (added 1294 days ago)
30 days: 6,089 (#19)
90 days: 15,528 (#20)
365 days: 61,576 (#23)

As it stands, either Powershell updates their dependency or we need to remove the cask (as it’s broken).

Is there an issue that points to a timeframe of them updating the dependency? Is it perhaps already live in a beta we could use?

@vitorgalvao - the impression I get is that the dependency is no longer needed?

PowerShell/PowerShell#6848
dotnet/corefx#17011

Thank you @dijitali.

PowerShell/PowerShell#6848 (comment)
#78101

This should not have been closed. I've tested it in the latest 7.0 and it's still broken

otool -L /usr/local/microsoft/powershell/7/libmi.dylib
libmi.dylib:
        @rpath/libmi.dylib (compatibility version 0.0.0, current version 0.0.0)
        /usr/lib/libSystem.B.dylib (compatibility version 1.0.0, current version 1238.60.2)
        /usr/lib/libpam.2.dylib (compatibility version 3.0.0, current version 3.0.0)
        /usr/local/opt/openssl/lib/libssl.1.0.0.dylib (compatibility version 1.0.0, current version 1.0.0)
        /usr/local/opt/openssl/lib/libcrypto.1.0.0.dylib (compatibility version 1.0.0, current version 1.0.0)
        /usr/lib/libz.1.dylib (compatibility version 1.0.0, current version 1.2.8)

Whilst the fix needs to be upstream, and I also understand that including openssl 1.0 is not an option, perhaps adding a message to the cask to inform people that functionality is broken until this issue is resolved.

The solution below worked on macOS BigSur 11.0 and PowerShell 7.0.3 with OpenSSL 1.1.1h and OpenSSL 1.0.2t side by side.

#1st install OpenSSL version 1.1.1h (run this once)
/usr/local/bin/brew install openssl

#1st install OpenSSL version 1.0.2t (run this once)
/usr/local/bin/brew extract --version 1.0.2t openssl company/team &&
/usr/local/bin/brew install company/team/openssl@1.0.2t &&
/usr/local/bin/brew pin openssl

Below works with Powershell 7.0.3. Place everything below this line in startup profile script, in a function, or run manually.

#Set link to OpenSSL version 1.0.2t
/bin/rm -Rf /usr/local/opt/openssl; /bin/ln -Ffs /usr/local/Cellar/openssl@1.0.2t/1.0.2t /usr/local/opt/openssl

#Run Powershell
/usr/local/bin/pwsh

#Restore link to OpenSSL version 1.1.1h
/bin/rm -Rf /usr/local/opt/openssl; /bin/ln -Ffs /usr/local/Cellar/openssl@1.1/1.1.1h /usr/local/opt/openssl

This continues to be an upstream matter.

My bash/zsh functions are below from .bash_profile.sh and .zsh_profile.sh

pwsh-openssl () {
brew extract --version 1.0.2t openssl company/team &&
brew install company/team/openssl@1.0.2t &&
brew pin openssl
}

pwsh-run () {
#Set link to OpenSSL version 1.0.2t
rm -Rf /usr/local/opt/openssl; ln -Ffs /usr/local/Cellar/openssl@1.0.2t/1.0.2t /usr/local/opt/openssl
/usr/local/bin/pwsh
#Restore link to OpenSSL version 1.1.1h
rm -Rf /usr/local/opt/openssl; ln -Ffs /usr/local/Cellar/openssl@1.1/1.1.1h /usr/local/opt/openssl
}