openssl@1.1 compatibility

[dchakro]

Please fill out the issue checklist below, and provide all of the requested information.

Please always follow these steps:

• Confirmed this is a problem with brew installing one, specific formula and not every time you run brew? If it's a general brew problem please file this issue at https://github.com/Homebrew/brew/issues/new or https://github.com/Linuxbrew/brew/issues/new.
• Ran brew update and retried your prior step?
• Ran brew doctor, fixed all issues and retried your prior step?
• Ran brew gist-logs <formula> (where <formula> is the name of the formula that failed) and included the output link?
• If brew gist-logs didn't work: ran brew config and brew doctor and included their output with your issue?

To help us debug your issue please explain:

• What you were trying to do (and why)
  rstudio-server installation broke on MacOS Catalina after brew upgrade upgraded openssl from version 1.0 to 1.1.

• Why did this happen?
  openssl 1.0 approached EOL at the end of 2019 and was consequently dropped from homebrew in favor of openssl 1.1.
  See: Remove OpenSSL 1.0 Homebrew/homebrew-core#46876

• What happened (include command output)

  • Active instance of rstudio-server starts giving an error on login screen about incorrect username or password (on entering correct username an password).
  • Running sudo rstudio-server restart gave error message complaining about missing library at /usr/local/opt/openssl/lib/libssl.1.0.0.dylib.

• What you expected to happen
  compatibility with openssl 1.1.

• Step-by-step reproduction instructions (by running brew install commands)
  Running following code will break current rstudio installation.

brew upgrade <openssl>
sudo rstudio-server start

Formula additions or changes

Solution for the problem:
Manually installing openssl 1.0.2t as identified to work here: aisingapore/TagUI#635

brew install https://github.com/tebelorg/Tump/releases/download/v1.0.0/openssl.rb

# Validate that openssl 1.0.2t is installed
ls -al /usr/local/Cellar/openssl*
# Start Rstudio again
sudo -k rstudio-server start

A more robust approach using homebrew's code base is:

brew install https://raw.githubusercontent.com/Homebrew/homebrew-core/8b9d6d688f483a0f33fcfc93d433de501b9c3513/Formula/openssl.rb

# or manually cloning the repo and installing
git clone https://github.com/Homebrew/homebrew-core.git
cd homebrew-core
git checkout 75b57384 Formula/openssl.rb
brew install Formula/openssl.rb

# Validate that it is installed
ls -al /usr/local/Cellar/openssl*

# Start Rstudio again
sudo -k rstudio-server start

[stale]

This issue has been automatically marked as stale because it has not had recent activity. It will be closed if no further activity occurs.

[dchakro]

Dropping this here (clone of my reply@ aisingapore/TagUI#635 (comment)), for users struggling to get openssl-1.0 working.

If you're getting errors llke:

brew extract or brew create and brew tap-new to create a formula file in a tap on GitHub instead.: Invalid usage: Non-checksummed download of openssl formula file from an arbitrary URL is unsupported! (UsageError)

OR

Invalid usage: Installation of openssl from a GitHub commit URL is unsupported! brew extract openssl to a stable tap on GitHub instead. (UsageError)

I found this blog post which shows how to properly use brew extract, homebrew doesn't have good documentation for such use cases:

brew tap-new $USER/local-openssl
brew extract --version=1.0.2t openssl $USER/local-openssl

# Install from your freshly created local repo
brew install openssl@1.0.2t
# builds openssl (as no bottle is available)