Fixing Rstudio Server

Here I’m enlisting a few tricks I have had to use from time to time to fix the rstudio-server installation on MacOS.

Fix error with openssl 1.0.x migration to 1.1.x

If you see a message like /usr/local/opt/openssl/lib/libssl.1.0.0.dylib is missing when running rstudio, and another symptom is that on the rstudio-server login screen it says userid and password are wrong.

Installing using brew extract

Setup a local tap and extract the formula.

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

# then install from your newly created local repository
brew install openssl@1.0.2t

The following methods are now deprecated in current versions of homebrew

To Fix you can try:

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

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

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

# Start Rstudio again
sudo -k rstudio-server start

If the above method fails try this:

curl -OJL https://github.com/tebelorg/Tump/releases/download/v1.0.0/openssl.rb
brewlog install openssl.rb

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

# Start Rstudio again
sudo -k rstudio-server start

There’s a chance that the error will still be displayed, and the reason is that the libraries from openssl 1.0 are not symlinked in the place where rstudio-server expects them to be. Resolve it by running:

ln -s '/usr/local/Cellar/openssl/1.0.2t/lib/libcrypto.1.0.0.dylib'  '/usr/local/opt/openssl/lib/libcrypto.1.0.0.dylib'
ln -s '/usr/local/Cellar/openssl/1.0.2t/lib/libssl.1.0.0.dylib'  '/usr/local/opt/openssl/lib/libssl.1.0.0.dylib'

If the above method fails try this:

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