Install curb 0.9.3 on MacOS Catalina

install_curb_0.9.3_on_macos_catalina.sh

# You'll probably also need to Install Ruby 2.3.x with OpenSSL 1.0 (on Catalina),
# follow this gist *before* you install curb: https://gist.github.com/sutanto/75a778f94edae116aeaa5ec56955ce58

# Recent Homebrew version no longer allow the `brew install formula` command, we'll need to create our own "custom" tap:
brew tap-new sutanto/homebrew-versions

# make sure that we don't use the "shallow" local homebrew repo
git -C "/usr/local/Homebrew/Library/Taps/homebrew/homebrew-core" fetch --unshallow

# extract the required curl version
brew extract --version 7.35.0 curl sutanto/homebrew-versions

# finally install it
# brew command below will fail with “Error: undefined method `strip' for :provided_by_osx:Symbol”, ignore this, the install is still completed successfully
brew install sutanto/homebrew-versions/curl@7.35.0

gem install curb -v '0.9.3' -- --with-openssl-dir=/usr/local/opt/openssl --with-curl-dir=/usr/local/opt/curl@7.35.0

I had similar issue of mix of curl(and curl-openssl).
It turns out, OpenSSL 1.1 isn’t compatible with Ruby 2.3.x, and I probably just accidentally installed 1.1 instead of 1.0

I can add my tries for you:

1. TRY 1: include pkg config for existing openssl and set options for rvm

PKG_CONFIG_PATH=/usr/local/opt/openssl@1.0/lib/pkgconfig rvm install 2.3.8  --with-openssl-lib=/usr/local/opt/openssl@1.0 --with-openssl-include=/usr/local/opt/openssl@1.0/include

2. TRY2: the brew solve problem with the commands:

brew update
brew uninstall openssl
brew install openssl101

if this is not worked at any step try:

brew install rbenv/tap/openssl@1.0
# Now ensure you are reload console to get new vars (or just open a new console)
rvm install ruby-2.3.8  --with-openssl-dir=`/usr/local/opt/openssl@1.0`

(or reinstall).

Use any path to your local ssl installation, like /usr/local/opt/openssl, mind not to set it to binaries folder but to relative root folder of openssl 1.0

3. The RVM issue:

UNINSTALL rvm with rvm implode - follow the post uninstall instructions, then install rvm from scratch, then:

rvm pkg install openssl
rvm install 2.3.8 --with-openssl-dir=$rvm_path/usr

4. Install curl-openssl:
   With brew and set --with-curl-dir=/usr/local/opt/curl-openssl (or any your path to it) option to $ rvm command. Yes its another curl called curl-openssl. Do not update $PATH or your *rc files with path to it unless you want curl-openssl by default

Finally:
bundle install

Notes:

• It may need mix commands from different steps above, i just ordered them as i tried to solve issue.
• Open a new console each time you install/uninstall rvm/openssl/curl
• Keep eye on paths (eg: which curl)

@alexey, in the gist above, I put a link to https://gist.github.com/sutanto/75a778f94edae116aeaa5ec56955ce58 which described how to install Ruby 2.3 with OpenSSL 1.0.
I'll change the comment in the gist above so it'll be more obvious.