A quick guide to downgrading OpenSSL with Homebrew

openssl_downgrade.md

OBSOLETE

THIS INFORMATION IS NOW OUT OF DATE, AND EXISTS HERE ONLY FOR ARCHIVAL PURPOSES

TROUBLESHOOTING

Excon Error

You may suffer an error that looks like this. It's possible you are setting up a new Mac, or you just recompiled your Ruby.

Excon::Errors::SocketError in ...
Bad address (Errno::EFAULT)

At fault is OpenSSL (or, an integration with it). You'll likely need to get a different version of it. Assuming you are using Homebrew, do the following...

$ brew tap homebrew/versions
$ brew versions openssl

You should see a number of versions listed, look for 1.0.1l...

...
1.0.1l   git checkout b5cffc8 /usr/local/Library/Formula/openssl.rb
...
# Get this version in your Library by doing...
$ cd /usr/local/Library/Formula/
$ git checkout b5cffc8 /usr/local/Library/Formula/openssl.rb

NOTE: Make sure you use your path and git-ref, not what is shown in this example.

Then rebuild ruby.

  $ rvm reinstall 2.1.0 # CHANGE TO YOUR RUBY VERSION

And that should fix it.

Looks like brew versions was removed:

Unknown command: versions

This is an alternative way:

brew update
brew uninstall openssl
brew install openssl101

(then reinstall ruby)

zubin, to gain access to brew versions command, you can run:

brew tap homebrew/boneyard

darrenboyd, I'm getting a no remote repository specified error.
Where should I be pointing /usr/local/Library/Formula/ at?

This whole guide doesn't work in 2020.

Odd how often things from the (technologically) distant past surface every once in awhile. I'll put a note at the very top of the post that this no longer works, if anyone has links to a better solution, please comment here, and I will add references to them. Since I no longer use brew (no longer on a Mac), I don't know what a good solution to this problem is.

Here is what worked for me:

brew install rbenv/tap/openssl@1.0
rvm reinstall 1.9.3-p551 --with-openssl-dir='/usr/local/opt/openssl@1.0'
gem update --system

Cheers!

@gulymaestro yes! was on this problem for a few hours and this was the fix, thankyou!

Here is what worked for me:

brew install rbenv/tap/openssl@1.0
rvm reinstall 1.9.3-p551 --with-openssl-dir='/usr/local/opt/openssl@1.0'
gem update --system

Cheers!

@gulymaestro I tried every other solution present online but did not work. This is the real fix. Thank you so much .

thank you

Here is what worked for me:

brew install rbenv/tap/openssl@1.0
rvm reinstall 1.9.3-p551 --with-openssl-dir='/usr/local/opt/openssl@1.0'
gem update --system

Cheers!

👍🏽

Here is what worked for me:

brew install rbenv/tap/openssl@1.0
rvm reinstall 1.9.3-p551 --with-openssl-dir='/usr/local/opt/openssl@1.0'
gem update --system

Cheers!

Thx a lot! 👍

I found the solution works for me on mac os x Catalina.

1. Download the file: https://github.com/tebelorg/Tump/releases/download/v1.0.0/openssl.rb
2. Run brew with the file downloaded: brew install openssl.rb

I found the solution works for me on mac os x Catalina.

1. Download the file: https://github.com/tebelorg/Tump/releases/download/v1.0.0/openssl.rb
2. Run brew with the file downloaded: brew install openssl.rb

thanks, this was the only suggestions from above that actually did work for me.

I found the solution works for me on mac os x Catalina.

1. Download the file: https://github.com/tebelorg/Tump/releases/download/v1.0.0/openssl.rb
2. Run brew with the file downloaded: brew install openssl.rb

Thank you! This was the only way working for me.

For people having trouble with downgrading openssl for installing old Ruby versions this guide might help
https://medium.com/@akforsn/installing-old-ruby-versions-on-apple-m1-step-by-step-guide-501bb893c843

Here is what worked for me:

brew install rbenv/tap/openssl@1.0
rvm reinstall 1.9.3-p551 --with-openssl-dir='/usr/local/opt/openssl@1.0'
gem update --system

Cheers!

@gulymaestro Saved my skin!

It didn't work for me. Showed me the error message below:
rbenv/homebrew-tap#4

Followed the #2 solution to successfully install it:
rbenv/homebrew-tap#2 (comment)

Cheers!

not working in mac m1 year 2022

brew install rbenv/tap/openssl@1.0
brew install rbenv/tap/openssl@1.0 not working anymore rbenv/homebrew-tap#1

@mahcloud , the solution you provided is not working anymore

$ brew tap homebrew/boneyard

==> Tapping homebrew/boneyard
Cloning into '/usr/local/Homebrew/Library/Taps/homebrew/homebrew-boneyard'...
remote: Repository not found.
fatal: repository 'https://github.com/Homebrew/homebrew-boneyard/' not found
Error: Failure while executing; `git clone https://github.com/Homebrew/homebrew-boneyard /usr/local/Homebrew/Library/Taps/homebrew/homebrew-boneyard --origin=origin --template= --config core.fsmonitor=false` exited with 128.

@mahcloud , the solution you provided is not working anymore

$ brew tap homebrew/boneyard

==> Tapping homebrew/boneyard
Cloning into '/usr/local/Homebrew/Library/Taps/homebrew/homebrew-boneyard'...
remote: Repository not found.
fatal: repository 'https://github.com/Homebrew/homebrew-boneyard/' not found
Error: Failure while executing; `git clone https://github.com/Homebrew/homebrew-boneyard /usr/local/Homebrew/Library/Taps/homebrew/homebrew-boneyard --origin=origin --template= --config core.fsmonitor=false` exited with 128.

sorry @Victorcorcos , it looks like this document has been labeled as obsolete