Cannot install Ruby versions < 2.4 because of openssl@1.1 dependency

[brandonfriess-stripe]

It seems the most recent change to ruby-build 20191002 homebrew formula to require openssl@1.1 breaks the install of Ruby versions that are < 2.4 (those require openssl 1.0.2q)

So, for macOS users who install ruby-build via homebrew, they will get openssl@1.1 installed as well.

If they then try to run rbenv install 2.1.10 for instance, it will fail with:

Last 10 log lines:
The Ruby openssl extension was not compiled.
ERROR: Ruby install aborted due to missing extensions
Configure options used:
  --prefix=/Users/username/.rbenv/versions/2.1.10
  --with-openssl-dir=/usr/local/opt/openssl@1.1
  --with-readline-dir=/usr/local/opt/readline
  CC=clang
  CFLAGS= -O3 -Wno-error=shorten-64-to-32 
  LDFLAGS=-L/Users/username/.rbenv/versions/2.1.10/lib 
  CPPFLAGS=-I/Users/username/.rbenv/versions/2.1.10/include 

Yeah, I know older versions are EOL but they still get used in some environments.

Seems like changing https://github.com/rbenv/ruby-build/blob/master/bin/ruby-build#L1023 to only check for openssl and not `openssl@1.1 could potentially fix this?

[hsbt]

I understand this issue too. But I didn't know the maintenance policy of ruby-build formula on homebrew.

I suggest you use git clone instead of brew install ruby-build

[gfguthrie]

Since I helped move the 1.1 change along:

The workaround for EOL Ruby versions (or any that won't build with 1.1) where you still want to use Homebrew is as follows:
brew install openssl
RUBY_CONFIGURE_OPTS="--with-openssl-dir=/usr/local/opt/openssl" rbenv install 2.3.8
Latest solution/workaround (March 2020): #1353 (comment)

(FWIW, the Homebrew formula was updated to use 1.1 at the end of August, the recent change was just to start looking for that version)

[brandonfriess-stripe]

Thanks! That will work and I am sure will be helpful for others who may land on this thread.

[aardvarkk]

I ran into this bug when trying to install Ruby 2.3.8 using the ASDF version manager. I was getting the following error when running:

asdf install ruby 2.3.8:

ERROR: Ruby install aborted due to missing extensions

Following the example above, I changed the command to the following and the installation worked correctly:

RUBY_CONFIGURE_OPTS="--with-openssl-dir=/usr/local/opt/openssl" asdf install ruby 2.3.8

[wekb]

Since I helped move the 1.1 change along:

The workaround for EOL Ruby versions (or any that won't build with 1.1) where you still want to use Homebrew is as follows:

brew install openssl
RUBY_CONFIGURE_OPTS="--with-openssl-dir=/usr/local/opt/openssl" rbenv install 2.3.8

(FWIW, the Homebrew formula was updated to use 1.1 at the end of August, the recent change was just to start looking for that version)

This is very helpful, but frankly this should not have been a breaking change. Adding logic, or at least some kind of user feedback, would have been trivial in this case.

[hraban]

Thanks for the explanation and solution.

Even just a link to this issue would be a great help to anyone using rbenv to install a <2.4.0 on mac. Many people will be running into this problem, not all of them confident enough to google the right error message (rbenv is usually part of a "run this to setup the repo" list in project READMEs).

[gfguthrie]

I've taken option 2 from my comment on the original PR and made a new PR (#1375) to stop looking for Homebrew openssl entirely so that the discussion can focus there about whether that's the approach ruby-build wants to move towards or not.

[hardvain]

Hello, I still seem to have this error. I am trying to instal ruby 2.3.7. My mac has openssl version 1.1.d 10 Sep 2019. I am getting the following error when trying to install ruby even after passing the above suggested method of including open-ssl-dir. The last few lines of the error is:

openssl_missing.c:39:18: error: expected ';' after top level declarator
EVP_MD_CTX_create(void)
                 ^
                 ;
2 warnings and 5 errors generated.
make[2]: *** [openssl_missing.o] Error 1
make[1]: *** [ext/openssl/all] Error 2
make[1]: *** Waiting for unfinished jobs....
installing default pathname libraries
compiling objspace.c
compiling objspace_dump.c
linking shared-object json/ext/parser.bundle
linking shared-object json/ext/generator.bundle
linking shared-object pathname.bundle
linking shared-object objspace.bundle
linking shared-object bigdecimal.bundle
linking shared-object nkf.bundle
linking shared-object date_core.bundle
make: *** [build-ext] Error 2

Am I missing anything? The command I am trying to run is RUBY_CONFIGURE_OPTS="--with-openssl-dir=/usr/local/opt/openssl" rbenv install 2.3.7

[gfguthrie]

@hardvain you probably don't need to pass the option at all. 2.3.7 I don't think will work with 1.1, and from the error it looks like you don't have anything in /usr/local/opt/openssl. If you don't pass in anything, ruby-build (assuming you have the current version) will just install the openssl that is needed for 2.3.7.

[jyr]

Hi,

I have the same error and tried with multiple options:

$ RUBY_CONFIGURE_OPTS="--with-openssl-dir=/usr/local/opt/openssl" rvm install ruby-2.1.2
$ rvm install --disable-binary  ruby-2.1.2 --autolibs=homebrew --with-openssl-dir=`brew --prefix openssl`
$ rvm install ruby-2.1.2 --autolibs=homebrew --with-openssl-dir=`brew --prefix openssl`

I have OpenSSL 1.1.1d 10 Sep 2019 and I'm using macOS High Sierra version 10.13.6

the error is:

++ printf %b 'command(6): command gem install /Users/jyr/.rvm/gem-cache/gem-wrappers-1.4.0.gem --local --no-document\n'
++ rvm_log 'installing gem /Users/jyr/.rvm/gem-cache/gem-wrappers-1.4.0.gem --local --no-document'
++ [[ '' == 1 ]]
++ printf %b 'installing gem /Users/jyr/.rvm/gem-cache/gem-wrappers-1.4.0.gem --local --no-document\n'
++ command gem install /Users/jyr/.rvm/gem-cache/gem-wrappers-1.4.0.gem --local --no-document
++ gem install /Users/jyr/.rvm/gem-cache/gem-wrappers-1.4.0.gem --local --no-document
ERROR:  Loading command: install (LoadError)
        cannot load such file -- openssl
ERROR:  While executing gem ... (NoMethodError)
    undefined method `invoke_with_build_args' for nil:NilClass
++ return 1
++ return 1
++ return 1
++ return 1

When I want to install openssl

$ rvm list
=> ruby-2.1.2 [ x86_64 ]
 * ruby-2.6.3 [ x86_64 ]

# => - current
# =* - current && default
#  * - default
$ gem install openssl
ERROR:  Loading command: install (LoadError)
	cannot load such file -- openssl
ERROR:  While executing gem ... (NoMethodError)
    undefined method `invoke_with_build_args' for nil:NilClass

And I have openssl via homebrew:

$ brew --prefix openssl
/usr/local/opt/openssl@1.1

Thanks a lot

[mislav]

@jyr There are multiple things wrong with what you are doing. First of all, you are using rvm, which is an entirely different tool for installing Ruby than this repo is (we are called "ruby-build", also known as "rbenv install").

Second, you clearly have OpenSSL 1.1 installed, and this whole thread is about Ruby 2.3 and lower not being compatible with OpenSSL 1.1. So your method of installation won't work until you install OpenSSL 1.0 on your system.

---

To others: Homebrew-core has removed their openssl@1.0 formula due to OpenSSL 1.0 reaching end of life last month. This makes it harder to install Ruby 2.3 and older on macOS. You can try the following and see if it works:

brew install rbenv/tap/openssl@1.0
RUBY_CONFIGURE_OPTS="--with-openssl-dir=$(brew --prefix openssl@1.0)" rbenv install 2.3.8

[sco11morgan]

Thanks @mislav . One small tweak and it worked for me

brew --prefix openssl@1.0
export LDFLAGS="-L/usr/local/opt/openssl@1.0/lib"
export CPPFLAGS="-I/usr/local/opt/openssl@1.0/include"
CONFIGURE_OPTS="--with-openssl-dir=$(brew --prefix openssl@1.0)" RUBY_CONFIGURE_OPTS="--with-openssl-dir=$(brew --prefix openssl@1.0)" rbenv install 2.3.8

[12masta]

@sco11morgan I am executed your command but I am receiving: Error: No available formula with the name "openssl@1.0" . How you resolved it?

[gfguthrie]

@12masta you have to install it first from the rbenv tap: brew install rbenv/tap/openssl@1.0

[chetstone]

I had a similar problem. After unfortunately doing "brew upgrade" I ended up with openssl 1.1.1 installed and a bunch of broken already-installed rubies. To fix those up, I installed openssl@1.0 from the tap as explained by @gfguthrie and @mislav , then, to fix them all, executed the following commands in ~/.rbenv/versions:

$ find . -name \*.bundle -exec /bin/sh -c "file {} | grep -q Mach-O " \; -exec /bin/sh -c "objdump -macho -dylibs-used {} |grep -q libcrypto.1.0 " \; -exec sudo install_name_tool -change /usr/local/opt/openssl/lib/libcrypto.1.0.0.dylib /usr/local/opt/openssl@1.0/lib/libcrypto.dylib {} \;
AND
$ find . -name \*.bundle -exec /bin/sh -c "file {} | grep -q Mach-O " \; -exec /bin/sh -c "objdump -macho -dylibs-used {} |grep -q libssl.1.0 " \; -exec  sudo install_name_tool -change /usr/local/opt/openssl/lib/libssl.1.0.0.dylib /usr/local/opt/openssl@1.0/lib/libssl.dylib {} \;

Before executing this, you might want to print a list of the files you're going to be working on:

find . -name \*.bundle -exec /bin/sh -c "file {} | grep -q Mach-O " \; -exec /bin/sh -c "objdump -macho -dylibs-used {} |grep -q libssl.1.0 " \; -print
AND
find . -name \*.bundle -exec /bin/sh -c "file {} | grep -q Mach-O " \; -exec /bin/sh -c "objdump -macho -dylibs-used {} |grep -q libcrypto.1.0 " \; -print

[burnettk]

@bfreezy confirmed, thanks a ton. i was indeed using version 12 of the command line tools, and downgrading to version 11 fixes rbenv install 2.2.5. i wonder what specifically about clang 12 causes this openssl/ruby breakage, and i wonder if people who have to deal with older rubies will be stuck depending on version 11 of the command line tools forever.

[Nucleotide]

I can also confirm as @bfreezy suggested that command line tools 12 was the issue for me when trying to install 2.1.10. Downgrading to 11.5. fixed install issues for me and I ran install with
RUBY_CONFIGURE_OPTS="--with-openssl-dir=$(brew --prefix openssl@1.0)" rbenv install 2.1.10
(On OS X 10.15.6)
Also I found out before downgrading that there might issues and the command line tools are loaded from a wrong path as suggested below (I had wrong path for version 12 tools initially).
#1473 (comment)

[vemuri-nath]

hii ,

does this fix works for 2.2.3 as well ??

[stephenZ22]

rbenv install 2.1.10

Downloading openssl-1.0.2u.tar.gz...
-> https://dqw8nmjcqpjn7.cloudfront.net/ecd0c6ffb493dd06707d38b14bb4d8c2288bb7033735606569d8f90f89669d16
Installing openssl-1.0.2u...

Installed openssl-1.0.2u to /Users/zhaofujun/.rbenv/versions/2.1.10

Downloading ruby-2.1.10.tar.bz2...
-> https://cache.ruby-lang.org/pub/ruby/2.1/ruby-2.1.10.tar.bz2
Installing ruby-2.1.10...

WARNING: ruby-2.1.10 is past its end of life and is now unsupported.
It no longer receives bug fixes or critical security updates.

ruby-build: using readline from homebrew

BUILD FAILED (Mac OS X 10.15.7 using ruby-build 20201005)

Inspect or clean up the working tree at /var/folders/cq/xmw2hj4d499c6zrcs7w_4wtw0000gn/T/ruby-build.20201014151416.69550.lZuVCh
Results logged to /var/folders/cq/xmw2hj4d499c6zrcs7w_4wtw0000gn/T/ruby-build.20201014151416.69550.log

Last 10 log lines:
make[2]: *** [ossl_pkcs7.o] Error 1
make[1]: *** [ext/openssl/all] Error 2
make[1]: *** Waiting for unfinished jobs....
compiling objspace_dump.c
installing default objspace libraries
linking shared-object objspace.bundle
linking shared-object nkf.bundle
13 warnings generated.
linking shared-object date_core.bundle
make: *** [build-ext] Error 2

[ksato0607]

I had an exactly same issue. When I ran rbenv install 2.3.3, I had this error:

Last 10 log lines:
The Ruby openssl extension was not compiled.
ERROR: Ruby install aborted due to missing extensions
Configure options used:
  --prefix=/Users/username/.rbenv/versions/2.3.3
  --with-openssl-dir=/usr/local/opt/openssl@1.1
  --with-readline-dir=/usr/local/opt/readline
  CC=clang
  CFLAGS= -O3 -Wno-error=shorten-64-to-32 
  LDFLAGS=-L/Users/username/.rbenv/versions/2.3.3/lib 
  CPPFLAGS=-I/Users/username/.rbenv/versions/2.3.3/include 

From the post by @bfreezy, I learned that the version of Command Line Tools should not be 12. (Thank you so much for the information!) In fact, this is what I had

$ clang --version
Apple clang version 12.0.0 (clang-1200.0.32.2)

Therefore, I downgraded my Commond Line Tools version to 11 by following this post and I confirmed the version is downgraded.

$ clang --version
Apple clang version 11.0.3 (clang-1103.0.32.62)

Now I expect that rbenv install 2.3.3 will work, but it still failed with the following error. (--verbose just logs additional details)

$ rbenv install 2.3.3 --verbose
...
Downloading openssl-1.0.2u.tar.gz...
dyld: Library not loaded: /usr/local/opt/openssl/lib/libssl.1.0.0.dylib
  Referenced from: /usr/local/bin/curl
  Reason: image not found
/usr/local/bin/ruby-build: line 337:  3227 Abort trap: 6           curl -qsILf ${CURL_OPTS} "$1" 1>&4 2>&1
...
error: failed to download openssl-1.0.2u.tar.gz

BUILD FAILED (Mac OS X 10.15.6 using ruby-build 20201005)

It seems like there is an issue with curl, so I tried to reinstall it with the following command.

$ brew install --force curl
Updating Homebrew...
Warning: curl 7.72.0 is already installed, it's just not linked
You can use `brew link curl` to link this version.

As you can see above, in my case, I already had the latest version installed, but it was not linked.
Therefore, I updated the path of the curl like below

$ export PATH="/usr/local/opt/curl/bin:$PATH"

And tried rbenv install 2.3.3 again and it worked!! Hope it helps!!

[wyattbenno777]

I was shown the same error.

For me it turned out that RVM and RBENV were both installed.
When I went into the directory RVM would change to the local ruby there, while globally I was using RBENV.

Uninstalled RVM and reentered the directory. Everything worked.

[mattneub]

I had a similar problem. After unfortunately doing "brew upgrade" I ended up with openssl 1.1.1 installed and a bunch of broken already-installed rubies.

This isn't entirely germane to the current thread, but the same thing just happened to me — I said brew upgrade and all my rbenv rubies stopped working. For example, saying gem install failed; lots of other stuff went wrong too; but it all came down to a complaint about OpenSSL.

I ended up having to blow away all my rubies and install them again. Not a huge pain, but a pain nonetheless.

I find it very surprising that something can happen miles away (in brew) and rbenv can be crippled in this way.

[rtoledo-dev-ao3]

readline.c:1781:37: error: use of undeclared identifier 'username_completion_function'; did you mean 'rl_username_completion_function'?

The biggest problem is the openssl 1.0 in M1 Apple. Trying install with

brew install rbenv/tap/openssl@1.0

or

arch -arm64 brew install rbenv/tap/openssl@1.0

Final result:

These open issues may also help:

brew install rbenv/tap/openssl@1.0 not working anymore https://github.com/rbenv/homebrew-tap/issues/1

So these commands aren't working too

RUBY_CONFIGURE_OPTS="--with-openssl-dir=$(brew --prefix openssl@1.1)" rbenv install 2.3.8`

or

RUBY_CONFIGURE_OPTS="--with-openssl-dir=$(brew --prefix openssl@1.0)" rbenv install 2.3.8

[gfguthrie]

The biggest problem is the openssl 1.0 in M1 Apple.

You're going to have to find your own solution for openssl 1.0 on Apple Silicon – they have no plans to backport building 1.0: openssl/openssl#12254 (comment)

There's probably an unofficial backport somewhere.

[ThomasKoppensteiner]

Inspired by this solution the following worked for me:

export optflags="-Wno-error=implicit-function-declaration"
rbenv install 2.1.2

Setting RUBY_CONFIGURE_OPTS or CFLAGS had no effect.

[namratasaun]

export optflags="-Wno-error=implicit-function-declaration"
rbenv install 2.1.2

I am installing 2.3.4 and it's showing me openssl error shown below. (I have macos 11.5.1 and xcode 12.0.5)

[kornate]

With Amazon Linux 2 on ARM/aarch you need to install openssl-devel.

[nicobrenner]

Can confirm that gcc-6 + openssl@1.0 works (on MacOS BigSur 11.2.1, with homebrew):

brew install gcc@6
brew install rbenv/tap/openssl@1.0
RUBY_CONFIGURE_OPTS="--with-openssl-dir=$(brew --prefix openssl@1.0)" CC=$(which gcc-6) rbenv install 2.0.0-p647

Also had Xcode 12 installed and if the above command didn't work, was going to downgrade to 11 to try again.

It seems like people using rvm are having the same issue and they've come up with a slightly different solution of passing an extra compiler flag (export optflags="-Wno-error=implicit-function-declaration"), see here: https://stackoverflow.com/a/64829129/7724157

Spoke too soon. After installation, running gem install bundler (or any gem) gives me the following error:

ERROR:  Loading command: install (LoadError)
	cannot load such file -- socket
ERROR:  While executing gem ... (NoMethodError)

Doing some searching it seems it's an issue with openssl... 🥲 back to square one.

Finally, this worked 😃:

export LDFLAGS="-L/usr/local/opt/openssl@1.0/lib"
export CPPFLAGS="-I/usr/local/opt/openssl@1.0/include"
CONFIGURE_OPTS="--with-openssl-dir=$(brew --prefix openssl@1.0)" RUBY_CONFIGURE_OPTS="--with-openssl-dir=$(brew --prefix openssl@1.0)" rbenv install 2.0.0-p647

[thr3a]

With the help of your report I also succeeded in installing ruby2.3.

• M1 (homebrew on arm64)
• MacOS Ventura
• Xcode Command Line Tools 14.2

brew install --build-from-source readline
brew install libffi

For installing ruby2.3, you need to install openssl 1.0.(ref)

brew install nutcracker/tap/openssl@1.0

export optflags="-Wno-error=implicit-function-declaration"
export LDFLAGS="-L$(brew --prefix libffi)/lib"
export CPPFLAGS="-I$(brew --prefix libffi)/include"
export PKG_CONFIG_PATH="$(brew --prefix libffi)/lib/pkgconfig"
export RUBY_CONFIGURE_OPTS="--with-openssl-dir=$(brew --prefix openssl@1.0)"
RUBY_CFLAGS="-w" rbenv install 2.3.8

[hellysmile]

Hey, I had same issue and prepared a patched version brew Formula

https://gist.github.com/hellysmile/f58a6e32656ac1101cf6a64d0674f2c8 with openssl 1.0.2 patch from https://github.com/lavabit/magma