Can't install ruby on M1 Mac "use of undeclared identifier 'RSA_SSLV23_PADDING'" #409

SteveTro · 2021-09-24T11:23:40Z

Description

Steps To Reproduce

Steps to reproduce the bug:

$ ruby-install ruby -- --with-openssl-dir=$(brew --prefix openssl)

Expected Behavior

ruby should be installed

Actual Behavior

ossl_pkey_rsa.c:950:5: error: use of undeclared identifier 'RSA_SSLV23_PADDING'
    DefRSAConst(SSLV23_PADDING);
    ^
ossl_pkey_rsa.c:885:58: note: expanded from macro 'DefRSAConst'
#define DefRSAConst(x) rb_define_const(cRSA, #x, INT2NUM(RSA_##x))
                                                         ^
<scratch space>:166:1: note: expanded from here
RSA_SSLV23_PADDING
^
110 warnings and 1 error generated.
make[2]: *** [ossl_pkey_rsa.o] Error 1
make[1]: *** [ext/openssl/all] Error 2
make: *** [build-ext] Error 2

Environment

$ ruby-install --version
ruby-install: 0.8.2
$ uname -a
Darwin macbook.fritz.box 20.3.0 Darwin Kernel Version 20.3.0: Thu Jan 21 00:06:51 PST 2021; root:xnu-7195.81.3~1/RELEASE_ARM64_T8101 arm64
$ cc --version
Apple clang version 12.0.5 (clang-1205.0.22.9)
Target: arm64-apple-darwin20.3.0
Thread model: posix
InstalledDir: /Library/Developer/CommandLineTools/usr/bin
$ openssl version
OpenSSL 3.0.0 7 sep 2021 (Library: OpenSSL 3.0.0 7 sep 2021)

The text was updated successfully, but these errors were encountered:

superx3man · 2021-09-24T14:52:31Z

Same issue observed for intel processor as well.

postmodern · 2021-09-24T15:27:57Z

This looks like a compatibility difference between the ruby and the version of openssl. Also, - --with-openssl-dir=$(brew --prefix openssl) is not necessary, as ruby-install already passes in --with-opt-dir="$(brew --prefix openssl):$(brew --prefix readline):$(brew --prefix libyaml):$(brew --prefix gdbm)".

Can you try reproducing this without ruby-install?

$ wget https://cache.ruby-lang.org/pub/ruby/3.0/ruby-3.0.2.tar.xz
$ tar -Jvf ruby-3.0.2.tar.xz
$ cd ruby-3.0.2/
$ ./configure --with-opt-dir="$(brew --prefix openssl):$(brew --prefix readline):$(brew --prefix libyaml):$(brew --prefix gdbm)"
$ make

If manually compiling also fails, than this issue needs to be reported upstream to https://bugs.ruby-lang.org/.

hkim3162 · 2021-09-24T15:58:17Z

hey folks same issue here. on an intel (big sur 11.6) getting issues with a simple ruby-install 2.7.2 where openssl failures appear.

ossl_pkey_rsa.c:942:5: error: use of undeclared identifier 'RSA_SSLV23_PADDING'
Using chruby + ruby-install

it appears that there is some weird symlink issue. I have already tried exporting flags and paths to my /usr/bin file where homebrew installed openssl but no luck. at other times i get

  Referenced from: /Users/hkim/src/ruby-2.7.2/.ext/x86_64-darwin20/openssl.bundle
  Expected in: flat namespace

dyld: Symbol not found: _EVP_MD_type

emptyflask · 2021-09-24T16:04:25Z

I had this issue with an intel mac too. It's because homebrew now defaults openssl to openssl@3 instead of openssl@1.1

Try this:

brew install openssl@1.1
ruby-install ruby-3.0.2 -- --with-openssl-dir=$(brew --prefix openssl@1.1)

grimm26 · 2021-09-24T16:10:58Z

manual build fails, too.

---
Configuration summary for ruby version 3.0.2

   * Installation prefix: /usr/local
   * exec prefix:         ${prefix}
   * arch:                x86_64-darwin20
   * site arch:           ${arch}
   * RUBY_BASE_NAME:      ruby
   * ruby lib prefix:     ${libdir}/${RUBY_BASE_NAME}
   * site libraries path: ${rubylibprefix}/${sitearch}
   * vendor path:         ${rubylibprefix}/vendor_ruby
   * target OS:           darwin20
   * compiler:            clang -fdeclspec
   * with pthread:        yes
   * with coroutine:      amd64
   * enable shared libs:  no
   * dynamic library ext: bundle
   * CFLAGS:              ${optflags} ${debugflags} ${warnflags}
   * LDFLAGS:             -L. -fstack-protector-strong -L/usr/local/lib \
                          -L/usr/local/opt/openssl@3/lib \
                          -L/usr/local/opt/readline/lib \
                          -L/usr/local/opt/libyaml/lib \
                          -L/usr/local/opt/gdbm/lib
   * DLDFLAGS:            -Wl,-undefined,dynamic_lookup \
                          -Wl,-multiply_defined,suppress \
                          -L/usr/local/opt/openssl@3/lib \
                          -L/usr/local/opt/readline/lib \
                          -L/usr/local/opt/libyaml/lib \
                          -L/usr/local/opt/gdbm/lib
   * optflags:            -O3
   * debugflags:          -ggdb3
   * warnflags:           -Wall -Wextra -Wdeprecated-declarations \
                          -Wdivision-by-zero \
                          -Wimplicit-function-declaration -Wimplicit-int \
                          -Wmisleading-indentation -Wpointer-arith \
                          -Wshorten-64-to-32 -Wwrite-strings \
                          -Wmissing-noreturn -Wno-constant-logical-operand \
                          -Wno-long-long -Wno-missing-field-initializers \
                          -Wno-overlength-strings -Wno-parentheses-equality \
                          -Wno-self-assign -Wno-tautological-compare \
                          -Wno-unused-parameter -Wno-unused-value \
                          -Wunused-variable -Wextra-tokens
   * strip command:       strip -A -n
   * install doc:         rdoc
   * JIT support:         yes
   * man page type:       doc
   * BASERUBY -v:         ruby 2.7.3p183 (2021-04-05 revision 6847ee089d) \
                          [x86_64-darwin20]

....

ossl_pkey_rsa.c:950:5: error: use of undeclared identifier 'RSA_SSLV23_PADDING'
    DefRSAConst(SSLV23_PADDING);
    ^
ossl_pkey_rsa.c:885:58: note: expanded from macro 'DefRSAConst'
#define DefRSAConst(x) rb_define_const(cRSA, #x, INT2NUM(RSA_##x))
                                                         ^
<scratch space>:49:1: note: expanded from here
RSA_SSLV23_PADDING
^
110 warnings and 1 error generated.
make[2]: *** [ossl_pkey_rsa.o] Error 1
make[1]: *** [ext/openssl/all] Error 2
make: *** [build-ext] Error 2

grimm26 · 2021-09-24T16:12:53Z

it seems this issue is covered by ruby/openssl#369

emptyflask · 2021-09-24T16:12:56Z

@grimm26 see my previous comment. Ruby doesn't support openssl 3 yet.

PeteHanner · 2021-09-24T16:33:45Z

After running brew uninstall openssl, brew uninstall openssl@3 and brew uninstall openssl@1.1, along with all the rm -rf suggestions along the way, I reinstalled openssl@1.1 and successfully ran ruby-install ruby-2.6.6 -- --with-openssl-dir=$(brew --prefix openssl@1.1)

dlegr250 · 2021-09-24T20:12:15Z

I had this issue with an intel mac too. It's because homebrew now defaults openssl to openssl@3 instead of openssl@1.1

Try this:
brew install openssl@1.1
ruby-install ruby-3.0.2 -- --with-openssl-dir=$(brew --prefix openssl@1.1)

I can verify that this also worked for me. Same issue, homebrew had openssl@3 installed; when I removed it and used openssl@1.1 to compile Ruby 3.0.2 it worked just fine.

postmodern · 2021-09-25T07:32:19Z

PR #410 has been merged which pins homebrew's openssl dependency to openssl@1.1. ruby-install-0.8.3 will be released shortly, then we just have to wait for homebrew to pickup the new version and for users to upgrade.

postmodern · 2021-09-25T08:34:02Z

ruby-install 0.8.3 has been released which pins the homebrew openssl dependency to openssl@1.1. Now we wait for homebrew to pull it in.

We temporarily removed the brewed versions of openssl in order to satisfy ruby-install. See postmodern/ruby-install#409 for details. By the time we need ruby-install again hopefully the issues with homebrew openssl will have sorted themselves out.

liijunwei · 2022-02-02T02:58:35Z

macos big sur

uninstall openssl@3
reinstall openssl@1.1
#open new shell
rvm reinstall "ruby-3.0.0" --with-openssl-dir=`brew --prefix openssl@1.1` --disable-binary # ok

this flow worked for me

paxperscientiam · 2022-10-21T05:58:57Z

After running brew uninstall openssl, brew uninstall openssl@3 and brew uninstall openssl@1.1, along with all the rm -rf suggestions along the way, I reinstalled openssl@1.1 and successfully ran ruby-install ruby-2.6.6 -- --with-openssl-dir=$(brew --prefix openssl@1.1)

Unfortunately, this isn't working for me (also M1 mac).

The only difference, I think, is that I'm using openssl 1.1 from macports.
ruby-install ruby -- --with-openssl-dir=/opt/local/libexec/openssl11

0xjacklove · 2023-05-24T07:35:17Z

brew install openssl@1.1
export LDFLAGS="-L/opt/homebrew/opt/openssl@1.1/lib"
export CPPFLAGS="-I/opt/homebrew/opt/openssl@1.1/include"
ruby-install ruby-3.0.2 -- --with-openssl-dir=$(brew --prefix openssl@1.1)
it works for me

AutumnChillHu · 2023-06-13T09:49:36Z

@emptyflask Thank you A LOT！！

chkhu · 2023-07-28T06:10:06Z

I had this issue with an intel mac too. It's because homebrew now defaults openssl to openssl@3 instead of openssl@1.1

Try this:
brew install openssl@1.1
ruby-install ruby-3.0.2 -- --with-openssl-dir=$(brew --prefix openssl@1.1)

This worked for me! thx🥰

sulaiman-pro · 2023-08-03T11:37:53Z

it also worked for me! thx

posiczko · 2023-08-16T19:05:44Z

FWIW, installation of legacy versions of ruby, say 2.6 or 2.7 which require openssl@1.1 may fail when openssl3 is present on a Mac. Specifying --with-openssl-dir=$(brew --prefix openssl@1.1) might not address the issue, because of how extensions detect openssl via autotools.

To fix, specify PKG_CONFIG_PATH pointing to $(brew --prefix openssl@1.1)/lib/pkgconfig which will force autotools in extensions to detect the correct path.

In addition, libffi binding may grumble of other issues, which can be fixed by setting CFLAGS to -DUSE_FFI_CLOSURE_ALLOC

In other words:

export CFLAGS="-DUSE_FFI_CLOSURE_ALLOC"
export PKG_CONFIG_PATH="$(brew --prefix openssl@1.1)/lib/pkgconfig"
ruby-install 2.6.5 -- --with-openssl-dir=$(brew --prefix openssl@1.1)

scifisamurai · 2023-08-17T05:46:31Z

I had this issue with an intel mac too. It's because homebrew now defaults openssl to openssl@3 instead of openssl@1.1

Try this:
brew install openssl@1.1
ruby-install ruby-3.0.2 -- --with-openssl-dir=$(brew --prefix openssl@1.1)

This worked on my M1 Mac as long as I uninstalled openssl@3 first ... otherwise it still failed oddly (possibly since I had /opt/homebrew/opt/openssl@3/bin in my PATH not sure ).

brew uninstall --ignore-dependencies openssl@3
ruby-install ruby-3.0.1 -- --with-openssl-dir=$(brew --prefix openssl@1.1) # I needed 3.0.1 rather than 3.0.2 but close enough
brew install openssl@3 # needed due to software already installed against openssl@3

Thank you!!

mr-liu-hunan · 2023-08-22T01:59:26Z

ruby-install 3.0.0

FWIW, installation of legacy versions of ruby, say 2.6 or 2.7 which require openssl@1.1 may fail when openssl3 is present on a Mac. Specifying --with-openssl-dir=$(brew --prefix openssl@1.1) might not address the issue, because of how extensions detect openssl via autotools.

To fix, specify PKG_CONFIG_PATH pointing to $(brew --prefix openssl@1.1)/lib/pkgconfig which will force autotools in extensions to detect the correct path.

In addition, libffi binding may grumble of other issues, which can be fixed by setting CFLAGS to -DUSE_FFI_CLOSURE_ALLOC

In other words:
export CFLAGS="-DUSE_FFI_CLOSURE_ALLOC"
export PKG_CONFIG_PATH="$(brew --prefix openssl@1.1)/lib/pkgconfig"
ruby-install 2.6.5 -- --with-openssl-dir=$(brew --prefix openssl@1.1)

很有帮助，谢谢

ziggear · 2023-12-11T07:53:32Z

mac os sonoma 14.1.2, for some other reason, I already have an openssl@3 installed in my homebrew, with an openssl@1.1 at the same time, so the comand:

rvm install 2.7.2 --with-openssl-dir=$(brew --prefix openssl@1.1)

not working for me

Then I uninstalled the openssl@3, everything is becoming OK

postmodern · 2023-12-11T13:48:18Z

@ziggear rvm is a different tool from ruby-install. ruby-install 0.9.3 should handle openssl@1.1 vs. openssl@3.

AppleCaffe · 2024-05-12T12:41:15Z

ruby-install 3.0.0
FWIW, installation of legacy versions of ruby, say 2.6 or 2.7 which require openssl@1.1 may fail when openssl3 is present on a Mac. Specifying --with-openssl-dir=$(brew --prefix openssl@1.1) might not address the issue, because of how extensions detect openssl via autotools.
To fix, specify PKG_CONFIG_PATH pointing to $(brew --prefix openssl@1.1)/lib/pkgconfig which will force autotools in extensions to detect the correct path.
In addition, libffi binding may grumble of other issues, which can be fixed by setting CFLAGS to -DUSE_FFI_CLOSURE_ALLOC
In other words:
export CFLAGS="-DUSE_FFI_CLOSURE_ALLOC"
export PKG_CONFIG_PATH="$(brew --prefix openssl@1.1)/lib/pkgconfig"
ruby-install 2.6.5 -- --with-openssl-dir=$(brew --prefix openssl@1.1)
很有帮助，谢谢
确实这个方法是有效的。This is the key approach, thank you!

SteveTro added the bug label Sep 24, 2021

postmodern added cruby openssl labels Sep 24, 2021

emptyflask mentioned this issue Sep 24, 2021

Force homebrew to use OpenSSL 1.1 #410

Merged

postmodern mentioned this issue Sep 25, 2021

ruby-install ruby 2.6.3 "ERR_get_line_data' is deprecated [-Werror, -Wdeprecated-declarations] #411

Closed

postmodern closed this as completed Sep 25, 2021

d12 mentioned this issue Jul 6, 2023

Ruby doesn't compile on macOS if openssl 3.1 is installed rvm/rvm#5365

Closed

holdenmatt mentioned this issue Sep 5, 2023

Jekyll build errors on M1 mac duckdb/duckdb-web#1090

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kwin mentioned this issue Feb 26, 2024

Support building site with Ruby 3.x Adobe-Consulting-Services/adobe-consulting-services.github.io#259

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Nightly build broken crystal-lang/distribution-scripts#318

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Can't install ruby on M1 Mac "use of undeclared identifier 'RSA_SSLV23_PADDING'" #409

Can't install ruby on M1 Mac "use of undeclared identifier 'RSA_SSLV23_PADDING'" #409

SteveTro commented Sep 24, 2021

superx3man commented Sep 24, 2021

postmodern commented Sep 24, 2021

hkim3162 commented Sep 24, 2021 •

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emptyflask commented Sep 24, 2021 •

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grimm26 commented Sep 24, 2021

grimm26 commented Sep 24, 2021

emptyflask commented Sep 24, 2021 •

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PeteHanner commented Sep 24, 2021

dlegr250 commented Sep 24, 2021

postmodern commented Sep 25, 2021

postmodern commented Sep 25, 2021 •

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liijunwei commented Feb 2, 2022

paxperscientiam commented Oct 21, 2022

0xjacklove commented May 24, 2023

AutumnChillHu commented Jun 13, 2023

chkhu commented Jul 28, 2023

sulaiman-pro commented Aug 3, 2023

posiczko commented Aug 16, 2023

scifisamurai commented Aug 17, 2023 •

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mr-liu-hunan commented Aug 22, 2023

ziggear commented Dec 11, 2023

postmodern commented Dec 11, 2023

AppleCaffe commented May 12, 2024

Can't install ruby on M1 Mac "use of undeclared identifier 'RSA_SSLV23_PADDING'" #409

Can't install ruby on M1 Mac "use of undeclared identifier 'RSA_SSLV23_PADDING'" #409

Comments

SteveTro commented Sep 24, 2021

Description

Steps To Reproduce

Expected Behavior

Actual Behavior

Environment

superx3man commented Sep 24, 2021

postmodern commented Sep 24, 2021

hkim3162 commented Sep 24, 2021 • edited Loading

emptyflask commented Sep 24, 2021 • edited Loading

grimm26 commented Sep 24, 2021

grimm26 commented Sep 24, 2021

emptyflask commented Sep 24, 2021 • edited Loading

PeteHanner commented Sep 24, 2021

dlegr250 commented Sep 24, 2021

postmodern commented Sep 25, 2021

postmodern commented Sep 25, 2021 • edited Loading

liijunwei commented Feb 2, 2022

paxperscientiam commented Oct 21, 2022

0xjacklove commented May 24, 2023

AutumnChillHu commented Jun 13, 2023

chkhu commented Jul 28, 2023

sulaiman-pro commented Aug 3, 2023

posiczko commented Aug 16, 2023

scifisamurai commented Aug 17, 2023 • edited Loading

mr-liu-hunan commented Aug 22, 2023

ziggear commented Dec 11, 2023

postmodern commented Dec 11, 2023

AppleCaffe commented May 12, 2024

hkim3162 commented Sep 24, 2021 •

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emptyflask commented Sep 24, 2021 •

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