Help with openssl@3 build failure (perl cant make socket?)

[jacktose]

Additional Info

• I am using Windows Subsystem for Linux

Output of brew config

brew config

HOMEBREW_VERSION: 4.6.4
ORIGIN: https://github.com/Homebrew/brew
HEAD: 160af073a53fcb23331d70d79785d17d13da41e7
Last commit: 4 days ago
Branch: stable
Core tap JSON: 21 Aug 23:10 UTC
HOMEBREW_PREFIX: /data/shared/lusers/jacktose/homebrew
HOMEBREW_REPOSITORY: /data/shared/lusers/jacktose/homebrew
HOMEBREW_CELLAR: /data/shared/lusers/jacktose/homebrew/Cellar
HOMEBREW_CASK_OPTS: []
HOMEBREW_CLEANUP_MAX_AGE_DAYS: 60
HOMEBREW_CLEANUP_PERIODIC_FULL_DAYS: 7
HOMEBREW_DISPLAY_INSTALL_TIMES: set
HOMEBREW_EDITOR: vim
HOMEBREW_FORBID_PACKAGES_FROM_PATHS: set
HOMEBREW_FORCE_BREWED_CURL: set
HOMEBREW_GITHUB_API_TOKEN: set
HOMEBREW_GIT_PATH: /usr/local/bin/git
HOMEBREW_MAKE_JOBS: 4
Homebrew Ruby: 3.4.5 => /data/shared/lusers/jacktose/homebrew/Library/Homebrew/vendor/portable-ruby/3.4.5/bin/ruby
CPU: quad-core 64-bit broadwell
Clang: N/A
Git: 2.31.1 => /usr/local/bin/git
Curl: 8.15.0 => /data/shared/lusers/jacktose/homebrew/opt/curl/bin/curl
Kernel: Linux 3.10.0-1160.90.1.el7.x86_64 x86_64 GNU/Linux
OS: CentOS Linux release 7.9.2009 (Core) (Core)
Host glibc: 2.17
/usr/bin/gcc: 4.8.5
/usr/bin/ruby: N/A
glibc: 2.35_1
gcc@11: N/A
gcc: 15.1.0
xorg: N/A

Output of brew doctor

brew doctor (Yes, it's messy. I don't control the system and don't have root.)

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Warning: Your system glibc 2.17 is too old.
We will need to automatically install a newer version.

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You can report Tier 2 unrelated issues to Homebrew/* repositories!
Read the above document instead before opening any issues or PRs.


Warning: Your Homebrew's prefix is not /home/linuxbrew/.linuxbrew.

Most of Homebrew's bottles (binary packages) can only be used with the default prefix.
Consider uninstalling Homebrew and reinstalling into the default prefix.

This is a Tier 3 configuration:
  https://docs.brew.sh/Support-Tiers#tier-3
You can report Tier 3 unrelated issues to Homebrew/* repositories!
Read the above document instead before opening any issues or PRs.


Warning: /usr/bin occurs before /data/shared/lusers/jacktose/homebrew/bin in your PATH.
This means that system-provided programs will be used instead of those
provided by Homebrew. Consider setting your PATH so that
/data/shared/lusers/jacktose/homebrew/bin occurs before /usr/bin. Here is a one-liner:
  echo 'export PATH="/data/shared/lusers/jacktose/homebrew/bin:$PATH"' >> /usr/lusers/jacktose/.bash_profile

The following tools exist at both paths:
  aclocal
  attr
  autoconf
  autoheader
  autom4te
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  awk
  bash
  bashbug
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  cal
  captoinfo
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  chrt
  clear
  col
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  colrm
  column
  compile_et
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  cpan
  curl
  curl-config
  dmesg
  dumpsexp
  eject
  envsubst
  fallocate
  findmnt
  flock
  funzip
  gawk
  getfacl
  getfattr
  getopt
  gettext
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  gss-client
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  json_pp
  k5srvutil
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  ksu
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  last
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  less
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  libtool
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  linux32
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Warning: Homebrew's "bin" was not found in your PATH.
Consider setting your PATH for example like so:
  echo 'export PATH="/data/shared/lusers/jacktose/homebrew/bin:$PATH"' >> /usr/lusers/jacktose/.bash_profile

Warning: Homebrew's "sbin" was not found in your PATH but you have installed
formulae that put executables in /data/shared/lusers/jacktose/homebrew/sbin.
Consider setting your PATH for example like so:
  echo 'export PATH="/data/shared/lusers/jacktose/homebrew/sbin:$PATH"' >> /usr/lusers/jacktose/.bash_profile

Description of issue

brew upgrade openssl@3 or brew install openssl@3 fails to build. It appears that some perl test script is failing to create sockets?

Details

Here's a log gist and here's the command output:

brew install --as-dependency openssl@3 output

==> Fetching downloads for: openssl@3
==> Downloading https://raw.githubusercontent.com/Homebrew/homebrew-core/dedb58bc7b79700ced4a991bb425957deadb4678/Formula/o/openssl@3.rb
Warning: Building openssl@3 from source as the bottle needs:
- `HOMEBREW_CELLAR=/home/linuxbrew/.linuxbrew/Cellar` (yours is /data/shared/lusers/jacktose/homebrew/Cellar)
- `HOMEBREW_PREFIX=/home/linuxbrew/.linuxbrew` (yours is /data/shared/lusers/jacktose/homebrew)
==> Fetching openssl@3
==> Downloading https://cpan.metacpan.org/authors/id/L/LE/LEONT/Test-Harness-3.52.tar.gz
==> Downloading https://cpan.metacpan.org/authors/id/E/EX/EXODIST/Test-Simple-1.302214.tar.gz
==> Downloading https://cpan.metacpan.org/authors/id/B/BI/BINGOS/ExtUtils-MakeMaker-7.76.tar.gz
==> Downloading https://github.com/openssl/openssl/releases/download/openssl-3.5.2/openssl-3.5.2.tar.gz
Already downloaded: /usr/lusers/jacktose/.cache/Homebrew/downloads/ade3b0cd5520e066abf867a4df49d9127a1fe73736a21f9b16ae658af9213f3b--openssl-3.5.2.tar.gz
==> perl Makefile.PL INSTALL_BASE=/var/tmp/opensslA3-20250821-7046-jvb2e3/openssl-3.5.2
==> make PERL5LIB=/var/tmp/opensslA3-20250821-7046-jvb2e3/openssl-3.5.2/lib/perl5 CC=gcc-15
==> make install
==> perl Makefile.PL INSTALL_BASE=/var/tmp/opensslA3-20250821-7046-jvb2e3/openssl-3.5.2
==> make PERL5LIB=/var/tmp/opensslA3-20250821-7046-jvb2e3/openssl-3.5.2/lib/perl5 CC=gcc-15
==> make install
==> perl Makefile.PL INSTALL_BASE=/var/tmp/opensslA3-20250821-7046-jvb2e3/openssl-3.5.2
==> make PERL5LIB=/var/tmp/opensslA3-20250821-7046-jvb2e3/openssl-3.5.2/lib/perl5 CC=gcc-15
==> make install
==> perl ./Configure --prefix=/data/shared/lusers/jacktose/homebrew/Cellar/openssl@3/3.5.2 --openssldir=/data/shared/lusers/jacktose/homebrew/etc/openssl@3 --libdir=lib no-ssl3 no-ssl3-method no-zlib linux-x86_64
==> make
==> make install MANDIR=/data/shared/lusers/jacktose/homebrew/Cellar/openssl@3/3.5.2/share/man MANSUFFIX=ssl
==> make HARNESS_JOBS=4 test TESTS=-test_afalg
Last 15 lines from /usr/lusers/jacktose/.cache/Homebrew/Logs/openssl@3/13.make.log:
  Non-zero exit status: 22
  Parse errors: No plan found in TAP output
70-test_tls13psk.t                    (Wstat: 5632 (exited 22) Tests: 0 Failed: 0)
  Non-zero exit status: 22
  Parse errors: No plan found in TAP output
70-test_tlsextms.t                    (Wstat: 5632 (exited 22) Tests: 0 Failed: 0)
  Non-zero exit status: 22
  Parse errors: No plan found in TAP output
Files=341, Tests=4229, 186 wallclock secs ( 8.76 usr  0.94 sys + 370.55 cusr 148.05 csys = 528.30 CPU)
Result: FAIL
make[2]: *** [Makefile:3919: run_tests] Error 1
make[2]: Leaving directory '/var/tmp/opensslA3-20250821-7046-jvb2e3/openssl-3.5.2'
make[1]: *** [Makefile:3916: _tests] Error 2
make[1]: Leaving directory '/var/tmp/opensslA3-20250821-7046-jvb2e3/openssl-3.5.2'
make: *** [Makefile:3914: tests] Error 2

READ THIS: https://docs.brew.sh/Troubleshooting

My troubleshooting

The last log file shows these errors:

# The results of this test will end up in test-runs/test_comp
Port 54422 in use - Name or service not known
Port 59512 in use - Name or service not known
Port 59692 in use - Name or service not known
Port 55676 in use - Name or service not known
Port 58773 in use - Name or service not known
Port 59592 in use - Name or service not known
Port 64337 in use - Name or service not known
Port 55833 in use - Name or service not known
Port 52991 in use - Name or service not known
Port 56892 in use - Name or service not known
Port 50703 in use - Name or service not known
Unable to find usable port for TLSProxy at /var/tmp/opensslA3-20250821-13970-wpl9dq/openssl-3.5.2/util/perl/TLSProxy/Proxy.pm line 159.70-test_comp.t .......................... 
Dubious, test returned 22 (wstat 5632, 0x1600)
No subtests run 

### similar things many times
### ...

Test Summary Report
-------------------
70-test_certtypeext.t                 (Wstat: 5632 (exited 22) Tests: 0 Failed: 0)
  Non-zero exit status: 22
  Parse errors: No plan found in TAP output

### similar things many times
### ...

Result: FAIL
make[2]: *** [Makefile:3919: run_tests] Error 1
make[2]: Leaving directory '/var/tmp/opensslA3-20250821-13970-wpl9dq/openssl-3.5.2'
make[1]: *** [Makefile:3916: _tests] Error 2
make[1]: Leaving directory '/var/tmp/opensslA3-20250821-13970-wpl9dq/openssl-3.5.2'
make: *** [Makefile:3914: tests] Error 2

If I follow the breadcrumb .../openssl-3.5.2/util/perl/TLSProxy/Proxy.pm line 159, that code looks like a 10x loop trying to open a socket on a random, high-numbered port. Apparently that fails every time.

I know no perl, but when I try a minimal replication of that test, it works fine:

$ ~/homebrew/bin/perl test.pl
Found available client port 60995
$ ~/homebrew/bin/perl test.pl
Found available client port 57227

Now what?

And I'm out of ideas. Why could this be failing? How can I fix it?

[carlocab]

That's weird. Maybe a system restart will help?

[jacktose]

I wish I had that option! It's a shared server at work.

Is there some way I can try to replicate it in an environment closer to the build process under homebrew? Maybe with --interactive?

[jacktose]

Okay, I got it to build!
The problem is the very old /usr/bin/perl on this system. Using brewed perl, the Proxy.pm stuff works fine. When using system perl, it fails to find ports, as above.
make was calling /usr/bin/perl—either explicitly or because homebrew messes with the PATH for the build environment.
I did brew edit openssl@3 and added depends_on "perl" => :build to add brew's perl to the path. And voila!

So, going forward, is there a better way to handle this situation?
Can homebrew automagically use brewed perl when system perl is too old or broken, like with curl or git? Or can I force it somehow? I don't see a HOMEBREW_FORCE_BREWED_PERL.
I'd rather not maintain the edited formula and the whole tap, but I expect this is too weird a case to warrant adding the perl build dependency for everyone.

details

This system has a fresh brewed perl first in path, and a very old system perl:

$ which -a perl
~/homebrew/bin/perl
/usr/bin/perl

$  /usr/bin/env perl --version
This is perl 5, version 40, subversion 2 (v5.40.2) built for x86_64-linux-thread-multi
Copyright 1987-2025, Larry Wall
...

$ ~/homebrew/bin/perl --version
This is perl 5, version 40, subversion 2 (v5.40.2) built for x86_64-linux-thread-multi
Copyright 1987-2025, Larry Wall
...

$ /usr/bin/perl --version
This is perl 5, version 16, subversion 3 (v5.16.3) built for x86_64-linux-thread-multi
(with 44 registered patches, see perl -V for more detail)
Copyright 1987-2012, Larry Wall
...

From the first failing test, I made a minimal test file, ptest.t:

#! /usr/bin/env perl
use TLSProxy::Proxy;
my $proxy = TLSProxy::Proxy->new();

It works when run (with the build environment's libraries) by brewed perl and fails (like the build does) when run by system perl:

$ PERL5LIB=/var/tmp/opensslA3-20251006-23281-ykf6q0/openssl-3.6.0/util/perl ~/homebrew/bin/perl ~/ptest.t
Found available client port 61007

$ PERL5LIB=/var/tmp/opensslA3-20251006-23281-ykf6q0/openssl-3.6.0/util/perl /usr/bin/perl ~/ptest.t
Port 61480 in use - Name or service not known
...
Unable to find usable port for TLSProxy at /var/tmp/opensslA3-20251006-23281-ykf6q0/openssl-3.6.0/util/perl/TLSProxy/Proxy.pm line 159.

It seems clear from the logs that the build uses /usr/bin/perl, but I also did puts ENV["PATH"] and puts which("perl") in the formula to confirm.
It looks like brew irb uses a similarly modified environment, which makes it pretty clear:

$ brew irb
==> Interactive Homebrew Shell
Example commands available with: `brew irb --examples`
brew(main):001> ENV["PATH"]
=> "/data/shared/lusers/jacktose/homebrew/Library/Homebrew/shims/shared:/usr/bin:/bin:/usr/sbin:/sbin"
brew(main):002> which "perl"
=> #<Pathname:/usr/bin/perl>
brew(main):003> system "perl", "--version"

This is perl 5, version 16, subversion 3 (v5.16.3) built for x86_64-linux-thread-multi
(with 44 registered patches, see perl -V for more detail)

Copyright 1987-2012, Larry Wall
...

=> true

$ ~/homebrew/Library/Homebrew/vendor/portable-ruby/current/bin/irb
irb(main):001> ENV["PATH"]
=> "/usr/lusers/jacktose/spack/bin:/usr/lusers/jacktose/.local/bin:/usr/lusers/jacktose/homebrew/bin:/usr/lusers/jacktose/homebrew/sbin:/netops/bin:/usr/lib64/qt-3.3/bin:/usr/local/bin:/usr/bin:/usr/local/sbin:/usr/sbin"
irb(main):002> system "perl", "--version"

This is perl 5, version 40, subversion 2 (v5.40.2) built for x86_64-linux-thread-multi

Copyright 1987-2025, Larry Wall
...

=> true

[jacktose]

openssl@3 updated and I had to remember how to do this again. Anybody got a better idea about a general solution?

[itsTurnip]

I've got just the same problem (but it happened to other perl packages) as you did and I used your soultion to fix it. Thanks for investigation!

For me it seems that adding depends_on "perl" => :build is the only option to allow build on any system.