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.)

Please note that these warnings are just used to help the Homebrew maintainers
with debugging if you file an issue. If everything you use Homebrew for is
working fine: please don't worry or file an issue; just ignore this. Thanks!

Warning: Unbrewed header files were found in /usr/local/include.
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Unexpected header files:
  /usr/local/include/ezs.h
  /usr/local/include/ezsthread.h
  /usr/local/include/node/*
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Warning: Unbrewed '.la' files were found in /usr/local/lib.
If you didn't put them there on purpose they could cause problems when
building Homebrew formulae and may need to be deleted.

Unexpected '.la' files:
  /usr/local/lib/libezs.la

Warning: Unbrewed '.pc' files were found in /usr/local/lib/pkgconfig.
If you didn't put them there on purpose they could cause problems when
building Homebrew formulae and may need to be deleted.

Unexpected '.pc' files:
  /usr/local/lib/pkgconfig/python-3.8-embed.pc
  /usr/local/lib/pkgconfig/python-3.8.pc

Warning: Unbrewed static libraries were found in /usr/local/lib.
If you didn't put them there on purpose they could cause problems when
building Homebrew formulae and may need to be deleted.

Unexpected static libraries:
  /usr/local/lib/libezs.a

Warning: Your /home directory is a symlink.
This is known to cause issues with formula linking, particularly when installing
multiple formulae that create symlinks in shared directories.

While this may be a standard directory structure in some distributions
(e.g. Fedora Silverblue) there are known issues as-is.

If you encounter linking issues, you may need to manually create conflicting
directories or use `brew link --overwrite` as a workaround.

We'd welcome a PR to fix this functionality.
See https://github.com/Homebrew/brew/issues/18036 for more context.

This is a Tier 2 configuration:
  https://docs.brew.sh/Support-Tiers#tier-2
You can report Tier 2 unrelated issues to Homebrew/* repositories!
Read the above document instead before opening any issues or PRs.


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

We recommend updating to a newer version via your distribution's
package manager, upgrading your distribution to the latest version,
or changing distributions.

This is a Tier 2 configuration:
  https://docs.brew.sh/Support-Tiers#tier-2
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
  automake
  autopoint
  autoreconf
  autoscan
  autoupdate
  awk
  bash
  bashbug
  bison
  bunzip2
  bzcat
  bzcmp
  bzdiff
  bzgrep
  bzip2
  bzip2recover
  bzless
  bzmore
  cal
  captoinfo
  chacl
  chmem
  chrt
  clear
  col
  colcrt
  colrm
  column
  compile_et
  corelist
  cpan
  curl
  curl-config
  dmesg
  dumpsexp
  eject
  envsubst
  fallocate
  findmnt
  flock
  funzip
  gawk
  getfacl
  getfattr
  getopt
  gettext
  gettext.sh
  gettextize
  gfortran
  gpg-error
  gpg-error-config
  gss-client
  h2ph
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  hexdump
  hmac256
  i386
  icu-config
  icuinfo
  ifnames
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  ionice
  ipcmk
  ipcrm
  ipcs
  isosize
  json_pp
  k5srvutil
  kadmin
  kdestroy
  kinit
  klist
  kpasswd
  krb5-config
  ksu
  kswitch
  ktutil
  kvno
  last
  lastb
  ldapadd
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  ldapexop
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  ldapmodrdn
  ldappasswd
  ldapsearch
  ldapurl
  ldapwhoami
  less
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  lesskey
  libgcrypt-config
  libnetcfg
  libtool
  libtoolize
  linux32
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  logger
  look
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  lscpu
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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?