Attempting to build Perl 5.38.2 on Mac OS X 10.2 Jaguar

[sevan]

Attempting to build Perl 5.38.2 on OS X 10.2.8 using GCC 3.1 from Dec 2002 Dev Tools fails after running ./Configure -des successfully.

% make
echo @`sh  cflags "optimize='-Os'" opmini.o`  -DPERL_IS_MINIPERL -DPERL_EXTERNAL_GLOB opmini.c
@cc -c -DPERL_CORE -std=gnu99 -fno-common -DPERL_DARWIN -fno-strict-aliasing -pipe -Os -Wall -DPERL_IS_MINIPERL -DPERL_EXTERNAL_GLOB opmini.c
charclass_invlists.h:36515: #endif outside an #if
op_reg_common.h:154: #error RXf_PMf_COMPILETIME is invalid
^[[Ccpp-precomp: warning: errors during smart preprocessing, retrying in basic mode
<built-in>:1:1: no macro name given in #define directive
make: *** [opmini.o] Error 1

More for the sake of archaeology.

[sevan]

Filed to keep record, in case anyone wondered.

[sevan]

Managed to make some progress with this. Needed to explicitly pass -no-cpp-precomp to the compiler, inspecting hints/darwin.sh it is only done for modules. So with ./Configure -des -Accflags=-no-cpp-precomp the build made progress. As with issue #21751 on OS X 10.3, I commented out undef bool in Dynaloader.xs otherwise GCC 3.1 would error due to undeclared type.
I'm currently stuck with the build failing at generating pod/perltoc.pod.

./miniperl -Ilib make_ext.pl lib/auto/threads/shared/shared.bundle  MAKE="make" LIBPERL_A=libperl.a LINKTYPE=dynamic
/Users/sme/Downloads/perl-5.38.2/dist/threads-shared/../../miniperl "-I../../lib" -MExtUtils::Command::MM -e 'cp_nonempty' -- shared.bs ../../lib/auto/threads/shared/shared.bs 644
./perl -Ilib -I. -f pod/buildtoc -q
dyld: ./perl multiple definitions of symbol _Perl_add_above_Latin1_folds
./perl definition of _Perl_add_above_Latin1_folds
lib/auto/re/re.bundle definition of _Perl_add_above_Latin1_folds
make: *** [pod/perltoc.pod] Trace/BPT trap

Date/Time:  2023-12-30 05:55:17 +0000
OS Version: 10.2.8 (Build 6R73)
Host:       Clampazzo.local.

Command:    perl
PID:        22976

Exception:  EXC_BREAKPOINT (0x0006)
Code[0]:    0x00000001Code[1]:    0x8fe01220

Thread 0 Crashed:
 #0   0x8fe01220 in halt
 #1   0x8fe0d12c in link_object_module
 #2   0x8fe120fc in _dyld_link_module
 #3   0x900169c8 in NSLinkModule
 #4   0x0004da6c in dlopen
 #5   0x0004dc0c in XS_DynaLoader_dl_load_file
 #6   0x00099aac in Perl_pp_entersub
 #7   0x001278cc in Perl_runops_standard
 #8   0x0004793c in Perl_call_sv
 #9   0x0004bd20 in Perl_call_list
 #10  0x00023514 in S_process_special_blocks
 #11  0x00023024 in Perl_newATTRSUB_x
 #12  0x0001cf0c in Perl_utilize
 #13  0x0015f068 in Perl_yyparse
 #14  0x000cba3c in S_doeval_compile
 #15  0x000ce264 in S_require_file
 #16  0x001278cc in Perl_runops_standard
 #17  0x0004793c in Perl_call_sv
 #18  0x0004bd20 in Perl_call_list
 #19  0x00023514 in S_process_special_blocks
 #20  0x00023024 in Perl_newATTRSUB_x
 #21  0x0001cf0c in Perl_utilize
 #22  0x0015f068 in Perl_yyparse
 #23  0x00046b4c in S_parse_body
 #24  0x00045bbc in perl_parse
 #25  0x00002954 in main
 #26  0x0000210c in _start (crt.c:267)
 #27  0x00001f8c in start

PPC Thread State:
  srr0: 0x8fe01220 srr1: 0x0002d030                vrsave: 0x00000000
   xer: 0x20000000   lr: 0x8fe09d98  ctr: 0x8fe293ac   mq: 0x00000000
    r0: 0x00000004   r1: 0xbfffdc50   r2: 0x00000005   r3: 0x000000bc
    r4: 0x00000000   r5: 0x000000bc   r6: 0x0000000a   r7: 0x6e315f66
    r8: 0x645f6162   r9: 0x00000000  r10: 0x0027cc34  r11: 0x00000040
   r12: 0x8fe71ae3  r13: 0x8fe4a427  r14: 0x00000000  r15: 0x8fe4850c
   r16: 0x8fe4850c  r17: 0x8fe4850c  r18: 0x8fe4852c  r19: 0x8fe4850c
   r20: 0x8fe4e4d0  r21: 0x00588fa0  r22: 0x8fe4e3e0  r23: 0x8fe4a446
   r24: 0x0027cc34  r25: 0x8fe4e53c  r26: 0x00000000  r27: 0x8fe4a427
   r28: 0x0058ae22  r29: 0x8fe484d4  r30: 0x00000000  r31: 0x8fe09c08

[sevan]

Attempting a DEBUGGING build doesn't make any difference.
make distclean && ./Configure -des -Dprefix=somewhere -Accflags=-no-cpp-precomp -DDEBUGGING && make install just takes longer to reach the same place and fail.

chmod 755 ../../lib/auto/threads/shared/shared.bundle
./perl -Ilib -I. -f pod/buildtoc -q
dyld: ./perl multiple definitions of symbol _Perl_add_above_Latin1_folds
./perl definition of _Perl_add_above_Latin1_folds
lib/auto/re/re.bundle definition of _Perl_add_above_Latin1_folds
make: *** [pod/perltoc.pod] Trace/BPT trap

[sevan]

Though I ran across it on OS X 10.2, I reproduced the issue on macOS 10.15 thanks to a hint by TonyC, forcing a static build of re using -Dstatic_ext=re

./miniperl -Ilib make_ext.pl lib/auto/re/re.a  MAKE="/Library/Developer/CommandLineTools/usr/bin/make" LIBPERL_A=libperl.a LINKTYPE=static CCCDLFLAGS=
Generating a Unix-style Makefile
Writing Makefile for re
"../../miniperl" "-I../../lib" "../../lib/ExtUtils/xsubpp" -noprototypes -typemap '/Users/sevan/Sandbox/perl5/ext/re/../../lib/ExtUtils/typemap'  re.xs > re.xsc
mv re.xsc re.c
cc -c   -fno-common -DPERL_DARWIN -mmacosx-version-min=10.15 -DNO_THREAD_SAFE_QUERYLOCALE -DNO_POSIX_2008_LOCALE -fno-strict-aliasing -pipe -fstack-protector-strong -I/usr/local/include -Wall -Werror=pointer-arith -Werror=vla -Wextra -Wno-long-long -Wno-declaration-after-statement -Wc++-compat -Wwrite-strings -Wno-error=implicit-function-declaration -O3   -DVERSION=\"0.45\" -DXS_VERSION=\"0.45\"  "-I../.."  -DPERL_EXT_RE_BUILD -DPERL_EXT_RE_DEBUG -DPERL_EXT re.c
rm -f re_comp.c
cp ../../regcomp.c re_comp.c
rm -f dquote.c
cp ../../dquote.c dquote.c
rm -f invlist_inline.h
cp ../../invlist_inline.h invlist_inline.h
cc -c   -fno-common -DPERL_DARWIN -mmacosx-version-min=10.15 -DNO_THREAD_SAFE_QUERYLOCALE -DNO_POSIX_2008_LOCALE -fno-strict-aliasing -pipe -fstack-protector-strong -I/usr/local/include -Wall -Werror=pointer-arith -Werror=vla -Wextra -Wno-long-long -Wno-declaration-after-statement -Wc++-compat -Wwrite-strings -Wno-error=implicit-function-declaration -O3   -DVERSION=\"0.45\" -DXS_VERSION=\"0.45\"  "-I../.."  -DPERL_EXT_RE_BUILD -DPERL_EXT_RE_DEBUG -DPERL_EXT re_comp.c
rm -f re_comp_invlist.c
cp ../../regcomp_invlist.c re_comp_invlist.c
cc -c   -fno-common -DPERL_DARWIN -mmacosx-version-min=10.15 -DNO_THREAD_SAFE_QUERYLOCALE -DNO_POSIX_2008_LOCALE -fno-strict-aliasing -pipe -fstack-protector-strong -I/usr/local/include -Wall -Werror=pointer-arith -Werror=vla -Wextra -Wno-long-long -Wno-declaration-after-statement -Wc++-compat -Wwrite-strings -Wno-error=implicit-function-declaration -O3   -DVERSION=\"0.45\" -DXS_VERSION=\"0.45\"  "-I../.."  -DPERL_EXT_RE_BUILD -DPERL_EXT_RE_DEBUG -DPERL_EXT re_comp_invlist.c
rm -f re_comp_study.c
cp ../../regcomp_study.c re_comp_study.c
cc -c   -fno-common -DPERL_DARWIN -mmacosx-version-min=10.15 -DNO_THREAD_SAFE_QUERYLOCALE -DNO_POSIX_2008_LOCALE -fno-strict-aliasing -pipe -fstack-protector-strong -I/usr/local/include -Wall -Werror=pointer-arith -Werror=vla -Wextra -Wno-long-long -Wno-declaration-after-statement -Wc++-compat -Wwrite-strings -Wno-error=implicit-function-declaration -O3   -DVERSION=\"0.45\" -DXS_VERSION=\"0.45\"  "-I../.."  -DPERL_EXT_RE_BUILD -DPERL_EXT_RE_DEBUG -DPERL_EXT re_comp_study.c
rm -f re_comp_trie.c
cp ../../regcomp_trie.c re_comp_trie.c
cc -c   -fno-common -DPERL_DARWIN -mmacosx-version-min=10.15 -DNO_THREAD_SAFE_QUERYLOCALE -DNO_POSIX_2008_LOCALE -fno-strict-aliasing -pipe -fstack-protector-strong -I/usr/local/include -Wall -Werror=pointer-arith -Werror=vla -Wextra -Wno-long-long -Wno-declaration-after-statement -Wc++-compat -Wwrite-strings -Wno-error=implicit-function-declaration -O3   -DVERSION=\"0.45\" -DXS_VERSION=\"0.45\"  "-I../.."  -DPERL_EXT_RE_BUILD -DPERL_EXT_RE_DEBUG -DPERL_EXT re_comp_trie.c
rm -f re_comp_debug.c
cp ../../regcomp_debug.c re_comp_debug.c
cc -c   -fno-common -DPERL_DARWIN -mmacosx-version-min=10.15 -DNO_THREAD_SAFE_QUERYLOCALE -DNO_POSIX_2008_LOCALE -fno-strict-aliasing -pipe -fstack-protector-strong -I/usr/local/include -Wall -Werror=pointer-arith -Werror=vla -Wextra -Wno-long-long -Wno-declaration-after-statement -Wc++-compat -Wwrite-strings -Wno-error=implicit-function-declaration -O3   -DVERSION=\"0.45\" -DXS_VERSION=\"0.45\"  "-I../.."  -DPERL_EXT_RE_BUILD -DPERL_EXT_RE_DEBUG -DPERL_EXT re_comp_debug.c
rm -f re_exec.c
cp ../../regexec.c re_exec.c
cc -c   -fno-common -DPERL_DARWIN -mmacosx-version-min=10.15 -DNO_THREAD_SAFE_QUERYLOCALE -DNO_POSIX_2008_LOCALE -fno-strict-aliasing -pipe -fstack-protector-strong -I/usr/local/include -Wall -Werror=pointer-arith -Werror=vla -Wextra -Wno-long-long -Wno-declaration-after-statement -Wc++-compat -Wwrite-strings -Wno-error=implicit-function-declaration -O3   -DVERSION=\"0.45\" -DXS_VERSION=\"0.45\"  "-I../.."  -DPERL_EXT_RE_BUILD -DPERL_EXT_RE_DEBUG -DPERL_EXT re_exec.c
rm -f "../../lib/auto/re/re.a"
/usr/bin/ar cr "../../lib/auto/re/re.a" re.o re_comp.o re_comp_invlist.o re_comp_study.o re_comp_trie.o re_comp_debug.o re_exec.o
ranlib "../../lib/auto/re/re.a"
chmod 755 ../../lib/auto/re/re.a
cc -o perl -mmacosx-version-min=10.15 -fstack-protector-strong -L/usr/local/lib  perlmain.o  lib/auto/re/re.a libperl.a `cat ext.libs` -lpthread -ldl -lm -lutil -lc 
duplicate symbol '_Perl_populate_anyof_bitmap_from_invlist' in:
    libperl.a(regcomp.o)
    lib/auto/re/re.a(re_comp.o)
duplicate symbol '_Perl_get_ANYOFHbbm_contents' in:
    libperl.a(regcomp.o)
    lib/auto/re/re.a(re_comp.o)
duplicate symbol '_Perl_get_ANYOFM_contents' in:
    libperl.a(regcomp.o)
    lib/auto/re/re.a(re_comp.o)
duplicate symbol '_Perl_add_above_Latin1_folds' in:
    libperl.a(regcomp.o)
    lib/auto/re/re.a(re_comp.o)
duplicate symbol '_Perl_set_ANYOF_arg' in:
    libperl.a(regcomp.o)
    lib/auto/re/re.a(re_comp.o)
duplicate symbol '_Perl_reg_add_data' in:
    libperl.a(regcomp.o)
    lib/auto/re/re.a(re_comp.o)
ld: 6 duplicate symbols for architecture x86_64
clang: error: linker command failed with exit code 1 (use -v to see invocation)
make: *** [perl] Error 1

[sevan]

Same on Ubuntu 23.10 (just for the sake of different toolchain)

./miniperl -Ilib make_ext.pl lib/auto/re/re.a  MAKE="make" LIBPERL_A=libperl.a LINKTYPE=static CCCDLFLAGS=                                                                                         
Generating a Unix-style Makefile                                                                                                                                                                   
Writing Makefile for re                                                                                                                                                                            
make[1]: Entering directory '/home/sme/perl-5.38.2/ext/re'                                                                                                                                       
"../../miniperl" "-I../../lib" "../../lib/ExtUtils/xsubpp" -noprototypes -typemap '/home/sme/perl-5.38.2/ext/re/../../lib/ExtUtils/typemap'  re.xs > re.xsc                                      
mv re.xsc re.c                                                                                                                                                                                     
cc -c   -fwrapv -fno-strict-aliasing -pipe -fstack-protector-strong -I/usr/local/include -D_LARGEFILE_SOURCE -D_FILE_OFFSET_BITS=64 -Wall -Werror=pointer-arith -Werror=vla -Wextra -Wno-long-long 
-Wno-declaration-after-statement -Wc++-compat -Wwrite-strings -Wno-use-after-free -O2   -DVERSION=\"0.44\" -DXS_VERSION=\"0.44\"  "-I../.."  -DPERL_EXT_RE_BUILD -DPERL_EXT_RE_DEBUG -DPERL_EXT re$
c                                                                                                                                                                                                  
rm -f re_comp.c                                                                                                                                                                                    
cp ../../regcomp.c re_comp.c                                                                                                                                                                       
rm -f dquote.c                                                                                                                                                                                     
cp ../../dquote.c dquote.c                                                                                                                                                                         
rm -f invlist_inline.h                                                                                                                                                                             
cp ../../invlist_inline.h invlist_inline.h                                                                                                                                                         
cc -c   -fwrapv -fno-strict-aliasing -pipe -fstack-protector-strong -I/usr/local/include -D_LARGEFILE_SOURCE -D_FILE_OFFSET_BITS=64 -Wall -Werror=pointer-arith -Werror=vla -Wextra -Wno-long-long 
-Wno-declaration-after-statement -Wc++-compat -Wwrite-strings -Wno-use-after-free -O2   -DVERSION=\"0.44\" -DXS_VERSION=\"0.44\"  "-I../.."  -DPERL_EXT_RE_BUILD -DPERL_EXT_RE_DEBUG -DPERL_EXT re_
comp.c                                                                                                                                                                                             
rm -f re_comp_invlist.c                                                                                                                                                                            
cp ../../regcomp_invlist.c re_comp_invlist.c                                                                                                                                                       
cc -c   -fwrapv -fno-strict-aliasing -pipe -fstack-protector-strong -I/usr/local/include -D_LARGEFILE_SOURCE -D_FILE_OFFSET_BITS=64 -Wall -Werror=pointer-arith -Werror=vla -Wextra -Wno-long-long 
-Wno-declaration-after-statement -Wc++-compat -Wwrite-strings -Wno-use-after-free -O2   -DVERSION=\"0.44\" -DXS_VERSION=\"0.44\"  "-I../.."  -DPERL_EXT_RE_BUILD -DPERL_EXT_RE_DEBUG -DPERL_EXT re_
comp_invlist.c                                                                                                                                                                                     
rm -f re_comp_study.c                                                                                                                                                                              
cp ../../regcomp_study.c re_comp_study.c                                                                                                                                                           
cc -c   -fwrapv -fno-strict-aliasing -pipe -fstack-protector-strong -I/usr/local/include -D_LARGEFILE_SOURCE -D_FILE_OFFSET_BITS=64 -Wall -Werror=pointer-arith -Werror=vla -Wextra -Wno-long-long 
-Wno-declaration-after-statement -Wc++-compat -Wwrite-strings -Wno-use-after-free -O2   -DVERSION=\"0.44\" -DXS_VERSION=\"0.44\"  "-I../.."  -DPERL_EXT_RE_BUILD -DPERL_EXT_RE_DEBUG -DPERL_EXT re_
comp_study.c                                                                                                                                                                                       
rm -f re_comp_trie.c                            
cp ../../regcomp_trie.c re_comp_trie.c                                                           
cc -c   -fwrapv -fno-strict-aliasing -pipe -fstack-protector-strong -I/usr/local/include -D_LARGEFILE_SOURCE -D_FILE_OFFSET_BITS=64 -Wall -Werror=pointer-arith -Werror=vla -Wextra -Wno-long-long -Wno-declaration-after-statement -Wc++-compat -Wwrite-strings -Wno-use-after-free -O2   -DVERSION=\"0.44\" -DXS_VERSION=\"0.44\"  "-I../.."  -DPERL_EXT_RE_BUILD -DPERL_EXT_RE_DEBUG -DPERL_EXT re_comp_trie.c                                     
rm -f re_comp_debug.c                           
cp ../../regcomp_debug.c re_comp_debug.c                                                         
cc -c   -fwrapv -fno-strict-aliasing -pipe -fstack-protector-strong -I/usr/local/include -D_LARGEFILE_SOURCE -D_FILE_OFFSET_BITS=64 -Wall -Werror=pointer-arith -Werror=vla -Wextra -Wno-long-long 
-Wno-declaration-after-statement -Wc++-compat -Wwrite-strings -Wno-use-after-free -O2   -DVERSION=\"0.44\" -DXS_VERSION=\"0.44\"  "-I../.."  -DPERL_EXT_RE_BUILD -DPERL_EXT_RE_DEBUG -DPERL_EXT re_
comp_debug.c                                    
rm -f re_exec.c                                 
cp ../../regexec.c re_exec.c                    
cc -c   -fwrapv -fno-strict-aliasing -pipe -fstack-protector-strong -I/usr/local/include -D_LARGEFILE_SOURCE -D_FILE_OFFSET_BITS=64 -Wall -Werror=pointer-arith -Werror=vla -Wextra -Wno-long-long 
-Wno-declaration-after-statement -Wc++-compat -Wwrite-strings -Wno-use-after-free -O2   -DVERSION=\"0.44\" -DXS_VERSION=\"0.44\"  "-I../.."  -DPERL_EXT_RE_BUILD -DPERL_EXT_RE_DEBUG -DPERL_EXT re_
exec.c                                          
rm -f "../../lib/auto/re/re.a"                                                                   
/usr/bin/ar cr "../../lib/auto/re/re.a" re.o re_comp.o re_comp_invlist.o re_comp_study.o re_comp_trie.o re_comp_debug.o re_exec.o                                                                  
: "../../lib/auto/re/re.a"                      
chmod 755 ../../lib/auto/re/re.a                                                                 
make[1]: Leaving directory '/home/sme/perl-5.38.2/ext/re'                                                                                                                                        
cc -o perl -fstack-protector-strong -L/usr/local/lib -Wl,-E perlmain.o  lib/auto/re/re.a libperl.a `cat ext.libs` -lpthread -ldl -lm -lcrypt -lutil -lc                                            
/usr/bin/ld: libperl.a(regcomp.o): in function `Perl_reg_add_data':                                                                                                                                
regcomp.c:(.text+0x60f6): multiple definition of `Perl_reg_add_data'; lib/auto/re/re.a(re_comp.o):re_comp.c:(.text+0x9be6): first defined here                                                     
/usr/bin/ld: libperl.a(regcomp.o): in function `Perl_populate_anyof_bitmap_from_invlist':                                                                                                          
regcomp.c:(.text+0x6844): multiple definition of `Perl_populate_anyof_bitmap_from_invlist'; lib/auto/re/re.a(re_comp.o):re_comp.c:(.text+0xa0dc): first defined here                               
/usr/bin/ld: libperl.a(regcomp.o): in function `Perl_add_above_Latin1_folds':                                                                                                                      
regcomp.c:(.text+0x6984): multiple definition of `Perl_add_above_Latin1_folds'; lib/auto/re/re.a(re_comp.o):re_comp.c:(.text+0xa3ba): first defined here                                           
/usr/bin/ld: libperl.a(regcomp.o): in function `Perl_set_ANYOF_arg':                                                                                                                               
regcomp.c:(.text+0x6d16): multiple definition of `Perl_set_ANYOF_arg'; lib/auto/re/re.a(re_comp.o):re_comp.c:(.text+0xa7b2): first defined here                                                    
/usr/bin/ld: libperl.a(regcomp.o): in function `Perl_get_ANYOFM_contents':                                                                                                                         
regcomp.c:(.text+0x8386): multiple definition of `Perl_get_ANYOFM_contents'; lib/auto/re/re.a(re_comp.o):re_comp.c:(.text+0xc352): first defined here                                              
/usr/bin/ld: libperl.a(regcomp.o): in function `Perl_get_ANYOFHbbm_contents':                                                                                                                      
regcomp.c:(.text+0x8434): multiple definition of `Perl_get_ANYOFHbbm_contents'; lib/auto/re/re.a(re_comp.o):re_comp.c:(.text+0xc400): first defined here                                           
/usr/bin/ld: libperl.a(regcomp_invlist.o): in function `Perl_populate_bitmap_from_invlist':                                                                                                        
regcomp_invlist.c:(.text+0x214): multiple definition of `Perl_populate_bitmap_from_invlist'; lib/auto/re/re.a(re_comp_invlist.o):re_comp_invlist.c:(.text+0x50): first defined here                
/usr/bin/ld: libperl.a(regcomp_invlist.o): in function `Perl_populate_invlist_from_bitmap':                                                                                                        
regcomp_invlist.c:(.text+0xed2): multiple definition of `Perl_populate_invlist_from_bitmap'; lib/auto/re/re.a(re_comp_invlist.o):re_comp_invlist.c:(.text+0x21c): first defined here               
collect2: error: ld returned 1 exit status                                                       
make: *** [makefile:392: perl] Error 1                     

[jkeenan]

Same on Ubuntu 23.10 (just for the sake of different toolchain)

Can you provide the exact spelling of your invocation of ./Configure on Ubuntu so that I can confirm your finding? Thanks.

[sevan]

./Configure -des -Dstatic_ext=re -Dusedevel should do it.

[jkeenan]

./Configure -des -Dstatic_ext=re -Dusedevel should do it.

First, I can confirm that the following fails on Perl 5 blead:

$ git describe
v5.39.6-126-g9035069470

$ sh ./Configure -des -Dstatic_ext=re -Dusedevel && make test_prep
...
cc -c   -fwrapv -fno-strict-aliasing -pipe -fstack-protector-strong -I/usr/local/include -D_LARGEFILE_SOURCE -D_FILE_OFFSET_BITS=64 -Wall -Werror=pointer-arith -Werror=vla -Wextra -Wno-long-long -Wno-declaration-after-statement -Wc++-compat -Wwrite-strings -O2   -DVERSION=\"0.45\" -DXS_VERSION=\"0.45\"  "-I../.."  -DPERL_EXT_RE_BUILD -DPERL_EXT_RE_DEBUG -DPERL_EXT re_exec.c
rm -f "../../lib/auto/re/re.a"
/usr/bin/ar cr "../../lib/auto/re/re.a" re.o re_comp.o re_comp_invlist.o re_comp_study.o re_comp_trie.o re_comp_debug.o re_exec.o
: "../../lib/auto/re/re.a"
chmod 755 ../../lib/auto/re/re.a
make[1]: Leaving directory '/home/jkeenan/gitwork/perl/ext/re'
cc -o perl -fstack-protector-strong -L/usr/local/lib -Wl,-E perlmain.o  lib/auto/re/re.a libperl.a `cat ext.libs` -lpthread -ldl -lm -lcrypt -lutil -lc 
/usr/bin/ld: libperl.a(regcomp.o): in function `Perl_reg_add_data':
regcomp.c:(.text+0x6540): multiple definition of `Perl_reg_add_data'; lib/auto/re/re.a(re_comp.o):re_comp.c:(.text+0x9070): first defined here
/usr/bin/ld: libperl.a(regcomp.o): in function `Perl_populate_anyof_bitmap_from_invlist':
regcomp.c:(.text+0x6ec0): multiple definition of `Perl_populate_anyof_bitmap_from_invlist'; lib/auto/re/re.a(re_comp.o):re_comp.c:(.text+0x9630): first defined here
/usr/bin/ld: libperl.a(regcomp.o): in function `Perl_add_above_Latin1_folds':
regcomp.c:(.text+0x7090): multiple definition of `Perl_add_above_Latin1_folds'; lib/auto/re/re.a(re_comp.o):re_comp.c:(.text+0x98c0): first defined here
/usr/bin/ld: libperl.a(regcomp.o): in function `Perl_set_ANYOF_arg':
regcomp.c:(.text+0x74e0): multiple definition of `Perl_set_ANYOF_arg'; lib/auto/re/re.a(re_comp.o):re_comp.c:(.text+0x9d90): first defined here
/usr/bin/ld: libperl.a(regcomp.o): in function `Perl_get_ANYOFM_contents':
regcomp.c:(.text+0x79d0): multiple definition of `Perl_get_ANYOFM_contents'; lib/auto/re/re.a(re_comp.o):re_comp.c:(.text+0xa580): first defined here
/usr/bin/ld: libperl.a(regcomp.o): in function `Perl_get_ANYOFHbbm_contents':
regcomp.c:(.text+0x7a90): multiple definition of `Perl_get_ANYOFHbbm_contents'; lib/auto/re/re.a(re_comp.o):re_comp.c:(.text+0xa640): first defined here
/usr/bin/ld: libperl.a(regcomp_invlist.o): in function `Perl_populate_bitmap_from_invlist':
regcomp_invlist.c:(.text+0x2e0): multiple definition of `Perl_populate_bitmap_from_invlist'; lib/auto/re/re.a(re_comp_invlist.o):re_comp_invlist.c:(.text+0xa0): first defined here
/usr/bin/ld: libperl.a(regcomp_invlist.o): in function `Perl_populate_invlist_from_bitmap':
regcomp_invlist.c:(.text+0x1360): multiple definition of `Perl_populate_invlist_from_bitmap'; lib/auto/re/re.a(re_comp_invlist.o):re_comp_invlist.c:(.text+0x310): first defined here
collect2: error: ld returned 1 exit status
make: *** [makefile:397: perl] Error 1

But it got similar failures on perl-5.30.3 and perl-5.24.3 (installed via perlbrew). So did this configuration ever work? Should we have expected it to work?

$ uname -mrs; gcc --version | head -1
Linux 6.2.0-39-generic x86_64
gcc (Ubuntu 11.4.0-1ubuntu1~22.04) 11.4.0

[sevan]

So did this configuration ever work? Should we have expected it to work?

I don't know about the history, was just provided with the means of reproducing the issue on modern system/hardware.
The OS I'm building on, shipped with Perl 5.6.0 and by the time 5.8.8 landed support for it was broken due to another, unrelated issue.
See how far you can go back before static builds start to work to answer if it ever worked?