--- .gdbinit.orig	2023-03-30 05:34:08.000000000 -0700
+++ .gdbinit	2023-04-24 16:24:34.000000000 -0700
@@ -1,4 +1,5 @@
-set startup-with-shell off
+# Move this to end, so failure on older gdbs doesn't blow the rest
+# set startup-with-shell off
 
 define hook-run
   set $color_type = 0
@@ -1344,3 +1345,6 @@ define print_flags
   printf "RUBY_FL_USER17      : %s\n", ((struct RBasic*)($arg0))->flags & RUBY_FL_USER17 ? "1" : "0"
   printf "RUBY_FL_USER18      : %s\n", ((struct RBasic*)($arg0))->flags & RUBY_FL_USER18 ? "1" : "0"
 end
+
+# Moved from beginning, since it fails on older gdbs
+set startup-with-shell off
--- configure.ac.orig	2023-03-30 05:34:08.000000000 -0700
+++ configure.ac	2023-04-24 16:24:34.000000000 -0700
@@ -2329,6 +2329,15 @@ AS_CASE([$rb_cv_coroutine], [yes|''], [
         [arm64-darwin*], [
             rb_cv_coroutine=arm64
         ],
+        [*86-darwin*], [
+            rb_cv_coroutine=x86
+        ],
+        [ppc*-darwin8*], [
+            rb_cv_coroutine=copy
+        ],
+        [universal-darwin8*], [
+            rb_cv_coroutine=copy
+        ],
         [x*64-linux*], [
             AS_CASE(["$ac_cv_sizeof_voidp"],
                 [8], [ rb_cv_coroutine=amd64 ],
--- dln.c.orig	2023-03-30 05:34:08.000000000 -0700
+++ dln.c	2023-04-24 16:24:34.000000000 -0700
@@ -1347,8 +1347,7 @@ dln_load(const char *file)
 	    if (dln_incompatible_library_p(handle)) {
 
 #   if defined __APPLE__ && \
-    defined(MAC_OS_X_VERSION_MIN_REQUIRED) && \
-    (MAC_OS_X_VERSION_MIN_REQUIRED < MAC_OS_X_VERSION_10_11)
+    __ENVIRONMENT_MAC_OS_X_VERSION_MIN_REQUIRED__ < 101100
 		/* dlclose() segfaults */
 		rb_fatal("%s - %s", incompatible, file);
 #   else
--- error.c.orig	2023-03-30 05:34:08.000000000 -0700
+++ error.c	2023-04-24 16:24:34.000000000 -0700
@@ -519,7 +519,7 @@ preface_dump(FILE *out)
 	"-- Crash Report log information "
 	"--------------------------------------------\n"
 	"   See Crash Report log file under the one of following:\n"
-# if MAC_OS_X_VERSION_MIN_REQUIRED < MAC_OS_X_VERSION_10_6
+# if MAC_OS_X_VERSION_MIN_REQUIRED < 1060
 	"     * ~/Library/Logs/CrashReporter\n"
 	"     * /Library/Logs/CrashReporter\n"
 # endif
@@ -544,7 +544,7 @@ postscript_dump(FILE *out)
 	"[IMPORTANT]"
 	/*" ------------------------------------------------"*/
 	"\n""Don't forget to include the Crash Report log file under\n"
-# if MAC_OS_X_VERSION_MIN_REQUIRED < MAC_OS_X_VERSION_10_6
+# if MAC_OS_X_VERSION_MIN_REQUIRED < 1060
 	"CrashReporter or "
 # endif
 	"DiagnosticReports directory in bug reports.\n"
--- file.c.orig	2023-03-30 05:34:08.000000000 -0700
+++ file.c	2023-04-24 16:24:34.000000000 -0700
@@ -156,6 +156,23 @@ int flock(int, int);
 #include <stdlib.h>
 #endif
 
+#if defined HAVE_REALPATH && defined __APPLE__ && \
+    __ENVIRONMENT_MAC_OS_X_VERSION_MIN_REQUIRED__ < 1060
+/* realpath() on OSX < 10.6 doesn't implement automatic allocation */
+#include <sys/syslimits.h>
+static char *
+realpath_wrapper(const char *file_name, char *resolved_name)
+{
+    if (resolved_name == NULL) {
+        resolved_name = malloc(PATH_MAX);
+        if (resolved_name == NULL) return NULL;
+    }
+    return realpath(file_name, resolved_name);
+}
+#else
+#define realpath_wrapper realpath
+#endif
+
 VALUE rb_cFile;
 VALUE rb_mFileTest;
 VALUE rb_cStat;
@@ -4417,7 +4434,8 @@ rb_check_realpath_internal(VALUE basedir
     }
     if (origenc) unresolved_path = TO_OSPATH(unresolved_path);
 
-    if ((resolved_ptr = realpath(RSTRING_PTR(unresolved_path), NULL)) == NULL) {
+    if ((resolved_ptr = realpath_wrapper(RSTRING_PTR(unresolved_path), NULL))
+        == NULL) {
         /* glibc realpath(3) does not allow /path/to/file.rb/../other_file.rb,
            returning ENOTDIR in that case.
            glibc realpath(3) can also return ENOENT for paths that exist,
--- io.c.orig	2023-03-30 05:34:08.000000000 -0700
+++ io.c	2023-04-24 16:24:34.000000000 -0700
@@ -119,6 +119,15 @@
 # include <copyfile.h>
 #endif
 
+/*
+ * Some OSes (e.g., OSX < 10.6) implement fcopyfile() but not
+ * COPYFILE_STATE_COPIED.  Since the only use of the former here
+ * requires the latter, we disable the former when the latter is undefined.
+ */
+#ifndef COPYFILE_STATE_COPIED
+#undef HAVE_FCOPYFILE
+#endif
+
 #include "ruby/util.h"
 
 #ifndef O_ACCMODE
--- lib/bundler/gem_helper.rb.orig	2023-03-30 05:34:08.000000000 -0700
+++ lib/bundler/gem_helper.rb	2023-04-24 16:24:34.000000000 -0700
@@ -210,7 +210,7 @@ module Bundler
     end
 
     def gem_command
-      ENV["GEM_COMMAND"] ? ENV["GEM_COMMAND"] : "gem"
+      ENV["GEM_COMMAND"] ? ENV["GEM_COMMAND"] : "gem2.7"
     end
   end
 end
--- random.c.orig	2023-03-30 05:34:08.000000000 -0700
+++ random.c	2023-04-24 16:24:34.000000000 -0700
@@ -340,6 +340,11 @@ fill_random_bytes_urandom(void *seed, si
 #if 0
 #elif defined MAC_OS_X_VERSION_10_7 && MAC_OS_X_VERSION_MIN_REQUIRED >= MAC_OS_X_VERSION_10_7
 #include <Security/Security.h>
+#ifndef kSecRandomDefault
+/* hack for missing kSecRandomDefault.
+   some old macOS SDKs do not import SecRandom.h in Security.h */
+#include <Security/SecRandom.h>
+#endif
 
 static int
 fill_random_bytes_syscall(void *seed, size_t size, int unused)
--- signal.c.orig	2023-03-30 05:34:08.000000000 -0700
+++ signal.c	2023-04-24 16:24:34.000000000 -0700
@@ -824,7 +824,8 @@ check_stack_overflow(int sig, const uint
     const greg_t bp = mctx->gregs[REG_EBP];
 #   endif
 # elif defined __APPLE__
-#   if __DARWIN_UNIX03
+#   include <AvailabilityMacros.h>
+#   if MAC_OS_X_VERSION_MAX_ALLOWED >= 1050
 #     define MCTX_SS_REG(reg) __ss.__##reg
 #   else
 #     define MCTX_SS_REG(reg) ss.reg
--- template/Makefile.in.orig	2023-03-30 05:34:08.000000000 -0700
+++ template/Makefile.in	2023-04-24 16:24:34.000000000 -0700
@@ -210,7 +210,7 @@ AR            = @AR@
 ARFLAGS       = @ARFLAGS@$(empty)
 RANLIB        = @RANLIB@
 AS            = @AS@
-ASFLAGS       = @ASFLAGS@ $(INCFLAGS)
+ASFLAGS       = @ASFLAGS@ $(ARCH_FLAG) $(INCFLAGS)
 IFCHANGE      = $(srcdir)/tool/ifchange
 OBJDUMP       = @OBJDUMP@
 OBJCOPY       = @OBJCOPY@
--- tool/m4/ruby_default_arch.m4.orig	2023-03-30 05:34:08.000000000 -0700
+++ tool/m4/ruby_default_arch.m4	2023-04-24 16:24:34.000000000 -0700
@@ -4,6 +4,7 @@ AC_MSG_CHECKING([arch option])
 AS_CASE([$1],
 	[*64],        [ARCH_FLAG=-m64],
 	[[i[3-6]86]], [ARCH_FLAG=-m32],
+	[ppc], [ARCH_FLAG=-m32],
 	[AC_MSG_ERROR(unknown target architecture: $target_archs)]
 	)
 AC_MSG_RESULT([$ARCH_FLAG])
--- tool/transform_mjit_header.rb.orig	2023-03-30 05:34:08.000000000 -0700
+++ tool/transform_mjit_header.rb	2023-04-24 16:24:34.000000000 -0700
@@ -176,7 +176,9 @@ module MJITHeader
   def self.conflicting_types?(code, cc, cflags)
     with_code(code) do |path|
       cmd = "#{cc} #{cflags} #{path}"
-      out = IO.popen(cmd, err: [:child, :out], &:read)
+      # As per gcc docs, set LC_ALL=C to avoid curly quotes in messages
+      cmd_env = {"LC_ALL" => "C"}
+      out = IO.popen(cmd_env, cmd, err: [:child, :out], &:read)
       !$?.success? &&
         (out.match?(/error: conflicting types for '[^']+'/) ||
          out.match?(/error: redefinition of parameter '[^']+'/))
--- vm_dump.c.orig	2023-03-30 05:34:08.000000000 -0700
+++ vm_dump.c	2023-04-24 16:24:34.000000000 -0700
@@ -459,7 +459,8 @@ rb_vmdebug_thread_dump_state(VALUE self)
 }
 
 #if defined __APPLE__
-# if __DARWIN_UNIX03
+# include <AvailabilityMacros.h>
+# if MAC_OS_X_VERSION_MAX_ALLOWED >= 1050
 #   define MCTX_SS_REG(reg) __ss.__##reg
 # else
 #   define MCTX_SS_REG(reg) ss.reg
@@ -470,7 +471,8 @@ rb_vmdebug_thread_dump_state(VALUE self)
 # ifdef HAVE_LIBUNWIND
 #  undef backtrace
 #  define backtrace unw_backtrace
-# elif defined(__APPLE__) && defined(__x86_64__) && defined(HAVE_LIBUNWIND_H)
+# elif defined(__APPLE__) && defined(__x86_64__) && defined(HAVE_LIBUNWIND_H) \
+       && MAC_OS_X_VERSION_MIN_REQUIRED >= 1060
 #  define UNW_LOCAL_ONLY
 #  include <libunwind.h>
 #  include <sys/mman.h>