--- .gdbinit.orig	2024-06-11 16:54:24.000000000 -0700
+++ .gdbinit	2024-06-14 19:51:49.000000000 -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
@@ -1345,3 +1346,6 @@ define print_flags
 end
 
 source misc/gdb.py
+
+# Moved from beginning, since it fails on older gdbs
+set startup-with-shell off
--- ext/digest/md5/md5cc.h.orig	2024-06-11 16:54:24.000000000 -0700
+++ ext/digest/md5/md5cc.h	2024-06-14 19:51:49.000000000 -0700
@@ -17,3 +17,11 @@ static DEFINE_FINISH_FUNC_FROM_FINAL(MD5
 #undef MD5_Finish
 #define MD5_Update rb_digest_MD5_update
 #define MD5_Finish rb_digest_MD5_finish
+
+/*
+ * Pre-10.6 defines are with args, which don't match the argless use in
+ * the function pointer inits.  Thus, we redefine MD5_Init as well.
+ * This is a NOP on 10.6+.
+ */
+#undef MD5_Init
+#define MD5_Init CC_MD5_Init
--- ext/digest/sha1/sha1cc.h.orig	2024-06-11 16:54:24.000000000 -0700
+++ ext/digest/sha1/sha1cc.h	2024-06-14 19:51:49.000000000 -0700
@@ -12,3 +12,11 @@ static DEFINE_FINISH_FUNC_FROM_FINAL(SHA
 #undef SHA1_Finish
 #define SHA1_Update rb_digest_SHA1_update
 #define SHA1_Finish rb_digest_SHA1_finish
+
+/*
+ * Pre-10.6 defines are with args, which don't match the argless use in
+ * the function pointer inits.  Thus, we redefine SHA1_Init as well.
+ * This is a NOP on 10.6+.
+ */
+#undef SHA1_Init
+#define SHA1_Init CC_SHA1_Init
--- ext/digest/sha2/sha2cc.h.orig	2024-06-11 16:54:24.000000000 -0700
+++ ext/digest/sha2/sha2cc.h	2024-06-14 19:51:49.000000000 -0700
@@ -1,6 +1,33 @@
 #define COMMON_DIGEST_FOR_OPENSSL 1
 #include <CommonCrypto/CommonDigest.h>
 
+/*
+ * Prior to 10.5, OpenSSL-compatible definitions are missing for
+ * SHA2 macros, though the CC_ versions are present.
+ * Add the missing definitions we actually use here if needed.
+ * Note that the definitions are the argless 10.6+-style.
+ * The weird CTX mismatch is copied from the 10.6 header.
+ */
+#ifndef SHA256_DIGEST_LENGTH
+#define SHA256_DIGEST_LENGTH		CC_SHA256_DIGEST_LENGTH
+#define SHA256_CTX					CC_SHA256_CTX
+#define SHA256_Update				CC_SHA256_Update
+#define SHA256_Final				CC_SHA256_Final
+#endif /* !defined SHA256_DIGEST_LENGTH */
+
+#ifndef SHA384_DIGEST_LENGTH
+#define SHA384_DIGEST_LENGTH		CC_SHA384_DIGEST_LENGTH
+#define SHA512_CTX					CC_SHA512_CTX
+#define SHA384_Update				CC_SHA384_Update
+#define SHA384_Final				CC_SHA384_Final
+#endif /* !defined SHA384_DIGEST_LENGTH */
+
+#ifndef SHA512_DIGEST_LENGTH
+#define SHA512_DIGEST_LENGTH		CC_SHA512_DIGEST_LENGTH
+#define SHA512_Update				CC_SHA512_Update
+#define SHA512_Final				CC_SHA512_Final
+#endif /* !defined SHA512_DIGEST_LENGTH */
+
 #define SHA256_BLOCK_LENGTH	CC_SHA256_BLOCK_BYTES
 #define SHA384_BLOCK_LENGTH	CC_SHA384_BLOCK_BYTES
 #define SHA512_BLOCK_LENGTH	CC_SHA512_BLOCK_BYTES
@@ -29,3 +56,15 @@ static DEFINE_FINISH_FUNC_FROM_FINAL(SHA
 #undef SHA512_Finish
 #define SHA512_Update rb_digest_SHA512_update
 #define SHA512_Finish rb_digest_SHA512_finish
+
+/*
+ * Pre-10.6 defines are with args, which don't match the argless use in
+ * the function pointer inits.  Thus, we redefine SHA*_Init as well.
+ * This is a NOP on 10.6+.
+ */
+#undef SHA256_Init
+#define SHA256_Init CC_SHA256_Init
+#undef SHA384_Init
+#define SHA384_Init CC_SHA384_Init
+#undef SHA512_Init
+#define SHA512_Init CC_SHA512_Init
--- lib/bundler/gem_helper.rb.orig	2024-06-11 16:54:24.000000000 -0700
+++ lib/bundler/gem_helper.rb	2024-06-14 19:51:49.000000000 -0700
@@ -231,7 +231,7 @@ module Bundler
     end
 
     def gem_command
-      ENV["GEM_COMMAND"]&.shellsplit || ["gem"]
+      ENV["GEM_COMMAND"]&.shellsplit || ["gem3.3"]
     end
   end
 end
--- signal.c.orig	2024-06-11 16:54:24.000000000 -0700
+++ signal.c	2024-06-14 19:51:49.000000000 -0700
@@ -803,7 +803,8 @@ 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
--- vm_dump.c.orig	2024-06-11 16:54:24.000000000 -0700
+++ vm_dump.c	2024-06-14 19:51:49.000000000 -0700
@@ -490,7 +490,8 @@ rb_vmdebug_thread_dump_state(FILE *errou
 }
 
 #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
@@ -502,7 +503,8 @@ rb_vmdebug_thread_dump_state(FILE *errou
 # ifdef HAVE_LIBUNWIND
 #  undef backtrace
 #  define backtrace unw_backtrace
-# elif defined(__APPLE__) && defined(HAVE_LIBUNWIND_H)
+# elif defined(__APPLE__) && defined(HAVE_LIBUNWIND_H) \
+       && MAC_OS_X_VERSION_MIN_REQUIRED >= 1060
 #  define UNW_LOCAL_ONLY
 #  include <libunwind.h>
 #  include <sys/mman.h>