diff --git a/lang/ruby33/Portfile b/lang/ruby33/Portfile
index 7c11254a53209..15610e65ee44f 100644
--- a/lang/ruby33/Portfile
+++ b/lang/ruby33/Portfile
@@ -17,7 +17,7 @@ legacysupport.newest_darwin_requires_legacy 14
 # This property should be preserved.
 
 set ruby_ver        3.3
-set ruby_patch      5
+set ruby_patch      6
 set ruby_ver_nodot  [string map {. {}} ${ruby_ver}]
 name                ruby${ruby_ver_nodot}
 version             ${ruby_ver}.${ruby_patch}
@@ -42,9 +42,9 @@ master_sites        ruby:${ruby_ver}
 distname            ruby-${version}
 dist_subdir         ruby${ruby_ver_nodot}
 
-checksums           rmd160  6b997a751809a5f84376ad653ea75e26734af085 \
-                    sha256  3781a3504222c2f26cb4b9eb9c1a12dbf4944d366ce24a9ff8cf99ecbce75196 \
-                    size    22129139
+checksums           rmd160  b77ffe3a13d630664a1ba91e5298575a430666f8 \
+                    sha256  8dc48fffaf270f86f1019053f28e51e4da4cce32a36760a0603a9aee67d7fd8d \
+                    size    22153657
 
 # Universal builds don't currently work, including via the approach used
 # in ruby30.
@@ -69,7 +69,7 @@ select.file         ${filespath}/ruby${ruby_ver_nodot}
 
 # patch-sources.diff: fixes for various issues.
 #
-# This diff is from v3_3_5 vs. macports-3_3_5.
+# This diff is from v3_3_6 vs. macports-3_3_6.
 #
 patchfiles-append   patch-sources.diff
 
diff --git a/lang/ruby33/files/patch-sources.diff b/lang/ruby33/files/patch-sources.diff
index e0f2452b7a5e5..9685733f85481 100644
--- a/lang/ruby33/files/patch-sources.diff
+++ b/lang/ruby33/files/patch-sources.diff
@@ -1,5 +1,5 @@
---- .gdbinit.orig	2024-09-02 09:09:08.000000000 -0700
-+++ .gdbinit	2024-09-14 16:02:32.000000000 -0700
+--- .gdbinit.orig	2024-11-04 16:49:11.000000000 -0800
++++ .gdbinit	2024-11-27 15:23:38.000000000 -0800
 @@ -1,4 +1,5 @@
 -set startup-with-shell off
 +# Move this to end, so failure on older gdbs doesn't blow the rest
@@ -14,8 +14,8 @@
 +
 +# Moved from beginning, since it fails on older gdbs
 +set startup-with-shell off
---- ext/digest/md5/md5cc.h.orig	2024-09-02 09:09:08.000000000 -0700
-+++ ext/digest/md5/md5cc.h	2024-09-14 16:02:32.000000000 -0700
+--- ext/digest/md5/md5cc.h.orig	2024-11-04 16:49:11.000000000 -0800
++++ ext/digest/md5/md5cc.h	2024-11-27 15:23:38.000000000 -0800
 @@ -17,3 +17,11 @@ static DEFINE_FINISH_FUNC_FROM_FINAL(MD5
  #undef MD5_Finish
  #define MD5_Update rb_digest_MD5_update
@@ -28,8 +28,8 @@
 + */
 +#undef MD5_Init
 +#define MD5_Init CC_MD5_Init
---- ext/digest/sha1/sha1cc.h.orig	2024-09-02 09:09:08.000000000 -0700
-+++ ext/digest/sha1/sha1cc.h	2024-09-14 16:02:32.000000000 -0700
+--- ext/digest/sha1/sha1cc.h.orig	2024-11-04 16:49:11.000000000 -0800
++++ ext/digest/sha1/sha1cc.h	2024-11-27 15:23:38.000000000 -0800
 @@ -12,3 +12,11 @@ static DEFINE_FINISH_FUNC_FROM_FINAL(SHA
  #undef SHA1_Finish
  #define SHA1_Update rb_digest_SHA1_update
@@ -42,8 +42,8 @@
 + */
 +#undef SHA1_Init
 +#define SHA1_Init CC_SHA1_Init
---- ext/digest/sha2/sha2cc.h.orig	2024-09-02 09:09:08.000000000 -0700
-+++ ext/digest/sha2/sha2cc.h	2024-09-14 16:02:32.000000000 -0700
+--- ext/digest/sha2/sha2cc.h.orig	2024-11-04 16:49:11.000000000 -0800
++++ ext/digest/sha2/sha2cc.h	2024-11-27 15:23:38.000000000 -0800
 @@ -1,6 +1,33 @@
  #define COMMON_DIGEST_FOR_OPENSSL 1
  #include <CommonCrypto/CommonDigest.h>
@@ -94,8 +94,8 @@
 +#define SHA384_Init CC_SHA384_Init
 +#undef SHA512_Init
 +#define SHA512_Init CC_SHA512_Init
---- lib/bundler/gem_helper.rb.orig	2024-09-02 09:09:08.000000000 -0700
-+++ lib/bundler/gem_helper.rb	2024-09-14 16:02:32.000000000 -0700
+--- lib/bundler/gem_helper.rb.orig	2024-11-04 16:49:11.000000000 -0800
++++ lib/bundler/gem_helper.rb	2024-11-27 15:23:38.000000000 -0800
 @@ -231,7 +231,7 @@ module Bundler
      end
  
@@ -105,8 +105,8 @@
      end
    end
  end
---- signal.c.orig	2024-09-02 09:09:08.000000000 -0700
-+++ signal.c	2024-09-14 16:02:32.000000000 -0700
+--- signal.c.orig	2024-11-04 16:49:11.000000000 -0800
++++ signal.c	2024-11-27 15:23:38.000000000 -0800
 @@ -803,7 +803,8 @@ check_stack_overflow(int sig, const uint
      const greg_t bp = mctx->gregs[REG_EBP];
  #   endif
@@ -117,8 +117,8 @@
  #     define MCTX_SS_REG(reg) __ss.__##reg
  #   else
  #     define MCTX_SS_REG(reg) ss.reg
---- vm_dump.c.orig	2024-09-02 09:09:08.000000000 -0700
-+++ vm_dump.c	2024-09-14 16:02:32.000000000 -0700
+--- vm_dump.c.orig	2024-11-04 16:49:11.000000000 -0800
++++ vm_dump.c	2024-11-27 15:23:38.000000000 -0800
 @@ -490,7 +490,8 @@ rb_vmdebug_thread_dump_state(FILE *errou
  }