diff --git a/security/ruby-rubyntlm/Makefile b/security/ruby-rubyntlm/Makefile
index b6746bac266b..f278e3be7a4e 100644
--- a/security/ruby-rubyntlm/Makefile
+++ b/security/ruby-rubyntlm/Makefile
@@ -1,6 +1,6 @@
-# $NetBSD: Makefile,v 1.2 2021/02/03 15:03:05 taca Exp $
+# $NetBSD: Makefile,v 1.3 2024/06/08 15:55:25 taca Exp $
 
-DISTNAME=	rubyntlm-0.6.3
+DISTNAME=	rubyntlm-0.6.4
 CATEGORIES=	security
 
 MAINTAINER=	minskim@NetBSD.org
diff --git a/security/ruby-rubyntlm/PLIST b/security/ruby-rubyntlm/PLIST
index baec4f5776e5..b61c9b180aae 100644
--- a/security/ruby-rubyntlm/PLIST
+++ b/security/ruby-rubyntlm/PLIST
@@ -1,8 +1,10 @@
-@comment $NetBSD: PLIST,v 1.1 2017/10/03 15:56:29 minskim Exp $
+@comment $NetBSD: PLIST,v 1.2 2024/06/08 15:55:25 taca Exp $
 ${GEM_HOME}/cache/${GEM_NAME}.gem
+${GEM_LIBDIR}/.devcontainer/devcontainer.json
+${GEM_LIBDIR}/.github/dependabot.yml
+${GEM_LIBDIR}/.github/workflows/build.yml
 ${GEM_LIBDIR}/.gitignore
 ${GEM_LIBDIR}/.rspec
-${GEM_LIBDIR}/.travis.yml
 ${GEM_LIBDIR}/CHANGELOG.md
 ${GEM_LIBDIR}/Gemfile
 ${GEM_LIBDIR}/LICENSE
@@ -23,11 +25,13 @@ ${GEM_LIBDIR}/lib/net/ntlm/field_set.rb
 ${GEM_LIBDIR}/lib/net/ntlm/int16_le.rb
 ${GEM_LIBDIR}/lib/net/ntlm/int32_le.rb
 ${GEM_LIBDIR}/lib/net/ntlm/int64_le.rb
+${GEM_LIBDIR}/lib/net/ntlm/md4.rb
 ${GEM_LIBDIR}/lib/net/ntlm/message.rb
 ${GEM_LIBDIR}/lib/net/ntlm/message/type0.rb
 ${GEM_LIBDIR}/lib/net/ntlm/message/type1.rb
 ${GEM_LIBDIR}/lib/net/ntlm/message/type2.rb
 ${GEM_LIBDIR}/lib/net/ntlm/message/type3.rb
+${GEM_LIBDIR}/lib/net/ntlm/rc4.rb
 ${GEM_LIBDIR}/lib/net/ntlm/security_buffer.rb
 ${GEM_LIBDIR}/lib/net/ntlm/string.rb
 ${GEM_LIBDIR}/lib/net/ntlm/target_info.rb
diff --git a/security/ruby-rubyntlm/distinfo b/security/ruby-rubyntlm/distinfo
index 0961f87c6244..ff195e77aeeb 100644
--- a/security/ruby-rubyntlm/distinfo
+++ b/security/ruby-rubyntlm/distinfo
@@ -1,5 +1,5 @@
-$NetBSD: distinfo,v 1.4 2021/10/26 11:17:59 nia Exp $
+$NetBSD: distinfo,v 1.5 2024/06/08 15:55:25 taca Exp $
 
-BLAKE2s (rubyntlm-0.6.3.gem) = 10f3521c497013a2787cc9179cdc2cdf384ec76bdb95fc285eeb8e10a94157ab
-SHA512 (rubyntlm-0.6.3.gem) = 7e50c1bf63477fead9189a5ade06db65a3fad04d82bccfbffb513517ab97766053c800af9551e027dedc3aee6fb35288c234d98b1a02815299bcbc463e0edd87
-Size (rubyntlm-0.6.3.gem) = 32768 bytes
+BLAKE2s (rubyntlm-0.6.4.gem) = b0b34bf4a28a30d54b6dc728f3b96ca659e7a174d2d01b4237fbcb1440e7113b
+SHA512 (rubyntlm-0.6.4.gem) = 04e0ffd6e34e2eeefcee065ccd15269a43a4c6ead743f5280106cdb9caad422604f7a39d81096d76ff98d28394e8f47cc85c7efae0b4b7d80c835e8291f52156
+Size (rubyntlm-0.6.4.gem) = 35840 bytes