diff --git a/sysutils/rubygem-bundler/Makefile b/sysutils/rubygem-bundler/Makefile
index cd061ecb2f79..532670976296 100644
--- a/sysutils/rubygem-bundler/Makefile
+++ b/sysutils/rubygem-bundler/Makefile
@@ -1,29 +1,29 @@
 PORTNAME=	bundler
-PORTVERSION=	2.6.5
+PORTVERSION=	2.6.6
 PORTEPOCH=	1
 CATEGORIES=	sysutils rubygems
 MASTER_SITES=	RG
 
 MAINTAINER=	ruby@FreeBSD.org
 COMMENT=	Tool that manages gem dependencies for Ruby applications
 WWW=		https://bundler.io/ \
 		https://github.com/rubygems/rubygems/tree/master/bundler
 
 LICENSE=	MIT
 LICENSE_FILE=	${WRKSRC}/LICENSE.md
 
 USES=		cpe gem
 
 NO_ARCH=	yes
 
 CONFLICTS_INSTALL=	go-tools # bin/bundle
 
 post-install:
 .for i in 1 5
 	for f in ${STAGEDIR}${PREFIX}/${GEM_LIB_DIR}/lib/bundler/man/*.${i}; do \
 		${GZIP_CMD} $${f}; \
 		${RLN} $${f}.gz ${STAGEDIR}${PREFIX}/share/man/man${i}/$$(basename $${f}).gz; \
 	done
 .endfor
 
 .include <bsd.port.mk>
diff --git a/sysutils/rubygem-bundler/distinfo b/sysutils/rubygem-bundler/distinfo
index 2e3bbaf12404..27c37e2556d9 100644
--- a/sysutils/rubygem-bundler/distinfo
+++ b/sysutils/rubygem-bundler/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1740836378
-SHA256 (rubygem/bundler-2.6.5.gem) = 9d0eef5779ee569c43f317484f034081f58e9cf7529af6cd59d15266e46a72a3
-SIZE (rubygem/bundler-2.6.5.gem) = 450048
+TIMESTAMP = 1742070848
+SHA256 (rubygem/bundler-2.6.6.gem) = 832b2ab8d2ad6e3d275138fb640df3d36d4818e142d13b277b44886711b89761
+SIZE (rubygem/bundler-2.6.6.gem) = 451072