diff --git a/security/rubygem-metasploit-payloads/Makefile b/security/rubygem-metasploit-payloads/Makefile
index d876109a9cd6..a155e2cf830e 100644
--- a/security/rubygem-metasploit-payloads/Makefile
+++ b/security/rubygem-metasploit-payloads/Makefile
@@ -1,5 +1,5 @@
 PORTNAME=	metasploit-payloads
-PORTVERSION=	2.0.166
+PORTVERSION=	2.0.189
 CATEGORIES=	security rubygems
 MASTER_SITES=	RG
 
diff --git a/security/rubygem-metasploit-payloads/distinfo b/security/rubygem-metasploit-payloads/distinfo
index 2c95e87558dc..4ac7bcb661a2 100644
--- a/security/rubygem-metasploit-payloads/distinfo
+++ b/security/rubygem-metasploit-payloads/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1714979911
-SHA256 (rubygem/metasploit-payloads-2.0.166.gem) = d312b257d192d2c7e7529b4c53d48c12ef7215fd2184190ce3c8278b5fcb0f39
-SIZE (rubygem/metasploit-payloads-2.0.166.gem) = 48062464
+TIMESTAMP = 1739885761
+SHA256 (rubygem/metasploit-payloads-2.0.189.gem) = 7bd1dd89263e6ad16ba142177fa64055cdcc5efe420c4a65c54d4030f41ab95b
+SIZE (rubygem/metasploit-payloads-2.0.189.gem) = 48089088