diff --git a/devel/rubygem-pry-byebug/Makefile b/devel/rubygem-pry-byebug/Makefile
index e037d5ac81da..6eb1c30822d2 100644
--- a/devel/rubygem-pry-byebug/Makefile
+++ b/devel/rubygem-pry-byebug/Makefile
@@ -1,21 +1,20 @@
 PORTNAME=	pry-byebug
-PORTVERSION=	3.9.0
-PORTREVISION=	1
+PORTVERSION=	3.10.1
 CATEGORIES=	devel rubygems
 MASTER_SITES=	RG
 
 MAINTAINER=	sunpoet@FreeBSD.org
 COMMENT=	Fast debugging with Pry
 
 LICENSE=	MIT
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
 RUN_DEPENDS=	rubygem-byebug>=11.0<12:devel/rubygem-byebug \
-		rubygem-pry>=0.13.0<1:devel/rubygem-pry
+		rubygem-pry>=0.13<0.15:devel/rubygem-pry
 
 USES=		gem
 USE_RUBY=	yes
 
 NO_ARCH=	yes
 
 .include <bsd.port.mk>
diff --git a/devel/rubygem-pry-byebug/distinfo b/devel/rubygem-pry-byebug/distinfo
index e2fe2ccf618d..453e155570ef 100644
--- a/devel/rubygem-pry-byebug/distinfo
+++ b/devel/rubygem-pry-byebug/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1585565032
-SHA256 (rubygem/pry-byebug-3.9.0.gem) = 3bba08f97fea15b89cc299f3b5136e3b85763cd18cf84960eac4fbfbeb2ede24
-SIZE (rubygem/pry-byebug-3.9.0.gem) = 15872
+TIMESTAMP = 1661599497
+SHA256 (rubygem/pry-byebug-3.10.1.gem) = c8f975c32255bfdb29e151f5532130be64ff3d0042dc858d0907e849125581f8
+SIZE (rubygem/pry-byebug-3.10.1.gem) = 15872
diff --git a/devel/rubygem-pry-byebug/files/patch-gemspec b/devel/rubygem-pry-byebug/files/patch-gemspec
deleted file mode 100644
index 5bcfe060f05c..000000000000
--- a/devel/rubygem-pry-byebug/files/patch-gemspec
+++ /dev/null
@@ -1,11 +0,0 @@
---- pry-byebug.gemspec.orig	2021-10-25 12:00:35 UTC
-+++ pry-byebug.gemspec
-@@ -25,7 +25,7 @@ Gem::Specification.new do |s|
- 
-   if s.respond_to? :add_runtime_dependency then
-     s.add_runtime_dependency(%q<byebug>.freeze, ["~> 11.0"])
--    s.add_runtime_dependency(%q<pry>.freeze, ["~> 0.13.0"])
-+    s.add_runtime_dependency(%q<pry>.freeze, ["~> 0.13"])
-   else
-     s.add_dependency(%q<byebug>.freeze, ["~> 11.0"])
-     s.add_dependency(%q<pry>.freeze, ["~> 0.13.0"])