diff --git a/www/ruby-unicorn/Makefile b/www/ruby-unicorn/Makefile
index 97c795dd5b9..659017b838a 100644
--- a/www/ruby-unicorn/Makefile
+++ b/www/ruby-unicorn/Makefile
@@ -1,11 +1,13 @@
-# $OpenBSD: Makefile,v 1.23 2018/06/13 22:26:53 jeremy Exp $
+# $OpenBSD: Makefile,v 1.24 2019/03/08 16:25:11 jeremy Exp $
 
 COMMENT =	ruby-rack HTTP server for Unix and fast clients
 
-DISTNAME =	unicorn-5.3.1
-REVISION =	0
+DISTNAME =	unicorn-5.5.0
 CATEGORIES =	www
 
+PATCHFILES =	unicorn_rails-5.5.0.patch{?id=6836d0674efdb1a6b79953285f10d8edd7e20432}:0
+PATCH_DIST_STRIP =	-p1
+
 HOMEPAGE =	https://bogomips.org/unicorn/
 
 MAINTAINER =	Jeremy Evans <jeremy@openbsd.org>
@@ -13,6 +15,8 @@ MAINTAINER =	Jeremy Evans <jeremy@openbsd.org>
 # Ruby/GPLv2
 PERMIT_PACKAGE_CDROM = Yes
 
+MASTER_SITES0 =	https://bogomips.org/unicorn.git/patch/
+
 MODULES =	lang/ruby
 
 BUILD_DEPENDS =	${RUN_DEPENDS}
@@ -27,10 +31,12 @@ post-install:
 		mv unicorn_rails.1 ${WRKINST}/${LOCALBASE}/man/man1/unicorn_rails${GEM_MAN_SUFFIX}.1
 	rm -r ${WRKINST}/${LOCALBASE}/${GEM_LIB}/gems/${DISTNAME}/man
 
-TEST_DEPENDS = devel/gmake \
-		  devel/ruby-isolate,${MODRUBY_FLAVOR}
+TEST_DEPENDS =	devel/gmake \
+		devel/ruby-isolate,${MODRUBY_FLAVOR} \
+		www/ruby-rack,${MODRUBY_FLAVOR}
+
 do-test:
-	cd ${WRKSRC} && RUBYOPT=-rubygems RUBY=${RUBY} MRI=${RUBY} \
-		MAKE='gmake -ek' gmake -ek test
+	cd ${WRKSRC} && RUBY=${RUBY} MRI=${RUBY} \
+		MAKE='gmake -ek' gmake -ek check
 
 .include <bsd.port.mk>
diff --git a/www/ruby-unicorn/distinfo b/www/ruby-unicorn/distinfo
index 8b1c03b1e8f..e5ed57d3c19 100644
--- a/www/ruby-unicorn/distinfo
+++ b/www/ruby-unicorn/distinfo
@@ -1,2 +1,4 @@
-SHA256 (unicorn-5.3.1.gem) = awP9QC//SHGSkijg7YruAWVtWcpxNfO0HgcWGCi0DTg=
-SIZE (unicorn-5.3.1.gem) = 217088
+SHA256 (unicorn-5.5.0.gem) = 75MIqhPrc378UQ9YL/VdlIWuF7jCwpu/G9kG6MFhyW0=
+SHA256 (unicorn_rails-5.5.0.patch) = L7FBYaJ9g7POx+wZ7knV8RDhYugyv6UaLqJTa6hrX2M=
+SIZE (unicorn-5.5.0.gem) = 220160
+SIZE (unicorn_rails-5.5.0.patch) = 1359
diff --git a/www/ruby-unicorn/patches/patch-test_unit_test_signals_rb b/www/ruby-unicorn/patches/patch-test_unit_test_signals_rb
new file mode 100644
index 00000000000..c55efc33565
--- /dev/null
+++ b/www/ruby-unicorn/patches/patch-test_unit_test_signals_rb
@@ -0,0 +1,16 @@
+$OpenBSD: patch-test_unit_test_signals_rb,v 1.1 2019/03/08 16:25:11 jeremy Exp $
+
+Set maximum sleep time in test.
+
+Index: test/unit/test_signals.rb
+--- test/unit/test_signals.rb.orig
++++ test/unit/test_signals.rb
+@@ -96,7 +96,7 @@ class SignalsTest < Test::Unit::TestCase
+ 
+   def test_timeout_slow_response
+     pid = fork {
+-      app = lambda { |env| sleep }
++      app = lambda { |env| sleep(61) }
+       opts = @server_opts.merge(:timeout => 3)
+       redirect_test_io { HttpServer.new(app, opts).start.join }
+     }
diff --git a/www/ruby-unicorn/pkg/PLIST b/www/ruby-unicorn/pkg/PLIST
index 278963ccdc3..50374c49ce9 100644
--- a/www/ruby-unicorn/pkg/PLIST
+++ b/www/ruby-unicorn/pkg/PLIST
@@ -1,4 +1,4 @@
-@comment $OpenBSD: PLIST,v 1.10 2017/03/27 14:40:13 jeremy Exp $
+@comment $OpenBSD: PLIST,v 1.11 2019/03/08 16:25:11 jeremy Exp $
 ${GEM_BIN}/unicorn${GEM_BIN_SUFFIX}
 ${GEM_BIN}/unicorn_rails${GEM_BIN_SUFFIX}
 ${GEM_LIB}/cache/${DISTNAME}.gem
@@ -132,6 +132,8 @@ ${GEM_LIB}/gems/${DISTNAME}/t/t0116-client_body_buffer_size.sh
 ${GEM_LIB}/gems/${DISTNAME}/t/t0116.ru
 ${GEM_LIB}/gems/${DISTNAME}/t/t0200-rack-hijack.sh
 ${GEM_LIB}/gems/${DISTNAME}/t/t0300-no-default-middleware.sh
+${GEM_LIB}/gems/${DISTNAME}/t/t0301-no-default-middleware-ignored-in-config.sh
+${GEM_LIB}/gems/${DISTNAME}/t/t0301.ru
 ${GEM_LIB}/gems/${DISTNAME}/t/t9000-preread-input.sh
 ${GEM_LIB}/gems/${DISTNAME}/t/t9001-oob_gc.sh
 ${GEM_LIB}/gems/${DISTNAME}/t/t9002-oob_gc-path.sh