diff --git a/ruby-3.3.1-Fix-test-session-reuse-but-expire.patch b/ruby-3.3.1-Fix-test-session-reuse-but-expire.patch
new file mode 100644
index 0000000..47e0440
--- /dev/null
+++ b/ruby-3.3.1-Fix-test-session-reuse-but-expire.patch
@@ -0,0 +1,45 @@
+From 047857d9cb44a0703b5582d502e45d585b9dfced Mon Sep 17 00:00:00 2001
+From: "NARUSE, Yui" <naruse@airemix.jp>
+Date: Sat, 3 Feb 2024 19:39:17 +0900
+Subject: [PATCH 1/2] Show OpenSSL version in the error message of assert_equal
+
+---
+ test/net/http/test_https.rb | 2 +-
+ 1 file changed, 1 insertion(+), 1 deletion(-)
+
+diff --git a/test/net/http/test_https.rb b/test/net/http/test_https.rb
+index 89d500118db24b..ccfa48b2a44ea8 100644
+--- a/test/net/http/test_https.rb
++++ b/test/net/http/test_https.rb
+@@ -182,7 +182,7 @@ def test_session_reuse_but_expire
+     http.get("/")
+ 
+     socket = http.instance_variable_get(:@socket).io
+-    assert_equal false, socket.session_reused?
++    assert_equal false, socket.session_reused?, "NOTE: OpenSSL library version is #{OpenSSL::OPENSSL_LIBRARY_VERSION}"
+ 
+     http.finish
+   end
+
+From 53b874d17b68d3f8566846a6df37fd6951a1873c Mon Sep 17 00:00:00 2001
+From: "NARUSE, Yui" <naruse@airemix.jp>
+Date: Sat, 3 Feb 2024 20:22:59 +0900
+Subject: [PATCH 2/2] OpenSSL 3.2.1 30 Jan 2024 is also broken
+
+---
+ test/net/http/test_https.rb | 2 +-
+ 1 file changed, 1 insertion(+), 1 deletion(-)
+
+diff --git a/test/net/http/test_https.rb b/test/net/http/test_https.rb
+index ccfa48b2a44ea8..6b3171d265997e 100644
+--- a/test/net/http/test_https.rb
++++ b/test/net/http/test_https.rb
+@@ -167,7 +167,7 @@ def test_session_reuse
+   def test_session_reuse_but_expire
+     # FIXME: The new_session_cb is known broken for clients in OpenSSL 1.1.0h.
+     omit if OpenSSL::OPENSSL_LIBRARY_VERSION.include?('OpenSSL 1.1.0h')
+-    omit if OpenSSL::OPENSSL_LIBRARY_VERSION.include?('OpenSSL 3.2.0')
++    omit if OpenSSL::OPENSSL_LIBRARY_VERSION.include?('OpenSSL 3.2.')
+ 
+     http = Net::HTTP.new(HOST, config("port"))
+     http.use_ssl = true
diff --git a/ruby.spec b/ruby.spec
index 403b325..5c8fd23 100644
--- a/ruby.spec
+++ b/ruby.spec
@@ -167,7 +167,7 @@
 Summary: An interpreter of object-oriented scripting language
 Name: ruby
 Version: %{ruby_version}%{?development_release}
-Release: 4%{?dist}
+Release: 5%{?dist}
 # BSD-3-Clause: missing/{crypt,mt19937,setproctitle}.c
 # ISC: missing/strl{cat,cpy}.c
 # Public Domain for example for: include/ruby/st.h, strftime.c, missing/*, ...
@@ -255,6 +255,10 @@ Patch12: ruby-3.4.0-fix-branch-protection-compilation-for-arm.patch
 # that is not present for us. Therefore we can safely revert the change.
 # https://bugs.ruby-lang.org/issues/20208
 Patch13: ruby-3.4.0-Revert-Set-AI_ADDRCONFIG-when-making-getaddrinfo.patch
+# Fix `TestNetHTTPS#test_session_reuse_but_expire` test failure cause by
+# to OpenSSL 3.2
+# https://github.com/ruby/ruby/pull/9824
+Patch14: ruby-3.3.1-Fix-test-session-reuse-but-expire.patch
 
 Requires: %{name}-libs%{?_isa} = %{version}-%{release}
 %{?with_rubypick:Suggests: rubypick}
@@ -728,6 +732,7 @@ analysis result in RBS format, a standard type description format for Ruby
 %patch 11 -p1
 %patch 12 -p1
 %patch 13 -p1
+%patch 14 -p1
 
 # Provide an example of usage of the tapset:
 cp -a %{SOURCE3} .
@@ -1663,6 +1668,9 @@ make -C %{_vpath_builddir} runruby TESTRUN_SCRIPT=" \
 
 
 %changelog
+* Wed Mar 06 2024 Vít Ondruch <vondruch@redhat.com> - 3.3.0-5
+- Fix FTBFS caused by OpenSSL 3.2.1 update.
+
 * Fri Jan 26 2024 Jarek Prokop <jprokop@redhat.com> - 3.3.0-4
 - Do not set AI_ADDRCONFIG by default when calling getaddrinfo(3).