diff --git a/lib/facter/openssl_version.rb b/lib/facter/openssl_version.rb
index c5d9c913..5a6ffef2 100644
--- a/lib/facter/openssl_version.rb
+++ b/lib/facter/openssl_version.rb
@@ -4,7 +4,8 @@
   setcode do
     if Facter::Util::Resolution.which('openssl')
       openssl_version = Facter::Util::Resolution.exec('openssl version 2>&1')
-      matches = %r{^OpenSSL ([\w.-]+)(\s+FIPS)?( +)([\d.]+)( +)([\w.]+)( +)([\d.]+)}.match(openssl_version)
+      # OracleLinux did some uppercase-lowercase-extras
+      matches = %r{^OpenSSL ([\w.]+)[ -]*(fips|FIPS|dev)? +([\d.]+) +([\w.]+) +([\d.]+) *(\([\w:. ]+\))?}.match(openssl_version)
       matches[1] if matches
     end
   end
diff --git a/spec/unit/openssl_version_spec.rb b/spec/unit/openssl_version_spec.rb
index 95ddbd2f..df4eb908 100644
--- a/spec/unit/openssl_version_spec.rb
+++ b/spec/unit/openssl_version_spec.rb
@@ -3,6 +3,77 @@
 require 'spec_helper'
 require 'facter'
 
+fact_matrix = {
+  'debian-11-x86_64' => {
+    return_string: 'OpenSSL 1.1.1w  11 Sep 2023',
+    version_string: '1.1.1w',
+  },
+  'debian-12-x86_64' => {
+    return_string: 'OpenSSL 3.0.15 3 Sep 2024 (Library: OpenSSL 3.0.15 3 Sep 2024)',
+    version_string: '3.0.15',
+  },
+  'ubuntu-20.04-x86_64' => {
+    return_string: 'OpenSSL 1.1.1f  31 Mar 2020',
+    version_string: '1.1.1f',
+  },
+  'ubuntu-22.04-x86_64' => {
+    return_string: 'OpenSSL 3.0.2 15 Mar 2022 (Library: OpenSSL 3.0.2 15 Mar 2022)',
+    version_string: '3.0.2',
+  },
+  'ubuntu-24.04-x86_64' => {
+    return_string: 'OpenSSL 3.0.13 30 Jan 2024 (Library: OpenSSL 3.0.13 30 Jan 2024)',
+    version_string: '3.0.13',
+  },
+  'redhat-8-legacy' => {
+    return_string: 'OpenSSL 1.1.1c FIPS  28 May 2019',
+    version_string: '1.1.1c',
+  },
+  'redhat-8-x86_64' => {
+    return_string: 'OpenSSL 1.1.1k  FIPS 25 Mar 2021',
+    version_string: '1.1.1k',
+  },
+  'redhat-9-x86_64' => {
+    return_string: 'OpenSSL 9.9.9zzz FIPS 1 Jan 2099',
+    version_string: '9.9.9zzz',
+  },
+  'oraclelinux-8-x86_64' => {
+    return_string: 'OpenSSL 1.1.1k  FIPS 25 Mar 2021',
+    version_string: '1.1.1k',
+  },
+  'oraclelinux-9-x86_64' => {
+    return_string: 'OpenSSL 3.2.2 4 Jun 2024 (Library: OpenSSL 3.2.2 4 Jun 2024)',
+    version_string: '3.2.2',
+  },
+  'rocky-8-x86_64' => {
+    return_string: 'OpenSSL 1.1.1k  FIPS 25 Mar 2021',
+    version_string: '1.1.1k',
+  },
+  'rocky-9-x86_64' => {
+    return_string: 'OpenSSL 3.2.2 4 Jun 2024 (Library: OpenSSL 3.2.2 4 Jun 2024)',
+    version_string: '3.2.2',
+  },
+  'almalinux-8-x86_64' => {
+    return_string: 'OpenSSL 1.1.1k  FIPS 25 Mar 2021',
+    version_string: '1.1.1k',
+  },
+  'almalinux-9-x86_64' => {
+    return_string: 'OpenSSL 3.2.2 4 Jun 2024 (Library: OpenSSL 3.2.2 4 Jun 2024)',
+    version_string: '3.2.2',
+  },
+  'centos-9-x86_64' => {
+    return_string: 'OpenSSL 1.0.2g  1 Mar 2016',
+    version_string: '1.0.2g',
+  },
+  'vanilla-openssl' => {
+    return_string: 'OpenSSL 3.5.0-dev  (Library: OpenSSL 3.5.0-dev )',
+    version_string: '3.5.0-dev',
+  },
+  'legacy' => {
+    return_string: 'OpenSSL 0.9.8zg 14 July 2015',
+    version_string: '0.9.8zg',
+  },
+}
+
 describe Facter.fact(:openssl_version) do
   on_supported_os.each do |os, facts|
     context "on #{os}" do
@@ -16,11 +87,11 @@
         context 'with value' do
           before do
             allow(Facter::Util::Resolution).to receive(:which).with('openssl').and_return(true)
-            allow(Facter::Util::Resolution).to receive(:exec).with('openssl version 2>&1').and_return('OpenSSL 0.9.8zg 14 July 2015')
+            allow(Facter::Util::Resolution).to receive(:exec).with('openssl version 2>&1').and_return(fact_matrix[os][:return_string])
           end
 
           it {
-            expect(Facter.value(:openssl_version)).to eq('0.9.8zg')
+            expect(Facter.value(:openssl_version)).to eq(fact_matrix[os][:version_string])
           }
         end
 
@@ -36,55 +107,27 @@
           }
         end
       end
+    end
+  end
 
-      describe 'openssl_version rhel' do
-        context 'with value' do
-          before do
-            allow(Facter::Util::Resolution).to receive(:which).with('openssl').and_return(true)
-            allow(Facter::Util::Resolution).to receive(:exec).with('openssl version 2>&1').and_return('OpenSSL 1.0.1e-fips 11 Feb 2013')
-          end
-
-          it {
-            expect(Facter.value(:openssl_version)).to eq('1.0.1e-fips')
-          }
-        end
-      end
-
-      describe 'openssl_version centos' do
-        context 'with value' do
-          before do
-            allow(Facter::Util::Resolution).to receive(:which).with('openssl').and_return(true)
-            allow(Facter::Util::Resolution).to receive(:exec).with('openssl version 2>&1').and_return('OpenSSL 1.0.2g  1 Mar 2016')
-          end
-
-          it {
-            expect(Facter.value(:openssl_version)).to eq('1.0.2g')
-          }
-        end
-      end
-
-      describe 'openssl_version rhel8' do
-        context 'with value' do
-          before do
-            allow(Facter::Util::Resolution).to receive(:which).with('openssl').and_return(true)
-            allow(Facter::Util::Resolution).to receive(:exec).with('openssl version 2>&1').and_return('OpenSSL 1.1.1c FIPS  28 May 2019')
-          end
+  filler_facts = on_supported_os['redhat-9-x86_64']
+  ['legacy', 'redhat-8-legacy'].each do |special_case|
+    context "on #{special_case}" do
+      let(:facts) { filler_facts }
 
-          it {
-            expect(Facter.value(:openssl_version)).to eq('1.1.1c')
-          }
-        end
+      before do
+        Facter.clear
       end
 
-      describe 'openssl_version rhel8 latest' do
+      describe 'openssl_version' do
         context 'with value' do
           before do
             allow(Facter::Util::Resolution).to receive(:which).with('openssl').and_return(true)
-            allow(Facter::Util::Resolution).to receive(:exec).with('openssl version 2>&1').and_return('OpenSSL 1.1.1k  FIPS 25 Mar 2021')
+            allow(Facter::Util::Resolution).to receive(:exec).with('openssl version 2>&1').and_return(fact_matrix[special_case][:return_string])
           end
 
           it {
-            expect(Facter.value(:openssl_version)).to eq('1.1.1k')
+            expect(Facter.value(:openssl_version)).to eq(fact_matrix[special_case][:version_string])
           }
         end
       end