diff --git a/Gemfile b/Gemfile
index df954669..3209ccfe 100644
--- a/Gemfile
+++ b/Gemfile
@@ -44,4 +44,15 @@ group :development do
   gem "ruby-lsp", require: false
   gem "simplecov-cobertura"
   gem "yard"
+
+  # Resolves https://github.com/ruby/openssl/issues/949 which we encounter when downloading gocaves on macOS on CI
+  # This has been fixed in openssl versions 3.1.2, 3.2.2, 3.3.1.
+  # The latest dot-patch version of Ruby 3.3 and 3.4 now comes with a new enough openssl version by default.
+  if RUBY_PLATFORM.include?("darwin")
+    if RUBY_VERSION.start_with?('3.2')
+      gem "openssl", "~> 3.2.2"
+    elsif RUBY_VERSION.start_with?('3.1')
+      gem "openssl", "~> 3.1.2"
+    end
+  end
 end