diff --git a/Gemfile b/Gemfile
index 7461ea33..d5c40033 100644
--- a/Gemfile
+++ b/Gemfile
@@ -4,6 +4,9 @@ gemspec
 
 gem "logger", "< 1.6" # 1.6 causes errors with mixlib-log < 3.1.1
 
+# Pin psych < 5.2 to avoid build issues on Windows Ruby 3.3 where libyaml headers are unavailable
+gem "psych", "< 5.2" if RUBY_PLATFORM.match?(/mingw|mswin/) && RUBY_VERSION.start_with?("3.3")
+
 group :test do
   gem "rake"
   gem "rspec", "~> 3.8"
@@ -17,7 +20,7 @@ end
 
 group :development do
   gem "pry"
-  gem "pry-byebug"
+  gem "pry-byebug", platforms: :ruby  # byebug doesn't work on Windows
   gem "rb-readline"
 end