diff --git a/Library/Homebrew/startup/bootsnap.rb b/Library/Homebrew/startup/bootsnap.rb
index 30064f196e..7cf031949a 100644
--- a/Library/Homebrew/startup/bootsnap.rb
+++ b/Library/Homebrew/startup/bootsnap.rb
@@ -5,9 +5,15 @@
 # rubocop:disable Rails
 homebrew_bootsnap_enabled = ENV["HOMEBREW_NO_BOOTSNAP"].nil? && !ENV["HOMEBREW_BOOTSNAP"].nil?
 
-# we need some development tools to build bootsnap native code
+# portable ruby doesn't play nice with bootsnap
+
+homebrew_bootsnap_enabled &&= !RUBY_PATH.to_s.include?("/vendor/portable-ruby/")
+
 homebrew_bootsnap_enabled &&= if ENV["HOMEBREW_MACOS_VERSION"]
-  File.directory?("/Applications/Xcode.app") || File.directory?("/Library/Developer/CommandLineTools")
+  # Apple Silicon doesn't play nice with bootsnap
+  ENV["HOMEBREW_PROCESSOR"] == "Intel" &&
+    # we need some development tools to build bootsnap native code
+    (File.directory?("/Applications/Xcode.app") || File.directory?("/Library/Developer/CommandLineTools"))
 else
   File.executable?("/usr/bin/clang") || File.executable?("/usr/bin/gcc")
 end