diff --git a/lib/vagrant.rb b/lib/vagrant.rb
index a346982a3..f790039d3 100644
--- a/lib/vagrant.rb
+++ b/lib/vagrant.rb
@@ -1,11 +1,12 @@
 # Copyright (c) HashiCorp, Inc.
 # SPDX-License-Identifier: BUSL-1.1
-
 require "log4r"
 
 # Add patches to log4r to support trace level
 require "vagrant/patches/log4r"
 require "vagrant/patches/net-ssh"
+require "vagrant/patches/rubygems"
+
 # Set our log levels and include trace
 require 'log4r/configurator'
 Log4r::Configurator.custom_levels(*(["TRACE"] + Log4r::Log4rConfig::LogLevels))
diff --git a/lib/vagrant/patches/builder/mkmf.rb b/lib/vagrant/patches/builder/mkmf.rb
new file mode 100644
index 000000000..7c7d9d9c0
--- /dev/null
+++ b/lib/vagrant/patches/builder/mkmf.rb
@@ -0,0 +1,116 @@
+# Copyright (c) HashiCorp, Inc.
+# SPDX-License-Identifier: BUSL-1.1
+
+# This custom mkmf.rb file is used on Windows platforms
+# to handle common path related build failures where
+# a space is included in the path. The default installation
+# location being in Program Files results in most many
+# extensions failing to build. These patches will attempt
+# to find unquoted paths in flags and quote them prior to
+# usage.
+
+# Start with locating the real mkmf.rb file and
+# loading it
+mkmf_paths = $LOAD_PATH.find_all { |x|
+  !x.start_with?(__dir__) &&
+  File.exist?(File.join(x, "mkmf.rb"))
+}.uniq
+
+# At this point the path collection should only consist
+# of a single entry. If there's more than one, load all
+# of them but include a warning message that more than
+# one was encountered. If none are found, then something
+# bad is going on so just bail.
+if mkmf_paths.size > 1
+  $stderr.puts "WARNING: Multiple mkmf.rb files located: #{mkmf_paths.inspect}"
+elsif mkmf_paths.empty?
+  raise "Failed to locate mkmf.rb file"
+end
+
+mkmf_paths.each do |mpath|
+  require File.join(mpath, "mkmf.rb")
+end
+
+# Attempt to detect and quote Windos paths found within
+# the given string of flags
+#
+# @param [String] flags Compiler/linker flags
+# @return [String] flags with paths quoted
+def flag_cleaner(flags)
+  parts = flags.split(" -")
+  parts.map! do |p|
+    if p !~ %r{[A-Za-z]:(/|\\)}
+      next p
+    elsif p =~ %r{"[A-Za-z]:(/|\\).+"$}
+      next p
+    end
+
+    p.gsub(%r{([A-Za-z]:(/|\\).+)$}, '"\1"')
+  end
+
+  parts.join(" -")
+end
+
+# Check values defined for CFLAGS, CPPFLAGS, LDFLAGS,
+# and INCFLAGS for unquoted Windows paths and quote
+# them.
+def clean_flags!
+  $CFLAGS = flag_cleaner($CFLAGS)
+  $CPPFLAGS = flag_cleaner($CPPFLAGS)
+  $LDFLAGS = flag_cleaner($LDFLAGS)
+  $INCFLAGS = flag_cleaner($INCFLAGS)
+end
+
+# Since mkmf loads the MakeMakefile module directly into the
+# current scope, apply patches directly in the scope
+def vagrant_create_makefile(*args)
+  clean_flags!
+
+  ruby_create_makefile(*args)
+end
+alias :ruby_create_makefile :create_makefile
+alias :create_makefile :vagrant_create_makefile
+
+def vagrant_append_cflags(*args)
+  result = ruby_append_cflags(*args)
+  clean_flags!
+  result
+end
+alias :ruby_append_cflags :append_cflags
+alias :append_cflags :vagrant_append_cflags
+
+def vagrant_append_cppflags(*args)
+  result = ruby_append_cppflags(*args)
+  clean_flags!
+  result
+end
+alias :ruby_append_cppflags :append_cppflags
+alias :append_cppflags :vagrant_append_cppflags
+
+def vagrant_append_ldflags(*args)
+  result = ruby_append_ldflags(*args)
+  clean_flags!
+  result
+end
+alias :ruby_append_ldflags :append_ldflags
+alias :append_ldflags :vagrant_append_ldflags
+
+def vagrant_cc_config(*args)
+  clean_flags!
+  ruby_cc_config(*args)
+end
+alias :ruby_cc_config :cc_config
+alias :cc_config :vagrant_cc_config
+
+def vagrant_link_config(*args)
+  clean_flags!
+  ruby_link_config(*args)
+end
+alias :ruby_link_config :link_config
+alias :link_config :vagrant_link_config
+
+# Finally, always append the flags that Vagrant has
+# defined via the environment
+append_cflags(ENV["CFLAGS"]) if ENV["CFLAGS"]
+append_cppflags(ENV["CPPFLAGS"]) if ENV["CPPFLAGS"]
+append_ldflags(ENV["LDFLAGS"]) if ENV["LDFLAGS"]
diff --git a/lib/vagrant/patches/rubygems.rb b/lib/vagrant/patches/rubygems.rb
new file mode 100644
index 000000000..3d844f0b5
--- /dev/null
+++ b/lib/vagrant/patches/rubygems.rb
@@ -0,0 +1,23 @@
+# Copyright (c) HashiCorp, Inc.
+# SPDX-License-Identifier: BUSL-1.1
+
+# This allows for effective monkey patching of the MakeMakefile
+# module when building gem extensions. When gem extensions are
+# built, the extconf.rb file is executed as a separate process.
+# To support monkey patching the MakeMakefile module, the ruby
+# executable path is adjusted to add a custom load path allowing
+# a customized mkmf.rb file to load the proper mkmf.rb file, and
+# then applying the proper patches.
+if Gem.win_platform?
+  Gem.class_eval do
+    class << self
+      def vagrant_ruby
+        cmd = ruby_ruby
+        "#{cmd} -I\"#{Vagrant.source_root.join("lib/vagrant/patches/builder")}\""
+      end
+
+      alias_method :ruby_ruby, :ruby
+      alias_method :ruby, :vagrant_ruby
+    end
+  end
+end