diff --git a/files/install_puppet.ps1 b/files/install_puppet.ps1
index 9e88c4c7d..393da4692 100644
--- a/files/install_puppet.ps1
+++ b/files/install_puppet.ps1
@@ -256,8 +256,9 @@ $service_names=@(
   "mcollective"
 )
 try {
+  $state_dir = (puppet.bat config print statedir)
   Write-Log "Installation PID:$PID"
-  $install_pid_lock = Join-Path -Path (Split-Path -Parent (puppet.bat config print agent_catalog_run_lockfile)) -ChildPath 'puppet_agent_upgrade.pid'
+  $install_pid_lock = Join-Path -Path $state_dir -ChildPath 'puppet_agent_upgrade.pid'
   Lock-Installation $install_pid_lock
   if ($PuppetPID) {
     # Wait for the puppet run to finish
@@ -342,6 +343,7 @@ try {
   if ($UseLockedFilesWorkaround) {
     Reset-PuppetresDLL $temp_puppetres
   }
+  "$_" | Out-File -FilePath (Join-Path -Path $state_dir -ChildPath 'puppet_agent_upgrade_failure.log')
 } finally {
   Reset-PuppetServices $services_before
   Unlock-Installation $install_pid_lock
diff --git a/lib/puppet/provider/upgrade_error/upgrade_error.rb b/lib/puppet/provider/upgrade_error/upgrade_error.rb
new file mode 100644
index 000000000..58f940b8d
--- /dev/null
+++ b/lib/puppet/provider/upgrade_error/upgrade_error.rb
@@ -0,0 +1,25 @@
+Puppet::Type.type(:upgrade_error).provide :upgrade_error do
+  def ensure_notexist
+    logfile = File.join(Puppet["statedir"].to_s, @resource[:name])
+    Puppet.debug "Checking for Error logfile #{logfile}"
+    not File.exists?(logfile)
+  end
+
+  def delete_file_and_read_content(filename)
+    logfile = File.join(Puppet["statedir"].to_s, filename)
+    Puppet.debug "Reading Error Log #{logfile}"
+    if Puppet.features.microsoft_windows?
+      # The file laid down by the installation script on windows will be UTF-16LE.
+      # In this scenario we need to open the file in binmode and read each line
+      # individually, then encode the result back to UTF-8 so we can sub out both
+      # the UTF-16 header \uFEFF and the \r\n line carriages.
+      content = File.open(logfile,"rb:UTF-16LE"){ |file| file.readlines }[0].encode!('UTF-8').gsub("\uFEFF",'').gsub("\r",'')
+    else
+      content = File.read(logfile)
+    end
+    Puppet.debug "Deleting Error Log"
+    File.delete(logfile)
+    return content
+  end
+
+end
diff --git a/lib/puppet/type/upgrade_error.rb b/lib/puppet/type/upgrade_error.rb
new file mode 100644
index 000000000..6eadb6c1a
--- /dev/null
+++ b/lib/puppet/type/upgrade_error.rb
@@ -0,0 +1,25 @@
+Puppet::Type.newtype(:upgrade_error) do
+  @doc = <<-DOC
+Fails when a previous backgroun installation failed. The type
+will check for the existance of an installation failure log
+and raise an error with the contents of the log if it exists
+DOC
+
+  newproperty(:ensure_notexist) do
+    desc "whether or not the error log exists"
+    def insync?(not_exist)
+      if not_exist
+        true
+      else
+        raise Puppet::Error.new("Failed previous installation with: #{provider.delete_file_and_read_content(@resource[:name])}")
+      end
+    end
+
+    defaultto { true }
+  end
+
+  newparam(:name) do
+    desc "The name of the failure log to check for in puppet's $statedir. If this log exists the resource will fail."
+    isnamevar
+  end
+end
diff --git a/manifests/windows/install.pp b/manifests/windows/install.pp
index 6f03e1bd5..7207f3e35 100644
--- a/manifests/windows/install.pp
+++ b/manifests/windows/install.pp
@@ -39,11 +39,12 @@
   debug ("Installing puppet from ${_msi_location}")
 
   $_installps1 = windows_native_path("${::env_temp_variable}/install_puppet.ps1")
+  upgrade_error { "puppet_agent_upgrade_failure.log": }
   file { "${_installps1}":
     ensure  => file,
     content => file('puppet_agent/install_puppet.ps1')
   }
-  -> exec { 'install_puppet.ps1':
+  exec { 'install_puppet.ps1':
     # The powershell execution uses -Command and not -File because -File will interpolate the quotes
     # in a context like cmd.exe: https://docs.microsoft.com/en-us/powershell/scripting/components/console/powershell.exe-command-line-help?view=powershell-6#-file--
     # Because of this it's much cleaner to use -Command and use single quotes for each powershell param
@@ -62,6 +63,10 @@
                           -InstallArgs '${_install_options}' \
                           ${_move_dll_workaround}",
     path    => $::path,
+    require => [
+      Upgrade_error['puppet_agent_upgrade_failure.log'],
+      File["${_installps1}"]
+    ]
   }
 
   # PUP-5480/PE-15037 Cache dir loses inheritable SYSTEM perms