diff --git a/lib/vagrant/util/powershell.rb b/lib/vagrant/util/powershell.rb
index 9afb4da65..8e48aad1d 100644
--- a/lib/vagrant/util/powershell.rb
+++ b/lib/vagrant/util/powershell.rb
@@ -20,12 +20,16 @@ module Vagrant
         if !defined?(@_powershell_executable)
           @_powershell_executable = "powershell"
 
-          # Try to use WSL interoperability if PowerShell is not symlinked to
-          # the container.
-          if Which.which(@_powershell_executable).nil? && Platform.wsl?
-            @_powershell_executable += ".exe"
+          if Which.which(@_powershell_executable).nil?
+            # Try to use WSL interoperability if PowerShell is not symlinked to
+            # the container.
+            if Platform.wsl?
+              @_powershell_executable += ".exe"
 
-            if Which.which(@_powershell_executable).nil?
+              if Which.which(@_powershell_executable).nil?
+                @_powershell_executable = nil
+              end
+            else
               @_powershell_executable = nil
             end
           end
@@ -41,6 +45,9 @@ module Vagrant
       # Execute a powershell script.
       #
       # @param [String] path Path to the PowerShell script to execute.
+      # @param [Array<String>] args Command arguments
+      # @param [Hash] opts Options passed to execute
+      # @option opts [Hash] :env Custom environment variables
       # @return [Subprocess::Result]
       def self.execute(path, *args, **opts, &block)
         validate_install!
@@ -57,7 +64,7 @@ module Vagrant
             "-NoProfile",
             "-NonInteractive",
             "-ExecutionPolicy", "Bypass",
-            "#{env}&('#{path}')",
+            "#{resize_console}#{env}&('#{path}')",
             args
           ].flatten
 
@@ -72,10 +79,16 @@ module Vagrant
       # Execute a powershell command.
       #
       # @param [String] command PowerShell command to execute.
+      # @param [Hash] opts Extra options
+      # @option opts [Hash] :env Custom environment variables
       # @return [nil, String] Returns nil if exit code is non-zero.
       #   Returns stdout string if exit code is zero.
-      def self.execute_cmd(command)
+      def self.execute_cmd(command, **opts)
         validate_install!
+        env = opts.delete(:env)
+        if env
+          env = env.map{|k,v| "$env:#{k}=#{v}"}.join(";") + "; "
+        end
         c = [
           executable,
           "-NoLogo",
@@ -83,7 +96,7 @@ module Vagrant
           "-NonInteractive",
           "-ExecutionPolicy", "Bypass",
           "-Command",
-          command
+          "#{resize_console}#{env}#{command}"
         ].flatten.compact
 
         r = Subprocess.execute(*c)
@@ -95,9 +108,14 @@ module Vagrant
       #
       # @param [String] command PowerShell command to execute.
       # @param [Hash] opts A collection of options for subprocess::execute
+      # @option opts [Hash] :env Custom environment variables
       # @param [Block] block Ruby block
       def self.execute_inline(*command, **opts, &block)
         validate_install!
+        env = opts.delete(:env)
+        if env
+          env = env.map{|k,v| "$env:#{k}=#{v}"}.join(";") + "; "
+        end
         c = [
           executable,
           "-NoLogo",
@@ -105,7 +123,7 @@ module Vagrant
           "-NonInteractive",
           "-ExecutionPolicy", "Bypass",
           "-Command",
-          command
+          "#{resize_console}#{env}#{command}"
         ].flatten.compact
         c << opts
 
@@ -224,6 +242,19 @@ module Vagrant
       def self.reset!
         instance_variables.each(&method(:remove_instance_variable))
       end
+
+      # @private
+      # This is a helper method that provides the PowerShell command to resize
+      # the "console" to prevent output wrapping or truncating. An environment
+      # variable guard is provided to disable the behavior in cases where it
+      # may cause unexpected results (VAGRANT_POWERSHELL_RESIZE_DISABLE)
+      def self.resize_console
+        if ENV["VAGRANT_POWERSHELL_RESIZE_DISABLE"]
+          ""
+        else
+          "$host.UI.RawUI.BufferSize = New-Object System.Management.Automation.Host.Size(512,50); "
+        end
+      end
     end
   end
 end