diff --git a/lib/vagrant/util/powershell.rb b/lib/vagrant/util/powershell.rb
index 2059e1ee9..55c7e5306 100644
--- a/lib/vagrant/util/powershell.rb
+++ b/lib/vagrant/util/powershell.rb
@@ -19,7 +19,7 @@ module Vagrant
       # Number of seconds to wait while attempting to get powershell version
       DEFAULT_VERSION_DETECTION_TIMEOUT = 30
       # Names of the powershell executable
-      POWERSHELL_NAMES = ["powershell", "pwsh"].map(&:freeze).freeze
+      POWERSHELL_NAMES = ["pwsh", "powershell"].map(&:freeze).freeze
       # Paths to powershell executable
       POWERSHELL_PATHS = [
         "%SYSTEMROOT%/System32/WindowsPowerShell/v1.0",
@@ -33,11 +33,29 @@ module Vagrant
       # @return [String|nil] a powershell executable, depending on environment
       def self.executable
         if !defined?(@_powershell_executable)
+          prefer_name = ENV["VAGRANT_PREFERRED_POWERSHELL"].to_s.sub(".exe", "")
+          if !POWERSHELL_NAMES.include?(prefer_name)
+            prefer_name = POWERSHELL_NAMES.first
+          end
+
+          LOGGER.debug("preferred powershell executable name: #{prefer_name}")
+
           # First start with detecting executable on configured path
-          POWERSHELL_NAMES.detect do |psh|
-            return @_powershell_executable = psh if Which.which(psh)
-            psh += ".exe"
-            return @_powershell_executable = psh if Which.which(psh)
+          found_shells = Hash.new.tap do |found|
+            POWERSHELL_NAMES.each do |psh|
+              psh_path = Which.which(psh)
+              psh_path = Which.which(psh + ".exe") if !psh_path
+              next if !psh_path
+
+              LOGGER.debug("detected powershell for #{psh.inspect} - #{psh_path}")
+              found[psh] = psh_path
+            end
+          end
+
+          # Done if preferred shell was found
+          if found_shells.key?(prefer_name)
+            LOGGER.debug("using preferred powershell #{prefer_name.inspect} - #{found_shells[prefer_name]}")
+            return @_powershell_executable = found_shells[prefer_name]
           end
 
           # Now attempt with paths
@@ -48,17 +66,29 @@ module Vagrant
 
           paths.each do |psh_path|
             POWERSHELL_NAMES.each do |psh|
+              next if found_shells.key?(psh)
+
               path = File.join(psh_path, psh)
-              return @_powershell_executable = path if Which.which(path)
-
-              path += ".exe"
-              return @_powershell_executable = path if Which.which(path)
-
-              # Finally test the msys2 style path
-              path = path.sub(/^([A-Za-z]):/, "/mnt/\\1")
-              return @_powershell_executable = path if Which.which(path)
+              [path, "#{path}.exe", path.sub(/^([A-Za-z]):/, "/mnt/\\1")].each do |full_path|
+                if File.executable?(full_path)
+                  found_shells[psh] = full_path
+                  break
+                end
+              end
             end
           end
+
+          # Done if preferred shell was found
+          if found_shells.key?(prefer_name)
+            LOGGER.debug("using preferred powershell #{prefer_name.inspect} - #{found_shells[prefer_name]}")
+            return @_powershell_executable = found_shells[prefer_name]
+          end
+
+          # Iterate names and return first found
+          POWERSHELL_NAMES.each do |psh|
+            LOGGER.debug("using powershell #{prefer_name.inspect} - #{found_shells[prefer_name]}")
+            return @_powershell_executable = found_shells[psh] if found_shells.key?(psh)
+          end
         end
         @_powershell_executable
       end
@@ -94,6 +124,7 @@ module Vagrant
             "-NoProfile",
             "-NonInteractive",
             "-ExecutionPolicy", "Bypass",
+            "-Command",
             "#{env}&('#{path}')",
             args
           ].flatten
diff --git a/test/unit/vagrant/util/powershell_test.rb b/test/unit/vagrant/util/powershell_test.rb
index bbe36df98..39ef3b30b 100644
--- a/test/unit/vagrant/util/powershell_test.rb
+++ b/test/unit/vagrant/util/powershell_test.rb
@@ -49,6 +49,7 @@ describe Vagrant::Util::PowerShell do
 
   describe ".executable" do
     before do
+      allow(ENV).to receive(:[]).with("VAGRANT_PREFERRED_POWERSHELL").and_return(nil)
       allow(Vagrant::Util::Which).to receive(:which).and_return(nil)
       allow(Vagrant::Util::Subprocess).to receive(:execute) do |*args|
         Vagrant::Util::Subprocess::Result.new(0, args.last.sub("echo ", ""), "")
@@ -57,7 +58,7 @@ describe Vagrant::Util::PowerShell do
 
     context "when powershell found in PATH" do
       before{ expect(Vagrant::Util::Which).to receive(:which).
-          with("powershell").and_return(true) }
+          with("powershell").and_return("powershell") }
 
       it "should return powershell string" do
         expect(described_class.executable).to eq("powershell")
@@ -66,7 +67,7 @@ describe Vagrant::Util::PowerShell do
 
     context "when pwsh found in PATH" do
       before { expect(Vagrant::Util::Which).to receive(:which).
-          with("pwsh").and_return(true) }
+          with("pwsh").and_return("pwsh") }
 
       it "should return pwsh string" do
         expect(described_class.executable).to eq("pwsh")
@@ -74,6 +75,8 @@ describe Vagrant::Util::PowerShell do
     end
 
     context "when not found in PATH" do
+      before { allow(File).to receive(:executable?) }
+
       it "should return nil" do
         expect(described_class.executable).to be_nil
       end
@@ -85,15 +88,46 @@ describe Vagrant::Util::PowerShell do
 
       it "should return powershell.exe when found" do
         expect(Vagrant::Util::Which).to receive(:which).
-          with("powershell.exe").and_return(true)
+          with("powershell.exe").and_return("powershell.exe")
         expect(described_class.executable).to eq("powershell.exe")
       end
 
       it "should check for powershell with full path" do
-        expect(Vagrant::Util::Which).to receive(:which).with(/WindowsPowerShell\/v1.0\/powershell.exe/)
+        expect(File).to receive(:executable?).with(/WindowsPowerShell\/v1.0\/powershell.exe/)
         described_class.executable
       end
     end
+
+    context "powershell preference" do
+      before do
+        allow(Vagrant::Util::Which).to receive(:which)
+        allow(File).to receive(:executable?)
+      end
+
+      it "should prefer pwsh found on in the PATH" do
+        expect(Vagrant::Util::Which).to receive(:which).with("pwsh.exe").and_return("pwsh.exe")
+        expect(described_class.executable).to eq("pwsh.exe")
+      end
+
+      it "should use powershell.exe when found on PATH and pwsh.exe is not" do
+        expect(Vagrant::Util::Which).to receive(:which).with("pwsh.exe").and_return("powershell.exe")
+        expect(described_class.executable).to eq("powershell.exe")
+      end
+
+      it "should prefer powershell.exe when env var is set and powershell.exe and pwsh.exe are on PATH" do
+        expect(ENV).to receive(:[]).with("VAGRANT_PREFERRED_POWERSHELL").and_return("powershell")
+        expect(Vagrant::Util::Which).to receive(:which).with("pwsh.exe").and_return("pwsh.exe")
+        expect(Vagrant::Util::Which).to receive(:which).with("powershell.exe").and_return("powershell.exe")
+        expect(described_class.executable).to eq("powershell.exe")
+      end
+
+      it "should use pwsh.exe when env var is set to powershell but only pwsh.exe is avaialble" do
+        expect(ENV).to receive(:[]).with("VAGRANT_PREFERRED_POWERSHELL").and_return("powershell")
+        expect(Vagrant::Util::Which).to receive(:which).with("pwsh.exe").and_return("pwsh.exe")
+        expect(Vagrant::Util::Which).to receive(:which).with("powershell.exe").and_return(nil)
+        expect(described_class.executable).to eq("pwsh.exe")
+      end
+    end
   end
 
   describe ".available?" do
diff --git a/website/content/docs/other/environmental-variables.mdx b/website/content/docs/other/environmental-variables.mdx
index 4ac9f3c20..4b9c86e37 100644
--- a/website/content/docs/other/environmental-variables.mdx
+++ b/website/content/docs/other/environmental-variables.mdx
@@ -268,6 +268,14 @@ detection.
 When setting this environment variable, its value will be in seconds. By default,
 it will use 30 seconds as a timeout.
 
+## `VAGRANT_PREFERRED_POWERSHELL`
+
+When executing PowerShell commands, Vagrant will prefer to use `pwsh.exe`
+over `powershell.exe` by default. This environment variable can be used to
+modify this preference and make Vagrant prefer `powershell.exe`. The value
+set in this environment variable are any supported PowerShell executables
+which currently are: `powershell` and `pwsh`.
+
 ## `VAGRANT_PREFERRED_PROVIDERS`
 
 This configures providers that Vagrant should prefer.