diff --git a/e2e/scenario_win_test.go b/e2e/scenario_win_test.go
index ed2454a3daf..f1a8cd34ca7 100644
--- a/e2e/scenario_win_test.go
+++ b/e2e/scenario_win_test.go
@@ -1,6 +1,9 @@
 package e2e
 
 import (
+	"context"
+	"fmt"
+	"strings"
 	"testing"
 
 	"github.com/Azure/agentbaker/e2e/config"
@@ -16,6 +19,9 @@ func Test_Windows2019Containerd(t *testing.T) {
 			VHD:                    config.VHDWindows2019Containerd,
 			VMConfigMutator:        func(vmss *armcompute.VirtualMachineScaleSet) {},
 			BootstrapConfigMutator: func(configuration *datamodel.NodeBootstrappingConfiguration) {},
+			Validator: func(ctx context.Context, s *Scenario) {
+				ValidateFileHasContentWindows(ctx, s, "c:/k/kubelet", "--rotate-server-certificates=true")
+			},
 		},
 	})
 }
@@ -42,7 +48,6 @@ func Test_Windows2022ContainerdGen2(t *testing.T) {
 			VHD:             config.VHDWindows2022ContainerdGen2,
 			VMConfigMutator: func(vmss *armcompute.VirtualMachineScaleSet) {},
 			BootstrapConfigMutator: func(configuration *datamodel.NodeBootstrappingConfiguration) {
-
 			},
 		},
 	})
@@ -75,3 +80,31 @@ func Test_Windows23H2Gen2(t *testing.T) {
 		},
 	})
 }
+
+func makeExecutablePowershellCommand(steps []string) string {
+	stepsWithEchos := make([]string, len(steps)*2)
+
+	for i, s := range steps {
+		stepsWithEchos[i*2] = fmt.Sprintf("echo '%s'", cleanse(s))
+		stepsWithEchos[i*2+1] = s
+	}
+
+	// quote " quotes and $ vars
+	joinedCommand := strings.Join(stepsWithEchos, " && ")
+	quotedCommand := strings.Replace(joinedCommand, "'", "'\"'\"'", -1)
+
+	command := fmt.Sprintf("pwsh -C '%s'", quotedCommand)
+
+	return command
+}
+
+func ValidateFileHasContentWindows(ctx context.Context, s *Scenario, fileName string, contents string) {
+	steps := []string{
+		fmt.Sprintf("dir %[1]s", fileName),
+		fmt.Sprintf("Get-Content %[1]s", fileName),
+		fmt.Sprintf("if (Select-String -Path .%s -Pattern \"%s\" -SimpleMatch -Quiet) { return 1 } else { return 0 }", fileName, contents),
+	}
+
+	command := makeExecutablePowershellCommand(steps)
+	execOnVMForScenarioValidateExitCode(ctx, s, command, 0, "could not validate file has contents - might mean file does not have contents, might mean something went wrong")
+}
diff --git a/e2e/validators.go b/e2e/validators.go
index 22159bbfddb..ed92c96e105 100644
--- a/e2e/validators.go
+++ b/e2e/validators.go
@@ -64,7 +64,7 @@ func ValidateFileHasContent(ctx context.Context, s *Scenario, fileName string, c
 		fmt.Sprintf("(sudo cat %[1]s | grep -q -F -e %[2]q)", fileName, contents),
 	}
 
-	command := makeExecutableCommand(steps)
+	command := makeExecutableBashCommand(steps)
 	execOnVMForScenarioValidateExitCode(ctx, s, command, 0, "could not validate file has contents - might mean file does not have contents, might mean something went wrong")
 }
 
@@ -77,7 +77,7 @@ func ValidateFileExcludesContent(ctx context.Context, s *Scenario, fileName stri
 		fmt.Sprintf("sudo cat %[1]s", fileName),
 		fmt.Sprintf("(sudo cat %[1]s | grep -q -v -F -e %[2]q)", fileName, contents),
 	}
-	command := makeExecutableCommand(steps)
+	command := makeExecutableBashCommand(steps)
 	execOnVMForScenarioValidateExitCode(ctx, s, command, 0, "could not validate file excludes contents - might mean file does have contents, might mean something went wrong")
 }
 
@@ -86,7 +86,7 @@ func cleanse(str string) string {
 	return strings.Replace(str, "'", "", -1)
 }
 
-func makeExecutableCommand(steps []string) string {
+func makeExecutableBashCommand(steps []string) string {
 	stepsWithEchos := make([]string, len(steps)*2)
 
 	for i, s := range steps {
@@ -131,7 +131,7 @@ func ServiceCanRestartValidator(ctx context.Context, s *Scenario, serviceName st
 		"if [[ \"$INITIAL_PID\" == \"$POST_PID\" ]]; then echo PID did not change after restart, failing validator. ; exit 1; fi",
 	}
 
-	command := makeExecutableCommand(steps)
+	command := makeExecutableBashCommand(steps)
 	execOnVMForScenarioValidateExitCode(ctx, s, command, 0, "command to restart service failed")
 }