diff --git a/.vsts-ci/templates/ci-build.yml b/.vsts-ci/templates/ci-build.yml
index cbbd5349417..e64ab4967a2 100644
--- a/.vsts-ci/templates/ci-build.yml
+++ b/.vsts-ci/templates/ci-build.yml
@@ -1,5 +1,5 @@
 parameters:
-  pool: 'vs2017-win2016'
+  pool: 'windows-latest'
   jobName: 'win_build'
   displayName: Windows Build
 
diff --git a/.vsts-ci/templates/credscan.yml b/.vsts-ci/templates/credscan.yml
index f6ed5b8fd23..60094ff3d77 100644
--- a/.vsts-ci/templates/credscan.yml
+++ b/.vsts-ci/templates/credscan.yml
@@ -1,12 +1,12 @@
 parameters:
-  pool: 'Hosted VS2017'
+  pool: 'windows-latest'
   jobName: 'credscan'
   displayName: Secret Scan
 
 jobs:
 - job: ${{ parameters.jobName }}
   pool:
-    name: ${{ parameters.pool }}
+    vmImage: ${{ parameters.pool }}
 
   displayName: ${{ parameters.displayName }}
 
diff --git a/.vsts-ci/templates/nanoserver.yml b/.vsts-ci/templates/nanoserver.yml
index c989d01c2f8..ae9f639b3b2 100644
--- a/.vsts-ci/templates/nanoserver.yml
+++ b/.vsts-ci/templates/nanoserver.yml
@@ -1,5 +1,5 @@
 parameters:
-  vmImage: 'windows-2019'
+  vmImage: 'windows-latest'
   jobName: 'Nanoserver_Tests'
   continueOnError: false
 
diff --git a/.vsts-ci/templates/verify-xunit.yml b/.vsts-ci/templates/verify-xunit.yml
index 9e09584d5c3..d2799f53ae0 100644
--- a/.vsts-ci/templates/verify-xunit.yml
+++ b/.vsts-ci/templates/verify-xunit.yml
@@ -1,6 +1,6 @@
 parameters:
   parentJobs: []
-  pool: 'vs2017-win2016'
+  pool: 'windows-latest'
   jobName: 'xunit_verify'
 
 jobs:
diff --git a/.vsts-ci/templates/windows-test.yml b/.vsts-ci/templates/windows-test.yml
index b316f8f360e..475c40c665c 100644
--- a/.vsts-ci/templates/windows-test.yml
+++ b/.vsts-ci/templates/windows-test.yml
@@ -1,5 +1,5 @@
 parameters:
-  pool: 'Hosted VS2017'
+  pool: 'windows-latest'
   parentJobs: []
   purpose: ''
   tagSet: 'CI'
@@ -9,7 +9,7 @@ jobs:
   dependsOn:
     ${{ parameters.parentJobs }}
   pool:
-    name: ${{ parameters.pool }}
+    vmImage: ${{ parameters.pool }}
 
   displayName: Windows Test - ${{ parameters.purpose }} - ${{ parameters.tagSet }}
 
diff --git a/.vsts-ci/windows-daily.yml b/.vsts-ci/windows-daily.yml
index 9171112b362..55470e6dd53 100644
--- a/.vsts-ci/windows-daily.yml
+++ b/.vsts-ci/windows-daily.yml
@@ -53,7 +53,7 @@ stages:
   jobs:
   - job: win_test
     pool:
-      vmImage: vs2017-win2016
+      vmImage: windows-latest
     displayName: Windows Test
     timeoutInMinutes: 90
 
diff --git a/.vsts-ci/windows/templates/windows-packaging.yml b/.vsts-ci/windows/templates/windows-packaging.yml
index 88a557ca032..832fe73af5e 100644
--- a/.vsts-ci/windows/templates/windows-packaging.yml
+++ b/.vsts-ci/windows/templates/windows-packaging.yml
@@ -1,6 +1,6 @@
 parameters:
   - name: pool
-    default: 'Hosted VS2017'
+    default: 'windows-latest'
   - name: jobName
     default: 'win_packaging'
   - name: runtimePrefix
@@ -24,7 +24,7 @@ jobs:
       value: $(Agent.BuildDirectory)\$(complianceRepoFolder)
 
   pool:
-    name: ${{ parameters.pool }}
+    vmImage: ${{ parameters.pool }}
 
   displayName: Windows Packaging - ${{ parameters.architecture }} - ${{ parameters.channel }}
 
diff --git a/test/powershell/Modules/Microsoft.PowerShell.Core/CompatiblePSEditions.Module.Tests.ps1 b/test/powershell/Modules/Microsoft.PowerShell.Core/CompatiblePSEditions.Module.Tests.ps1
index f9094254ec3..61f9f8e0f9f 100644
--- a/test/powershell/Modules/Microsoft.PowerShell.Core/CompatiblePSEditions.Module.Tests.ps1
+++ b/test/powershell/Modules/Microsoft.PowerShell.Core/CompatiblePSEditions.Module.Tests.ps1
@@ -600,9 +600,14 @@ Describe "Additional tests for Import-Module with WinCompat" -Tag "Feature" {
 
         It "NoClobber WinCompat import works for an engine module through -UseWindowsPowerShell parameter" {
 
+            # pre-test cleanup
+            Get-Module -Name Microsoft.PowerShell.Management | Remove-Module
+            Import-Module -Name Microsoft.PowerShell.Management # import the one that comes with PSCore
+
             Import-Module Microsoft.PowerShell.Management -UseWindowsPowerShell
 
             $modules = Get-Module -Name Microsoft.PowerShell.Management
+
             $modules.Count | Should -Be 2
             $proxyModule = $modules | Where-Object {$_.ModuleType -eq 'Script'}
             $coreModule = $modules | Where-Object {$_.ModuleType -eq 'Manifest'}
@@ -703,6 +708,10 @@ Remove-Module $desktopModuleToUse
             Restore-ModulePath
         }
 
+        BeforeEach {
+            Get-PSSession -Name WinPSCompatSession -ErrorAction SilentlyContinue | Remove-PSSession
+        }
+
         AfterEach {
             Get-Module $allModules | Remove-Module -Force
         }
diff --git a/test/powershell/Modules/Microsoft.WSMan.Management/CredSSP.Tests.ps1 b/test/powershell/Modules/Microsoft.WSMan.Management/CredSSP.Tests.ps1
index e440c8093f8..0f13e8e6aad 100644
--- a/test/powershell/Modules/Microsoft.WSMan.Management/CredSSP.Tests.ps1
+++ b/test/powershell/Modules/Microsoft.WSMan.Management/CredSSP.Tests.ps1
@@ -1,5 +1,8 @@
 # Copyright (c) Microsoft Corporation.
 # Licensed under the MIT License.
+
+Import-Module HelpersCommon
+
 Describe "CredSSP cmdlet tests" -Tags 'Feature','RequireAdminOnWindows' {
 
     BeforeAll {
@@ -44,21 +47,27 @@ Describe "CredSSP cmdlet tests" -Tags 'Feature','RequireAdminOnWindows' {
     }
 
     It "Enable-WSManCredSSP works: <description>" -Skip:($NotEnglish -or $IsToBeSkipped) -TestCases @(
-        @{params=@{Role="Client";DelegateComputer="*"};description="client"},
-        @{params=@{Role="Server"};description="server"}
+        @{ params = @{ Role="Client"; DelegateComputer="*" }; description = "client"; expected = "The machine is configured to allow delegating fresh credentials to the following target\(s\):wsman/\*" },
+        @{ params = @{ Role="Server" };                       description = "server"; expected = "This computer is configured to receive credentials from a remote client computer" }
     ) {
-        param ($params)
+        param ($params, $description, $expected)
+
         $c = Enable-WSManCredSSP @params -Force
         $c.CredSSP | Should -BeTrue
 
-        $c = Get-WSManCredSSP
         if ($params.Role -eq "Client")
         {
-            $c[0] | Should -Match "The machine is configured to allow delegating fresh credentials to the following target\(s\):wsman/\*"
+            Wait-UntilTrue -IntervalInMilliseconds 500 -sb {
+                $c = Get-WSManCredSSP
+                $c[0] -match $expected
+            } | Should -BeTrue -Because "WSManCredSSP should have been enabled to allow delegating fresh credentials to wsman/*, but it was not."
         }
         else
         {
-            $c[1] | Should -Match "This computer is configured to receive credentials from a remote client computer"
+            Wait-UntilTrue -IntervalInMilliseconds 500 -sb {
+                $c = Get-WSManCredSSP
+                $c[1] -match $expected
+            } | Should -BeTrue -Because "WSManCredSSP should have been enabled to allow receiving credentials from a remote client computer, but it was not."
         }
     }