diff --git a/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1 b/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1
index 5deb9308bd2..2b2968ea3da 100644
--- a/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1
+++ b/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1
@@ -4218,26 +4218,32 @@ Describe 'Invoke-WebRequest and Invoke-RestMethod support Cancellation through C
             [string]$Command = 'Invoke-WebRequest',
             [string]$Arguments = '',
             [uri]$Uri,
-            [int]$DelayMs = 100,
+            [int]$DelayBeforeStopSimulationMs = 5000,
             [switch]$WillComplete
         )
 
         $pwsh = [PowerShell]::Create()
         $invoke = "`$result = $Command -Uri `"$Uri`" $Arguments"
         $task = $pwsh.AddScript($invoke).InvokeAsync()
-        Start-Sleep -Milliseconds $DelayMs
+        $delay = [System.Threading.Tasks.Task]::Delay($DelayBeforeStopSimulationMs)
+
+        # Simulate CTRL-C as soon as the timeout expires or the main task ends
+        $null = [System.Threading.Tasks.Task]::WaitAny($task, $delay)
         $task.IsCompleted | Should -Be $WillComplete.ToBool()
         $pwsh.Stop()
+
+        # The download stall is normally 30 seconds from the web listener based
+        # on the first slash separated parameter in the -TestValue provided to
+        # Get-WebListenerUrl -test Stall -TestValue duration/content-type.
         Wait-UntilTrue { [bool]($Task.IsCompleted) } | Should -BeTrue
         $result = $pwsh.Runspace.SessionStateProxy.GetVariable('result')
         $pwsh.Dispose()
-
         return $result
     }
 
     It 'Invoke-WebRequest: CTRL-C Cancels request before request headers received' {
         $uri = Get-WebListenerUrl -test Delay -TestValue 30
-        RunWithCancellation -Uri $uri -DelayMs 0
+        RunWithCancellation -Uri $uri -DelayBeforeStopSimulationMs 1000
     }
 
     It 'Invoke-WebRequest: CTRL-C Cancels request after request headers received' {
@@ -4250,20 +4256,32 @@ Describe 'Invoke-WebRequest and Invoke-RestMethod support Cancellation through C
         RunWithCancellation -Uri $uri -Arguments "-SkipCertificateCheck"
     }
 
-    It 'Invoke-WebRequest: Compression CTRL-C Cancels request after request headers' {
+    It 'Invoke-WebRequest: Brotli Compression CTRL-C Cancels request after request headers' {
         $uri = Get-WebListenerUrl -Test StallBrotli -TestValue '30/application%2fjson'
         RunWithCancellation -Uri $uri
+    }
+
+    It 'Invoke-WebRequest: Gzip Compression CTRL-C Cancels request after request headers' {
         $uri = Get-WebListenerUrl -Test StallGzip -TestValue '30/application%2fjson'
         RunWithCancellation -Uri $uri
+    }
+
+    It 'Invoke-WebRequest: Defalate Compression CTRL-C Cancels request after request headers' {
         $uri = Get-WebListenerUrl -Test StallDeflate -TestValue '30/application%2fjson'
         RunWithCancellation -Uri $uri
     }
 
-    It 'Invoke-WebRequest: HTTPS with compression CTRL-C Cancels request after request headers' {
+    It 'Invoke-WebRequest: HTTPS with Brotli compression CTRL-C Cancels request after request headers' {
         $uri = Get-WebListenerUrl -Https -Test StallBrotli -TestValue '30/application%2fjson'
         RunWithCancellation -Uri $uri -Arguments '-SkipCertificateCheck'
+    }
+
+    It 'Invoke-WebRequest: HTTPS with Gzip compression CTRL-C Cancels request after request headers' {
         $uri = Get-WebListenerUrl -Https -Test StallGzip -TestValue '30/application%2fjson'
         RunWithCancellation -Uri $uri -Arguments '-SkipCertificateCheck'
+    }
+
+    It 'Invoke-WebRequest: HTTPS with Defalte compression CTRL-C Cancels request after request headers' {
         $uri = Get-WebListenerUrl -Https -Test StallDeflate -TestValue '30/application%2fjson'
         RunWithCancellation -Uri $uri -Arguments '-SkipCertificateCheck'
     }
@@ -4271,7 +4289,7 @@ Describe 'Invoke-WebRequest and Invoke-RestMethod support Cancellation through C
     It 'Invoke-WebRequest: CTRL-C Cancels file download request after request headers received' {
         $uri = Get-WebListenerUrl -Test Stall -TestValue '30'
         $outFile = Join-Path $TestDrive "output.txt"
-        RunWithCancellation -Uri $uri -Arguments "-OutFile $outFile" -DelayMs 300
+        RunWithCancellation -Uri $uri -Arguments "-OutFile $outFile"
         # No guarantee the file will be present since the D/L is interrupted
         if (Test-Path -Path $outFile) {
             Remove-Item -Path $outFile
@@ -4281,14 +4299,14 @@ Describe 'Invoke-WebRequest and Invoke-RestMethod support Cancellation through C
     It 'Invoke-WebRequest: CTRL-C after stalled file download completes gives entire file' {
         $uri = Get-WebListenerUrl -test Stall -TestValue '1'
         $outFile = Join-Path $TestDrive "output.txt"
-        RunWithCancellation -Uri $uri -Arguments "-OutFile $outFile" -DelayMs 1200 -WillComplete
+        RunWithCancellation -Uri $uri -Arguments "-OutFile $outFile" -WillComplete
         Get-content -Path $outFile | should -be 'Hello worldHello world'
         Remove-Item -Path $outFile
     }
 
     It 'Invoke-RestMethod: CTRL-C Cancels request before request headers received' {
         $uri = Get-WebListenerUrl -test Delay -TestValue 30
-        RunWithCancellation -Command 'Invoke-RestMethod' -Uri $uri -DelayMs 0
+        RunWithCancellation -Command 'Invoke-RestMethod' -Uri $uri -DelayBeforeStopSimulationMs 1000
     }
 
     It 'Invoke-RestMethod: CTRL-C Cancels request after JSON request headers received' {
@@ -4298,7 +4316,7 @@ Describe 'Invoke-WebRequest and Invoke-RestMethod support Cancellation through C
 
     It 'Invoke-RestMethod: CTRL-C after stalled JSON download processes JSON response' {
         $uri = Get-WebListenerUrl -test Stall -TestValue '1/application%2fjson'
-        $result = RunWithCancellation -Command 'Invoke-RestMethod' -Uri $uri -DelayMs 1200 -WillComplete
+        $result = RunWithCancellation -Command 'Invoke-RestMethod' -Uri $uri -WillComplete
         $result.name3 | should -be 'value3'
     }
 
@@ -4309,7 +4327,7 @@ Describe 'Invoke-WebRequest and Invoke-RestMethod support Cancellation through C
 
     It 'Invoke-RestMethod: CTRL-C after stalled atom feed download processes atom response' {
         $uri = Get-WebListenerUrl -test Stall -TestValue '1/application%2fxml'
-        $result = RunWithCancellation -Command 'Invoke-RestMethod' -Uri $uri -DelayMs 1200 -WillComplete
+        $result = RunWithCancellation -Command 'Invoke-RestMethod' -Uri $uri -WillComplete
         $result.title | should -be 'Atom-Powered Robots Run Amok'
     }