diff --git a/test/tools/Modules/WebListener/WebListener.psm1 b/test/tools/Modules/WebListener/WebListener.psm1
index 7f9c69e30..26ede1a95 100644
--- a/test/tools/Modules/WebListener/WebListener.psm1
+++ b/test/tools/Modules/WebListener/WebListener.psm1
@@ -60,12 +60,20 @@ function Start-WebListener
         $serverPfx           = 'ServerCert.pfx'
         $serverPfxPassword   = 'password'
         $initCompleteMessage = 'Now listening on'
+        $sleepMilliseconds   = 100
 
         $serverPfxPath = Join-Path $MyInvocation.MyCommand.Module.ModuleBase $serverPfx
-        $timeOut = (get-date).AddSeconds($initTimeoutSeconds)
         $Job = Start-Job {
-            $path = Split-Path -parent (get-command WebListener).Path
-            Push-Location $path
+            $path = Split-Path -parent (get-command WebListener).Path -Verbose
+            Push-Location $path -Verbose
+            'appDLL: {0}' -f $using:appDll
+            'serverPfxPath: {0}' -f $using:serverPfxPath
+            'serverPfxPassword: {0}' -f $using:serverPfxPassword
+            'HttpPort: {0}' -f $using:HttpPort
+            'Https: {0}' -f $using:HttpsPort
+            'Tls11Port: {0}' -f $using:Tls11Port
+            'TlsPort: {0}' -f $using:TlsPort
+            $env:ASPNETCORE_ENVIRONMENT = 'Development'
             dotnet $using:appDll $using:serverPfxPath $using:serverPfxPassword $using:HttpPort $using:HttpsPort $using:Tls11Port $using:TlsPort
         }
         $Script:WebListener = [WebListener]@{
@@ -75,20 +83,28 @@ function Start-WebListener
             TlsPort   = $TlsPort
             Job       = $Job
         }
-        # Wait until the app is running or until the initTimeoutSeconds have been reached
+
+        # Count iterations of $sleepMilliseconds instead of using system time to work around possible CI VM sleep/delays
+        $sleepCountRemaining = $initTimeoutSeconds * 1000 / $sleepMilliseconds
         do
         {
-            Start-Sleep -Milliseconds 100
+            Start-Sleep -Milliseconds $sleepMilliseconds
             $initStatus = $Job.ChildJobs[0].Output | Out-String
             $isRunning = $initStatus -match $initCompleteMessage
+            $sleepCountRemaining--
         }
-        while (-not $isRunning -and (get-date) -lt $timeOut)
+        while (-not $isRunning -and $sleepCountRemaining -gt 0)
 
         if (-not $isRunning)
         {
-            $Job | Stop-Job -PassThru | Receive-Job
-            $Job | Remove-Job
-            throw 'WebListener did not start before the timeout was reached.'
+            $jobErrors = $Job.ChildJobs[0].Error | Out-String
+            $jobOutput =  $Job.ChildJobs[0].Output | Out-String
+            $jobVerbose =  $Job.ChildJobs[0].Verbose | Out-String
+            $Job | Stop-Job
+            $Job | Remove-Job -Force
+            $message = 'WebListener did not start before the timeout was reached.{0}Errors:{0}{1}{0}Output:{0}{2}{0}Verbose:{0}{3}' -f
+                ([System.Environment]::NewLine), $jobErrors, $jobOutput, $jobVerbose
+            throw $message
         }
         return $Script:WebListener
     }