diff --git a/.github/workflows/dotnet-ec2-windows-test.yml b/.github/workflows/dotnet-ec2-windows-test.yml
index dc592e201..4572d2f78 100644
--- a/.github/workflows/dotnet-ec2-windows-test.yml
+++ b/.github/workflows/dotnet-ec2-windows-test.yml
@@ -185,10 +185,10 @@ jobs:
           echo "REMOTE_SERVICE_INSTANCE_ID=$(terraform output remote_service_instance_id)" >> $GITHUB_ENV
 
 # A standard Windows Deployment Script are Expect to run ~5min, plus waiting for SSM to be setup in EC2 instance ~2min
-# 12 Min loose upper timeout bound is designed to allow for a rate situation: in a very small chance,
+# 15 Min loose upper timeout bound is designed to allow for a rate situation: in a very small chance,
 # It's possible for SSM document to take up to 8min to run and still produce expect setup outcome
       - name: Monitor EC2 instances readiness and SSM execute status in Systems Manager
-        timeout-minutes: 12
+        timeout-minutes: 15
         run: |
           # Allow up to 5 min for EC2 instance connect to SSM
           max_attempts=30
diff --git a/sample-apps/dotnet/dotnet-ec2-win-main-setup.ps1 b/sample-apps/dotnet/dotnet-ec2-win-main-setup.ps1
index c11513f68..c5c230c5c 100644
--- a/sample-apps/dotnet/dotnet-ec2-win-main-setup.ps1
+++ b/sample-apps/dotnet/dotnet-ec2-win-main-setup.ps1
@@ -14,13 +14,14 @@ param (
 $ProgressPreference = 'SilentlyContinue'
 
 # Install Dotnet
+Write-Host "Installing Dotnet" | %{ "{0:HH:mm:ss:fff}: {1}" -f (Get-Date), $_ }
 wget -O dotnet-install.ps1 https://dot.net/v1/dotnet-install.ps1
 .\dotnet-install.ps1 -Version 8.0.302
 
 # Install and start Cloudwatch Agent
-Invoke-Expression $GetCloudwatchAgentCommand
+Invoke-Expression $GetCloudwatchAgentCommand | %{ "{0:HH:mm:ss:fff}: {1}" -f (Get-Date), $_ }
 
-Write-Host "Installing Cloudwatch Agent"
+Write-Host "Installing Cloudwatch Agent" | %{ "{0:HH:mm:ss:fff}: {1}" -f (Get-Date), $_ }
 msiexec /i amazon-cloudwatch-agent.msi
 $timeout = 30
 $interval = 5
@@ -33,6 +34,7 @@ while ($elapsedTime -lt $timeout) {
         Write-Host "Install Finished"
         break
     } else {
+        $call_cloudwatch = & "C:\Program Files\Amazon\AmazonCloudWatchAgent\amazon-cloudwatch-agent-ctl.ps1"
         Write-Host "Cloudwatch Agent not found: $filePath. Checking again in $interval seconds..."
         Start-Sleep -Seconds $interval
         $elapsedTime += $interval
@@ -43,7 +45,7 @@ if ($elapsedTime -ge $timeout) {
     Write-Host "CloudWatch not found after $timeout seconds."
 }
 
-Write-Host "Install Finished"
+Write-Host "Install Finished" | %{ "{0:HH:mm:ss:fff}: {1}" -f (Get-Date), $_ }
 
 # Even after this step, it only expose 8080 to localhost and local (EC2) network on current config, so it's safe
 # Leave it here for Debug purpose
@@ -52,11 +54,11 @@ New-NetFirewallRule -DisplayName "Allow TCP 8080" -Direction Inbound -Protocol T
 & "C:\Program Files\Amazon\AmazonCloudWatchAgent\amazon-cloudwatch-agent-ctl.ps1" -a fetch-config -m ec2 -s -c file:./amazon-cloudwatch-agent.json
 
 # Get Instrumentation Artifacts and Sample App
-Invoke-Expression $GetAdotDistroCommand
+Invoke-Expression $GetAdotDistroCommand | %{ "{0:HH:mm:ss:fff}: {1}" -f (Get-Date), $_ }
 
-Invoke-Expression $GetSampleAppCommand
+Invoke-Expression $GetSampleAppCommand | %{ "{0:HH:mm:ss:fff}: {1}" -f (Get-Date), $_ }
 
-Expand-Archive -Path .\dotnet-sample-app.zip -DestinationPath .\ -Force
+Expand-Archive -Path .\dotnet-sample-app.zip -DestinationPath .\ -Force | %{ "{0:HH:mm:ss:fff}: {1}" -f (Get-Date), $_ }
 
 # Config Env variable for Windows EC2
 
@@ -82,7 +84,7 @@ $env:OTEL_TRACES_SAMPLER = "always_on"
 $env:ASPNETCORE_URLS = "http://0.0.0.0:8080"
 
 
-dotnet build
+dotnet build | %{ "{0:HH:mm:ss:fff}: {1}" -f (Get-Date), $_ }
 
 
 Start-Process -FilePath "dotnet" -ArgumentList "bin/Debug/netcoreapp8.0/asp_frontend_service.dll"
@@ -93,18 +95,18 @@ Start-Sleep -Seconds 10
 # Deploy Traffic Generator
 
 # Install node and setup path for node
-wget -O nodejs.zip https://nodejs.org/dist/v20.16.0/node-v20.16.0-win-x64.zip
-Expand-Archive -Path .\nodejs.zip -DestinationPath .\nodejs -Force
+wget -O nodejs.zip https://nodejs.org/dist/v20.16.0/node-v20.16.0-win-x64.zip | %{ "{0:HH:mm:ss:fff}: {1}" -f (Get-Date), $_ }
+Expand-Archive -Path .\nodejs.zip -DestinationPath .\nodejs -Force | %{ "{0:HH:mm:ss:fff}: {1}" -f (Get-Date), $_ }
 $currentdir = Get-Location
-Write-Host $currentdir
+Write-Host $currentdir | %{ "{0:HH:mm:ss:fff}: {1}" -f (Get-Date), $_ }
 $env:Path += ";$currentdir" + "\nodejs\node-v20.16.0-win-x64"
 
 # Bring in the traffic generator files to EC2 Instance
 aws s3 cp "s3://aws-appsignals-sample-app-prod-$AWSRegion/traffic-generator.zip" "./traffic-generator.zip"
-Expand-Archive -Path "./traffic-generator.zip" -DestinationPath "./" -Force
+Expand-Archive -Path "./traffic-generator.zip" -DestinationPath "./" -Force | %{ "{0:HH:mm:ss:fff}: {1}" -f (Get-Date), $_ }
 
 # Install the traffic generator dependencies
-npm install
+npm install | %{ "{0:HH:mm:ss:fff}: {1}" -f (Get-Date), $_ }
 
 # Start traffic generator
 $env:MAIN_ENDPOINT = "localhost:8080"
diff --git a/sample-apps/dotnet/dotnet-ec2-win-remote-setup.ps1 b/sample-apps/dotnet/dotnet-ec2-win-remote-setup.ps1
index b4af24791..87797841b 100644
--- a/sample-apps/dotnet/dotnet-ec2-win-remote-setup.ps1
+++ b/sample-apps/dotnet/dotnet-ec2-win-remote-setup.ps1
@@ -12,13 +12,14 @@ param (
 $ProgressPreference = 'SilentlyContinue'
 
 # Install Dotnet
+Write-Host "Installing Dotnet" | %{ "{0:HH:mm:ss:fff}: {1}" -f (Get-Date), $_ }
 wget -O dotnet-install.ps1 https://dot.net/v1/dotnet-install.ps1
 .\dotnet-install.ps1 -Version 8.0.302
 
 # Install and start Cloudwatch Agent
-Invoke-Expression $GetCloudwatchAgentCommand
+Invoke-Expression $GetCloudwatchAgentCommand | %{ "{0:HH:mm:ss:fff}: {1}" -f (Get-Date), $_ }
 
-Write-Host "Installing Cloudwatch Agent"
+Write-Host "Installing Cloudwatch Agent" | %{ "{0:HH:mm:ss:fff}: {1}" -f (Get-Date), $_ }
 msiexec /i amazon-cloudwatch-agent.msi
 $timeout = 30
 $interval = 5
@@ -31,6 +32,7 @@ while ($elapsedTime -lt $timeout) {
         Write-Host "Install Finished"
         break
     } else {
+        $call_cloudwatch = & "C:\Program Files\Amazon\AmazonCloudWatchAgent\amazon-cloudwatch-agent-ctl.ps1"
         Write-Host "Cloudwatch Agent not found: $filePath. Checking again in $interval seconds..."
         Start-Sleep -Seconds $interval
         $elapsedTime += $interval
@@ -44,14 +46,14 @@ if ($elapsedTime -ge $timeout) {
 & "C:\Program Files\Amazon\AmazonCloudWatchAgent\amazon-cloudwatch-agent-ctl.ps1" -a fetch-config -m ec2 -s -c file:./amazon-cloudwatch-agent.json
 
 # Get Instrumentation Artifacts and Sample App
-Invoke-Expression $GetAdotDistroCommand
+Invoke-Expression $GetAdotDistroCommand | %{ "{0:HH:mm:ss:fff}: {1}" -f (Get-Date), $_ }
 
-Invoke-Expression $GetSampleAppCommand
+Invoke-Expression $GetSampleAppCommand | %{ "{0:HH:mm:ss:fff}: {1}" -f (Get-Date), $_ }
 
-Expand-Archive -Path .\dotnet-sample-app.zip -DestinationPath .\ -Force
+Expand-Archive -Path .\dotnet-sample-app.zip -DestinationPath .\ -Force | %{ "{0:HH:mm:ss:fff}: {1}" -f (Get-Date), $_ }
 
 # Allow income traffic from main-service
-New-NetFirewallRule -DisplayName "Allow TCP 8081" -Direction Inbound -Protocol TCP -LocalPort 8081 -Action Allow
+New-NetFirewallRule -DisplayName "Allow TCP 8081" -Direction Inbound -Protocol TCP -LocalPort 8081 -Action Allow | %{ "{0:HH:mm:ss:fff}: {1}" -f (Get-Date), $_ }
 
 $current_dir = Get-Location
 Write-Host $current_dir
@@ -76,7 +78,7 @@ $env:OTEL_TRACES_SAMPLER = "always_on"
 $env:ASPNETCORE_URLS = "http://0.0.0.0:8081"
 
 
-dotnet build
+dotnet build | %{ "{0:HH:mm:ss:fff}: {1}" -f (Get-Date), $_ }
 
 
 Start-Process -FilePath "dotnet" -ArgumentList "bin/Debug/netcoreapp8.0/asp_remote_service.dll"