diff --git a/eng/common/testproxy/test-proxy-standalone-tool.yml b/eng/common/testproxy/test-proxy-standalone-tool.yml
index 596add2b5..fb9696e6d 100644
--- a/eng/common/testproxy/test-proxy-standalone-tool.yml
+++ b/eng/common/testproxy/test-proxy-standalone-tool.yml
@@ -32,37 +32,54 @@ steps:
       }
 
       Write-Host "Installing test-proxy version $version"
+      Write-Host "${{ parameters.templateRoot }}/eng/common/testproxy/install-test-proxy.ps1 -Version $version -InstallDirectory $(Build.BinariesDirectory)/test-proxy"
       ${{ parameters.templateRoot }}/eng/common/testproxy/install-test-proxy.ps1 -Version $version -InstallDirectory $(Build.BinariesDirectory)/test-proxy
     displayName: "Install test-proxy"
     condition: and(succeeded(), ${{ parameters.condition }})
 
   - pwsh: |
+      Write-Host "Prepending path with the test proxy tool install location: '$(Build.BinariesDirectory)/test-proxy'"
       Write-Host "##vso[task.prependpath]$(Build.BinariesDirectory)/test-proxy"
     displayName: "Prepend path with test-proxy tool install location"
 
   - ${{ if eq(parameters.runProxy, 'true') }}:
     - pwsh: |
+        Write-Host "Setting ASPNETCORE_Kestrel__Certificates__Default__Path to '${{ parameters.templateRoot }}/eng/common/testproxy/dotnet-devcert.pfx'"
         Write-Host "##vso[task.setvariable variable=ASPNETCORE_Kestrel__Certificates__Default__Path]${{ parameters.templateRoot }}/eng/common/testproxy/dotnet-devcert.pfx"
+        Write-Host "Setting ASPNETCORE_Kestrel__Certificates__Default__Password to 'password'"
         Write-Host "##vso[task.setvariable variable=ASPNETCORE_Kestrel__Certificates__Default__Password]password"
+        Write-Host "Setting PROXY_MANUAL_START to 'true'"
         Write-Host "##vso[task.setvariable variable=PROXY_MANUAL_START]true"
       displayName: 'Configure Kestrel and PROXY_MANUAL_START Variables'
       condition: and(succeeded(), ${{ parameters.condition }})
 
     - pwsh: |
+        $invocation = @"
+        Start-Process $(PROXY_EXE)
+          -ArgumentList `"start -u --storage-location ${{ parameters.rootFolder }}`"
+          -NoNewWindow -PassThru -RedirectStandardOutput ${{ parameters.rootFolder }}/test-proxy.log
+          -RedirectStandardError ${{ parameters.rootFolder }}/test-proxy-error.log
+        "@
+        Write-Host $invocation
+
         $Process = Start-Process $(PROXY_EXE) `
           -ArgumentList "start -u --storage-location ${{ parameters.rootFolder }}" `
           -NoNewWindow -PassThru -RedirectStandardOutput ${{ parameters.rootFolder }}/test-proxy.log `
           -RedirectStandardError ${{ parameters.rootFolder }}/test-proxy-error.log
 
+        Write-Host "Setting PROXY_PID to $($Process.Id)"
         Write-Host "##vso[task.setvariable variable=PROXY_PID]$($Process.Id)"
       displayName: 'Run the testproxy - windows'
       condition: and(succeeded(), eq(variables['Agent.OS'],'Windows_NT'), ${{ parameters.condition }})
 
     # nohup does NOT continue beyond the current session if you use it within powershell
     - bash: |
+        echo "nohup $(PROXY_EXE) 1>${{ parameters.rootFolder }}/test-proxy.log 2>${{ parameters.rootFolder }}/test-proxy-error.log &"
         nohup $(PROXY_EXE) 1>${{ parameters.rootFolder }}/test-proxy.log 2>${{ parameters.rootFolder }}/test-proxy-error.log &
 
         echo $! > $(Build.SourcesDirectory)/test-proxy.pid
+
+        echo "Setting PROXY_PID to $(cat $(Build.SourcesDirectory)/test-proxy.pid)"
         echo "##vso[task.setvariable variable=PROXY_PID]$(cat $(Build.SourcesDirectory)/test-proxy.pid)"
       displayName: "Run the testproxy - linux/mac"
       condition: and(succeeded(), ne(variables['Agent.OS'],'Windows_NT'), ${{ parameters.condition }})
@@ -71,7 +88,9 @@ steps:
     - pwsh: |
         for ($i = 0; $i -lt 10; $i++) {
             try {
+                Write-Host "Invoke-WebRequest -Uri `"http://localhost:5000/Admin/IsAlive`" | Out-Null"
                 Invoke-WebRequest -Uri "http://localhost:5000/Admin/IsAlive" | Out-Null
+                Write-Host "Successfully connected to the test proxy on port 5000."
                 exit 0
             } catch {
                 Write-Warning "Failed to successfully connect to test proxy. Retrying..."
diff --git a/eng/common/testproxy/test-proxy-tool.yml b/eng/common/testproxy/test-proxy-tool.yml
index db1bba2f4..03c9dbaa0 100644
--- a/eng/common/testproxy/test-proxy-tool.yml
+++ b/eng/common/testproxy/test-proxy-tool.yml
@@ -33,6 +33,14 @@ steps:
 
       Write-Host "Installing test-proxy version $version"
 
+      $invocation = @"
+      dotnet tool install azure.sdk.tools.testproxy `
+        --tool-path $(Build.BinariesDirectory)/test-proxy `
+        --add-source https://pkgs.dev.azure.com/azure-sdk/public/_packaging/azure-sdk-for-net/nuget/v3/index.json `
+        --version $version
+      "@
+      Write-Host $invocation
+
       dotnet tool install azure.sdk.tools.testproxy `
         --tool-path $(Build.BinariesDirectory)/test-proxy `
         --add-source https://pkgs.dev.azure.com/azure-sdk/public/_packaging/azure-sdk-for-net/nuget/v3/index.json `
@@ -41,23 +49,36 @@ steps:
     condition: and(succeeded(), ${{ parameters.condition }})
 
   - pwsh: |
+      Write-Host "Prepending path with the test proxy tool install location: '$(Build.BinariesDirectory)/test-proxy'"
       Write-Host "##vso[task.prependpath]$(Build.BinariesDirectory)/test-proxy"
     displayName: "Prepend path with test-proxy tool install location"
 
   - ${{ if eq(parameters.runProxy, 'true') }}:
     - pwsh: |
+        Write-Host "Setting ASPNETCORE_Kestrel__Certificates__Default__Path to '${{ parameters.templateRoot }}/eng/common/testproxy/dotnet-devcert.pfx'"
         Write-Host "##vso[task.setvariable variable=ASPNETCORE_Kestrel__Certificates__Default__Path]${{ parameters.templateRoot }}/eng/common/testproxy/dotnet-devcert.pfx"
+        Write-Host "Setting ASPNETCORE_Kestrel__Certificates__Default__Password to 'password'"
         Write-Host "##vso[task.setvariable variable=ASPNETCORE_Kestrel__Certificates__Default__Password]password"
+        Write-Host "Setting PROXY_MANUAL_START to 'true'"
         Write-Host "##vso[task.setvariable variable=PROXY_MANUAL_START]true"
       displayName: 'Configure Kestrel and PROXY_MANUAL_START Variables'
       condition: and(succeeded(), ${{ parameters.condition }})
 
     - pwsh: |
+        $invocation = @"
+        Start-Process $(Build.BinariesDirectory)/test-proxy/test-proxy.exe
+          -ArgumentList `"start -u --storage-location ${{ parameters.rootFolder }}`"
+          -NoNewWindow -PassThru -RedirectStandardOutput ${{ parameters.rootFolder }}/test-proxy.log
+          -RedirectStandardError ${{ parameters.rootFolder }}/test-proxy-error.log
+        "@
+        Write-Host $invocation
+
         $Process = Start-Process $(Build.BinariesDirectory)/test-proxy/test-proxy.exe `
           -ArgumentList "start -u --storage-location ${{ parameters.rootFolder }}" `
           -NoNewWindow -PassThru -RedirectStandardOutput ${{ parameters.rootFolder }}/test-proxy.log `
           -RedirectStandardError ${{ parameters.rootFolder }}/test-proxy-error.log
 
+        Write-Host "Setting PROXY_PID to $($Process.Id)"
         Write-Host "##vso[task.setvariable variable=PROXY_PID]$($Process.Id)"
       displayName: 'Run the testproxy - windows'
       condition: and(succeeded(), eq(variables['Agent.OS'],'Windows_NT'), ${{ parameters.condition }})
@@ -69,6 +90,8 @@ steps:
         nohup $(Build.BinariesDirectory)/test-proxy/test-proxy 1>${{ parameters.rootFolder }}/test-proxy.log 2>${{ parameters.rootFolder }}/test-proxy-error.log &
 
         echo $! > $(Build.SourcesDirectory)/test-proxy.pid
+
+        echo "Setting PROXY_PID to $(cat $(Build.SourcesDirectory)/test-proxy.pid)"
         echo "##vso[task.setvariable variable=PROXY_PID]$(cat $(Build.SourcesDirectory)/test-proxy.pid)"
       displayName: "Run the testproxy - linux/mac"
       condition: and(succeeded(), ne(variables['Agent.OS'],'Windows_NT'), ${{ parameters.condition }})
@@ -79,7 +102,9 @@ steps:
     - pwsh: |
         for ($i = 0; $i -lt 10; $i++) {
             try {
+                Write-Host "Invoke-WebRequest -Uri `"http://localhost:5000/Admin/IsAlive`" | Out-Null"
                 Invoke-WebRequest -Uri "http://localhost:5000/Admin/IsAlive" | Out-Null
+                Write-Host "Successfully connected to the test proxy on port 5000."
                 exit 0
             } catch {
                 Write-Warning "Failed to successfully connect to test proxy. Retrying..."