diff --git a/eng/common/scripts/Prepare-Release.ps1 b/eng/common/scripts/Prepare-Release.ps1
index b3b62e9f96e9..2c7b61522048 100644
--- a/eng/common/scripts/Prepare-Release.ps1
+++ b/eng/common/scripts/Prepare-Release.ps1
@@ -136,6 +136,11 @@ if ($null -eq $newVersionParsed)
   -packageType $packageProperties.SDKType `
   -packageNewLibrary $packageProperties.IsNewSDK
 
+if ($LASTEXITCODE -ne 0) {
+  Write-Error "Updating of the Devops Release WorkItem failed."
+  exit 1
+}
+
 if ($releaseTrackingOnly)
 {
   Write-Host
diff --git a/eng/common/scripts/Update-DevOps-Release-WorkItem.ps1 b/eng/common/scripts/Update-DevOps-Release-WorkItem.ps1
index 92f9a41106ad..b1a45abffa2e 100644
--- a/eng/common/scripts/Update-DevOps-Release-WorkItem.ps1
+++ b/eng/common/scripts/Update-DevOps-Release-WorkItem.ps1
@@ -19,11 +19,17 @@ param(
 Set-StrictMode -Version 3
 
 if (!(Get-Command az -ErrorAction SilentlyContinue)) {
-  Write-Host 'You must have the Azure CLI installed: https://aka.ms/azure-cli'
+  Write-Error 'You must have the Azure CLI installed: https://aka.ms/azure-cli'
   exit 1
 }
 
-az extension show -n azure-devops > $null
+az account show *> $null
+if (!$?) {
+  Write-Host 'Running az login...'
+  az login *> $null
+}
+
+az extension show -n azure-devops *> $null
 if (!$?){
   Write-Host 'Installing azure-devops extension'
   az extension add --name azure-devops