diff --git a/.github/workflows/deploy-web.yml b/.github/workflows/deploy-web.yml
index 4bc0cc0a7b..040ad3f1b3 100644
--- a/.github/workflows/deploy-web.yml
+++ b/.github/workflows/deploy-web.yml
@@ -19,6 +19,10 @@ on:
         description: "Branch or Tag name to deploy (examples: 'main', 'feature/sm', 'web-v2023.12.0')"
         type: string
         default: main
+      invert-default-sync-delete-destination-files-value:
+        description: "Invert the default sync-delete-destination-files value"
+        type: boolean
+        default: false
       debug:
         description: "Debug mode"
         type: boolean
@@ -34,10 +38,14 @@ on:
         description: "Branch or Tag name to deploy (examples: 'main', 'feature/sm', 'web-v2023.12.0')"
         type: string
         default: main
+      invert-default-sync-delete-destination-files-value:
+        description: "Invert the default sync-delete-destination-files value"
+        type: boolean
+        default: false
       debug:
         description: "Debug mode"
         type: boolean
-        default: false
+        default: true
 
 permissions:
   deployments: write
@@ -54,6 +62,7 @@ jobs:
       azure-login-creds: ${{ steps.config.outputs.azure-login-creds }}
       retrieve-secrets-keyvault: ${{ steps.config.outputs.retrieve-secrets-keyvault }}
       sync-utility: ${{ steps.config.outputs.sync-utility }}
+      sync-delete-destination-files: ${{ steps.config.outputs.sync-delete-destination-files }}
     steps:
       - name: Configure
         id: config
@@ -61,6 +70,15 @@ jobs:
           ENV_NAME_LOWER=$(echo "${{ inputs.environment }}" | awk '{print tolower($0)}')
           echo "configuring the Web deploy for ${{ inputs.environment }}"
           echo "environment=${{ inputs.environment }}" >> $GITHUB_OUTPUT
+
+          # Invert the default value for sync-delete-destination-files
+          if [ ${{ inputs.invert-default-sync-delete-destination-files-value }} ]; then
+            echo "sync-delete-destination-files=true" >> $GITHUB_OUTPUT
+          else
+          # This is the default value for USQA, EUQA, USPROD, and EUPROD
+          echo "sync-delete-destination-files=false" >> $GITHUB_OUTPUT
+          fi
+
           case ${{ inputs.environment }} in
             "USQA")
               echo "azure-login-creds=AZURE_KV_US_QA_SERVICE_PRINCIPAL" >> $GITHUB_OUTPUT
@@ -96,6 +114,13 @@ jobs:
               echo "environment-artifact=web-*-cloud-usdev.zip" >> $GITHUB_OUTPUT
               echo "environment-name=Web Vault - US Development Cloud" >> $GITHUB_OUTPUT
               echo "environment-url=http://vault.$ENV_NAME_LOWER.bitwarden.pw" >> $GITHUB_OUTPUT
+
+              if [ ${{ inputs.invert-default-sync-delete-destination-files-value }} ]; then
+                echo "sync-delete-destination-files=false" >> $GITHUB_OUTPUT
+              else
+                # This is the default value for USDEV
+                echo "sync-delete-destination-files=true" >> $GITHUB_OUTPUT
+              fi
               ;;
           esac
           # Set the sync utility to use for deployment to the environment (az-sync or azcopy)
@@ -259,7 +284,8 @@ jobs:
           az storage blob sync \
             --source "./build" \
             --container '$web' \
-            --connection-string "${{ steps.retrieve-secrets-az-sync.outputs.sa-bitwarden-web-vault-dev-key-temp }}"
+            --connection-string "${{ steps.retrieve-secrets-az-sync.outputs.sa-bitwarden-web-vault-dev-key-temp }}" \
+            --delete-destination=${{ needs.setup.outputs.sync-delete-destination-files }}
 
       - name: Sync to Azure Storage Account using azcopy
         if: ${{ needs.setup.outputs.sync-utility == 'azcopy' }}
@@ -271,7 +297,7 @@ jobs:
           AZCOPY_TENANT_ID: ${{ steps.retrieve-secrets-azcopy.outputs.sp-bitwarden-web-vault-tenant }}
         run: |
           azcopy sync ./build 'https://${{ steps.retrieve-secrets-azcopy.outputs.sa-bitwarden-web-vault-name }}.blob.core.windows.net/$web/' \
-            --delete-destination=true
+            --delete-destination=${{ needs.setup.outputs.sync-delete-destination-files }}
 
       - name: Debug sync logs
         if: ${{ inputs.debug }}