diff --git a/.azure-pipelines/templates/jobs/packaging-jobs.yml b/.azure-pipelines/templates/jobs/packaging-jobs.yml
index 8da30b1f5..f6caefa2a 100644
--- a/.azure-pipelines/templates/jobs/packaging-jobs.yml
+++ b/.azure-pipelines/templates/jobs/packaging-jobs.yml
@@ -31,6 +31,24 @@ jobs:
           path: $(Build.ArtifactStagingDirectory)
           artifact: docker_$(DOCKER_ARCH)
         displayName: Store Docker artifact
+  - job: docker_run
+    dependsOn: docker_build
+    pool:
+      vmImage: ubuntu-18.04
+    steps:
+      - task: DownloadPipelineArtifact@2
+        inputs:
+          artifact: docker_amd64
+          path: $(Build.SourcesDirectory)
+        displayName: Retrieve Docker images
+      - bash: set -e && docker load --input $(Build.SourcesDirectory)/images.tar
+        displayName: Load Docker images
+      - bash: |
+          set -e
+          DOCKER_IMAGES=$(docker images --filter reference='*/certbot' --filter reference='*/dns-*' --format '{{.Repository}}')
+          for $DOCKER_IMAGE in DOCKER_IMAGES
+            do docker run --rm $DOCKER_IMAGE plugin --prepare
+          done
   - job: installer_build
     pool:
       vmImage: vs2017-win2016