diff --git a/changelogs/unreleased/improve_auto_devops_migration_debug.yml b/changelogs/unreleased/improve_auto_devops_migration_debug.yml
new file mode 100644
index 0000000000000..96a788083616e
--- /dev/null
+++ b/changelogs/unreleased/improve_auto_devops_migration_debug.yml
@@ -0,0 +1,6 @@
+---
+title: 'Auto DevOps: Add echo for each branch of the deploy() function where we run
+  helm upgrade'
+merge_request: 23499
+author:
+type: changed
diff --git a/lib/gitlab/ci/templates/Auto-DevOps.gitlab-ci.yml b/lib/gitlab/ci/templates/Auto-DevOps.gitlab-ci.yml
index c90976b20409b..49f03d2ae19d9 100644
--- a/lib/gitlab/ci/templates/Auto-DevOps.gitlab-ci.yml
+++ b/lib/gitlab/ci/templates/Auto-DevOps.gitlab-ci.yml
@@ -658,6 +658,7 @@ rollout 100%:
     fi
 
     if [[ -n "$DB_INITIALIZE" && -z "$(helm ls -q "^$name$")" ]]; then
+      echo "Deploying first release with database initialization..."
       helm upgrade --install \
         --wait \
         --set service.enabled="$service_enabled" \
@@ -680,6 +681,7 @@ rollout 100%:
         "$name" \
         chart/
 
+      echo "Deploying second release..."
       helm upgrade --reuse-values \
         --wait \
         --set application.initializeCommand="" \
@@ -688,6 +690,7 @@ rollout 100%:
         "$name" \
         chart/
     else
+      echo "Deploying new release..."
       helm upgrade --install \
         --wait \
         --set service.enabled="$service_enabled" \