diff --git a/.changelog/3820.txt b/.changelog/3820.txt
new file mode 100644
index 00000000000..2cfa010f445
--- /dev/null
+++ b/.changelog/3820.txt
@@ -0,0 +1,4 @@
+```release-note:bug
+upgrade: Update ECS server upgrade to respect -ecs-server-image flag when the
+existing server image is hashicorp/waypoint:latest
+```
\ No newline at end of file
diff --git a/internal/serverinstall/ecs.go b/internal/serverinstall/ecs.go
index 175fc280b93..48864eeb9b3 100644
--- a/internal/serverinstall/ecs.go
+++ b/internal/serverinstall/ecs.go
@@ -536,8 +536,7 @@ func (i *ECSInstaller) Upgrade(
 	s = sg.Add("Updating task definition")
 	defer func() { s.Abort() }()
 
-	// assume upgrade to latest
-	if *containerDef.Image == installutil.DefaultServerImage {
+	if containerDef != nil && *containerDef.Image == installutil.DefaultServerImage && upgradeImg == installutil.DefaultServerImage {
 		// we can just update/force-deploy the service
 		_, err := ecsSvc.UpdateService(&ecs.UpdateServiceInput{
 			ForceNewDeployment:            aws.Bool(true),