diff --git a/dask_kubernetes/operator/controller/controller.py b/dask_kubernetes/operator/controller/controller.py
index c34aa0ce..ef0c3d61 100644
--- a/dask_kubernetes/operator/controller/controller.py
+++ b/dask_kubernetes/operator/controller/controller.py
@@ -10,6 +10,7 @@
 from uuid import uuid4
 
 import aiohttp
+import anyio
 import dask.config
 import kopf
 import kr8s
@@ -646,16 +647,19 @@ async def daskworkergroup_replica_update(
     # Replica updates can come in quick succession and the changes must be applied atomically to ensure
     # the number of workers ends in the correct state
     async with worker_group_scale_locks[f"{namespace}/{name}"]:
-        current_workers = len(
-            await kr8s.asyncio.get(
-                "deployments",
-                namespace=namespace,
-                label_selector={"dask.org/workergroup-name": name},
-            )
+        current_workers = await kr8s.asyncio.get(
+            "deployments",
+            namespace=namespace,
+            label_selector={"dask.org/workergroup-name": name},
+        )
+        # Sorting workers to ensure long-lived workers are the first on list
+        current_workers = sorted(
+            current_workers,
+            key=lambda d: datetime.fromisoformat(d.metadata["creationTimestamp"]),
         )
         assert isinstance(new, int)
         desired_workers = new
-        workers_needed = desired_workers - current_workers
+        workers_needed = desired_workers - len(current_workers)
         labels = _get_labels(meta)
         annotations = _get_annotations(meta)
         worker_spec = spec["worker"]
@@ -695,22 +699,48 @@ async def daskworkergroup_replica_update(
             )
         logger.info(f"Scaled worker group {name} up to {desired_workers} workers.")
         if workers_needed < 0:
-            worker_ids = await retire_workers(
-                n_workers=-workers_needed,
-                scheduler_service_name=SCHEDULER_NAME_TEMPLATE.format(
-                    cluster_name=cluster_name
-                ),
-                worker_group_name=name,
-                namespace=namespace,
-                logger=logger,
-            )
-            logger.info(f"Workers to close: {worker_ids}")
-            for wid in worker_ids:
-                worker_deployment = await Deployment(wid, namespace=namespace)
-                await worker_deployment.delete()
-            logger.info(
-                f"Scaled worker group {name} down to {desired_workers} workers."
-            )
+            # We prioritize the deletion of newly created and unready deployments
+            recent_workers = current_workers[::-1]
+
+            unready_deployments = []
+            for idx in range(-workers_needed):
+                if idx > len(recent_workers):
+                    break
+                deployment = recent_workers[idx]
+                if not (
+                    deployment.raw["status"].get("observedGeneration", 0)
+                    >= deployment.raw["metadata"]["generation"]
+                    and deployment.raw["status"].get("readyReplicas", 0)
+                    == deployment.replicas
+                ):
+                    unready_deployments.append(deployment)
+
+            async with anyio.create_task_group() as tg:
+                for deployment in unready_deployments:
+                    tg.start_soon(deployment.delete)
+
+            if unready_deployments:
+                logger.info(f"Deleted unready {len(unready_deployments)} workers.")
+
+            n_workers = -workers_needed - len(unready_deployments)
+
+            if n_workers > 0:
+                worker_ids = await retire_workers(
+                    n_workers=n_workers,
+                    scheduler_service_name=SCHEDULER_NAME_TEMPLATE.format(
+                        cluster_name=cluster_name
+                    ),
+                    worker_group_name=name,
+                    namespace=namespace,
+                    logger=logger,
+                )
+                logger.info(f"Workers to close: {worker_ids}")
+                for wid in worker_ids:
+                    worker_deployment = await Deployment(wid, namespace=namespace)
+                    await worker_deployment.delete()
+                logger.info(
+                    f"Scaled worker group {name} down to {desired_workers} workers."
+                )
 
 
 @kopf.on.delete("daskworkergroup.kubernetes.dask.org", optional=True)