diff --git a/lib/microwaveprop/workers/backfill_enqueue_worker.ex b/lib/microwaveprop/workers/backfill_enqueue_worker.ex
index c88266de..eeb58110 100644
--- a/lib/microwaveprop/workers/backfill_enqueue_worker.ex
+++ b/lib/microwaveprop/workers/backfill_enqueue_worker.ex
@@ -24,7 +24,7 @@ defmodule Microwaveprop.Workers.BackfillEnqueueWorker do
       Contact
       |> where([c], not is_nil(c.pos1) or not is_nil(c.grid1))
       |> where(^type_filter(types))
-      |> order_by([c], desc: c.qso_timestamp)
+      |> order_by(^status_priority_order(types))
       |> limit(^limit)
       |> Repo.all()
 
@@ -48,6 +48,16 @@ defmodule Microwaveprop.Workers.BackfillEnqueueWorker do
 
   defp parse_types(_), do: [:hrrr, :weather, :terrain, :iemre]
 
+  defp status_priority_order(types) do
+    # Prioritize pending/failed over queued so real work happens first
+    field = :"#{hd(types)}_status"
+
+    [
+      asc: dynamic([c], fragment("CASE ? WHEN 'pending' THEN 0 WHEN 'failed' THEN 1 ELSE 2 END", field(c, ^field))),
+      desc: dynamic([c], c.qso_timestamp)
+    ]
+  end
+
   defp type_filter(types) do
     Enum.reduce(types, dynamic(false), fn type, acc ->
       field = :"#{type}_status"