diff --git a/lib/oban/engines/basic.ex b/lib/oban/engines/basic.ex
index 83a17e29..638e09dc 100644
--- a/lib/oban/engines/basic.ex
+++ b/lib/oban/engines/basic.ex
@@ -153,9 +153,10 @@ defmodule Oban.Engines.Basic do
     subquery =
       queryable
       |> select([:id, :queue, :state])
-      |> where([j], j.state in ~w(completed cancelled discarded))
+      |> where([j], j.state == "completed" and j.scheduled_at < ^time)
+      |> or_where([j], j.state == "cancelled" and j.cancelled_at < ^time)
+      |> or_where([j], j.state == "discarded" and j.discarded_at < ^time)
       |> where([j], not is_nil(j.queue))
-      |> where([j], j.scheduled_at < ^time)
       |> limit(^limit)
 
     query =
diff --git a/lib/oban/engines/lite.ex b/lib/oban/engines/lite.ex
index 5c62e1a6..23a08a77 100644
--- a/lib/oban/engines/lite.ex
+++ b/lib/oban/engines/lite.ex
@@ -146,8 +146,9 @@ defmodule Oban.Engines.Lite do
     select_query =
       queryable
       |> select([j], map(j, [:id, :queue, :state]))
-      |> where([j], j.state in ~w(completed cancelled discarded))
-      |> where([j], j.scheduled_at < ^time)
+      |> where([j], j.state == "completed" and j.scheduled_at < ^time)
+      |> or_where([j], j.state == "cancelled" and j.cancelled_at < ^time)
+      |> or_where([j], j.state == "discarded" and j.discarded_at < ^time)
       |> limit(^limit)
 
     pruned = Repo.all(conf, select_query)
diff --git a/test/oban/engine_test.exs b/test/oban/engine_test.exs
index 1ca091be..ffeb7bd0 100644
--- a/test/oban/engine_test.exs
+++ b/test/oban/engine_test.exs
@@ -445,7 +445,13 @@ for engine <- [Oban.Engines.Basic, Oban.Engines.Lite] do
         TelemetryHandler.attach_events(span_type: [:job, [:engine, :prune_jobs]])
 
         for state <- Job.states(), seconds <- 59..61 do
-          opts = [state: to_string(state), scheduled_at: seconds_ago(seconds)]
+          opts = [
+            state: to_string(state),
+            completed_at: seconds_ago(seconds),
+            discarded_at: seconds_ago(seconds),
+            cancelled_at: seconds_ago(seconds),
+            scheduled_at: seconds_ago(seconds)
+          ]
 
           # Insert one job at a time to avoid a "Cell-wise defaults" error in SQLite.
           Oban.insert!(name, Worker.new(%{}, opts))
diff --git a/test/oban/plugins/pruner_test.exs b/test/oban/plugins/pruner_test.exs
index 60356626..783b5fcc 100644
--- a/test/oban/plugins/pruner_test.exs
+++ b/test/oban/plugins/pruner_test.exs
@@ -27,17 +27,26 @@ defmodule Oban.Plugins.PrunerTest do
     test "historic jobs are pruned when they are older than the configured age" do
       TelemetryHandler.attach_events()
 
-      %Job{id: _id_} = insert!(%{}, state: "completed", scheduled_at: seconds_ago(61))
-      %Job{id: _id_} = insert!(%{}, state: "cancelled", scheduled_at: seconds_ago(61))
-      %Job{id: _id_} = insert!(%{}, state: "discarded", scheduled_at: seconds_ago(61))
-      %Job{id: id_1} = insert!(%{}, state: "completed", scheduled_at: seconds_ago(59))
+      %Job{id: _id_} = insert_historical("cancelled", :cancelled_at, 61, 61)
+      %Job{id: _id_} = insert_historical("cancelled", :cancelled_at, 61, 59)
+      %Job{id: _id_} = insert_historical("discarded", :discarded_at, 61, 61)
+      %Job{id: _id_} = insert_historical("discarded", :discarded_at, 61, 59)
+      %Job{id: _id_} = insert_historical("completed", :completed_at, 61, 61)
+      %Job{id: _id_} = insert_historical("completed", :completed_at, 59, 61)
+
+      %Job{id: id_1} = insert_historical("cancelled", :cancelled_at, 59, 61)
+      %Job{id: id_2} = insert_historical("cancelled", :cancelled_at, 59, 59)
+      %Job{id: id_3} = insert_historical("discarded", :discarded_at, 59, 61)
+      %Job{id: id_4} = insert_historical("discarded", :discarded_at, 59, 59)
+      %Job{id: id_5} = insert_historical("completed", :completed_at, 59, 59)
+      %Job{id: id_6} = insert_historical("completed", :completed_at, 61, 59)
 
       start_supervised_oban!(plugins: [{Pruner, interval: 10, max_age: 60}])
 
       assert_receive {:event, :stop, _, %{plugin: Pruner} = meta}
-      assert %{pruned_count: 3, pruned_jobs: [_ | _]} = meta
+      assert %{pruned_count: 6, pruned_jobs: [_ | _]} = meta
 
-      assert [id_1] ==
+      assert [id_1, id_2, id_3, id_4, id_5, id_6] ==
                Job
                |> select([j], j.id)
                |> order_by(asc: :id)
diff --git a/test/support/case.ex b/test/support/case.ex
index 184e2333..36440056 100644
--- a/test/support/case.ex
+++ b/test/support/case.ex
@@ -102,6 +102,19 @@ defmodule Oban.Case do
     Oban.insert!(oban, changeset)
   end
 
+  # Pruning test helpers
+
+  def insert_historical(state, timestamp_field, timestamp_age, scheduled_age) do
+    opts =
+      Keyword.put(
+        [state: state, scheduled_at: seconds_ago(scheduled_age)],
+        timestamp_field,
+        seconds_ago(timestamp_age)
+      )
+
+    insert!(%{}, opts)
+  end
+
   # Time
 
   def seconds_from_now(seconds) do