diff --git a/lib/jackalope/persistent_work_list.ex b/lib/jackalope/persistent_work_list.ex
index ebc23c4..7540164 100644
--- a/lib/jackalope/persistent_work_list.ex
+++ b/lib/jackalope/persistent_work_list.ex
@@ -17,13 +17,10 @@ defmodule Jackalope.PersistentWorkList do
     @type t :: %__MODULE__{
             # The maximum number of items that can be persisted as files
             max_size: non_neg_integer(),
-            # The lowest index of an unexpired, not-pending item. No pending item has an index >= bottom_index.
+            # The lowest index of an unexpired, not-pending item. No pending item has an index >= bottom_index. Monotonic.
             bottom_index: non_neg_integer(),
-            # The index at which the next item will be pushed
+            # The index at which the next item will be pushed. Monotonic.
             next_index: non_neg_integer(),
-            # Indices greater than bottom_index of (maybe prematurely and forcibly) expired items.
-            # Used to get a correct count of work items (i.e. not pending).
-            expired: [],
             # Cache of item expiration times for all persisted items (pending and not)
             expirations: %{required(non_neg_integer()) => integer},
             # Indices of pending items mapped by their references.
@@ -32,19 +29,21 @@ defmodule Jackalope.PersistentWorkList do
             data_dir: String.t(),
             # The function to use to get an expiration given the item
             expiration_fn: fun(),
-            # The function to use to update an item's expiration
-            update_expiration_fn: fun()
+            # Delta between the (approximate) monotonic time at last reboot and the monotomic time at startup
+            delta_time: integer(),
+            # The highest index of a recovered item, -1 if none
+            recovery_index: integer
           }
 
     defstruct bottom_index: 0,
               next_index: 0,
-              expired: [],
               expirations: %{},
               pending: %{},
               data_dir: nil,
               max_size: nil,
               expiration_fn: nil,
-              update_expiration_fn: nil
+              delta_time: 0,
+              recovery_index: -1
   end
 
   @doc "Create a new work list"
@@ -63,11 +62,11 @@ defmodule Jackalope.PersistentWorkList do
       %State{
         max_size: Keyword.get(opts, :max_size),
         data_dir: Keyword.fetch!(opts, :data_dir),
-        expiration_fn: Keyword.fetch!(opts, :expiration_fn),
-        update_expiration_fn: Keyword.fetch!(opts, :update_expiration_fn)
+        expiration_fn: Keyword.fetch!(opts, :expiration_fn)
       }
       |> recover()
 
+    record_time_now(initial_state)
     {:ok, initial_state}
   end
 
@@ -121,10 +120,7 @@ defmodule Jackalope.PersistentWorkList do
 
       index ->
         {:ok, item} = stored_item_at(index, state, remove: true)
-
-        updated_state =
-          %State{state | pending: Map.delete(state.pending, ref)}
-          |> clean_up()
+        updated_state = %State{state | pending: Map.delete(state.pending, ref)}
 
         {:reply, item, updated_state}
     end
@@ -156,7 +152,13 @@ defmodule Jackalope.PersistentWorkList do
   ## PRIVATE
 
   defp count(state) do
-    (state.next_index - state.bottom_index - length(state.expired))
+    expired_count =
+      Enum.count(
+        state.bottom_index..(state.next_index - 1),
+        &expired?(&1, state)
+      )
+
+    (state.next_index - state.bottom_index - expired_count)
     |> max(0)
   end
 
@@ -175,14 +177,12 @@ defmodule Jackalope.PersistentWorkList do
 
   # Peek at oldest non-pending work item
   defp peek_oldest(state) do
-    cond do
-      empty?(state) ->
-        nil
-
-      true ->
-        # If this fails, let it crash
-        {:ok, item} = stored_item_at(state.bottom_index, state)
-        item
+    if empty?(state) do
+      nil
+    else
+      # If this fails, let it crash
+      {:ok, item} = stored_item_at(state.bottom_index, state)
+      item
     end
   end
 
@@ -206,7 +206,6 @@ defmodule Jackalope.PersistentWorkList do
 
     %State{state | expirations: Map.delete(state.expirations, index)}
     |> move_bottom_index()
-    |> clean_up()
   end
 
   # Move bottom index up until it is not an expired
@@ -217,7 +216,7 @@ defmodule Jackalope.PersistentWorkList do
       next_bottom_index > state.next_index ->
         state
 
-      next_bottom_index in state.expired ->
+      expired?(next_bottom_index, state) ->
         %State{
           state
           | bottom_index: next_bottom_index
@@ -235,32 +234,13 @@ defmodule Jackalope.PersistentWorkList do
   # No non-pending items?
   defp empty?(state), do: state.bottom_index == state.next_index
 
-  defp bottom_pending_index(state) do
-    if Enum.empty?(state.pending), do: nil, else: Enum.min(Map.values(state.pending))
-  end
-
-  # Maybe reset indices to initial values and cleanup expired list
-  defp clean_up(state) do
-    if empty?(state) and Enum.empty?(state.pending) do
-      %State{state | bottom_index: 0, next_index: 0, expired: []}
-    else
-      cleanup_expired(state)
-    end
+  defp expired?(index, state) do
+    path = item_file_path(index, state)
+    not File.exists?(path)
   end
 
-  # Remove from expired all indices smaller than the smallest index of a persisted item
-  defp cleanup_expired(state) do
-    expired_index_min =
-      case bottom_pending_index(state) do
-        nil -> state.bottom_index
-        index -> min(index, state.bottom_index)
-      end
-
-    updated_expired =
-      state.expired
-      |> Enum.reject(&(&1 < expired_index_min))
-
-    %State{state | expired: updated_expired}
+  defp bottom_pending_index(state) do
+    if Enum.empty?(state.pending), do: nil, else: Enum.min(Map.values(state.pending))
   end
 
   defp store_item(item, index, state) do
@@ -330,11 +310,16 @@ defmodule Jackalope.PersistentWorkList do
     end
   end
 
+  defp expiration(index, state) do
+    expiration = Map.fetch!(state.expirations, index)
+    if index <= state.recovery_index, do: expiration + state.delta_time, else: expiration
+  end
+
   defp maybe_expire(index, state) do
-    if index in state.expired do
+    if expired?(index, state) do
       state
     else
-      expiration = Map.fetch!(state.expirations, index)
+      expiration = expiration(index, state)
 
       if Expiration.after?(expiration, Expiration.now()) do
         state
@@ -355,9 +340,9 @@ defmodule Jackalope.PersistentWorkList do
     else
       live_indices =
         state.bottom_index..(state.next_index - 1)
-        |> Enum.reject(&(&1 in state.expired))
+        |> Enum.reject(&expired?(&1, state))
         |> Enum.sort(fn index1, index2 ->
-          Map.fetch!(state.expirations, index1) <= Map.fetch!(state.expirations, index2)
+          expiration(index1, state) <= expiration(index2, state)
         end)
         |> Enum.take(excess_count)
 
@@ -383,63 +368,79 @@ defmodule Jackalope.PersistentWorkList do
           move_bottom_index(state)
 
         true ->
-          %State{state | expired: [index | state.expired]}
+          state
       end
 
     %State{updated_state | expirations: Map.delete(state.expirations, index)}
-    |> clean_up()
   end
 
   defp pending_item?(index, state), do: Map.has_key?(state.pending, index)
 
   defp recover(state) do
     :ok = File.mkdir_p!(state.data_dir)
-    now = Expiration.now()
-
-    item_files =
-      File.ls!(state.data_dir) |> Enum.filter(&Regex.match?(~r/.*\.item/, &1)) |> Enum.sort()
 
-    item_files
-    |> Enum.reduce(
-      reset_state(state),
-      fn file, acc ->
-        recover_file(Path.join(state.data_dir, file), now, acc)
-      end
-    )
-    |> bound_items()
-  end
+    delta_time = Expiration.now() - latest_time(state)
+
+    expirations =
+      File.ls!(state.data_dir)
+      |> Enum.filter(&Regex.match?(~r/.*\.item/, &1))
+      |> Enum.reduce(
+        [],
+        fn item_file, acc ->
+          index = index_of_item_file(item_file)
+
+          case stored_item_at(index, state) do
+            {:ok, item} ->
+              expiration = state.expiration_fn.(item)
+              [{index, expiration} | acc]
+
+            {:error, reason} ->
+              Logger.warn(
+                "Failed to recover item in #{inspect(item_file)}: #{inspect(reason)}. Removing it."
+              )
+
+              _ = File.rm(item_file_path(index, state))
+              acc
+          end
+        end
+      )
+      |> Enum.into(%{})
 
-  defp reset_state(state) do
-    %State{state | bottom_index: 0, next_index: 0, expired: [], pending: %{}, expirations: %{}}
-  end
+    item_indices = Map.keys(expirations)
 
-  defp recover_file(file, now, state) do
-    binary = File.read!(file)
-    :ok = File.rm!(file)
+    if Enum.empty?(item_indices) do
+      reset_state(state)
+    else
+      bottom_index = Enum.min(item_indices)
+      last_index = Enum.max(item_indices)
 
-    updated_state =
-      case item_from_binary(binary) do
-        {:ok, item} ->
-          index = state.next_index
-          # TODO - do some version checking...
-          rebased_expiration =
-            Expiration.rebase_expiration(state.expiration_fn.(item), latest_time(state), now)
-
-          rebased_item = state.update_expiration_fn.(item, rebased_expiration)
-          :ok = store_item(rebased_item, index, state)
-
-          %State{
-            state
-            | next_index: index + 1,
-              expirations: Map.put(state.expirations, index, rebased_expiration)
-          }
+      %State{
+        state
+        | bottom_index: bottom_index,
+          next_index: last_index + 1,
+          recovery_index: last_index,
+          delta_time: delta_time,
+          expirations: expirations
+      }
+      |> bound_items()
+    end
+  end
 
-        {:error, :invalid} ->
-          # Ignore invalid item file
-          state
-      end
+  defp index_of_item_file(item_file) do
+    [index_s, _] = String.split(item_file, ".")
+    {index, _} = Integer.parse(index_s)
+    index
+  end
 
-    updated_state
+  defp reset_state(state) do
+    %State{
+      state
+      | bottom_index: 0,
+        next_index: 0,
+        pending: %{},
+        expirations: %{},
+        recovery_index: -1
+    }
   end
 
   defp latest_time(state) do
diff --git a/lib/jackalope/session.ex b/lib/jackalope/session.ex
index 80731c7..dd26f86 100644
--- a/lib/jackalope/session.ex
+++ b/lib/jackalope/session.ex
@@ -79,9 +79,6 @@ defmodule Jackalope.Session do
     work_list =
       Keyword.merge(opts,
         expiration_fn: fn {_cmd, opts} -> Keyword.fetch!(opts, :expiration) end,
-        update_expiration_fn: fn {cmd, opts}, expiration ->
-          {cmd, Keyword.put(opts, :expiration, expiration)}
-        end,
         max_size: max_work_list_size
       )
       |> work_list_mod.new()
diff --git a/test/jackalope_test.exs b/test/jackalope_test.exs
index d4751e2..2c54bf2 100644
--- a/test/jackalope_test.exs
+++ b/test/jackalope_test.exs
@@ -175,9 +175,6 @@ defmodule JackalopeTest do
     work_list =
       Jackalope.PersistentWorkList.new(
         expiration_fn: fn {_cmd, opts} -> Keyword.fetch!(opts, :expiration) end,
-        update_expiration_fn: fn {cmd, opts}, expiration ->
-          {cmd, Keyword.put(opts, :expiration, expiration)}
-        end,
         max_size: 10,
         data_dir: "/tmp/jackalope"
       )
@@ -193,6 +190,7 @@ defmodule JackalopeTest do
         )
       end)
 
+    assert WorkList.count(work_list) == 10
     ref = make_ref()
     work_list = WorkList.pending(work_list, ref)
     :ok = GenServer.stop(work_list, :normal)
@@ -200,9 +198,6 @@ defmodule JackalopeTest do
     work_list =
       Jackalope.PersistentWorkList.new(
         expiration_fn: fn {_cmd, opts} -> Keyword.fetch!(opts, :expiration) end,
-        update_expiration_fn: fn {cmd, opts}, expiration ->
-          {cmd, Keyword.put(opts, :expiration, expiration)}
-        end,
         max_size: 5,
         data_dir: "/tmp/jackalope"
       )