diff --git a/src/khepri_adv.erl b/src/khepri_adv.erl
index d98d9080..969071df 100644
--- a/src/khepri_adv.erl
+++ b/src/khepri_adv.erl
@@ -332,11 +332,18 @@ put(StoreId, PathPattern, Data) ->
 %% in the path pattern is not met, an error is returned and the tree structure
 %% is not modified.
 %%
-%% The returned `{ok, NodeProps}' tuple contains a map with the properties and
-%% payload (if any) of the targeted tree node: the payload was the one before
-%% the update, other properties like the payload version correspond to the
-%% updated node. If the targeted tree node didn't exist, `NodeProps' will be
-%% an empty map.
+%% The returned `{ok, NodePropsMap}' tuple contains a map where keys correspond
+%% to the path to a node affected by the put operation. Each key points to a
+%% map containing the properties and prior payload (if any) of a tree node
+%% created, updated or deleted by the put operation. If the put results in the
+%% creation of a tree node this props map will be empty. If the put updates an
+%% existing tree node then the props map will contain the payload of the tree
+%% node (if any) before the update while the other properties like the payload
+%% version correspond to the updated node. The `NodePropsMap' map might also
+%% contain deletions if the put operation leads to an existing tree node's
+%% keep-while condition becoming unsatisfied. The props map for any nodes
+%% deleted because of an expired keep-while condition will contain a
+%% `delete_reason' key set to `keep_while'.
 %%
 %% The payload must be one of the following form:
 %% <ul>
@@ -452,11 +459,18 @@ put_many(StoreId, PathPattern, Data) ->
 %% in the path pattern is not met, an error is returned and the tree structure
 %% is not modified.
 %%
-%% The returned `{ok, NodePropsMap}' tuple contains a map where keys
-%% correspond to the path to a tree node matching the path pattern. Each key
-%% then points to a map containing the properties and payload (if any) of the
-%% targeted tree node: the payload was the one before the update, other
-%% properties like the payload version correspond to the updated node.
+%% The returned `{ok, NodePropsMap}' tuple contains a map where keys correspond
+%% to the path to a node affected by the put operation. Each key points to a
+%% map containing the properties and prior payload (if any) of a tree node
+%% created, updated or deleted by the put operation. If the put results in the
+%% creation of a tree node this props map will be empty. If the put updates an
+%% existing tree node then the props map will contain the payload of the tree
+%% node (if any) before the update while the other properties like the payload
+%% version correspond to the updated node. The `NodePropsMap' map might also
+%% contain deletions if the put operation leads to an existing tree node's
+%% keep-while condition becoming unsatisfied. The props map for any nodes
+%% deleted because of an expired keep-while condition will contain a
+%% `delete_reason' key set to `keep_while'.
 %%
 %% The payload must be one of the following form:
 %% <ul>
@@ -831,9 +845,15 @@ delete(PathPattern, Options) when is_map(Options) ->
 %% one tree node would match at the time. If you want to delete multiple nodes
 %% at once, use {@link delete_many/3}.
 %%
-%% The returned `{ok, NodeProps}' tuple contains a map with the properties and
-%% payload (if any) of the targeted tree node as they were before the delete.
-%% If the targeted tree node didn't exist, `NodeProps' will be an empty map.
+%% The returned `{ok, NodePropsMap}' tuple contains a map where keys
+%% correspond to the path to a deleted tree node. Each key then points to a
+%% map containing the properties and payload (if any) of that deleted tree
+%% node as they were before the delete. Tree nodes in this map which were
+%% the target of the delete command will have a `delete_reason' key set to
+%% `explicit' in their associated props map. Any tree nodes deleted because
+%% their keep-while condition became unsatisfied due to the deletion will have
+%% the `delete_reason' key set to `keep_while' instead. (See {@link
+%% khepri_condition:keep_while()}.)
 %%
 %% When doing an asynchronous update, the {@link handle_async_ret/1}
 %% function should be used to handle the message received from Ra.
@@ -842,7 +862,8 @@ delete(PathPattern, Options) when is_map(Options) ->
 %% ```
 %% %% Delete the tree node at `/:foo/:bar'.
 %% {ok, #{data := value,
-%%        payload_version := 1}} = khepri_adv:delete(StoreId, [foo, bar]).
+%%        payload_version := 1,
+%%        delete_reason := explicit}} = khepri_adv:delete(StoreId, [foo, bar]).
 %% '''
 %%
 %% @param StoreId the name of the Khepri store.
@@ -925,18 +946,25 @@ delete_many(PathPattern, Options) when is_map(Options) ->
 %% The returned `{ok, NodePropsMap}' tuple contains a map where keys
 %% correspond to the path to a deleted tree node. Each key then points to a
 %% map containing the properties and payload (if any) of that deleted tree
-%% node as they were before the delete.
+%% node as they were before the delete. Tree nodes in this map which were
+%% the target of the delete command will have a `delete_reason' key set to
+%% `explicit' in their associated props map. Any tree nodes deleted because
+%% their keep-while condition became unsatisfied due to the deletion will have
+%% the `delete_reason' key set to `keep_while' instead. (See {@link
+%% khepri_condition:keep_while()}.)
 %%
 %% When doing an asynchronous update, the {@link handle_async_ret/1}
 %% function should be used to handle the message received from Ra.
 %%
 %% Example:
 %% ```
-%% %% Delete the tree node at `/:foo/:bar'.
+%% %% Delete all tree nodes matching `/*/:bar'.
 %% {ok, #{[foo, bar] := #{data := value,
-%%                        payload_version := 1},
-%%        [baz, bar] := #{payload_version := 1}}} = khepri_adv:delete_many(
-%%                                                    StoreId, [foo, bar]).
+%%                        payload_version := 1,
+%%                        delete_reason := explicit},
+%%        [baz, bar] := #{payload_version := 1,
+%%                        delete_reason := explicit}}} =
+%% khepri_adv:delete_many(StoreId, [?KHEPRI_WILDCARD_STAR, bar]).
 %% '''
 %%
 %% @param StoreId the name of the Khepri store.
diff --git a/src/khepri_tree.erl b/src/khepri_tree.erl
index 22f76236..f97cef57 100644
--- a/src/khepri_tree.erl
+++ b/src/khepri_tree.erl
@@ -1343,7 +1343,9 @@ handle_keep_while_for_parent_update(
 handle_keep_while_for_parent_update(
   #walk{tree = Tree,
         node = ParentNode,
-        reversed_path = ReversedPath} = Walk,
+        reversed_path = ReversedPath,
+        tree_options = TreeOptions,
+        fun_acc = Acc} = Walk,
   AppliedChangesAcc) ->
     ParentPath = lists:reverse(ReversedPath),
     IsMet = is_keep_while_condition_met_on_self(
@@ -1356,7 +1358,11 @@ handle_keep_while_for_parent_update(
             %% This parent node must be removed because it doesn't meet its
             %% own keep_while condition. keep_while conditions for nodes
             %% depending on this one will be evaluated with the recursion.
-            Walk1 = Walk#walk{node = delete},
+            {ok, delete, Acc1} = delete_matching_nodes_cb(
+                                   ParentPath, ParentNode,
+                                   TreeOptions, keep_while, Acc),
+            Walk1 = Walk#walk{node = delete,
+                              fun_acc = Acc1},
             walk_back_up_the_tree(Walk1, AppliedChangesAcc)
     end.
 
@@ -1540,14 +1546,27 @@ remove_expired_nodes([], Walk) ->
     {ok, Walk};
 remove_expired_nodes(
   [PathToDelete | Rest],
-  #walk{tree = Tree, applied_changes = AppliedChanges} = Walk) ->
-    case delete_matching_nodes(Tree, PathToDelete, AppliedChanges, #{}) of
-        {ok, Tree1, AppliedChanges1, _Acc} ->
+  #walk{tree = Tree,
+        applied_changes = AppliedChanges,
+        tree_options = TreeOptions,
+        fun_acc = Acc} = Walk) ->
+    %% See `delete_matching_nodes/4'. This is the same except that the
+    %% accumulator is passed through and the `DeleteReason' is provided as
+    %% `keep_while'.
+    Fun = fun(Path, Node, Result) ->
+                  delete_matching_nodes_cb(
+                    Path, Node, TreeOptions, keep_while, Result)
+          end,
+    Result = walk_down_the_tree(
+               Tree, PathToDelete, TreeOptions, AppliedChanges, Fun, Acc),
+    case Result of
+        {ok, Tree1, AppliedChanges1, Acc1} ->
             AppliedChanges2 = merge_applied_changes(
                                 AppliedChanges, AppliedChanges1),
             Walk1 = Walk#walk{tree = Tree1,
                               node = Tree1#tree.root,
-                              applied_changes = AppliedChanges2},
+                              applied_changes = AppliedChanges2,
+                              fun_acc = Acc1},
             remove_expired_nodes(Rest, Walk1)
     end.
 
diff --git a/test/delete_command.erl b/test/delete_command.erl
index 6cc84d53..76108334 100644
--- a/test/delete_command.erl
+++ b/test/delete_command.erl
@@ -139,12 +139,18 @@ delete_a_node_deep_into_the_tree_test() ->
             child_list_version => 3},
           child_nodes = #{}},
        Root),
-    ?assertEqual(
-      {ok, #{[foo, bar, baz] => #{payload_version => 1,
-                                  child_list_version => 1,
-                                  child_list_length => 1,
-                                  delete_reason => explicit}}},
-      Ret),
+    ?assertEqual({ok, #{[foo, bar, baz] => #{payload_version => 1,
+                                             child_list_version => 1,
+                                             child_list_length => 1,
+                                             delete_reason => explicit},
+                        [foo, bar] => #{payload_version => 1,
+                                        child_list_version => 2,
+                                        child_list_length => 0,
+                                        delete_reason => keep_while},
+                        [foo] => #{payload_version => 1,
+                                   child_list_version => 2,
+                                   child_list_length => 0,
+                                   delete_reason => keep_while}}}, Ret),
     ?assertEqual([], SE).
 
 delete_existing_node_with_condition_true_test() ->
diff --git a/test/keep_while_conditions.erl b/test/keep_while_conditions.erl
index ee450b0a..127df540 100644
--- a/test/keep_while_conditions.erl
+++ b/test/keep_while_conditions.erl
@@ -260,7 +260,8 @@ keep_while_now_false_after_command_test() ->
                  #node{props = ?INIT_NODE_PROPS,
                        payload = khepri_payload:data(bar_value)}}}}},
        Root),
-    ?assertEqual({ok, #{[foo, bar] => #{}}}, Ret),
+    ?assertEqual({ok, #{[foo, bar] => #{},
+                        [baz] => #{delete_reason => keep_while}}}, Ret),
     ?assertEqual([], SE).
 
 recursive_automatic_cleanup_test() ->
@@ -292,13 +293,21 @@ recursive_automatic_cleanup_test() ->
             child_list_version => 3},
           child_nodes = #{}},
        Root),
-    ?assertEqual(
-      {ok, #{[foo, bar, baz] => #{data => baz_value,
-                                  payload_version => 1,
-                                  child_list_version => 1,
-                                  child_list_length => 0,
-                                  delete_reason => explicit}}},
-      Ret),
+    ?assertEqual({ok, #{[foo, bar, baz] => #{data => baz_value,
+                                             payload_version => 1,
+                                             child_list_version => 1,
+                                             child_list_length => 0,
+                                             delete_reason => explicit},
+                        [foo, bar] => #{data => bar_value,
+                                        payload_version => 1,
+                                        child_list_version => 3,
+                                        child_list_length => 0,
+                                        delete_reason => keep_while},
+                        [foo] => #{data => foo_value,
+                                   payload_version => 1,
+                                   child_list_version => 3,
+                                   child_list_length => 0,
+                                   delete_reason => keep_while}}}, Ret),
     ?assertEqual([], SE).
 
 keep_while_now_false_after_delete_command_test() ->
@@ -330,7 +339,12 @@ keep_while_now_false_after_delete_command_test() ->
                                    payload_version => 1,
                                    child_list_version => 1,
                                    child_list_length => 0,
-                                   delete_reason => explicit}}}, Ret),
+                                   delete_reason => explicit},
+                        [baz] => #{data => baz_value,
+                                   payload_version => 1,
+                                   child_list_version => 1,
+                                   child_list_length => 0,
+                                   delete_reason => keep_while}}}, Ret),
     ?assertEqual([], SE).
 
 automatic_reclaim_of_useless_nodes_works_test() ->
@@ -349,8 +363,9 @@ automatic_reclaim_of_useless_nodes_works_test() ->
             child_list_version => 3},
           child_nodes = #{}},
        Root),
-    ?assertEqual(
-      {ok, #{[foo, bar, baz] => #{delete_reason => explicit}}}, Ret),
+    ?assertEqual({ok, #{[foo, bar, baz] => #{delete_reason => explicit},
+                        [foo, bar] => #{delete_reason => keep_while},
+                        [foo] => #{delete_reason => keep_while}}}, Ret),
     ?assertEqual([], SE).
 
 automatic_reclaim_keeps_relevant_nodes_1_test() ->
@@ -379,8 +394,8 @@ automatic_reclaim_keeps_relevant_nodes_1_test() ->
                   payload = khepri_payload:data(relevant),
                   child_nodes = #{}}}},
        Root),
-    ?assertEqual(
-      {ok, #{[foo, bar, baz] => #{delete_reason => explicit}}}, Ret),
+    ?assertEqual({ok, #{[foo, bar, baz] => #{delete_reason => explicit},
+                        [foo, bar] => #{delete_reason => keep_while}}}, Ret),
     ?assertEqual([], SE).
 
 automatic_reclaim_keeps_relevant_nodes_2_test() ->
@@ -415,6 +430,7 @@ automatic_reclaim_keeps_relevant_nodes_2_test() ->
                           child_nodes = #{}}}}}},
        Root),
     ?assertEqual(
-      {ok, #{[foo, bar, baz, qux] => #{delete_reason => explicit}}},
+      {ok, #{[foo, bar, baz, qux] => #{delete_reason => explicit},
+             [foo, bar, baz] => #{delete_reason => keep_while}}},
       Ret),
     ?assertEqual([], SE).