diff --git a/test/livebook/live_markdown/export_test.exs b/test/livebook/live_markdown/export_test.exs
index 0bd2be45b..02ee83500 100644
--- a/test/livebook/live_markdown/export_test.exs
+++ b/test/livebook/live_markdown/export_test.exs
@@ -1,6 +1,8 @@
 defmodule Livebook.LiveMarkdown.ExportTest do
   use ExUnit.Case, async: true
 
+  import Livebook.TestHelpers
+
   alias Livebook.LiveMarkdown.Export
   alias Livebook.Notebook
 
@@ -1327,7 +1329,7 @@ defmodule Livebook.LiveMarkdown.ExportTest do
 
   describe "file entries" do
     test "persists file entries" do
-      file = Livebook.FileSystem.File.new(Livebook.FileSystem.Local.new(), "/document.pdf")
+      file = Livebook.FileSystem.File.new(Livebook.FileSystem.Local.new(), p("/document.pdf"))
 
       notebook = %{
         Notebook.new()
@@ -1340,7 +1342,7 @@ defmodule Livebook.LiveMarkdown.ExportTest do
       }
 
       expected_document = """
-      <!-- livebook:{"file_entries":[{"name":"data.csv","type":"url","url":"https://example.com/data.csv"},{"file":{"file_system_id":"local","path":"/document.pdf"},"name":"document.pdf","type":"file"},{"name":"image.jpg","type":"attachment"}]} -->
+      <!-- livebook:{"file_entries":[{"name":"data.csv","type":"url","url":"https://example.com/data.csv"},{"file":{"file_system_id":"local","path":"#{p("/document.pdf")}"},"name":"document.pdf","type":"file"},{"name":"image.jpg","type":"attachment"}]} -->
 
       # My Notebook
       """
diff --git a/test/livebook_web/live/app_live_test.exs b/test/livebook_web/live/app_live_test.exs
index 4b6be821a..d355f4b44 100644
--- a/test/livebook_web/live/app_live_test.exs
+++ b/test/livebook_web/live/app_live_test.exs
@@ -42,6 +42,12 @@ defmodule LivebookWeb.AppLiveTest do
 
       Livebook.Session.app_deactivate(session_pid2)
 
+      assert_receive {:app_updated,
+                      %{
+                        pid: ^app_pid,
+                        sessions: [%{app_status: %{lifecycle: :deactivated}}, _]
+                      }}
+
       {:ok, view, _} = live(conn, ~p"/apps/#{slug}")
 
       assert render(view) =~ ~p"/apps/#{slug}/#{session_id1}"
diff --git a/test/livebook_web/live/session_live_test.exs b/test/livebook_web/live/session_live_test.exs
index 081a254c6..efb90ca12 100644
--- a/test/livebook_web/live/session_live_test.exs
+++ b/test/livebook_web/live/session_live_test.exs
@@ -1524,6 +1524,8 @@ defmodule LivebookWeb.SessionLiveTest do
     @tag :tmp_dir
     test "adding :attachment file entry from file",
          %{conn: conn, session: session, tmp_dir: tmp_dir} do
+      Session.subscribe(session.id)
+
       path = Path.join(tmp_dir, "image.jpg")
       File.write!(path, "content")
 
@@ -1543,6 +1545,8 @@ defmodule LivebookWeb.SessionLiveTest do
       |> element(~s{#add-file-entry-form})
       |> render_submit(%{"data" => %{"name" => "image.jpg", "copy" => "true"}})
 
+      assert_receive {:operation, {:add_file_entries, _client_id, [%{name: "image.jpg"}]}}
+
       assert %{notebook: %{file_entries: [%{type: :attachment, name: "image.jpg"}]}} =
                Session.get_data(session.pid)
 
@@ -1579,6 +1583,8 @@ defmodule LivebookWeb.SessionLiveTest do
     end
 
     test "adding :attachment file entry from url", %{conn: conn, session: session} do
+      Session.subscribe(session.id)
+
       bypass = Bypass.open()
       file_url = "http://localhost:#{bypass.port}/image.jpg"
 
@@ -1603,6 +1609,8 @@ defmodule LivebookWeb.SessionLiveTest do
         "data" => %{"name" => "image.jpg", "copy" => "true", "url" => file_url}
       })
 
+      assert_receive {:operation, {:add_file_entries, _client_id, [%{name: "image.jpg"}]}}
+
       assert %{notebook: %{file_entries: [%{type: :attachment, name: "image.jpg"}]}} =
                Session.get_data(session.pid)
 
@@ -1703,6 +1711,8 @@ defmodule LivebookWeb.SessionLiveTest do
 
     @tag :tmp_dir
     test "transferring file entry", %{conn: conn, session: session, tmp_dir: tmp_dir} do
+      Session.subscribe(session.id)
+
       tmp_dir = FileSystem.File.local(tmp_dir <> "/")
       image_file = FileSystem.File.resolve(tmp_dir, "image.jpg")
       :ok = FileSystem.File.write(image_file, "content")
@@ -1716,11 +1726,13 @@ defmodule LivebookWeb.SessionLiveTest do
       |> element(~s/[data-el-files-list] menu button/, "Copy to files")
       |> render_click()
 
-      assert {:ok, true} = FileSystem.File.exists?(image_file)
+      assert_receive {:operation, {:add_file_entries, _client_id, [%{name: "image.jpg"}]}}
 
       assert %{notebook: %{file_entries: [%{type: :attachment, name: "image.jpg"}]}} =
                Session.get_data(session.pid)
 
+      assert {:ok, true} = FileSystem.File.exists?(image_file)
+
       assert FileSystem.File.resolve(session.files_dir, "image.jpg") |> FileSystem.File.read() ==
                {:ok, "content"}
     end