diff --git a/lib/livebook_web/live/session_live.ex b/lib/livebook_web/live/session_live.ex
index eeb3a234a..64905cdd4 100644
--- a/lib/livebook_web/live/session_live.ex
+++ b/lib/livebook_web/live/session_live.ex
@@ -6,7 +6,7 @@ defmodule LivebookWeb.SessionLive do
   import Livebook.Utils, only: [format_bytes: 1]
 
   alias Livebook.{Sessions, Session, Delta, Notebook, Runtime, LiveMarkdown}
-  alias Livebook.Notebook.Cell
+  alias Livebook.Notebook.{Cell, ContentLoader}
   alias Livebook.JSInterop
 
   @impl true
@@ -1242,7 +1242,8 @@ defmodule LivebookWeb.SessionLive do
         |> redirect_to_self()
 
       resolution_location ->
-        origin = Notebook.ContentLoader.resolve_location(resolution_location, relative_path)
+        origin = ContentLoader.resolve_location(resolution_location, relative_path)
+        fallback_locations = fallback_relative_locations(resolution_location, relative_path)
 
         case session_id_by_location(origin) do
           {:ok, session_id} ->
@@ -1252,7 +1253,7 @@ defmodule LivebookWeb.SessionLive do
             push_redirect(socket, to: redirect_path)
 
           {:error, :none} ->
-            open_notebook(socket, origin, requested_url)
+            open_notebook(socket, origin, fallback_locations, requested_url)
 
           {:error, :many} ->
             origin_str =
@@ -1282,12 +1283,12 @@ defmodule LivebookWeb.SessionLive do
     end
   end
 
-  defp open_notebook(socket, origin, requested_url) do
-    case Notebook.ContentLoader.fetch_content_from_location(origin) do
+  defp open_notebook(socket, origin, fallback_locations, requested_url) do
+    case fetch_content_with_fallbacks(origin, fallback_locations) do
       {:ok, content} ->
         {notebook, messages} = Livebook.LiveMarkdown.notebook_from_livemd(content)
 
-        # If the current session has no path, fork the notebook
+        # If the current session has no file, fork the notebook
         fork? = socket.private.data.file == nil
         {file, notebook} = file_and_notebook(fork?, origin, notebook)
         url_hash = get_url_hash(requested_url)
@@ -1308,6 +1309,32 @@ defmodule LivebookWeb.SessionLive do
     end
   end
 
+  def fallback_relative_locations({:file, _}, _relative_path), do: []
+
+  def fallback_relative_locations(resolution_location, relative_path) do
+    # Other locations to check in case the relative location doesn't
+    # exist. For example, in ExDoc all pages (including notebooks) are
+    # flat, regardless of how they are structured in the file system
+
+    name = relative_path |> String.split("/") |> Enum.at(-1)
+    flat_location = ContentLoader.resolve_location(resolution_location, name)
+    [flat_location]
+  end
+
+  defp fetch_content_with_fallbacks(location, fallbacks) do
+    case ContentLoader.fetch_content_from_location(location) do
+      {:ok, content} ->
+        {:ok, content}
+
+      error ->
+        fallbacks
+        |> Enum.reject(&(&1 == location))
+        |> Enum.find_value(error, fn fallback ->
+          with {:error, _} <- ContentLoader.fetch_content_from_location(fallback), do: nil
+        end)
+    end
+  end
+
   defp file_and_notebook(fork?, origin, notebook)
   defp file_and_notebook(false, {:file, file}, notebook), do: {file, notebook}
   defp file_and_notebook(true, {:file, _file}, notebook), do: {nil, Notebook.forked(notebook)}
diff --git a/test/livebook_web/live/session_live_test.exs b/test/livebook_web/live/session_live_test.exs
index 4d7d34da5..33f0151e6 100644
--- a/test/livebook_web/live/session_live_test.exs
+++ b/test/livebook_web/live/session_live_test.exs
@@ -834,6 +834,34 @@ defmodule LivebookWeb.SessionLiveTest do
       close_session_by_id(session_id)
     end
 
+    test "when a remote URL cannot be loaded, attempts to resolve a flat URL", %{conn: conn} do
+      bypass = Bypass.open()
+
+      # Multi-level path is not available
+      Bypass.expect_once(bypass, "GET", "/nested/path/to/notebook.livemd", fn conn ->
+        Plug.Conn.resp(conn, 500, "Error")
+      end)
+
+      # A flat path is available
+      Bypass.expect_once(bypass, "GET", "/notebook.livemd", fn conn ->
+        conn
+        |> Plug.Conn.put_resp_content_type("text/plain")
+        |> Plug.Conn.resp(200, "# My notebook")
+      end)
+
+      index_url = url(bypass.port) <> "/index.livemd"
+      {:ok, session} = Sessions.create_session(origin: {:url, index_url})
+
+      assert {:error, {:live_redirect, %{to: "/sessions/" <> session_id}}} =
+               result = live(conn, "/sessions/#{session.id}/nested/path/to/notebook.livemd")
+
+      {:ok, view, _} = follow_redirect(result, conn)
+      assert render(view) =~ "My notebook"
+
+      Session.close(session.pid)
+      close_session_by_id(session_id)
+    end
+
     test "renders an error message if relative remote notebook cannot be loaded", %{conn: conn} do
       bypass = Bypass.open()