When it seems time entries are missing, it is usually because you are using a different View than normal.  There two view modes, Date and Task.  When in date view, entries are displayed for the date selected in the calendar.  When in task view, entries are displayed for the selected task.

When restarting Timeless Time & Expense in a different view than normal, the entry list may show blank when starting in task view because the top level task item is selected.  In date view the same can happen if not entries have been made for the current day.

To check if this is the problem, click the View menu to see which view is selected.  The view selected is also shown by the Task and Date view buttons on the toolbar.