The behavior of recurring tasks and reminders confuses a lot of users – when a reminder for a task is dismissed, all that happens is the reminder is dismissed on the current occurrence. The task is not marked complete and the next task is not generated. If the task is later marked complete, the next occurrence will not have a reminder set.
In order to generate a new task with a reminder, mark the task complete – this will dismiss the current reminder and generate next recurrence.
To mark the task complete, right click on the reminder and choose Mark Complete or open the task and set the Status to Complete.