@curtis-r You have left out some important details…
Assuming that your sensor.wake_time_1 returns just a time in HH:MM:SS or HH:MM format:
value_template: >
{{ now() >= today_at( states('sensor.wake_time_1')) - timedelta(minutes = 30) }}
If you’re using the standard sensor.time, there is no point using it… just use now().
For time comparison based Template triggers it is best to use a “>=” instead of “==” so you aren’t limiting the trigger to having to hit the time value exactly.