As quoted from Megger "Application guide for power factor testing of power & distribution transformers" and attached to this post for reference:
"Never perform electrical tests of any kind on a unit under vacuum. Flashovers can occur at voltages as low as 250 volts."
As quoted from "Transformers: Basics, Maintenance, and Diagnostics"
"Transformers must not be sampled if there is a negative pressure(vacuum) at the sample valve. If there is a vacuum at the bottom, air will be pulled in when the sample valve is opened. Wait until the pressure gauge reads positive before sampling. Pulling in a volume of air could be disastrous if the transformer is energized."
Transformers_AG_en_V01.PDF