Probably yes.
Hyenas lack an external vagina. Their clitoris is a pseudopenis about 15 cm long. This is the route through which the young must emerge into the world. Unfortunately, the young are quite large for mammals of this size, and this isn't made any easier by the fact that the opening is about 2 cm in diameter. A fetus ready to emerge has 6-8 of them.
For this reason, the first birth ends with a rupture of the foramen, which results in the death of new mothers in 10–20% of cases.
Worse still, only 25% of puppies survive birth.
Additional problems await 'deeper' - the hyena's birth canal is 60 cm (a lot) and the umbilical cord is much shorter, which means that the birth must be quick so that the fetus does not die from lack of oxygen.
So do hyenas have the most cruel childbirth in the animal world?
I think the inglorious crown goes to our feathered colleague from New Zealand:
The photo shows the skeleton of a kiwi bird, along with the egg it needs to give birth to.
You see, the kiwi's ancestors included the Madagascar ostrich (3 meters tall, 500 kg), and its cousins include the cassowary and the emu. The kiwi's isolation on islands has had an evolutionary impact on its size—known as island dwarfism. Everything about the kiwi has shrunk—except for the size of its egg.
If I remember correctly, his bones and internal organs 'regroup' during labor to allow for the expulsion of this colossal baby.