Use when you expect something to fail or end badly, not just for literal crying. Ignoring the warning signs, they went ahead, but it's bound to end in tears.
Pro Tip 2/3
Emotional Outcome
Implies a strong emotional response, like disappointment or sadness, not just physical tears. The farewell party was bittersweet, knowing it would ultimately end in tears.
Pro Tip 3/3
Figurative Use
It's often used figuratively, meaning the situation could be very upsetting or disastrous. Taking such a risky shortcut might save time, but it will probably end in tears.