Looking up...
Prima ho perso le chiavi, poi ho bucato una gomma, e ora piove sul bagnato: ho trovato la mia macchina inondata!
First I lost my keys, then I got a flat tire, and now it's raining when it pours: I found my car flooded!
a situation where misfortunes or difficulties follow one after another, often worsening the original problem
Dopo aver perso il lavoro, gli hanno anche rubato la macchina: proprio piove sul bagnato!
After losing his job, they also stole his car: it's just when it rains it pours!
Used to express frustration or irony when additional problems compound existing ones.
The phrase is always figurative in modern usage. Never use it to describe actual weather (e.g., 'it's raining on the already wet ground').
The phrase plays on the literal image of rain falling on already wet ground, intensifying the wetness. It reflects a cultural tendency to personify misfortune as relentless.