dovevi essere

you were supposed to be; you must have been

→ dovere
phrase Rare #24,483
you were supposed to be; you must have been Used for a past expectation or obligation (“you were supposed to be”) and, depending on context, for an inference about the past (“you must have been”).
IT: Dovevi essere stanco dopo il viaggio.
EN: You must have been tired after the trip.

In ogni caso, dovevi essere pronto.

In any case, you had to be ready.

— TÁR (2022)

Dovevi essere con Tom ieri pomeriggio.

You were supposed to be with Tom yesterday afternoon.

Non dovevi essere in custodia alla polizia?

Weren’t you supposed to be in police custody?

— The Man from Nowhere (2010)

Tu dovevi essere preparata.

You should have been prepared.

Dovevi essere preparato.

You had to be prepared.

Non dovevi essere alla festa di Elton John.

You weren't supposed to be at Elton John's party.

— Love Actually - L'amore davvero (2003)

Non dovevi essere in Salvador?

Weren't you supposed to be in El Salvador?

— Tutto su mia madre (1999)

Quando l'hai scritto, dovevi essere molto innamorato.

When you wrote it, you must have been very much in love.

— La grande bellezza (2013)

Tu dovevi essere con Tom ieri pomeriggio.

You were supposed to be with Tom yesterday afternoon.

Dovevi essere molto divertente.

You must have been so funny.

— Mosca non crede alle lacrime (1980)

Dovevi essere tu.

It had to be you.

— La storia fantastica (1987)