@Georgy предложный падеж........ in most of my encounters with this, it is referred to as the prepositional case in English but I’ve heard the term locative case before

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What is the difference between он на крышу and он на крыше ?Feel free to just provide example sentences.

он на крышу - куда? (направление)он на крыше - где?

Он поднимается на крышу.Он поднялся на крышу.Он находится на крыше.

Where is he going/climbing? На крышу (direction)Where is he? На крыше (location)

@Anthony_Rahming You’re absolutely right! Different cases for different situations:)

он на крышу - куда? (направление)
он на крыше - где?

Он поднимается на крышу.
Он поднялся на крышу.
Он находится на крыше.

Where is he going/climbing? На крышу (direction)
Where is he? На крыше (location)