Unless you test things, and provide feed back, is is difficult to analyze the situation. For instance, If you can test the cyl, and verify whether good or bad that will lead you to the next possibility. You can eliminate the cyl by doing the needle valve test. Use a needle valve or gate high pressure valve, and install in the A port/base end. Connect the outrigger cyl hose to the needle valve. Start the engine, and raise the machine up on the outriggers, and close down the needle valve. If the unit stays up, then you can assume that the cyl is good.
Is there any auto leveling system installed for the outriggers? .