Is that picture now or when it was new? Because it looks pretty healthy to me. Lower leaves will die off naturally even under the best conditions. Btw it’s a Dracaena massangeana in case you didn’t have a name for it. If it is an old photo, can we see a current one?

Dracaenas are very strong plants. bulletproof.

Dracaena fragrans 'Massangeana'

Agree, it looks wonderful! Loss of older leaves is normal as the trunk lignifies.

Thanks. I stand corrected on the full name.

I'm assuming the main pot has drainage and the cache pot doesn't. There's a problem if the pot that holds the plant sits in the effluent that has passed through the soil and out of the drain. Dracaena doesn't deal well with a high level of salts in the soil solution, and it doesn't react well to fluoride, which is accumulative in plant tissues. If you want the water in the cache pot to evaporate, you should set the pot holding the plant up on blocks, so there is no pathway by which the effluent can make its way back into the soil.

You should wait until the soil is nearly but not quite dry before you water. I suggest that you water at the sink and apply enough water that at least 15-20% of the entire volume of water used to wet the soil exits the drain hole(s). Then, tilt the pot at a 54* angle until it stops draining. If there isn't a drain hole through the bottom of the pot where it transitions to the sidewall, make one; and make sure it's the lowest point when you tip the pot. You can see in the picture below, how much additional water exits the pot when you tip it by comparing B to A.

Try using a 5/16" wooden dowel rod (any hardware or stores like Lowe's, Home Depot, Menards, ....) cut in half and ends sharpened in a pencil sharpener as a 'tell' By sticking it deep into the soil, it will 'tell' you what moisture conditions are deeper than a finger's depth from the top. Water when it's almost completely dry.

You also should maintain a good nutritional supplementation (fertilizer) program that meshes with your watering habits. More on that if you have interest. You can also employ objects like bricks or empty soda bottles as 'ballast' in the pot bottom to help reduce the amount of excess water your soil can hold. It's extremely effective if properly implemented. Again, more on that if you have interest.

Al