How do I handle this situation with my landlord and a leaky air conditioner?

Bypass the maintenance guy and call the property owner directly. I’m sure they’ll be interested in the wall damage at the very least and hopefully they’ll light a fire under maintenance to get it repaired. You might check to see if there’s a tenant’s union in your area and find out if you can get compensation for your damaged property. Make sure you document every time you called about this issue and take pictures of the damage.

To speak up on behalf of the maintenance guy, because he should have said this himself, perhaps: the sealing, to be effective, should have been done from the outside anyway (point number 1) and (point number 2) water leaks through and around windows in cases like this are some of the more difficult issues to resolve, because there are so many places in and around the window where the leak could be starting, such as the top of the window or any of various places around the sash (and if it’s an old, warn or loose-fitting window in the first place, then there’s just no telling where the water can be coming from until every possibility is sealed, one by one).

But @Blueroses probably has the best usable advice for you for now: contact the landlord or owner directly and file a claim for damages with them. They may not give you a new mattress, but they might give you some cash for the damage and the inconvenience you’ve been put through – and they definitely need to get the window leak fixed, as well as get the wallboard repaired (after the leak is fixed).

@WasCy I wondered if maybe it had be sealed from the outside. I would have no way of checking since we’re on the 2nd floor and I’d need a ladder. And yes, I assume it’s probably difficult to locate where exactly the leak is coming from. That’s why I called while it was actually happening. I assumed he’d want to come see for himself the exact spot it was dripping from. But he instead said “tomorrow”. I can show him the part where it drips from, but that probably doesn’t help much.

@ItalianPrincess1217

You’re right. Showing him the point where you see water entering / leaking (inside) only tells him that it’s coming from some place above that. So if the leak is at the bottom of the window, then he would not have learned much to exclude.

@WasCy That’s what I figured. Let’s say I plugged in my air conditioner again and ran it. If water dripped on the electrical outlet while it was running, what could potentially happen? I don’t intend on trying this out. Just curious.

Can you turn power off to the problem outlet without turning it off to the AC? Your breaker box should have labels as to what goes where. Or is the problem outlet to AC outlet?

@klutzaroo The outlet that the ac plugs into is the same one that the water is leaking on. It’s the only outlet on the whole wall.

@ItalianPrincess1217 Could you duct tape the cord up out of the way of the drip line and run an extension cord to another outlet temporarily?

@Blueroses I wish it were that easy. The plug needs a special outlet. It’s not a normal universal one that can go in any outlet.

Oh, of course it is. I thought of that right after I posted. What a pain. How about duct tape and plastic to seal off the outlet from the drips?

@Blueroses Good plan! That would work. Although I wonder if I should make sure the outlet dries out completely before sticking anything in there. It got rained on for quite awhile.

Since you turned it off at the fuse, you should be able to pull the outlet cover off and dry it out enough with paper towels.