Sorry, quick follow up, this doesn't

[hidden nova]

Could you share your Layers panel please? Not sure to understand what's happening on your end.

[thorn dew]

Here are my main layers and the layers for this object specifically

Would it be helpful if I sent over a copy of my file to you?

[hidden nova]

If it's not too large... You can try...

Are you trying to mask the "Layer 0" in the Boat.psd file? If so the mask seems to be a regular layer mask so pen tool is not really the best tool to work in this type of mask.... I'm a bit lost.

[thorn dew]

May I email the file to you so you can analyze better?

[hidden nova]

is it large?

[thorn dew]

Yes it's over 300MB

I don't have Discord premium so it won't let me send it here

[hidden nova]

Ouch! no forget about that... I don't have Nitro too.

Your Layer 0 is not a Smart object so technique shown in the video should work. I dont understand the first layer panel you've sent... Are you trying to mask something shown in this screen shot?

[thorn dew]

The first screenshot covered this entire composition, of which the boat was a single layer.

[hidden nova]

Ok. Can you show me in this file where is the layer of the boat?

[thorn dew]

Yes

As you can see, it's a smart object with the smart object thumbnail attached to the layer

[hidden nova]

Thanks. Now double click on the thumbnail => It should open a window named Speedboat.psb

[thorn dew]

Yes

[hidden nova]

So it's not the same file than the one you shared (it was named "Boat.psd".
Can you share the screen shot of your Speed boat.psb?

[thorn dew]

Oh but when I double click the smart object layer, it opens 'boat.psd'

I recorded a quick video with a mobile device for demonstration

[hidden nova]

When you've placed the boat picture in your "Party Resort Island" file it was a psd file or a flat image (jpg or png)?

[thorn dew]

Initially it was a flat image, but it was converted to a smart object

[hidden nova]

Ok that's correct to work like this but honnestly double clicking a smart object should open it in a .psb file...
Anyway, could you make a quick selection with lasso tool (as shown in the video) > then with selection active click on the mask thumbnail (black square beside the layer thumbnail) > paint black inside a share a screen shot of the final result?

In the boat .psd

[thorn dew]

This is what happens when I attempt to do that

[hidden nova]

Ok I think I understand what's hapenning check your selection behavior is set like this one.

If you are using the pen tool with the circled mode you get an "inverted selection"

Here is a short video exemple... Hope we found the problem 'cause I'm going to bed now. Let us know if it's solved.

[thorn dew]

Thank you so much, this seems to have solved it

[autumn tiger]

Gave +1 Creative Carma to @hidden nova (current: #9 - 586)

[hidden nova]

Happy to hear that!

[thorn dew]

I really appreciate all your help!

[thorn dew]

Hi, may I ask another question please