I'm trying to turn this:

into this:

Put into words, I want the map to be the clipping mask of the lines. And then, I want the circle to be the clipping mask of that other clipping mask. I want to mask a mask. Note the blue outline map is a map duplicate in another layer, since clipping masks cannot clip something and at the same time have a stroke applied.

Illustrator doesn't allow multiple clipping masks as far as I know. So what I'm doing right now is:

1. Ungroup every shape in the map, then select them all and turn them into a compound shape.
2. Paste the lines on top of the map, select both, right click -> make clipping mask.
3. Export both a "with lines" and a "without lines" versions, mask in Photoshop.

Is there any way to do this directly in Adobe Illustrator?

• I'm a bit confused as to why you need to mask it in PS. Just duplicate the map layer, have one with lines and one without, then use the circle to mask the one with the lines. – Cai Oct 4 '16 at 10:08
• Yeah, that's what I was trying to do, hence my question. Turns out the file was bugged, seemed weird to me that Illustrator wouldn't let me do such a simple thing. But, since Illustrator has some weird workflows, I thought it couldn't be done. So yeah. It was a bug. – MrMerrick Oct 4 '16 at 12:11
• Well, glad you got it sorted! :) – Cai Oct 4 '16 at 12:14

First things first: A clipping mask CAN in fact have a stroke. Just apply the clipping mask, direct select the mask path and then apply the stroke. It can have a fill too if you like. Also, you can achieve multiple clipping masks by having a mask inside a mask inside a mask... Not best practice, but doable.

Secondly, you may be overcomplicating this. There is no need for the map to act as a clipping mask, it can just have a white fill. If you do it that way then you just need a circle with the lines clipped inside it behind the map and then one with the key line in front of the map. Simple, tidy and nice and flexible if you need to move the circle or add more circles.

I'd also suggest setting up your stripes as a pattern swatch to make things even easier.

• You're right about the stroke and the clipping mask. For some reason Illustrator didn't let me. Same with the mask within mask, Illustrator wouldn't let me but I tried reproducing this in a newly created document and I can do it now. It's like the other file bugged out. Weird. As for overcomplicating this: it all depends on your needs. I needed this to be a mask inside a mask, it was the quickest way to do and maintain it. That's what I asked about, not the workflow itself. – MrMerrick Oct 4 '16 at 12:05

As it turns out, it looks like it was an Illustrator bug. Just tried creating a new document and recreate what I was trying to do and now it gives me the option to create a mask inside a mask where before it would only let me "group" and "ungroup".

If you encounter this problem, try recreating what you're after in a new document.