Bleed

Yes, as @Earth Oliver suggested, create a selection of the pumpkin, inverse selection, content aware fill (left hand image below), inverse the selection, expand and mask. Work in layers so that you separate the original image from the added bleed and retouching etc.

You may then wish to retouch the area where the die will meet the bleed so that there is better content where content aware fill didn't do so well, as suggested by @Kevin Stohlmeyer.

A very quick example with the marching ants selections visible to indicate the diecut line and the original + bleed:

What am I missing here?  You have what appears to be a selection of the pumpkin that has been expanded.  Is that what you would like to achieve?

You have a white background so an easy selection with Select Subject or The Object Selection Tool.

Then Select > Modify > Expand

I used a value of 20 pixels for this

I must be missing something though.

Hi!

Are you wanting to duplicate the dashed cut line that is 1/8 of an inch outside the image? 

Here is a simple way to do that.

1. Make sure your artwork is on a layer by itself with transparency.

2. Command click on your image in the layers panel to get a selection marquee. Then go to the Select menu and choose Modify>Expand, and I used a number of 25, but depending on the resolution of your image, that number might change.

This will give you a selection that is approximately the 1/8 inch bleed area. 

3. Next, you will want to add a layer underneath your image, then choose Stroke from the edit menu and again the number you put in will be dependant on your resolution. I used 1 pixel and hit ok.

Unfortunately, I can't help you with a dotted or dashed line, but there might be someone else here on the forum who can!

Hope that helps!

Michelle

In addition to these ideas, be sure to protect this layer. Duplicate it and work on that or do all the painting / CAF on a separate layer.

~ Jane

you're just going to have to scale it up, then trim off some of your original image. Or you could try something more experimental and content aware fill all the edges...

This will have to be done manually.

You could try to duplicate the layer and scale the graphic up, but I'm guessing it wont create a consistent bleed.

I would paint the area in with the colors from the pumpkin or use the Stamp tool to extend it.