Newb cutlines Software question

Hi , I use a Roland sp540v and can’t believe how hard it is to create a cut line around a image .

is there a easy way to take a image from goggle let’s say a a nice text logo and create a cut line ?

I am new to this and have managed to make a box cut contour with the Roland swatches , but I have tried putting a circle using the circle tool
And selecting the Roland cut colour but it still does not cut a circle

In versa works I know I can select cut image boundaries but this only seems works on square Artwork .

I would be happy to pay someone to do a Skype video call if they can show me a quick and easier way to creat a cut lines using illustrator.