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What I normally do is:
1. Stamp the image in BLACK ink on WHITE paper.
2. Scan it and save it as a JPG
3. Import it into my Cameo software.
4. Trace it and give it a bit of a margin (as I prefer).
I don't normally color it. This usually works with some tweaking.
Unless I'm not understanding your query. If so, sorry!
__________________ "Satan trembles when he sees the weakest saint on his knees."
The way I make cut files for stamps is to stamp, scan and then trace in the software to get a cut file.
Once I've cut file, then I cut first and then stamp. You mentioned that with your stamp, it might be hard to do so. I can't think of any other way of doing it unless and until your machine uses registration marks to do the cut. In which case, you can stamp, add registration marks and then cut. Here's what I'm talking about: Stamp and cut with a Silhouette | Clever Someday