This is the image I made for the project. So, yeah… compromises were made. 
So of course I downloaded your image to see if I could replicate your problem.
And of course it transformed just fine. I added an image and flattened; that transformed just fine. I added text on top of that, and the whole thing transformed.
It’s clear you’re having bad juju. Sometimes computers take an evil glee in foiling our plans. I know my inkjet printer hates me.
My brother gave me his old desktop; I only use it for Photoshop. It isn’t up to running the slicer software, so I had to load Linux on my chromebook. That worked for a while, then refused. I found an online slicer, and that’s working now. I wonder what will go wrong next.
I am not sure to be honest… but I see you made it.
I am using Sketchbook for making my pictures first, then just importing to Design Space, so not very familiar with the program. Also, I am mainly using it for cutting wool-blend felt 
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I experimented in Photoshop too, but I have the latest, greatest, version. I get to work in Photoshop, Illustrator, InDesign for my job. It’s Ice Cream! all the time. I do eLearning and use Storyline these days, but editing photos makes it all easier. I don’t know what I will do when I retire, probably pay for a subscription though it’s rather spendy for the core products. But I love them. Maybe someone will leave me some money!
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@grabacoffee Yeah, I usually make something in Photoshop to import because it’s what I have and am used to. Mostly I cut paper.
@marionberries Lucky! I was able to buy the last hard copy version back in the day through a friend who worked for Adobe at the time. Employees got a certain number of discounts/year and she shared one with me and it was a HUGE discount. Alas… it is no more.
I’m sorry I didn’t read this sooner, as this info is probably no longer useful, but there’s also a “warp”
option on the Edit>Transform menu, and that allows you to actually curve the object. I hadn’t seen anyone mention it. It was added in version CS2, so it should be in your version.
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THANK YOU! I think this will be great info to have in the future!!!
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PS 6.0 doesn’t have the warp option. Sigh.
And my printer died today. Sigh.
I feel your pain. Our all-in-one printer died about a year and a half-to-two years ago and I can’t work up the interest to research a new one. We’re limping along with a black-only laser printer and taking the occasional thumb drive to Staples.
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Two hours of google-fu, experimentation, and judicious cussing got the printer working. Although the error message I was getting AND the tech help line said the printer needed professional attention, it turned out it just needed new print cartridges. I didn’t have new ones, but was able to refill some grotty old ones and print the forms I needed.
Computers, making our lives easier.
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