Think that I once read that one can use "Fray check" or a similar product on the underside, to keep the umbrella waterproof, but I have not tried it.
*4u!
Jacqueline

Or maybe you could spray it with those products that seal tents.

I hope you succeed! I will then like to copy you!

The visual I have for hooping it is hysterical in my head! GL and post a pic of it.

I know that 10tje did one, mebey you can send her a PM and can she help you.

The bit at the end 'will I end up with a leak' made me laugh. Somewhere I saw a piece about umberellas but at the moment I dont know where. Have fun with the project and hope it works well

There is a product to waterproof leather/shoes for wearing in dewey grass. I've used it on the shoes I wore camping and it works. I don't remember the name, but it was in the shoe department. Wouldn't that prevent leaks???

I did one. I had to go to a friend's house and borrow her commercial machine, because of having to hold it while open to embroider on. I had to stand there and hold it the entire time since it would have been too heavy to let go of. Used sticky stabilizer and tent sealer on the inside. I actually used one of the redwork ladies in the rain from this site and put initials on it. It was for the friend that owns the machine. She said she loved it, but wasn't going to do any more due to the time taken in having to hold it. I haven't tried it again either.;)

I saw once an embroidered umbrella and it was beautiful(do not remember where), that is one of my future projects too, I do not know how to, but I woould think you will have to take the umbrella apart so can hoop it, find the right design one that does not have too much density, hoop and embroider it. ( Well i think), that my idea maybe someone has a better one.

I have not, however, sounds as tho many others have. H&*