How do I keep wrinkles out of tubeless rim tape?

Question

I just set up my Surly My Other Brother Daryl rims to run tubeless. They are 80mm rims and this is my first time setting up tubeless. I used Surly's official tubeless kit for those rims. I believe it uses Whiskey Parts tape. My first comment is that it's really hard to wrap the tape without wrinkles. The tape is flat, stiff and non-pliable. It doesn't want to mold in to a concave shape. I pulled hard and took my time, but there are definitely wrinkles. I tried to make sure that the tape is as wrinkle free as possible on the edges.

Got the tires mounted with a compressor. The front holds fine, but the rear loses pressure quickly as I ride (10 psi down to 6 is a few minutes). I must admit that there was a bit of a wrinkle at the valve. I assumed that the sealant would take care of it. No sealant is escaping anywhere (I think used 4oz per 5" tire).

I guess I have a few questions here:

1. Why is tubeless rim tape so stiff? I feel like I'd get easier results from Gorilla tape.
2. If there's a wrinkle at the sidewall or by the valve, is that the kiss of death?
3. If a tubeless setup is losing pressure while riding, will it most likely seal up after a few rides or do I need to pull everything off and start again?

Answer 1

1. I don't know why it's so stiff, but other brands of tubeless tape are also stiff. Many riders do choose to use Gorilla tape.
2. If the wrinkle only creates a small air bubble, but is sealed at both edges of the tape you are probably ok. If the wrinkle reaches the edge of the tape, i'd redo it. I found keeping the tape taught, but not with too much tension, and coming behind and really pressing it onto the rim an inch at a time works well for me.
3. It really depends what the problem is. I've had tubeless setups seal immediately, i've had one that took a full week of the 'shake and turn' technique and i've had one that did indeed finally seal after 2 weeks of riding.

If you are losing pressure that quickly (4psi in a few mins) there is definitely something wrong with your setup - generally even without any sealant the losses are in the region of 0.5-1psi/hour if things are setup right. Take the wheel and either stand it upright in the bath and slowly rotate to find leaks (don't dunk the hub!), or liberally coat it in soapy water and look for bubbles