I haven't had any pictures yet on tubeless, but according to Tom A. you may need a tubeless patch kit if you are having trouble with punctures that don't seal

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Keep riding and lean the bike from side to side (fishtail) to get the sealant to hit the hole.

Put more sealant in before you get a puncture.

Your initial thought is the way that's worked for me in the mt bike world. I have only had one road tubeless puncture in several years of trying. You want to get as much of the 'stuff' as possible at the puncture site. Holding the puncture against the road, letting gravity drop sealant towards the puncture, and giving it some time to plug works. You may lose a lot of air before it's sealed if it's a larger puncture. Road tubeless is sort of a different beast because of how high pressure the system is. Tom A. was one of the first to recommend the tubeless tire repair inserts for a puncture that wouldn't seal. I carry them now, but haven't ever had to use one.

I 'practiced' on an old Vittoria Corsa tubular filled with sealant in the past (before dropping them in the trash). It wasn't the most scientific, but I would jam it with a tack. The thumbtack puncture almost always sealed just while spinning. Then I started using a nail. The nail puncture would not seal very well unless I held it against the ground, but it held air just fine after sealing. Spinning the tire post-nail was usually good for a whooshing noise and making more of a mess. I bet I punctured that tire 20-30 times that day. All punctures were directly through the tread, not the sidewall. I also had a bit more sealant in there than standard. I'm guessing 2-3oz which is quite a bit for a 21mm tubular. I know it's a tire with a latex tube and not apples to apples, but it was close enough for me. It was fun making a mess out in the driveway too.

Thanks for sharing that testing info. Holding the puncture against the road seemed to work for me. The sealant sprays everywhere if I just keep riding, although I have had very small punctures seal this way, too.

I have read that some folks put a small amount of glitter in the tire along with sealant to help close larger holes.

These plugs work great for bigger punctures that don't seal right away, or in the sidewall of the tire where sealant doesn't pool as well. Inserting a plug takes about 2 seconds. If you have a co2 canister ready and a plug already through the eye of the tool, you can usually get off the bike, find the puncture (based on where the sealant is spraying from), insert a plug, and be back on your bike in under a minute.

Small punctures usually seal by themselves if you are running enough sealant, and a good sealant like Stan's Race Day.

If i don't have a plug kit with me and its a big puncture, I'll usually spin the tire with no weight on it. From what I've heard, the mixture of air and sealant helps get a good seal. When it stop spraying (usually a few seconds) I put the puncture at the lowest part and let sealant sit there for a minute or so, then spin it again. Then I'll fill it back up with air and try again. Even with good sealant, some punctures just won't seal without a plug to put in.

If you're racing tubeless, it's definitely a good idea to always carry those plugs and a spare tube, just in case.

This is true.

Some things to keep in mind:
-Glitter may not be environmentally friendly. Others advocate ground black pepper.
-It will not go through any injector or valve stem. Its job is to 'clog' and it will clog those two immediately. It has to be poured or scooped directly into the tire.
-Hitting the tire with a big shot of air when seating your tires in a tubeless manner can shoot glitter out of the sides before it seals.
-Glitter will not come off the inside of your tires (if you care). It's also messy in general and hard to clean.

In addition to pointing it down, anecdotally I've had best luck with the sealant when it's dry. When you flat in the wet, try to get the puncture site dry or in the sun. If you have beaded water on/around the hole it's much less likely to clot, IME.