I’ve had to put a tube in 3 times - once on my first ever tubeless ride and again a few weeks later, both before I bought a DynaPlug 
. The third time was about 2 miles into a 50 mile gravel sportive, the plug sealed it fine but as I was pumping it back up the tape around the valve hole split and it wouldn’t hold air for love nor money.
I’ve ever had to make “the call,” was this year. And it wasnt even because of a mechanical. I’d gone out for a ride probably a bit too closely after being sick. Got about 40 miles in, on way back home…10 miles from home, and just ran out of gas and motivation. Stopped in a brewery within sight of the bike path, had 2 beers, at which time it started raining. Given I had zero motivation to keep riding in the dry…the rain was the dealbreaker. It was Uber or my wife at that point. I wasnt going to get on my bike to go to the end of the block 
I like how you think!
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you got me on that one LOL
Have been using Tubeless on the road for about 5 years, and never had a problem getting the tire off and an innertube on the 2 occasions where this have been needed.
It is great, especially for us heavier riders, as it allows running lower pressures and still avoiding pinch flats, which is a bit of a problem on UK roads.
I do have a question for the hive mind.
What kind of patches do you recommend for those cases when a puncture is a bit bigger and need it. I have been using Lezyne patches, and they don’t seem to like Stans sealer very much as it seems to come part after a little while…
any ideas on this very much appreciated
Try Dynaplugs - they’ve worked great for multiple larger punctures and effectively form a permanent seal.
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Just replaced the rear tire yesterday GP5K STR for the same, and it went absolutely fine, piece of cake to mount.
I use normal inner tube patches. (Cheap ones I got from Wilkos - need to find somewhere else to buy from now 
)
I also use Stans, I’ve never had a patch come off. I’ve found that they don’t stick well initially (likely because the inside tyre casing isn’t rubber), but I just leave the tyre overnight, before putting it back on and adding sealant.
I’m just going to pile on. Carry a tube for a last resort. Dyna plugs work great. I’ve seen two people abandon a group ride with flats while tubeless. first took a roofing nail through the rim and tore up the rim tape pretty bad. Even if we took the effort to fix it all, it would have been a process tubeless or tubed. The guy said F it right away when he pulled the nail out and called for a ride. The other flatted, when I pulled his tire off, the sealant was completely gone and dry. He already had 3 dynaplugs in the tire. I pulled out 2 stables as well. Mounted a tube that failed not much further down the road. I am guessing we missed another staple or glass in the tire.
I’ve seen a few flats that took a tube, and my end thought on road tubeless is this now: if you have to run over 70 psi due to rider weight or tire size, just stick to tubes. ideally your bike will fit 30s and most everyone should be able to ride tubeless then.
Knock on wood, since going tubeless 5 years ago, I have never punctured. Use a quality tire, on a quality rim with quality sealant and the system works great. A properly designed rim is no harder to mount a TLR tire than a standard clincher, but it requires proper technique.
I woulda said “F it” even if I was riding a tubed wheel!
My LBS gave up trying to fit mine. It took 2 people, an oven tyre grippers and a couple of heavier duty tyre levers to get mine on. I wouldn’t even attempt to try and take it off at the roadside to put a inner tube in. Plugs and a pump is all I take.
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What was your wheel/tire combo?
I finally had to live out that “what if” scenario with a puncture that wouldn’t seal (sealant in the tyre had dried up, so my mistake) on my gravel bike which had tyre liners, on a 150km gravel ride. I thought if this ever happened, I would have to stick the liner up the back of my jersey (I tested this at home). It worked out on the road 
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I feel like the denizens of this thread should have a pitched battle with those of the “hookless = dangerous” thread.
If a tyre is easy to mount by hand it is easy to dismount at high shear forces or speeds and is dangerous.
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Hooked rim
Tire mounted too easy a week before (January 2018), but I “didn’t get the memo”
Blow off at 25mph, thankfully I was scrubbing speed because it was January and my hands were cold
19 miles from my car, on a logging road in the middle of nowhere
thankfully it was a well attended group ride and I only waited an hour to get rescued
never ever ride a tire that goes on too easy!
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“Easy” is hard to define. I can easily remove a tire from my wheels, just requires the right technique. I’m not worried about the tire blowing off.
I stopped carrying a tube, though I think I’ll start packing one just in case. I’ve had a slashed tire (only the second I can think of in 100,000+ miles) that I recently called a ride for and a couple pinch flats, only one I called a ride for. Only times I can think of where I called for a ride.
But also, I have a feeling that my tires are so full of thorns and other debris that a tube will instantly flat.
Personally, I don’t intend to run tire liners for road use - not sure if anyone here is thinking of it, but my reasoning is that they make removing tires harder, and I do want to be able to get a tube in.
So far, my experience has not been mind-blowing. I got two sidewall cuts that refused to seal with two Dynaplugs each. That said, that would also defeat a tubed tire. First cut I got a tire boot (I have a cut up section of tire in my flat kit) and a tube in there. Second cut, the sidewall seemed to seal at first, but it would go flat at my desired inflation pressure. I should have just booted that tire, but I kept trying to see if it would hold.
Anyway, those were Vittoria Corsa Pros, which are not hard to mount and which have very soft sidewalls. I replaced the damaged rear with a Conti GP 5000 AS TR, and I’m going to run the front Corsa Pro until it’s worn out. The Conti was markedly harder to initially mount. Haven’t needed to service it on the road yet.
My first experience with Vittoria AirLiner road inserts:
More importantly, my scariest flats have been in the mountains above 25mph.
First was with Conti GP4KSII tires and tubes at about 35mph:
rudely interrupted a ~16 minute HC descent (~3200’ / 975m descent).
Tubes 
Could have been a total disaster - with tubes or tubeless - but I brought the bike to a controlled stop.
Thats why I use inserts. The safety of tubulars without the hassle.
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So, your Air Liners let you go 30 miles at 12mph. In my view, an alternative is to boot the tire and put a tube in it.
Anyway, I see you had another sidewall tear that didn’t seal, and maybe sidewall tears are just a lost cause.