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I’ve had trouble with crap Specialized hybrid tyres and Veloflex on tubeless rims before.
@edscoble has had fun with Vittoria Randonneurs :D
I recommend a couple of Pedros tyre levers, by far the best normal lever I’ve used. And for tubeless rims one of these:
miro_o
edscoble
I need help... struggled massively to get these tyres on, obviously damaged both tubes in the process as some brute force was needed and now I can't get bloody things off again now. Any suggestions before I lose it and sack off the whole bike