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Converted a couple of wheels to tubeless using rim strips and specialized 2Bliss tyres.
They went up no problem.
I then tried doing a ghetto tubeless conversion with a 18" inner tube, effectively making my own rim strip.
With the specialized tyres it went up fine.
I've tried some other tyres (both wire bead) and there is no chance of them going up.
Do wire bead tyres not work well with tubeless?
The tyres in question are Michelin wild grippers and some wtb timberwolfs, both used if that makes any difference.
I've got a ghetto tl conversion on my bonty rims. And I'm running a 2.4 mk on rear and a 2.2 rubber queen on the front. Both wire bead and both went up off track pump with ease. But from what you said about using a sliced tube I'm guessing the lack of non removable valve core is restricting any kind of mass air flow. Afaik wire beads are best for ghetto tl. But could be wrong.
Compressor
The tubes I bought have a removable valve core and are threaded so I can lock the valve down.
Only thing I haven't got is a compressor so think I'll have to invest.
Just surprised at how easy the specialized tyres go up and how impossible it is with the non tuneless ready tyres.
I did the ghetto method once but it was a PITA. A recent post had this and it worked well: