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It depends on the bike. I'm pretty sure I was running 32T with the shortcage Ultegra Di2 RD before I went to the long cage version and ran a 36T. I now run 40 and 42T with the shadow cage version of the Ultegra RD and still no Wolftooth. Longer chain and it's worth a try before buying a Wolfie. Oh, at some point I also went to 46/34 chainrings so that might have helped with the massive cassettes.
hippy
My old man runs a Di2 9070 RD with 11-28T cassette and 50-34T DA cranks up front. He needs a 32T rear cog.
Can he go with a Wolf Tooth Roadlink and install a 11-32T without issues? Should he try without a roadlink, just maxing out on the B-screw? He never really cross-shifts, but I guess the chain will still be a bit loose every now and then. Any other options? He's also considering this, but we're after a simpler solution.
(I already told him to just get a medium-cage Ultegra RD but he's reluctant. :P )