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I wonder what 'pushing it' would risk me
If you get the upper pulley to clear a sprocket that's 4 teeth bigger than design, either by messing with the B-tension screw or extending the hanger with something like a Wolftooth road link, you risk having shit shifting at the top end because the pulley will now be too far from the small sprockets. You might also run out of total capacity - an RD6800GS with an 11-36 cassette can only handle a 12T difference up front because you only have a total capacity of 37T
https://bike.shimano.com/en-EU/product/component/ultegra-6800/RD-6800-GS.html
32 by design, 34 will nearly always work, 36 might be pushing it.