Indeed. Consider a variant of the thought experiment where in the "actual" world you used a very reliable process, that's only wrong 1 time in a trillion, while in the counterfactual you're offered to control, you know only of an old calculator that is wrong 1 time in 10, and indicated a different answer from what you worked out. Updateless analysis says that you still have to go with old calculator's result.
Knowledge seems to apply only to the event that produced it, even "logical" knowledge. Even if you prove something, you can't be absolutely sure, so in the counterfactual you trust an old calculator instead of your proof. This would actually be a good variant of this thought experiment ("Counterfactual Proof"), interesting in its own right, by showing that "logical knowledge" has the same limitations, and perhaps further highlighting the nature of these limitations.
Do you build counterfactuals the Judea Pearl way, or some other way (for example the Gary Drescher way of chap. 5 "Good and Real")? Or do you think our current formalisms do not "transfer" to handling logical uncertainty (i.e. are not good analogues of a theory of logical uncertainty)?
Consider the following thought experiment ("Counterfactual Calculation"):
Should you write "even" on the counterfactual test sheet, given that you're 99% sure that the answer is "even"?
This thought experiment contrasts "logical knowledge" (the usual kind) and "observational knowledge" (what you get when you look at a calculator display). The kind of knowledge you obtain by observing things is not like the kind of knowledge you obtain by thinking yourself. What is the difference (if there actually is a difference)? Why does observational knowledge work in your own possible worlds, but not in counterfactuals? How much of logical knowledge is like observational knowledge, and what are the conditions of its applicability? Can things that we consider "logical knowledge" fail to apply to some counterfactuals?
(Updateless analysis would say "observational knowledge is not knowledge" or that it's knowledge only in the sense that you should bet a certain way. This doesn't analyze the intuition of knowing the result after looking at a calculator display. There is a very salient sense in which the result becomes known, and the purpose of this thought experiment is to explore some of counterintuitive properties of such knowledge.)