For what it's worth, prospect theory helps explain this paradox.
The first aspect is how probability functions in the mind. In experiment one, you're comparing 1% to 10%. A 1% objective probability gets stretched drastically to a 10% subjective probability, while a 10% probability gets stretched to 15%. Functionally, your brain feels like there's a 1.5x difference in probability when there's really a 10x difference in probability. In experiment two, you're comparing 10% to 11%. The subjective probabilities are going to be almost equally stretched (say, 10%->15% and 11%->16%). Functionally, your brain feels like there's an 1.06x difference between them when there's really a 1.10x difference. In other terms your brain discounts the difference between 1% and 10% disproportionately to the difference between 10% and 11%.
The second aspect has to do with how we compress expected values. In experiment two, we're comparing an expected gain of $1m with $5m. If the most utilons we can gain or lose is 100, then $5m would be around 90 utilons (best thing ever!) and $1m would be 70 utilons (omg great thing!), a difference of 20 utilons. In experiment one, we're looking at gaining 90 utilons (win $5m, best thing ever!) or losing 90 utilons (lose $1m, worst thing ever!) for a 180 utilon difference. Basically, losses and gains are compressed separately differently, and our expect utilities are based on whatever our set point is.
Combined, your brain feels like experiment one is asking you to choose between 70 expected utilons (70 utilons @ 100%) or ~67 expected utilons (70 utilons @ 89% plus 90 utilons @ 15% minus 90 utilons @ 10%). Experiment two feels like choosing between 11.2 expected utilons (70 utilons at 16%) or 13.5 expected utilons (90 utilons @ 15%). In other words, the math roughly matches out with a being 'really close, but I'd rather have the sure thing' in experiment one and 'yeah, the better payoff overcomes less odds' in experiment two.
I'm not trying to say if this is how we should calculate subjective probabilities, but it seems to be how we actually do it. Personally, this decision feels so right that I'd err on the side of evolution for now. I would not be surprised if the truly rational answer is to trust our heuristics because the naively rational answer only works in hypothetical models.
There are a number of experiments that throughout the years has shown that expected utility theory EUT fails to predict actual observed behavior of people in decision situations. Take for example Allais paradox. Whether or not an average human being can be considered a rational agent has been under debate for a long time, and critics of EUT points out the inconsistency between theory and observation and concludes that theory is flawed. I will begin from Allais paradox, but the aim of this discussion is actually to reach something much broader. Asking if it should be included in a chain of reasoning, the distrust in the ability to reason.
From Wikipedia:
I would say that there is a difference between E1 and E2 that EUT does not take into account. That is that in E1 understanding 1B is a more complex computational task than understanding 1A while in E2 understanding 2A and 2B is more equal. There could therefore exist a bunch of semi-rational people out there that have difficulties in understanding the details of 1B and therefore assign a certain level of uncertainty to their own "calculations". 1A involves no calculations; they are sure to receive 1 000 000! This uncertainty then makes it rational to choose the alternative they are more comfortable in. Whereas in E2 the task is simpler, almost a no-brainer.
Now if by rational agents considering any information processing entity capable of making choices, human or AI etc and considering more complex cases, it would be reasonable to assume that this uncertainty grows with the complexity of the computational task. This then should at some point make it rational to make the "irrational" set of choices when weighing in the agents uncertainty in the its own ability to make calculated choices!
Usually decision models takes into account external factors of uncertainty and risk for dealing with rational choices, expected utility, risk aversion etc. My question is: Shouldn't a rational agent also take into account an internal (introspective) analysis of its own reasoning when making choices? (Humans may well do - and that would explain Allais paradox as an effect of rational behavior).
Basically - Could decision models including these kinds of introspective analysis do better in: 1. Explaining human behavior, 2. Creating AI's?