Somehow got irb history broken.
Googling brought a solution
Here’s the simplified version of the fix I’ve came with:
module IRB
def HistorySavingAbility.extended(obj);
Kernel.at_exit{ HistorySavingAbility.create_finalizer.call }
obj.load_history
obj
end
end
Put it into .irbrc
Turns out that finalizer is not guaranteed to run, so Kernetl.at_exit hook should be used instead, to persist history