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Yeah, I've seen this as well - it seems to get compounded by the fact that restarting the attempt over and over makes the conversation longer, which means eventually you'll hit the limit with fairly little work done and it asks you to summarize it... which I expect then makes the overload worse.

Yeah, that retry button seems to just start the task flow from the very top instead of picking up where it left off in the task flow. Then it pulls a bunch of context and eats lots of tokens to get started again.