Is the query just insanely complex? Like the plan would be some simply titanic amount of RAM?
I don't think it's even possible to have a plan that large, but who knows?
I'd check the amount of memory being used by SQL Server vs the amount allocated to the OS and other processes. It sounds like you may have already done that, but allocating more memory isn't the same as checking those two things, so I wasn't quite sure if you had.
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