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system
how do i track 401k rollovers in quicken?
user
you definitely should not do what you are doing now (#2) since this is not a reflection of what actually is going on.  (unless you actually did transfer the equities themselves and not the cash.)    your first option is correct solution. as noted by mpenrow you need to make sure that the target account is also tax deferred.  if that still doesn't work and there is a bug you should still do it this way anyway. if it messes up your tax planner just make sure to include a comment so that everyone knows what is really going on. when i have had issues like this in the past i always try to stick to whatever is the closest indication of what actually occurred.
assistant