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How do I track 401k rollovers in Quicken?
When I did this I sold the stock out of my 401k account.  Then transferred the cash to my rollover IRA account.  No tax event was created for me.  Make sure your rollover IRA account is listed as tax deferred.  If this still doesn't work for you then it could be a bug in Quicken and your best bet is the Quicken forums.  Good luck.