Why won't Quicken 'insert transaction' work?

I am told Insert transaction only works when you sort transactions by 'date'.

I sorted by 'date & order entered' for many years and insert transaction would work most of the time but lately insert transaction works only when you sort transactions by 'date'.

I used Quicken 2009 since 2009. I used Quicken 2012 for a few months.

Quicken should allow insert transaction to work no matter the sorting method