Q2009 Bug Report - Placeholder Transactions Invalid w/Validate Command

I don't believe there is any fundamental new behavior here (Q2008 and Q2007 work the same); I think your Quicken "Preferences" are different (including the possibility that you upgraded from a version which didn't have the Preference that allows control of the display of placeholders).

Placeholders are never "replaced": the only way to get rid of a placeholder is to manually delete it.

But Quicken will "hide" a placeholder whose number of adjustment shares is zero if not told otherwise. In Q2005 (and earlier), there was no way to tell Quicken to display a "satisfied" placeholder (one with zero adjusted shares) ... you could only force the display by entering a transaction that caused the number of adjusted shares to be non-zero.

I'm pretty sure that Q2006 (and I know Q2007 and later) allowed the user to always display "hidden" investment transactions. If you turn that preference on, you'll see your placeholders, and your "backfill cash transaction"s in the account "Transactions" tab.

Edit > Preferences > Quicken Program > Investment transactions

Put a check mark in the "Show hidden transactions" box.

The backfill cash transaction is Quicken's way of insuring that a transaction, entered to satisfy a placeholder, will have no effect on the cash balance in the account. I think they were always there, but if your version was old enough, probably hidden.