Running the latest client 0.7.0 on OSX 10.7.4, opened the client roughly 1000 blocks behind the chain, and started syncing. However once the client had caught up to the chain, the Estimated total blocks was still less than the current total blocks.
I realise that when you open the client the estimated total blocks is just an estimate, however it should never be displayed as less than the current number of downloaded blocks, otherwise it might cause some concern for users.