So I created a separate wallet a couple days ago as my "secure" wallet and I sent some small sums of bitcoins to it to test it out (in 2-10 amounts). In my regular wallet, I see 100 or so confirmations of my sent transactions, but I still have 0 confirmations in my secure wallet. Is there any reason why I'm not seeing any confirmations?
I did the exact same thing today and had the same 'problem'. I didn't know about that rescan option, so I don't know if it will work. I just deleted the block data and the client redownloaded it. When you import a wallet and already have blocks, the wallet you imported 'missed' the transactions, so it will not display them. If you redownload the block chain while the imported wallet is loaded, the wallet will see the transactions that belong to it as the client redownloads the blocks that affect this wallet. This had been my observation at least.
Let me know how rescan works if you use it.
Also, try putting the involved addresses into http://blockexplorer.com/
. If the transactions show up, they are confirmed (I believe).