rhdpZH9CS8tKExLU9VmLDFaYmAHQfhnC6j

Unfortunately, I securely deleted the plain text wallet before I realized there was an issue, so it was probably overwritten many times with random bits.  I was basically following the steps I found in a thread describing how to create a secure savings wallet.  

I guess I can confirm this bug, and I demonstrated it in a spectacular fashion.  

The sad thing is, I think the 100-address pool is meant to help protect against loss like happened to this guy:
http://forum.bitcoin.org/index.php?topic=782.0

But if this 100-address pseudo protection didn't exist, I would have been obsessively making completely new backups after every transaction.  The 100-address pool sort of tricked me into a false sense of security.

I know it's my fault for relying on the pool without verifying that it actually existed.  I don't think I've ever been this depressed, I'm actually crying.  I can't believe this happened.

I tried starting Bitcoin with only wallet.dat and let it rebuild from scratch, but it only has the 0.02 BTC.

The problem is that I initially created a new empty savings wallet, encrypted it, and backed it up.  That encrypted savings wallet apparently only had 1 single address.  I only have a copy of that initial encrypted savings wallet with one address (although I thought it was supposed to have 100 addresses).

After my large transfers to the savings wallet, I did delete my later copy of the wallet.dat.  I thought my initial encrypted copy of the savings wallet had 100 pre-generated addresses, but it didn't.  Newly created wallets DO NOT actually have a key pool of 100 address, they just have 1 single address.  

Yes, unfortunately.  I hate to admit it, but I lost 7208 BTC.  At least for me, that's a lot.  My savings just got destroyed.  Ugggggghhhh.  I seriously can't believe it.  I'm totally screwed.

Thanks for confirming.  This makes me very depressed.  Everything I had read made me believe that 100 pre-generated addresses were created for new wallets.

If I re-open the Bitcoin application with this wallet.dat, wait for it to show my 0.02 BTC transaction, then quit Bitcoin, I can use dbdump.py to see that it now has 100 addresses.  However, none of them are the addresses where I transferred all my savings.  I guess the pool of 100 addresses isn't created until a transaction is completed.  We should update the Wiki to clarify this.  I would edit the Wiki myself, but I'm busy contemplating jumping out a window in despair.

I'm using Mac OS 10.6.7.  I definitely backed up the directory containing the actual wallet.dat file.  My initial 0.02 BTC transfer showed up in the wallet.dat file that I restored from my Bitcoin-savings-encrypted. 

On a Mac, the Bitcoin directory is at:
/Users/username/Library/Application\ Support/Bitcoin

I think I just managed to lose a large number of BTC.  Here's what happened:

1. I had a wallet with all my BTC.  I quit Bitcoin (version 0.3.21) and renamed the entire Bitcoin directory Bitcoin-checking.
2. I re-opened Bitcoin, which created a new Bitcoin directory and downloaded all the blocks again.
3. I copied the address shown, quit Bitcoin, renamed this directory Bitcoin-savings, encrypted it as Bitcoin-savings-encrypted, and saved it in multiple remote locations.
4. I renamed Bitcoin-checking to Bitcoin, then restarted the Bitcoin application.
5. I sent 0.02 BTC to the address from step 3.
6. I quit Bitcoin and renamed the Bitcoin directory to Bitcoin-checking.
7. I unencrypted a copy of Bitcoin-savings-encrypted, renamed the directory to Bitcoin, and restarted the Bitcoin application.
8. My 0.02 BTC showed up in this savings wallet.
9. I copied another address, quit Bitcoin again, renamed the directory as Bitcoin-savings, swapped in Bitcoin-checking and sent lots of BTC to this new savings address.
10. I never updated the Bitcoin-savings-encrypted file after step 3, because I thought the wallet automatically contained 100 pre-generated addresses to start.
11. I securely deleted my unencrypted Bitcoin-savings directory with multiple passes.
12. Later I unencrypted a copy of the Bitcoin-savings-encrypted directory, renamed it Bitcoin, opened the Bitcoin app, and only my original 0.02 BTC are shown even after all the new blocks are downloaded.

So it looks like I lost all the BTC I transferred to my savings wallet!  I downloaded bitcointools from here:
https://github.com/gavinandresen/bitcointools
and viewed the contents of my savings wallet.dat from Bitcoin-savings-encrypted with this command:
python dbdump.py --wallet

The output only shows a single PubKey and PrivKey pair (where I sent 0.02 BTC).  It also shows two lines that say "Unknown key type: bestblock".

I was under the impression that wallets automatically have 100 pre-generated keys as soon as the wallet is created as mentioned here:
https://en.bitcoin.it/wiki/Securing_your_wallet

So why did my savings wallet that I encrypted in step 3 only have a single address?  I clearly completely screwed up by not updating Bitcoin-savings-encrypted after the large transfers, but I thought I only needed to do that after 100 keys had been used for 100 transactions.  What went wrong?  When does the Bitcoin application actually create those 100 queued keys?  Does it only created the pool of pre-generated keys after the first address is actually used?

- Very Sad Puppy