There is a security option in Mac OS X to require you to enter your password when waking from sleep. I have this enabled. This option, unfortunately, has some rather annoying side effects.
A number of apps that use the system keychain (Adium, Shrook, Chicken of the VNC) all require you to re-authenticate as they wake up and attempt to re-connect to various services. When these apps need authentication, they pop up a password dialog.
So when the machine wakes from sleep, you first get a system username/password dialog. As you’re typing into that dialog, the application keychain access dialogs start popping-up in the background and I’m guessing that these steal the focus from the dialog you’re typing in.
This means you almost always have to re-focus into the login dialog to complete the login, or 
try again 
after the focus jumping around has causes the login to fail.
I’ve heard a lot of new Mac users complain about this, and I don’t blame them. I really can’t think of a good reason why this couldn’t be fixed. Or maybe there is a fix and I just don’t know about it?
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Joseph Scott adds this Comment:
I must have my PowerBook setup differently then. I’ve had the password required after sleep turned on since day one and never had to re-authenticate apps using keychain. Same thing for the screen saver, regular password window pops up, but I’ve never had to re-auth other apps.
Perhaps there is a difference in the way we are using keychain?
November 6th, 2006 at 9:08 am
Alex adds this Comment:
Different apps seem to do it differently. For example, Mail hardly ever prompts me to enter a password.
November 6th, 2006 at 9:11 am
PatrickQG adds this Comment:
I also must’ve set up my PowerBook (and consequently my MBP) differently - as I don’t see that happen here either.
Are you telling keychain to lock on screensaver? SSHKeychain can be setup to do this, for example. Possibly even by default, I really can’t remember.
However… that doesn’t really discount that this is possibly a security issue (nothing should be able to take input away from the security unlock window thingy, surely?)
November 6th, 2006 at 12:25 pm
sandro adds this Comment:
Provided you’re running 10.4.x (and possibly 10.3.x although i can’t remember), open up:
applications > utilities > keychain access
then from the menubar select:
Edit > Change settings for keychain “XXX” (where XXX is the name of your active keychain)
this will open a dialog box with 2 deeply annoying checkboxes: lock when inactive for X mins, and lock when sleeping. uncheck and enjoy…
November 6th, 2006 at 7:39 pm
Alex adds this Comment:
Now we’re talking!
November 7th, 2006 at 1:47 am