Yes, I have this issue with Password Manager as well, even though there is an option to sychronize it wireless, I've never had any of it stay wirelessly.
If you still have the old device, hook it up to the Desktop Manager and backup just the password keeper (you may have to have the user go into the device and pw keeper and turn off the wireless synch), then you can restore it back onto his new device. I've had to do that for several of my users who use pw keeper.
Only issue with this, is you better hope the user doesn't accidently wipe his device, being the pw keeper isn't synched online. Hope that helps,