[andrewaylett]

I'm concerned (but not qualified to judge) that changing your password and keyfile may not be as beneficial as it appears.

A password for an encryption key is very different to a password for a server. Once you change your password on a server, there's little harm in publishing it -- it can't be used any more. But the key is a file that may still exist (see also Wikileaks' key being published by David Leigh).

Consider: your database exists as a file. If someone is able to gain access to a copy, that copy remains valid as long as at least one password within it remains unchanged. So you need a strong key, because it's subject to offline bruteforcing. Now they get a second copy of your database, with a different password. If any of your passwords are ever published or cracked, your database is exposed. If you have to change your password regularly, it's going to be tempting to make it weaker, or to store it somewhere less securely. If you're using key files, they only need to get one of your files. It seems to me that the more key material you need to secure, the more difficult it's going to be?

Anyone who knows better want to chime in?

[asquabventured]

The key it seems to me is by using both a master password and a key file. If a site gets cracked and they find your site specific password that won't help them determine your keepass database master password &/or generated key file that you only store offline and never sync to the cloud.

In order to open the database you need both the correct master password and the correct keyfile. If the attacker doesn't have both, they should not be able to get into the database.

[jcline]

I'm also no qualified to judge, but I would say it's important that in addition to rotating the password and key file used to encrypt the password database, one also rotates the all the passwords in the database regularly. This way, if someone obtains a copy of your database, they have a limited time before all the passwords in the database become useless.

[asquabventured]

This is true, as well as enable 2-factor authentication for sites that support it.