How to store a crypto key securely?

If you are encrypting fields that you only need to verify (not recall), then simple hash with SHA or one-way encrypt with DES, or IDEA using a salt to prevent a rainbow table to actually reveal them. This is useful for passwords or other access secrets.

Python and webapps makes me think of GAE, so you may want something that is not doing an encrypt/decrypt on every DB transaction since these are already un-cheap on GAE.

Best practice for an encrypted databased is to encrypt the fields with the users own secret, but to include an asymmetric backdoor that encrypts the users secret key so you (and not anyone who has access to the DB source files, or the tables) can unencrypt the users key with your secret key, should recovery or something else necessitate.

In that case, the user (or you or trusted delegate) can retireve and unencrypt their own information only. You may want to be more stringent in validating user secrets if you are thinking you need to secure their fields by encryption.

In this regards, a passphrase (as opposed to a password) of some secret words such "in the jungle the mighty Jungle" is a good practice to encourage.

EDIT: Just saw your update. The best way to store OAuth is to give them a short lifespan, only request resources your need and re-request them over getting long tokens. It's better to design around getting authenticated, getting your access and getting out, than leaving the key under the backdoor for 10 years.

Since, if you need to recall OAuth when the user comes online, you can do as above and encrypt with a user specfic secret. You could also keygen from an encrypted counter (encrypted with the user secret) so the actual encryption key changes at each transaction, and the counter is stored in plaintext. But check specific crypto algo discussion of this mode before using. Some algorithms may not play nice with this.

Symmetric encryption is indeed useless, as you have noticed; however for certain fields, using asymmetric encryption or a trapdoor function may be usable:

• if the web application does not need to read back the data, then use asymmetric encryption. This is useful e.g. for credit card data: your application would encrypt the data with the public key of the order processing system, which is on a separate machine that is not publically accessible.

• if all you need is equality comparison, use a trapdoor function, such as a message digest, ideally with a salt value. This is good for passwords that should be unrecoverable on the server.

Before you can determine what crypto approach is the best, you have to think about what you are trying to protect and how much effort an attacker will be ready to put into getting the key/information from your system.

What is the attack scenario that you are trying to remedy by using crypto? A stolen database file?