Why can't I seem to generate identical password based encryption keys?

The InvalidKeyException being thrown indicates to me that I would look at how the key is being used on the receiving end. Are you storing it in a database or file? Are you sure it is in the same encoding that was used to encrypt the data?

The password used to generate the key is stored in plaintext, then read into the application and passed through the key generation function. – GradysGhost Nov 14 at 14:47.

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