Encryption strength veracrypt vs keepass?

Question

can you please explain the strength of veracrypt and keepass compared?

1. Whats theoretically easier to break if both use the exact same password for their respective containers, the vcrypt or keepass file?

2. Are they both still considered in the dev community as "unbroken" and safe encryption tools for storing data? Or are there successful attacks publicly known? Do they currently have any known weaknesses in their code bases?

3. Lets say you have a Text.txt file. In one case this txt file is stored in the vcrypt container. And a second time in the keepass kdb as an attachement. Now, when you open both on your windows system (mounting vcrypt and opening keepass kdb), which one is in this "opened state" more vulnerable to what kind of attacks? Which one isolates .txt file in a better way? Here you can consider that you are connected to the Internet while those files are open and you can consider any other attacks.

4. In case of veracrypt: Is the file safety somehow decreased, when we start opening the text .txt file from within the vcrypt container? How does that impact potential unwanted file access?

5. what difference does it make in vcrypt selecting algorithms in different order? eg serpent-aes or aes-serpent. What impact does the order have on bruteforcing attacks?

Answer 1

Both products uses strong encryption, but there are a few fundamental differences in their designs.

Assuming that there's no big in the implementation, then Keepass has a slight advantage in its cipher mode, as it uses CBC while full disk encryption like Veracrypt used XTS/XEX to support random access.

Cipher mode like CBC that's used in Keepass means that it has to rewrite the entire encrypted database from scratch on every writes. CBC supports random reads but not random writes. For the use case of password managers, where the file size typically only range in the megabytes, this is fine, but a full disk encryption has to work with files in the size of gigabytes, terabytes, or even petabytes that is constantly updated.

For those reasons, XTS/XEX is used in full disk encryption to support fast random writes, it is the state of the art cipher mode for full disk encryption and is not known to be broken, but because it has to support random writes, it has a few weaknesses/tradeoffs and leakages that cipher modes that doesn't need to support random writes don't have. You can read further about the challenges with full disk encryption in "You Don't Want XTS".