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Pinentry: Offer to generate a password
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In T4346#122374, @dkg wrote:

I think it would be great if gpg-agent (or pinentry?), when it knows it is prompting for a new password, to auto-generate a memorable, high-entropy passphrase from the user's native locale and provide it as initial prompt. If the user selects this pre-generated passphrase, then they should also be prompted for it while it is not being shown to the user, to verify that they do actually know it. Choosing high-entropy passphrases for people is super useful because people are terrible at choosing passphrases.

I would not go so far as to provide it as "initial prompt" but I would very much like a button for it. Especially for symmetric encryption which we offer in the GUI since Gpg4win 3

This might go hand in hand with the proposed quality bar improvement in T2103