Steve on 19 Apr, 2017 05:24 PM
Mike, I have split your comment into a separate discussion.
I'll try to answer your questions:
1) Can you give more details on the scenario you are referring to? When you say you set a caching time, have you entered the password so that it resides in the cache for the given time? The fact that you may be asked for your password twice is expected since signing and decryption maybe done using different parts of your key. Once you entered the password (once or twice) the caching should indeed work as expected. Is that not the case for you?
2) LastPass has received some attention from Tavis Ormandy from the Google Project Zero team recently. E.g. https://twitter.com/taviso/status/843965519371812864 etc. So it may be a good idea to keep an eye on that and which of the issues are fixed and which remain open.
3) I answered that part in Discussion #50834 which is about the security of macOS keychain.
I hope this somewhat answers your questions. Let me know how the caching experiments go.
I set the "remember my password" length in gpgPreferences.prefPane for 1200 seconds (see attached image of my settings). I have to enter my password much more than twice, and certainly nothing is remembered for 12000 seconds. So, yes, it is the case for me that the caching is not working.
Thanks for the Lastpass and MasOS keychain resources!