Hi Steven, Am Donnerstag 27 Mai 2021 17:44:23 schrieb Steven Dudley via Gnupg-users: > Windows 7 home premium > service pack 1 > 8 gb of ram > 64-bit > > GnuPG 1.4.23 > GPG Config 1.33 > GPG Shell 3.78
(Note that I cannot find a current info on GPG Shell are you shure this is still security supported?) > When I right click on a file and send to GPG Tools, pick my OLD DEFAULT > (being phased out) email, GPG runs and a *.gpg file is created. I double > click on it, I'm asked for a passphrase, I enter it, and my file is > decrypted. > > When I encrypt to my NEW key, my *.gpg file is created, I double click on > it, GPG NEVER asks for a passphrase, it just decrypts the file. Try to operate "gpg" on the command line to see more messages which may help you to find out if this is a frontend issue or something else. example gpg -vv --decrypt x.gpg Newer GnuPG version on windows would cache a passphrase for a while, I cannot say what GPG Shell does (as far as I remember it isn't Free Software). Best Regards, Bernhard -- www.intevation.de/~bernhard +49 541 33 508 3-3 Intevation GmbH, Osnabrück, DE; Amtsgericht Osnabrück, HRB 18998 Geschäftsführer Frank Koormann, Bernhard Reiter, Dr. Jan-Oliver Wagner
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