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I have set up keychain to use an id_rsa key. After latest world updates, I am asked for a passphrase repeatedly. I got the following files/entries: ~/.ssh: authorized_keys config id_rsa id_rsa.pub known_hosts .. /etc/ssh/sshd_config (perhaps irrelevant here, however, it is the same setup used in other system into which I ssh from the current one) PermitRootLogin no PubkeyAuthentication yes PasswordAuthentication no PermitEmptyPasswords no UsePAM no AllowTcpForwarding yes X11Forwarding yes AcceptEnv LANG LC_* ~/.gnupg: gpg-agent.conf no-grab default-cache-ttl 28800z default-cache-ttl-ssh 28800z max-cache-ttl 28800z max-cache-ttl-ssh 28800z gpg.conf # GnuPG config file created by KGpg use-agent default-key 9053534B693C4FB3 encrypt-to 9053534B693C4FB3 private-keys-v1.d (directory) pubring.gpg random_seed secring.gpg trustdb.gpg .. ~/.keychain/ .. tpx1c2g-sh tpx1c2g-sh-gpg ~/bash_profile # GPG #export GPG_TTY=`tty` export GNUPGHOME=~/.gnupg export GPGKEY=693C4FB3 eval `keychain --noask --eval --timeout 180 id_rsa` source ~/.keychain/$HOSTNAME-sh source ~/.keychain/$HOSTNAME-sh-gpg I have added the Key, again, via ssh-add to be sure it is used. I am still not sure why it stopped working, nor why it is not working now, even after checking that ssh-agent is (already) running. What else should I check?