diff --git a/hosts/pinwheel/modules/git/default.nix b/hosts/pinwheel/modules/git/default.nix
index ae17f47..94feecf 100644
--- a/hosts/pinwheel/modules/git/default.nix
+++ b/hosts/pinwheel/modules/git/default.nix
@@ -6,6 +6,38 @@
 }:
 let
   enabled = config.mod.git.enable;
+
+  # Wrapper around `ssh-keygen` used as git's SSH signing program. Before a
+  # signing operation it ensures the passphrase-protected signing key is loaded
+  # into the agent — `ssh-keygen -Y sign` reads the key from disk and re-prompts
+  # every commit otherwise, since `AddKeysToAgent` only ever caches auth keys.
+  # Loading it once (through the GUI askpass) lets later commits reuse the
+  # cached key from the agent. Verification and every other op pass straight
+  # through to the real ssh-keygen untouched.
+  sshSignWrapper = pkgs.writeShellApplication {
+    name = "git-ssh-sign";
+    runtimeInputs = [
+      pkgs.openssh
+      pkgs.gawk
+      pkgs.gnugrep
+    ];
+    text = ''
+      key="${config.age.secrets."alex.pinwheel-github.com-signing".path}"
+
+      case " $* " in
+        *" -Y sign "*)
+          fp=""
+          fp="$(ssh-keygen -lf "$key.pub" 2>/dev/null | awk '{print $2}')" || true
+          if [ -n "$fp" ] && ! ssh-add -l 2>/dev/null | grep -qF "$fp"; then
+            # </dev/null detaches stdin so ssh-add uses SSH_ASKPASS (the GUI).
+            ssh-add "$key" </dev/null || true
+          fi
+          ;;
+      esac
+
+      exec ssh-keygen "$@"
+    '';
+  };
 in
 {
   options = {
@@ -33,6 +65,11 @@ in
 
           # Tells Git to use SSH instead of the default GPG
           gpg.format = "ssh";
+
+          # Sign via a wrapper that loads the signing key into the agent on
+          # first use, so subsequent signed commits reuse the cached key
+          # instead of re-prompting for the passphrase every time.
+          gpg.ssh.program = "${sshSignWrapper}/bin/git-ssh-sign";
         };
       };
 
diff --git a/hosts/pinwheel/modules/ssh/default.nix b/hosts/pinwheel/modules/ssh/default.nix
index 5c7082f..fb8cf03 100644
--- a/hosts/pinwheel/modules/ssh/default.nix
+++ b/hosts/pinwheel/modules/ssh/default.nix
@@ -13,6 +13,20 @@
       components = [ "secrets" ];
     };
 
+    home.sessionVariables = {
+      # gnome-keyring's PAM hooks export SSH_AUTH_SOCK pointing at a dead gcr
+      # socket (gcr-ssh-agent is disabled above), which shadows openssh's own
+      # agent and silently breaks passphrase caching. Force it back to the
+      # openssh agent started by `programs.ssh.startAgent`.
+      SSH_AUTH_SOCK = "$XDG_RUNTIME_DIR/ssh-agent";
+
+      # Route passphrase prompts through seahorse's GUI askpass instead of the
+      # terminal. `prefer` uses the GUI even when a tty is attached (ssh only
+      # falls back to askpass with no controlling terminal otherwise).
+      SSH_ASKPASS = "${pkgs.seahorse}/libexec/seahorse/ssh-askpass";
+      SSH_ASKPASS_REQUIRE = "prefer";
+    };
+
     programs.ssh = {
       enable = true;
       enableDefaultConfig = false;
diff --git a/hosts/pinwheel/modules/zsh/default.nix b/hosts/pinwheel/modules/zsh/default.nix
index 52fdb68..6211b36 100644
--- a/hosts/pinwheel/modules/zsh/default.nix
+++ b/hosts/pinwheel/modules/zsh/default.nix
@@ -56,6 +56,14 @@ in
 
         initContent = lib.strings.concatStringsSep "\n" [
           "export KEYTIMEOUT=1"
+
+          # Point every interactive shell at openssh's ssh-agent. home-manager's
+          # session vars set this too, but hm-session-vars runs once and is then
+          # inherited — so a tmux server that outlives this change (or started
+          # with the stale gcr socket) hands new panes a dead SSH_AUTH_SOCK.
+          # Re-exporting the fixed path per-shell keeps every pane on the same
+          # agent, so each key is only ever prompted for once per session.
+          ''export SSH_AUTH_SOCK="$XDG_RUNTIME_DIR/ssh-agent"''
           "bindkey -v '^?' backward-delete-char"
           "bindkey '^a' beginning-of-line"
           "bindkey '^e' end-of-line"