diff --git a/nixos/lib/test-driver/test_driver/machine.py b/nixos/lib/test-driver/test_driver/machine.py
index 8f01833bffb4..0db7930f496b 100644
--- a/nixos/lib/test-driver/test_driver/machine.py
+++ b/nixos/lib/test-driver/test_driver/machine.py
@@ -1,4 +1,4 @@
-from contextlib import _GeneratorContextManager
+from contextlib import _GeneratorContextManager, nullcontext
 from pathlib import Path
 from queue import Queue
 from typing import Any, Callable, Dict, Iterable, List, Optional, Tuple
@@ -406,25 +406,23 @@ class Machine:
         return rootlog.nested(msg, my_attrs)
 
     def wait_for_monitor_prompt(self) -> str:
-        with self.nested("waiting for monitor prompt"):
-            assert self.monitor is not None
-            answer = ""
-            while True:
-                undecoded_answer = self.monitor.recv(1024)
-                if not undecoded_answer:
-                    break
-                answer += undecoded_answer.decode()
-                if answer.endswith("(qemu) "):
-                    break
-            return answer
+        assert self.monitor is not None
+        answer = ""
+        while True:
+            undecoded_answer = self.monitor.recv(1024)
+            if not undecoded_answer:
+                break
+            answer += undecoded_answer.decode()
+            if answer.endswith("(qemu) "):
+                break
+        return answer
 
     def send_monitor_command(self, command: str) -> str:
         self.run_callbacks()
-        with self.nested(f"sending monitor command: {command}"):
-            message = f"{command}\n".encode()
-            assert self.monitor is not None
-            self.monitor.send(message)
-            return self.wait_for_monitor_prompt()
+        message = f"{command}\n".encode()
+        assert self.monitor is not None
+        self.monitor.send(message)
+        return self.wait_for_monitor_prompt()
 
     def wait_for_unit(
         self, unit: str, user: Optional[str] = None, timeout: int = 900
@@ -547,7 +545,7 @@ class Machine:
         self.shell.send("echo ${PIPESTATUS[0]}\n".encode())
         rc = int(self._next_newline_closed_block_from_shell().strip())
 
-        return (rc, output.decode())
+        return (rc, output.decode(errors="replace"))
 
     def shell_interact(self, address: Optional[str] = None) -> None:
         """Allows you to interact with the guest shell for debugging purposes.
@@ -685,9 +683,9 @@ class Machine:
             retry(tty_matches)
 
     def send_chars(self, chars: str, delay: Optional[float] = 0.01) -> None:
-        with self.nested(f"sending keys '{chars}'"):
+        with self.nested(f"sending keys {repr(chars)}"):
             for char in chars:
-                self.send_key(char, delay)
+                self.send_key(char, delay, log=False)
 
     def wait_for_file(self, filename: str) -> None:
         """Waits until the file exists in machine's file system."""
@@ -860,11 +858,15 @@ class Machine:
                 if matches is not None:
                     return
 
-    def send_key(self, key: str, delay: Optional[float] = 0.01) -> None:
+    def send_key(
+        self, key: str, delay: Optional[float] = 0.01, log: Optional[bool] = True
+    ) -> None:
         key = CHAR_TO_KEY.get(key, key)
-        self.send_monitor_command(f"sendkey {key}")
-        if delay is not None:
-            time.sleep(delay)
+        context = self.nested(f"sending key {repr(key)}") if log else nullcontext()
+        with context:
+            self.send_monitor_command(f"sendkey {key}")
+            if delay is not None:
+                time.sleep(delay)
 
     def send_console(self, chars: str) -> None:
         assert self.process
diff --git a/nixos/tests/all-tests.nix b/nixos/tests/all-tests.nix
index 7ee83be6672e..d8eb00d54537 100644
--- a/nixos/tests/all-tests.nix
+++ b/nixos/tests/all-tests.nix
@@ -248,6 +248,7 @@ in {
   gnome = handleTest ./gnome.nix {};
   gnome-flashback = handleTest ./gnome-flashback.nix {};
   gnome-xorg = handleTest ./gnome-xorg.nix {};
+  gnupg = handleTest ./gnupg.nix {};
   go-neb = handleTest ./go-neb.nix {};
   gobgpd = handleTest ./gobgpd.nix {};
   gocd-agent = handleTest ./gocd-agent.nix {};
diff --git a/nixos/tests/gnupg.nix b/nixos/tests/gnupg.nix
new file mode 100644
index 000000000000..65a9a93007fd
--- /dev/null
+++ b/nixos/tests/gnupg.nix
@@ -0,0 +1,118 @@
+import ./make-test-python.nix ({ pkgs, lib, ...}:
+
+{
+  name = "gnupg";
+  meta = with lib.maintainers; {
+    maintainers = [ rnhmjoj ];
+  };
+
+  # server for testing SSH
+  nodes.server = { ... }: {
+    imports = [ ../modules/profiles/minimal.nix ];
+
+    users.users.alice.isNormalUser = true;
+    services.openssh.enable = true;
+  };
+
+  # machine for testing GnuPG
+  nodes.machine = { pkgs, ... }: {
+    imports = [ ../modules/profiles/minimal.nix ];
+
+    users.users.alice.isNormalUser = true;
+    services.getty.autologinUser = "alice";
+
+    environment.shellInit = ''
+      # preset a key passphrase in gpg-agent
+      preset_key() {
+        # find all keys
+        case "$1" in
+          ssh) grips=$(awk '/^[0-9A-F]/{print $1}' "''${GNUPGHOME:-$HOME/.gnupg}/sshcontrol") ;;
+          pgp) grips=$(gpg --with-keygrip --list-secret-keys | awk '/Keygrip/{print $3}') ;;
+        esac
+
+        # try to preset the passphrase for each key found
+        for grip in $grips; do
+          "$(gpgconf --list-dirs libexecdir)/gpg-preset-passphrase" -c -P "$2" "$grip"
+        done
+      }
+    '';
+
+    programs.gnupg.agent.enable = true;
+    programs.gnupg.agent.enableSSHSupport = true;
+  };
+
+  testScript =
+    ''
+      import shlex
+
+
+      def as_alice(command: str) -> str:
+          """
+          Wraps a command to run it as Alice in a login shell
+          """
+          quoted = shlex.quote(command)
+          return "su --login alice --command " + quoted
+
+
+      start_all()
+
+      with subtest("Wait for the autologin"):
+          machine.wait_until_tty_matches("1", "alice@machine")
+
+      with subtest("Can generate a PGP key"):
+          # Note: this needs a tty because of pinentry
+          machine.send_chars("gpg --gen-key\n")
+          machine.wait_until_tty_matches("1", "Real name:")
+          machine.send_chars("Alice\n")
+          machine.wait_until_tty_matches("1", "Email address:")
+          machine.send_chars("alice@machine\n")
+          machine.wait_until_tty_matches("1", "Change")
+          machine.send_chars("O\n")
+          machine.wait_until_tty_matches("1", "Please enter")
+          machine.send_chars("pgp_p4ssphrase\n")
+          machine.wait_until_tty_matches("1", "Please re-enter")
+          machine.send_chars("pgp_p4ssphrase\n")
+          machine.wait_until_tty_matches("1", "public and secret key created")
+
+      with subtest("Confirm the key is in the keyring"):
+          machine.wait_until_succeeds(as_alice("gpg --list-secret-keys | grep -q alice@machine"))
+
+      with subtest("Can generate and add an SSH key"):
+          machine.succeed(as_alice("ssh-keygen -t ed25519 -f alice -N ssh_p4ssphrase"))
+
+          # Note: apparently this must be run before using the OpenSSH agent
+          # socket for the first time in a tty. It's not needed for `ssh`
+          # because there's a hook that calls it automatically (only in NixOS).
+          machine.send_chars("gpg-connect-agent updatestartuptty /bye\n")
+
+          # Note: again, this needs a tty because of pinentry
+          machine.send_chars("ssh-add alice\n")
+          machine.wait_until_tty_matches("1", "Enter passphrase")
+          machine.send_chars("ssh_p4ssphrase\n")
+          machine.wait_until_tty_matches("1", "Please enter")
+          machine.send_chars("ssh_agent_p4ssphrase\n")
+          machine.wait_until_tty_matches("1", "Please re-enter")
+          machine.send_chars("ssh_agent_p4ssphrase\n")
+
+      with subtest("Confirm the SSH key has been registered"):
+          machine.wait_until_succeeds(as_alice("ssh-add -l | grep -q alice@machine"))
+
+      with subtest("Can preset the key passphrases in the agent"):
+          machine.succeed(as_alice("echo allow-preset-passphrase > .gnupg/gpg-agent.conf"))
+          machine.succeed(as_alice("pkill gpg-agent"))
+          machine.succeed(as_alice("preset_key pgp pgp_p4ssphrase"))
+          machine.succeed(as_alice("preset_key ssh ssh_agent_p4ssphrase"))
+
+      with subtest("Can encrypt and decrypt a message"):
+          machine.succeed(as_alice("echo Hello | gpg -e -r alice | gpg -d | grep -q Hello"))
+
+      with subtest("Can log into the server"):
+          # Install Alice's public key
+          public_key = machine.succeed(as_alice("cat alice.pub"))
+          server.succeed("mkdir /etc/ssh/authorized_keys.d")
+          server.succeed(f"printf '{public_key}' > /etc/ssh/authorized_keys.d/alice")
+
+          server.wait_for_open_port(22)
+          machine.succeed(as_alice("ssh -i alice -o StrictHostKeyChecking=no server exit"))
+    '';
+})
diff --git a/pkgs/tools/security/gnupg/23.nix b/pkgs/tools/security/gnupg/23.nix
index 2030e8195e68..0f56c4a8c15b 100644
--- a/pkgs/tools/security/gnupg/23.nix
+++ b/pkgs/tools/security/gnupg/23.nix
@@ -1,5 +1,6 @@
 { fetchurl, fetchpatch, lib, stdenv, pkg-config, libgcrypt, libassuan, libksba
 , libgpg-error, libiconv, npth, gettext, texinfo, buildPackages
+, nixosTests
 , guiSupport ? stdenv.isDarwin, enableMinimal ? false
 , adns, bzip2, gnutls, libusb1, openldap
 , pinentry, readline, sqlite, zlib
@@ -85,6 +86,8 @@ stdenv.mkDerivation rec {
 
   enableParallelBuilding = true;
 
+  passthru.tests.connman = nixosTests.gnupg;
+
   meta = with lib; {
     homepage = "https://gnupg.org";
     description = "Modern release of the GNU Privacy Guard, a GPL OpenPGP implementation";