diff --git a/external-sop/src/test/java/sop/external/ExternalDetachedSignVerifyRoundTripTest.java b/external-sop/src/test/java/sop/external/ExternalDetachedSignVerifyRoundTripTest.java
index 5dca76d..63638cc 100644
--- a/external-sop/src/test/java/sop/external/ExternalDetachedSignVerifyRoundTripTest.java
+++ b/external-sop/src/test/java/sop/external/ExternalDetachedSignVerifyRoundTripTest.java
@@ -67,24 +67,12 @@ public class ExternalDetachedSignVerifyRoundTripTest extends AbstractExternalSOP
     }
 
     @Test
-    public void signVerifyWithFreshEncryptedKey() throws IOException {
-        ignoreIf("sqop", Is.leq, "0.26.1"); // --with-key-password not supported
-
+    public void signVerifyWithEncryptedKey() throws IOException {
         byte[] message = "Hello, World!\n".getBytes(StandardCharsets.UTF_8);
-        byte[] keyPassword = "sw0rdf1sh".getBytes(StandardCharsets.UTF_8);
-        byte[] key = getSop().generateKey()
-                .userId("Alice <alice@openpgp.org>")
-                .withKeyPassword(keyPassword)
-                .generate()
-                .getBytes();
-
-        byte[] cert = getSop().extractCert()
-                .key(key)
-                .getBytes();
 
         byte[] signature = getSop().detachedSign()
-                .key(key)
-                .withKeyPassword(keyPassword)
+                .key(TestKeys.PASSWORD_PROTECTED_KEY.getBytes(StandardCharsets.UTF_8))
+                .withKeyPassword(TestKeys.PASSWORD)
                 .data(message)
                 .toByteArrayAndResult()
                 .getBytes();
@@ -92,7 +80,7 @@ public class ExternalDetachedSignVerifyRoundTripTest extends AbstractExternalSOP
         assertArrayStartsWith(signature, BEGIN_PGP_SIGNATURE_BYTES);
 
         List<Verification> verificationList = getSop().detachedVerify()
-                .cert(cert)
+                .cert(TestKeys.PASSWORD_PROTECTED_CERT.getBytes(StandardCharsets.UTF_8))
                 .signatures(signature)
                 .data(message);
 
@@ -169,24 +157,36 @@ public class ExternalDetachedSignVerifyRoundTripTest extends AbstractExternalSOP
 
 
     @Test
-    public void signVerifyWithFreshEncryptedKeyWithoutPassphraseFails() throws IOException {
+    public void signVerifyWithEncryptedKeyWithoutPassphraseFails() {
         ignoreIf("sqop", Is.leq, "0.27.2"); // does not return exit code 67 for encrypted keys without passphrase
 
-        byte[] keyPassword = "sw0rdf1sh".getBytes(StandardCharsets.UTF_8);
-        byte[] key = getSop().generateKey()
-                .userId("Alice <alice@openpgp.org>")
-                .withKeyPassword(keyPassword)
-                .generate()
-                .getBytes();
-
-        byte[] message = "Hello, World!\n".getBytes(StandardCharsets.UTF_8);
-
         assertThrows(SOPGPException.KeyIsProtected.class, () ->
                 getSop().detachedSign()
-                        .key(key)
-                        .data(message)
+                        .key(TestKeys.PASSWORD_PROTECTED_KEY.getBytes(StandardCharsets.UTF_8))
+                        .data("Hello, World!\n".getBytes(StandardCharsets.UTF_8))
                         .toByteArrayAndResult()
                         .getBytes());
     }
 
+    @Test
+    public void signWithProtectedKeyAndMultiplePassphrasesTest()
+            throws IOException {
+        byte[] message = "Hello, World!\n".getBytes(StandardCharsets.UTF_8);
+
+        byte[] signature = getSop().sign()
+                .key(TestKeys.PASSWORD_PROTECTED_KEY.getBytes(StandardCharsets.UTF_8))
+                .withKeyPassword("wrong")
+                .withKeyPassword(TestKeys.PASSWORD) // correct
+                .withKeyPassword("wrong2")
+                .data(message)
+                .toByteArrayAndResult()
+                .getBytes();
+
+        assertFalse(getSop().verify()
+                .cert(TestKeys.PASSWORD_PROTECTED_CERT.getBytes(StandardCharsets.UTF_8))
+                .signatures(signature)
+                .data(message)
+                .isEmpty());
+    }
+
 }
diff --git a/external-sop/src/test/java/sop/external/TestKeys.java b/external-sop/src/test/java/sop/external/TestKeys.java
index 1a2bb94..b7f73c3 100644
--- a/external-sop/src/test/java/sop/external/TestKeys.java
+++ b/external-sop/src/test/java/sop/external/TestKeys.java
@@ -304,4 +304,75 @@ public class TestKeys {
             "1FkOSekLi8WNMdUx3XMyvP8nJ65P2Q==\n" +
             "=Xj8h\n" +
             "-----END PGP PRIVATE KEY BLOCK-----\n";
+
+    public static final String PASSWORD_PROTECTED_KEY = "-----BEGIN PGP PRIVATE KEY BLOCK-----\n" +
+            "Comment: FC63 688A 5E69 8C29 40AF  7029 7C62 2B00 D459 2657\n" +
+            "Comment: Password Protected <protected@openpgp.org>\n" +
+            "\n" +
+            "xYYEY8qfmxYJKwYBBAHaRw8BAQdAv5atAPgP3WOvjoeEGAXIpX+k9LbX1+roEQQE\n" +
+            "WaQfbMv+CQMI7d4yuArkBqz/J/UllaSoHN2kYdJE4Biiqgto2d39B8JRCrb0LSeX\n" +
+            "25TolXynV3bdiTsVKtnNOOcCzP09kDMu8uCMpregFrMdI511iR+dysLAEQQfFgoA\n" +
+            "gwWCY8qfmwWJBZ+mAAMLCQcJEHxiKwDUWSZXRxQAAAAAAB4AIHNhbHRAbm90YXRp\n" +
+            "b25zLnNlcXVvaWEtcGdwLm9yZ5Rt+kxLFFiFbTaZO2Rbf52K6FEcetqiht8jk9Vt\n" +
+            "DObSAxUKCAKbAQIeARYhBPxjaIpeaYwpQK9wKXxiKwDUWSZXAABTzQEA9Vy2e5eU\n" +
+            "dFj+gfwPULtwEJqMpj29eN37J0VfwF1RdW0BAMeXutE1dzL5PdIIX8VJAIv9RXVR\n" +
+            "lw5TujtjLhr8uzEKzSpQYXNzd29yZCBQcm90ZWN0ZWQgPHByb3RlY3RlZEBvcGVu\n" +
+            "cGdwLm9yZz7CwBQEExYKAIYFgmPKn5sFiQWfpgADCwkHCRB8YisA1FkmV0cUAAAA\n" +
+            "AAAeACBzYWx0QG5vdGF0aW9ucy5zZXF1b2lhLXBncC5vcmdTOuFjGL7cyOIVEfem\n" +
+            "5b/gCJLP6LFKTy3P/gFGRB7VEAMVCggCmQECmwECHgEWIQT8Y2iKXmmMKUCvcCl8\n" +
+            "YisA1FkmVwAARXsBAP4jwRWnAqEe59BV+0WviYzC8NhKpIjXwRQIM5yD6E90AQCQ\n" +
+            "wfhqsexB2rVQGw0siW2c/3DUhmnK8osNK5f8iLv5BceGBGPKn5sWCSsGAQQB2kcP\n" +
+            "AQEHQM/fv1zxwMjruKiq9W7PcMUbcMKQ3lbFdqPtwEJ16LxY/gkDCA3yM1VPvA6b\n" +
+            "/1vqf8sxU96j7CAMZaQRutdRd1xwFxx9ZIvhrPjm23nCcURzmnPflnKdx/p8/QVj\n" +
+            "jTQufQbnZkrmo/fg+eZURLX6O3Op2svCwMUEGBYKATcFgmPKn5sFiQWfpgAJEHxi\n" +
+            "KwDUWSZXRxQAAAAAAB4AIHNhbHRAbm90YXRpb25zLnNlcXVvaWEtcGdwLm9yZ0X3\n" +
+            "iVnya1OCsmkt7OijGLXSTv9FRbFVf+fcQGSMzViBApsCvqAEGRYKAG8FgmPKn5sJ\n" +
+            "EGiGL7kPBxZbRxQAAAAAAB4AIHNhbHRAbm90YXRpb25zLnNlcXVvaWEtcGdwLm9y\n" +
+            "Z62UKDMX/Uh2ywrGJjKi3Ex6jpghyED+kPlNuxS8uMs6FiEE2PHLwmEzUNGnZtNf\n" +
+            "aIYvuQ8HFlsAAPgiAPwIlVOxTF7J80KAiHrApEgfLHsEeGivjEtnkKO6eUa2awEA\n" +
+            "5qlATwB3bQVkMFYa893MxrjVmmasil81uwMiU8gtRQoWIQT8Y2iKXmmMKUCvcCl8\n" +
+            "YisA1FkmVwAAktwBAOEXjAXOZaFM8PoSNtrKVLakPXCadY8zduAqqgmp5PBwAP0R\n" +
+            "EpO9g0mQuCCmg6eeXm2GxChWORWArh9of7l/epycAceLBGPKn5sSCisGAQQBl1UB\n" +
+            "BQEBB0DDEzY37G8GNXIJqbVsawutIqNTZcizObXrau9F0H5wHQMBCAf+CQMI9ppA\n" +
+            "+RYt5Sv/gIPNmVm7UraBpK75qOC/tN9h/uNaaadcgrWEXMr6+YWjvBmH+iCV61/y\n" +
+            "b9Gkfxn2V/lw8asgch86Y6tN0Rhy+uXTFKMHecLABgQYFgoAeAWCY8qfmwWJBZ+m\n" +
+            "AAkQfGIrANRZJldHFAAAAAAAHgAgc2FsdEBub3RhdGlvbnMuc2VxdW9pYS1wZ3Au\n" +
+            "b3JnYeL3YzJjnG3vwSjzVnzgbFCe5QyC0/mFnqML7+hQi0kCmwwWIQT8Y2iKXmmM\n" +
+            "KUCvcCl8YisA1FkmVwAAbRcA/3haEwnnHhitQNbvDs2DqzVvz0QtjEW59ZKFgzX2\n" +
+            "PUMXAQDJzcz9GoPTqU8hioiSBoQUjN883qv6sJHiEveRyDbMDQ==\n" +
+            "=xHUd\n" +
+            "-----END PGP PRIVATE KEY BLOCK-----\n";
+    public static final String PASSWORD_PROTECTED_CERT = "-----BEGIN PGP PUBLIC KEY BLOCK-----\n" +
+            "Comment: FC63 688A 5E69 8C29 40AF  7029 7C62 2B00 D459 2657\n" +
+            "Comment: Password Protected <protected@openpgp.org>\n" +
+            "\n" +
+            "xjMEY8qfmxYJKwYBBAHaRw8BAQdAv5atAPgP3WOvjoeEGAXIpX+k9LbX1+roEQQE\n" +
+            "WaQfbMvCwBEEHxYKAIMFgmPKn5sFiQWfpgADCwkHCRB8YisA1FkmV0cUAAAAAAAe\n" +
+            "ACBzYWx0QG5vdGF0aW9ucy5zZXF1b2lhLXBncC5vcmeUbfpMSxRYhW02mTtkW3+d\n" +
+            "iuhRHHraoobfI5PVbQzm0gMVCggCmwECHgEWIQT8Y2iKXmmMKUCvcCl8YisA1Fkm\n" +
+            "VwAAU80BAPVctnuXlHRY/oH8D1C7cBCajKY9vXjd+ydFX8BdUXVtAQDHl7rRNXcy\n" +
+            "+T3SCF/FSQCL/UV1UZcOU7o7Yy4a/LsxCs0qUGFzc3dvcmQgUHJvdGVjdGVkIDxw\n" +
+            "cm90ZWN0ZWRAb3BlbnBncC5vcmc+wsAUBBMWCgCGBYJjyp+bBYkFn6YAAwsJBwkQ\n" +
+            "fGIrANRZJldHFAAAAAAAHgAgc2FsdEBub3RhdGlvbnMuc2VxdW9pYS1wZ3Aub3Jn\n" +
+            "UzrhYxi+3MjiFRH3puW/4AiSz+ixSk8tz/4BRkQe1RADFQoIApkBApsBAh4BFiEE\n" +
+            "/GNoil5pjClAr3ApfGIrANRZJlcAAEV7AQD+I8EVpwKhHufQVftFr4mMwvDYSqSI\n" +
+            "18EUCDOcg+hPdAEAkMH4arHsQdq1UBsNLIltnP9w1IZpyvKLDSuX/Ii7+QXOMwRj\n" +
+            "yp+bFgkrBgEEAdpHDwEBB0DP379c8cDI67ioqvVuz3DFG3DCkN5WxXaj7cBCdei8\n" +
+            "WMLAxQQYFgoBNwWCY8qfmwWJBZ+mAAkQfGIrANRZJldHFAAAAAAAHgAgc2FsdEBu\n" +
+            "b3RhdGlvbnMuc2VxdW9pYS1wZ3Aub3JnRfeJWfJrU4KyaS3s6KMYtdJO/0VFsVV/\n" +
+            "59xAZIzNWIECmwK+oAQZFgoAbwWCY8qfmwkQaIYvuQ8HFltHFAAAAAAAHgAgc2Fs\n" +
+            "dEBub3RhdGlvbnMuc2VxdW9pYS1wZ3Aub3JnrZQoMxf9SHbLCsYmMqLcTHqOmCHI\n" +
+            "QP6Q+U27FLy4yzoWIQTY8cvCYTNQ0adm019ohi+5DwcWWwAA+CIA/AiVU7FMXsnz\n" +
+            "QoCIesCkSB8sewR4aK+MS2eQo7p5RrZrAQDmqUBPAHdtBWQwVhrz3czGuNWaZqyK\n" +
+            "XzW7AyJTyC1FChYhBPxjaIpeaYwpQK9wKXxiKwDUWSZXAACS3AEA4ReMBc5loUzw\n" +
+            "+hI22spUtqQ9cJp1jzN24CqqCank8HAA/RESk72DSZC4IKaDp55ebYbEKFY5FYCu\n" +
+            "H2h/uX96nJwBzjgEY8qfmxIKKwYBBAGXVQEFAQEHQMMTNjfsbwY1cgmptWxrC60i\n" +
+            "o1NlyLM5tetq70XQfnAdAwEIB8LABgQYFgoAeAWCY8qfmwWJBZ+mAAkQfGIrANRZ\n" +
+            "JldHFAAAAAAAHgAgc2FsdEBub3RhdGlvbnMuc2VxdW9pYS1wZ3Aub3JnYeL3YzJj\n" +
+            "nG3vwSjzVnzgbFCe5QyC0/mFnqML7+hQi0kCmwwWIQT8Y2iKXmmMKUCvcCl8YisA\n" +
+            "1FkmVwAAbRcA/3haEwnnHhitQNbvDs2DqzVvz0QtjEW59ZKFgzX2PUMXAQDJzcz9\n" +
+            "GoPTqU8hioiSBoQUjN883qv6sJHiEveRyDbMDQ==\n" +
+            "=xlgc\n" +
+            "-----END PGP PUBLIC KEY BLOCK-----\n";
+    public static final String PASSWORD = "sw0rdf1sh";
 }
diff --git a/external-sop/src/test/java/sop/external/UnsupportedSubcommandTest.java b/external-sop/src/test/java/sop/external/UnsupportedSubcommandTest.java
index 8196871..55e13e2 100644
--- a/external-sop/src/test/java/sop/external/UnsupportedSubcommandTest.java
+++ b/external-sop/src/test/java/sop/external/UnsupportedSubcommandTest.java
@@ -39,7 +39,7 @@ public class UnsupportedSubcommandTest extends AbstractExternalSOPTest {
         private final String binary;
         private final Properties environment;
 
-        public UnsupportedSubcommandExternal(String binaryName, Properties environment) {
+        UnsupportedSubcommandExternal(String binaryName, Properties environment) {
             this.binary = binaryName;
             this.environment = environment;
         }