diff --git a/pgpainless-cli/src/test/java/org/pgpainless/cli/commands/RoundTripEncryptDecryptCmdTest.java b/pgpainless-cli/src/test/java/org/pgpainless/cli/commands/RoundTripEncryptDecryptCmdTest.java
index 8c294e59..3caa81ae 100644
--- a/pgpainless-cli/src/test/java/org/pgpainless/cli/commands/RoundTripEncryptDecryptCmdTest.java
+++ b/pgpainless-cli/src/test/java/org/pgpainless/cli/commands/RoundTripEncryptDecryptCmdTest.java
@@ -644,4 +644,30 @@ public class RoundTripEncryptDecryptCmdTest extends CLITest {
         int exitCode = executeCommand("decrypt");
         assertEquals(SOPGPException.MissingArg.EXIT_CODE, exitCode);
     }
+
+    @Test
+    public void testEncryptDecryptWithFreshRSAKey() throws IOException {
+        // Generate key
+        File passwordFile = writeFile("password", "sw0rdf1sh");
+        File keyFile = pipeStdoutToFile("key.asc");
+        assertSuccess(executeCommand("generate-key", "--profile=rfc4880", "--with-key-password", passwordFile.getAbsolutePath(), "Alice <alice@example.org>"));
+
+        File certFile = pipeStdoutToFile("cert.asc");
+        pipeFileToStdin(keyFile);
+        assertSuccess(executeCommand("extract-cert"));
+
+        // Write plaintext
+        File plaintextFile = writeFile("msg.txt", "Hello, World!\n");
+
+        // Encrypt
+        File ciphertextFile = pipeStdoutToFile("msg.asc");
+        pipeFileToStdin(plaintextFile);
+        assertSuccess(executeCommand("encrypt", "--profile=rfc4880", certFile.getAbsolutePath()));
+
+        ByteArrayOutputStream decrypted = pipeStdoutToStream();
+        pipeFileToStdin(ciphertextFile);
+        assertSuccess(executeCommand("decrypt", "--with-key-password", passwordFile.getAbsolutePath(), keyFile.getAbsolutePath()));
+
+        assertEquals("Hello, World!\n", decrypted.toString());
+    }
 }