From a46f1706369c3bceb3abaaabd12a4b37427d3cfa Mon Sep 17 00:00:00 2001
From: Paul Schaub <vanitasvitae@fsfe.org>
Date: Thu, 15 May 2025 14:50:21 +0200
Subject: [PATCH] Test edge-cases in inline-detach operation

---
 .../org/pgpainless/sop/InlineDetachTest.java  | 66 +++++++++++++++++++
 1 file changed, 66 insertions(+)

diff --git a/pgpainless-sop/src/test/java/org/pgpainless/sop/InlineDetachTest.java b/pgpainless-sop/src/test/java/org/pgpainless/sop/InlineDetachTest.java
index acbba821..ebb39694 100644
--- a/pgpainless-sop/src/test/java/org/pgpainless/sop/InlineDetachTest.java
+++ b/pgpainless-sop/src/test/java/org/pgpainless/sop/InlineDetachTest.java
@@ -5,6 +5,8 @@
 package org.pgpainless.sop;
 
 import static org.junit.jupiter.api.Assertions.assertArrayEquals;
+import static org.junit.jupiter.api.Assertions.assertFalse;
+import static org.junit.jupiter.api.Assertions.assertThrows;
 
 import java.io.ByteArrayInputStream;
 import java.io.ByteArrayOutputStream;
@@ -23,10 +25,16 @@ import org.bouncycastle.openpgp.PGPSecretKeyRing;
 import org.bouncycastle.openpgp.PGPSignature;
 import org.bouncycastle.openpgp.PGPSignatureList;
 import org.bouncycastle.openpgp.api.OpenPGPImplementation;
+import org.bouncycastle.openpgp.api.OpenPGPKey;
 import org.bouncycastle.util.io.Streams;
 import org.junit.jupiter.api.Test;
 import org.pgpainless.PGPainless;
+import org.pgpainless.algorithm.CompressionAlgorithm;
+import org.pgpainless.encryption_signing.EncryptionStream;
+import org.pgpainless.encryption_signing.ProducerOptions;
+import org.pgpainless.encryption_signing.SigningOptions;
 import org.pgpainless.key.OpenPgpV4Fingerprint;
+import org.pgpainless.key.protection.SecretKeyRingProtector;
 import sop.ByteArrayAndResult;
 import sop.SOP;
 import sop.Signatures;
@@ -201,4 +209,62 @@ public class InlineDetachTest {
 
         assertArrayEquals(data, message);
     }
+
+    @Test
+    public void detachSignaturesFromCompressedMessage() throws PGPException, IOException {
+        PGPainless api = PGPainless.getInstance();
+        OpenPGPKey key = api.generateKey()
+                .modernKeyRing("Alice <alice@pgpainless.org>");
+        byte[] cert = key.toCertificate().getEncoded();
+
+        ByteArrayOutputStream bOut = new ByteArrayOutputStream();
+        EncryptionStream eOut = api.generateMessage()
+                .onOutputStream(bOut)
+                .withOptions(ProducerOptions.sign(
+                        SigningOptions.get().addInlineSignature(SecretKeyRingProtector.unprotectedKeys(), key)
+                ).overrideCompressionAlgorithm(CompressionAlgorithm.ZIP));
+        eOut.write("Hello, World!\n".getBytes(StandardCharsets.UTF_8));
+        eOut.close();
+
+        ByteArrayAndResult<Signatures> result = sop.inlineDetach()
+                .message(bOut.toByteArray())
+                .toByteArrayAndResult();
+
+        byte[] message = result.getBytes();
+        byte[] signatures = result.getResult().getBytes();
+
+        List<Verification> verifications = sop.detachedVerify()
+                .cert(cert)
+                .signatures(signatures)
+                .data(message);
+
+        assertFalse(verifications.isEmpty());
+    }
+
+    @Test
+    public void detachMissingSignaturesFails() throws PGPException, IOException {
+        PGPainless api = PGPainless.getInstance();
+
+        ByteArrayOutputStream bOut = new ByteArrayOutputStream();
+        EncryptionStream eOut = api.generateMessage()
+                .onOutputStream(bOut)
+                .withOptions(ProducerOptions.noEncryptionNoSigning()
+                        .overrideCompressionAlgorithm(CompressionAlgorithm.ZIP));
+
+        eOut.write("Hello, World!\n".getBytes(StandardCharsets.UTF_8));
+        eOut.close();
+
+        assertThrows(SOPGPException.BadData.class, () ->
+                sop.inlineDetach()
+                        .message(bOut.toByteArray())
+                        .toByteArrayAndResult());
+    }
+
+    @Test
+    public void detachBadDataFails() {
+        byte[] bytes = "Hello, World\n".getBytes(StandardCharsets.UTF_8);
+        assertThrows(SOPGPException.BadData.class, () ->
+                sop.inlineDetach().message(bytes)
+                        .toByteArrayAndResult());
+    }
 }