diff --git a/pgpainless-core/src/test/java/org/pgpainless/signature/OnePassSignatureBracketingTest.java b/pgpainless-core/src/test/java/org/pgpainless/signature/OnePassSignatureBracketingTest.java
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+++ b/pgpainless-core/src/test/java/org/pgpainless/signature/OnePassSignatureBracketingTest.java
@@ -0,0 +1,161 @@
+/*
+ * Copyright 2021 Paul Schaub.
+ *
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ * You may obtain a copy of the License at
+ *
+ *     http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+package org.pgpainless.signature;
+
+import static org.junit.jupiter.api.Assertions.assertEquals;
+import static org.junit.jupiter.api.Assertions.assertNotNull;
+
+import java.io.ByteArrayInputStream;
+import java.io.ByteArrayOutputStream;
+import java.io.IOException;
+import java.io.InputStream;
+import java.nio.charset.StandardCharsets;
+import java.security.InvalidAlgorithmParameterException;
+import java.security.NoSuchAlgorithmException;
+
+import org.bouncycastle.openpgp.PGPEncryptedData;
+import org.bouncycastle.openpgp.PGPEncryptedDataList;
+import org.bouncycastle.openpgp.PGPException;
+import org.bouncycastle.openpgp.PGPLiteralData;
+import org.bouncycastle.openpgp.PGPObjectFactory;
+import org.bouncycastle.openpgp.PGPOnePassSignature;
+import org.bouncycastle.openpgp.PGPOnePassSignatureList;
+import org.bouncycastle.openpgp.PGPPrivateKey;
+import org.bouncycastle.openpgp.PGPPublicKeyEncryptedData;
+import org.bouncycastle.openpgp.PGPPublicKeyRing;
+import org.bouncycastle.openpgp.PGPSecretKey;
+import org.bouncycastle.openpgp.PGPSecretKeyRing;
+import org.bouncycastle.openpgp.PGPSignature;
+import org.bouncycastle.openpgp.PGPSignatureList;
+import org.bouncycastle.openpgp.PGPUtil;
+import org.bouncycastle.openpgp.bc.BcPGPObjectFactory;
+import org.bouncycastle.openpgp.operator.PublicKeyDataDecryptorFactory;
+import org.bouncycastle.openpgp.operator.bc.BcPublicKeyDataDecryptorFactory;
+import org.bouncycastle.util.io.Streams;
+import org.junit.jupiter.params.ParameterizedTest;
+import org.junit.jupiter.params.provider.MethodSource;
+import org.pgpainless.PGPainless;
+import org.pgpainless.algorithm.DocumentSignatureType;
+import org.pgpainless.algorithm.HashAlgorithm;
+import org.pgpainless.algorithm.PublicKeyAlgorithm;
+import org.pgpainless.algorithm.SignatureType;
+import org.pgpainless.encryption_signing.EncryptionOptions;
+import org.pgpainless.encryption_signing.EncryptionStream;
+import org.pgpainless.encryption_signing.ProducerOptions;
+import org.pgpainless.encryption_signing.SigningOptions;
+import org.pgpainless.implementation.ImplementationFactory;
+import org.pgpainless.key.protection.SecretKeyRingProtector;
+import org.pgpainless.key.protection.UnlockSecretKey;
+
+public class OnePassSignatureBracketingTest {
+
+    @ParameterizedTest
+    @MethodSource("org.pgpainless.util.TestImplementationFactoryProvider#provideImplementationFactories")
+    public void onePassSignaturePacketsAndSignaturesAreBracketedTest(ImplementationFactory implementationFactory) throws PGPException, InvalidAlgorithmParameterException, NoSuchAlgorithmException, IOException {
+        ImplementationFactory.setFactoryImplementation(implementationFactory);
+
+        PGPSecretKeyRing key1 = PGPainless.generateKeyRing().modernKeyRing("Alice", null);
+        PGPSecretKeyRing key2 = PGPainless.generateKeyRing().modernKeyRing("Bob", null);
+        PGPPublicKeyRing cert1 = PGPainless.extractCertificate(key1);
+
+        ByteArrayOutputStream out = new ByteArrayOutputStream();
+        EncryptionStream encryptionStream = PGPainless.encryptAndOrSign()
+                .onOutputStream(out)
+                .withOptions(ProducerOptions.signAndEncrypt(
+                        EncryptionOptions.encryptCommunications()
+                                .addRecipient(cert1),
+                        SigningOptions.get()
+                                .addInlineSignature(SecretKeyRingProtector.unprotectedKeys(), key1, DocumentSignatureType.BINARY_DOCUMENT)
+                                .addInlineSignature(SecretKeyRingProtector.unprotectedKeys(), key2, DocumentSignatureType.BINARY_DOCUMENT)
+                ).setAsciiArmor(true));
+
+        ByteArrayInputStream data = new ByteArrayInputStream("Hello, World!".getBytes(StandardCharsets.UTF_8));
+        Streams.pipeAll(data, encryptionStream);
+        encryptionStream.close();
+
+        ByteArrayInputStream ciphertextIn = new ByteArrayInputStream(out.toByteArray());
+
+        InputStream inputStream = PGPUtil.getDecoderStream(ciphertextIn);
+        PGPObjectFactory objectFactory = new BcPGPObjectFactory(inputStream);
+
+        PGPOnePassSignatureList onePassSignatures = null;
+        PGPSignatureList signatures = null;
+
+        outerloop: while (true) {
+            Object next = objectFactory.nextObject();
+            if (next == null) {
+                break outerloop;
+            }
+            if (next instanceof PGPEncryptedDataList) {
+                PGPEncryptedDataList encryptedDataList = (PGPEncryptedDataList) next;
+                for (PGPEncryptedData encryptedData : encryptedDataList) {
+                    if (encryptedData instanceof PGPPublicKeyEncryptedData) {
+                        PGPPublicKeyEncryptedData publicKeyEncryptedData = (PGPPublicKeyEncryptedData) encryptedData;
+                        PGPSecretKey secretKey = key1.getSecretKey(publicKeyEncryptedData.getKeyID());
+                        PGPPrivateKey privateKey = UnlockSecretKey.unlockSecretKey(secretKey, SecretKeyRingProtector.unprotectedKeys());
+                        PublicKeyDataDecryptorFactory decryptorFactory = new BcPublicKeyDataDecryptorFactory(privateKey);
+                        InputStream decryptionStream = publicKeyEncryptedData.getDataStream(decryptorFactory);
+                        objectFactory = new BcPGPObjectFactory(decryptionStream);
+                        continue outerloop;
+                    }
+                }
+            } else if (next instanceof PGPOnePassSignatureList) {
+                onePassSignatures = (PGPOnePassSignatureList) next;
+                continue outerloop;
+            } else if (next instanceof PGPLiteralData) {
+                continue outerloop;
+            } else if (next instanceof PGPSignatureList) {
+                signatures = (PGPSignatureList) next;
+                continue outerloop;
+            }
+        }
+
+        assertNotNull(onePassSignatures);
+        assertNotNull(signatures);
+
+        assertEquals(signatures.size(), onePassSignatures.size());
+        assertEquals(2, signatures.size());
+
+        for (int i = 0; i < signatures.size(); i++) {
+
+            // CHECK BRACKETING
+
+            // OnePassSignatures and Signatures are bracketed
+            //  eg. (OPS1, OPS2, LiteralData, Sig2, Sig1)
+            PGPOnePassSignature onePassSignature = onePassSignatures.get(i);
+            PGPSignature signature = signatures.get(signatures.size() - 1 - i);
+            assertEquals(onePassSignature.getKeyID(), signature.getKeyID());
+            byte[] encoded = onePassSignature.getEncoded();
+
+            // CHECK NESTED-NESS
+
+            // 0,1 are header
+            // 2 is version number
+            assertEquals(3, encoded[2]);
+            // 3 is sig type
+            assertEquals(SignatureType.BINARY_DOCUMENT.getCode(), encoded[3]);
+            // 4 is hash algo
+            assertEquals(HashAlgorithm.SHA512.getAlgorithmId(), encoded[4]);
+            // 5 is public key algo
+            assertEquals(PublicKeyAlgorithm.EDDSA.getAlgorithmId(), encoded[5]);
+            // [6,7,8,9,10,11,12,13] are key-id
+
+            boolean last = i == signatures.size() - 1;
+            // 14 is nested
+            assertEquals(last ? 1 : 0, encoded[14]);
+        }
+    }
+}