diff --git a/pgpainless-core/src/main/java/org/pgpainless/decryption_verification/DecryptionStreamFactory.java b/pgpainless-core/src/main/java/org/pgpainless/decryption_verification/DecryptionStreamFactory.java
index 130eb537..b991d316 100644
--- a/pgpainless-core/src/main/java/org/pgpainless/decryption_verification/DecryptionStreamFactory.java
+++ b/pgpainless-core/src/main/java/org/pgpainless/decryption_verification/DecryptionStreamFactory.java
@@ -201,7 +201,12 @@ public final class DecryptionStreamFactory {
                             pbeEncryptedData.getSymmetricAlgorithm(passphraseDecryptor));
                     resultBuilder.setSymmetricKeyAlgorithm(symmetricKeyAlgorithm);
                     resultBuilder.setIntegrityProtected(pbeEncryptedData.isIntegrityProtected());
-                    return pbeEncryptedData.getDataStream(passphraseDecryptor);
+
+                    try {
+                        return pbeEncryptedData.getDataStream(passphraseDecryptor);
+                    } catch (PGPException e) {
+                        LOGGER.log(LEVEL, "Probable passphrase mismatch, skip PBE encrypted data block", e);
+                    }
                 }
 
             } else if (encryptedData instanceof PGPPublicKeyEncryptedData) {
@@ -225,7 +230,7 @@ public final class DecryptionStreamFactory {
         }
 
         if (decryptionKey == null) {
-            throw new PGPException("Decryption failed - No suitable decryption key found");
+            throw new PGPException("Decryption failed - No suitable decryption key or passphrase found");
         }
 
         PublicKeyDataDecryptorFactory keyDecryptor = new BcPublicKeyDataDecryptorFactory(decryptionKey);
diff --git a/pgpainless-core/src/test/java/org/pgpainless/symmetric_encryption/MultiPassphraseSymmetricEncryptionTest.java b/pgpainless-core/src/test/java/org/pgpainless/symmetric_encryption/MultiPassphraseSymmetricEncryptionTest.java
new file mode 100644
index 00000000..aee992f2
--- /dev/null
+++ b/pgpainless-core/src/test/java/org/pgpainless/symmetric_encryption/MultiPassphraseSymmetricEncryptionTest.java
@@ -0,0 +1,65 @@
+/*
+ * Copyright 2020 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.symmetric_encryption;
+
+import java.io.ByteArrayInputStream;
+import java.io.ByteArrayOutputStream;
+import java.io.IOException;
+import java.nio.charset.StandardCharsets;
+
+import org.bouncycastle.openpgp.PGPException;
+import org.bouncycastle.util.io.Streams;
+import org.junit.jupiter.api.Test;
+import org.pgpainless.PGPainless;
+import org.pgpainless.decryption_verification.DecryptionStream;
+import org.pgpainless.encryption_signing.EncryptionStream;
+import org.pgpainless.util.Passphrase;
+
+public class MultiPassphraseSymmetricEncryptionTest {
+
+    @Test
+    public void test() throws IOException, PGPException {
+        String message = "Here we test if during decryption of a message that was encrypted with two passphrases, " +
+                "the decryptor finds the session key encrypted for the right passphrase.";
+        ByteArrayInputStream plaintextIn = new ByteArrayInputStream(message.getBytes(StandardCharsets.UTF_8));
+        ByteArrayOutputStream ciphertextOut = new ByteArrayOutputStream();
+        EncryptionStream encryptor = PGPainless.encryptAndOrSign()
+                .onOutputStream(ciphertextOut)
+                .forPassphrases(Passphrase.fromPassword("p1"), Passphrase.fromPassword("p2"))
+                .usingSecureAlgorithms()
+                .doNotSign()
+                .noArmor();
+
+        Streams.pipeAll(plaintextIn, encryptor);
+        encryptor.close();
+
+        byte[] ciphertext = ciphertextOut.toByteArray();
+
+        // decrypting the p1 package with p2 first will not work. Test if it is handled correctly.
+        for (Passphrase passphrase : new Passphrase[] {Passphrase.fromPassword("p2"), Passphrase.fromPassword("p1")}) {
+            DecryptionStream decryptor = PGPainless.decryptAndOrVerify().onInputStream(new ByteArrayInputStream(ciphertext))
+                    .decryptWith(passphrase)
+                    .doNotVerify()
+                    .build();
+
+            ByteArrayOutputStream plaintextOut = new ByteArrayOutputStream();
+
+            Streams.pipeAll(decryptor, plaintextOut);
+
+            decryptor.close();
+        }
+    }
+}