diff --git a/k9mail-library/src/main/java/com/fsck/k9/mail/transport/smtp/SmtpTransport.java b/k9mail-library/src/main/java/com/fsck/k9/mail/transport/smtp/SmtpTransport.java
index 11086eb03..b2cd02793 100644
--- a/k9mail-library/src/main/java/com/fsck/k9/mail/transport/smtp/SmtpTransport.java
+++ b/k9mail-library/src/main/java/com/fsck/k9/mail/transport/smtp/SmtpTransport.java
@@ -651,22 +651,30 @@ public class SmtpTransport extends Transport {
     }
 
     private void readPipelinedResponse(Queue<String> pipelinedCommands) throws IOException, MessagingException {
-        int noOfPipelinedResponse = pipelinedCommands.size();
         String responseLine = null;
         List<String> results = new ArrayList<>();
-        while (noOfPipelinedResponse > 0) {
-            noOfPipelinedResponse--;
+        NegativeSmtpReplyException negativeRecipient = null;
+        for (String command : pipelinedCommands) {
             results.clear();
             responseLine = readCommandResponseLine(results);
             try {
                 responseLineToCommandResponse(responseLine, results);
 
             } catch (MessagingException exception) {
-                if (noOfPipelinedResponse == 0) {
+                if (command.equals("DATA")) {
                     throw exception;
                 }
-                Timber.d("SMTP <<< " + exception.getMessage());
-                //continue reading response till DATA response .
+                if (command.startsWith("RCPT")) {
+                    negativeRecipient = (NegativeSmtpReplyException) exception;
+                }
+            }
+        }
+
+        if (negativeRecipient != null) {
+            try {
+                executeCommand(".");
+            } catch (NegativeSmtpReplyException e) {
+                throw negativeRecipient;
             }
         }
 
diff --git a/k9mail-library/src/test/java/com/fsck/k9/mail/helpers/TestMessage.java b/k9mail-library/src/test/java/com/fsck/k9/mail/helpers/TestMessage.java
index e44f283d7..c867b0fba 100644
--- a/k9mail-library/src/test/java/com/fsck/k9/mail/helpers/TestMessage.java
+++ b/k9mail-library/src/test/java/com/fsck/k9/mail/helpers/TestMessage.java
@@ -61,7 +61,15 @@ class TestMessage extends MimeMessage {
         bufferedSink.emit();
     }
 
-    private static Address[] toAddressArray(String email) {
-        return email == null ? new Address[0] : new Address[] { new Address(email) };
+    private static Address[] toAddressArray(String[] emails) {
+        return emails == null ? new Address[0] : stringArrayToAddressArray(emails);
+    }
+
+    private static Address[] stringArrayToAddressArray(String[] emails) {
+        Address addresses[] = new Address[emails.length];
+        for (int i = 0; i < emails.length; i++) {
+            addresses[i] = new Address(emails[i]);
+        }
+        return addresses;
     }
 }
diff --git a/k9mail-library/src/test/java/com/fsck/k9/mail/helpers/TestMessageBuilder.java b/k9mail-library/src/test/java/com/fsck/k9/mail/helpers/TestMessageBuilder.java
index 9a28fcc23..f8d545e2e 100644
--- a/k9mail-library/src/test/java/com/fsck/k9/mail/helpers/TestMessageBuilder.java
+++ b/k9mail-library/src/test/java/com/fsck/k9/mail/helpers/TestMessageBuilder.java
@@ -5,18 +5,18 @@ import com.fsck.k9.mail.Message;
 
 
 public class TestMessageBuilder {
-    String from;
-    String to;
+    String[] from;
+    String[] to;
     boolean hasAttachments;
     long messageSize;
 
 
-    public TestMessageBuilder from(String email) {
+    public TestMessageBuilder from(String... email) {
         from = email;
         return this;
     }
 
-    public TestMessageBuilder to(String email) {
+    public TestMessageBuilder to(String... email) {
         to = email;
         return this;
     }
diff --git a/k9mail-library/src/test/java/com/fsck/k9/mail/transport/smtp/SmtpTransportTest.java b/k9mail-library/src/test/java/com/fsck/k9/mail/transport/smtp/SmtpTransportTest.java
index 196067dea..fd8323f2a 100644
--- a/k9mail-library/src/test/java/com/fsck/k9/mail/transport/smtp/SmtpTransportTest.java
+++ b/k9mail-library/src/test/java/com/fsck/k9/mail/transport/smtp/SmtpTransportTest.java
@@ -745,17 +745,23 @@ public class SmtpTransportTest {
         server.expect("RCPT TO:<user2@localhost>");
         server.expect("DATA");
         server.output("250 OK");
-        server.output("421 4.7.0 Temporary system problem");
+        server.output("550 remote mail to <user2@localhost> not allowed");
         server.output("354 End data with <CR><LF>.<CR><LF>");
-        server.expect("[message data]");
         server.expect(".");
-        server.output("250 OK: queued as 12345");
+        server.output("554 no valid recipients");
         server.expect("QUIT");
         server.output("221 BYE");
         server.closeConnection();
         SmtpTransport transport = startServerAndCreateSmtpTransport(server);
 
-        transport.sendMessage(message);
+        try {
+            transport.sendMessage(message);
+            fail("Expected exception");
+        } catch (NegativeSmtpReplyException e) {
+            assertEquals(550, e.getReplyCode());
+            assertEquals("remote mail to <user2@localhost> not allowed", e.getReplyText());
+        }
+
 
         server.verifyConnectionClosed();
         server.verifyInteractionCompleted();
@@ -788,6 +794,38 @@ public class SmtpTransportTest {
         server.verifyInteractionCompleted();
     }
 
+    @Test
+    public void sendMessagePipelining_with250and550ReplyforRecipients_shouldThrow() throws Exception {
+        Message message = getMessageWithTwoRecipients();
+        MockSmtpServer server = createServerAndSetupForPlainAuthentication("PIPELINING");
+        server.expect("MAIL FROM:<user@localhost>");
+        server.expect("RCPT TO:<user2@localhost>");
+        server.expect("RCPT TO:<user3@localhost>");
+        server.expect("DATA");
+        server.output("250 OK");
+        server.output("250 OK");
+        server.output("550 remote mail to <user3@localhost> not allowed");
+        server.output("354 End data with <CR><LF>.<CR><LF>");
+        server.expect(".");
+        server.output("554 no valid recipients given");
+        server.expect("QUIT");
+        server.output("221 BYE");
+        server.closeConnection();
+        SmtpTransport transport = startServerAndCreateSmtpTransport(server);
+
+        try {
+            transport.sendMessage(message);
+            fail("Expected exception");
+        } catch (NegativeSmtpReplyException e) {
+            assertEquals(550, e.getReplyCode());
+            assertEquals("remote mail to <user3@localhost> not allowed", e.getReplyText());
+        }
+
+        server.verifyConnectionClosed();
+        server.verifyInteractionCompleted();
+    }
+
+
     private SmtpTransport startServerAndCreateSmtpTransport(MockSmtpServer server) throws IOException,
             MessagingException {
         return startServerAndCreateSmtpTransport(server, AuthType.PLAIN, ConnectionSecurity.NONE);
@@ -840,6 +878,13 @@ public class SmtpTransportTest {
         return getDefaultMessageBuilder().build();
     }
 
+    private Message getMessageWithTwoRecipients() {
+        return new TestMessageBuilder()
+                .from("user@localhost")
+                .to("user2@localhost", "user3@localhost")
+                .build();
+    }
+
     private MockSmtpServer createServerAndSetupForPlainAuthentication(String... extensions) {
         MockSmtpServer server = new MockSmtpServer();