Merge pull request #2344 from philipwhiuk/smtpTransportResponseHandling

SMTP Transport improvements

k9mail-library/src/main/java/com/fsck/k9/mail/Transport.java

@@ -1,13 +1,8 @@
 
 package com.fsck.k9.mail;
 
-import android.content.Context;
-
-import com.fsck.k9.mail.oauth.OAuth2TokenProvider;
-import com.fsck.k9.mail.ssl.DefaultTrustedSocketFactory;
-import com.fsck.k9.mail.store.StoreConfig;
 import com.fsck.k9.mail.ServerSettings.Type;
-import com.fsck.k9.mail.transport.SmtpTransport;
+import com.fsck.k9.mail.transport.smtp.SmtpTransport;
 import com.fsck.k9.mail.transport.WebDavTransport;
 
 import java.io.UnsupportedEncodingException;

k9mail-library/src/main/java/com/fsck/k9/mail/TransportProvider.java

@@ -6,7 +6,7 @@ import android.content.Context;
 import com.fsck.k9.mail.oauth.OAuth2TokenProvider;
 import com.fsck.k9.mail.ssl.DefaultTrustedSocketFactory;
 import com.fsck.k9.mail.store.StoreConfig;
-import com.fsck.k9.mail.transport.SmtpTransport;
+import com.fsck.k9.mail.transport.smtp.SmtpTransport;
 import com.fsck.k9.mail.transport.WebDavTransport;
 
 public class TransportProvider {

k9mail-library/src/main/java/com/fsck/k9/mail/transport/smtp/EnhancedNegativeSmtpReplyException.java

@@ -0,0 +1,18 @@
+package com.fsck.k9.mail.transport.smtp;
+
+
+class EnhancedNegativeSmtpReplyException extends NegativeSmtpReplyException {
+    private final StatusCodeClass statusCodeClass;
+    private final StatusCodeSubject statusCodeSubject;
+    private final StatusCodeDetail statusCodeDetail;
+
+
+    EnhancedNegativeSmtpReplyException(int replyCode, StatusCodeClass statusCodeClass,
+            StatusCodeSubject statusCodeSubject, StatusCodeDetail statusCodeDetail,
+            String replyText) {
+        super(replyCode, replyText);
+        this.statusCodeClass = statusCodeClass;
+        this.statusCodeSubject = statusCodeSubject;
+        this.statusCodeDetail = statusCodeDetail;
+    }
+}

k9mail-library/src/main/java/com/fsck/k9/mail/transport/smtp/NegativeSmtpReplyException.java

@@ -0,0 +1,41 @@
+package com.fsck.k9.mail.transport.smtp;
+
+
+import android.text.TextUtils;
+
+import com.fsck.k9.mail.MessagingException;
+
+
+/**
+ * Exception that is thrown when the server sends a negative reply (reply codes 4xx or 5xx).
+ */
+class NegativeSmtpReplyException extends MessagingException {
+    private static final long serialVersionUID = 8696043577357897135L;
+
+
+    private final int replyCode;
+    private final String replyText;
+
+
+    public NegativeSmtpReplyException(int replyCode, String replyText) {
+        super(buildErrorMessage(replyCode, replyText), isPermanentSmtpError(replyCode));
+        this.replyCode = replyCode;
+        this.replyText = replyText;
+    }
+
+    private static String buildErrorMessage(int replyCode, String replyText) {
+        return TextUtils.isEmpty(replyText) ? "Negative SMTP reply: " + replyCode : replyText;
+    }
+
+    private static boolean isPermanentSmtpError(int replyCode) {
+        return replyCode >= 500 && replyCode <= 599;
+    }
+
+    public int getReplyCode() {
+        return replyCode;
+    }
+
+    public String getReplyText() {
+        return replyText;
+    }
+}

k9mail-library/src/main/java/com/fsck/k9/mail/transport/smtp/SmtpTransport.java

@@ -1,5 +1,5 @@
 
-package com.fsck.k9.mail.transport;
+package com.fsck.k9.mail.transport.smtp;
 
 
 import java.io.BufferedInputStream;
@@ -49,6 +49,7 @@ import com.fsck.k9.mail.oauth.XOAuth2ChallengeParser;
 import com.fsck.k9.mail.ssl.TrustedSocketFactory;
 import com.fsck.k9.mail.store.StoreConfig;
 import javax.net.ssl.SSLException;
+import org.apache.commons.io.IOUtils;
 
 import static com.fsck.k9.mail.CertificateValidationException.Reason.MissingCapability;
 import static com.fsck.k9.mail.K9MailLib.DEBUG_PROTOCOL_SMTP;
@@ -211,6 +212,7 @@ public class SmtpTransport extends Transport {
     private PeekableInputStream mIn;
     private OutputStream mOut;
     private boolean m8bitEncodingAllowed;
+    private boolean mEnhancedStatusCodesProvided;
     private int mLargestAcceptableMessage;
     private boolean retryXoauthWithNewToken;
 
@@ -269,7 +271,7 @@ public class SmtpTransport extends Transport {
             mOut = new BufferedOutputStream(mSocket.getOutputStream(), 1024);
 
             // Eat the banner
-            executeSimpleCommand(null);
+            executeCommand(null);
 
             InetAddress localAddress = mSocket.getLocalAddress();
             String localHost = getCanonicalHostName(localAddress);
@@ -293,11 +295,11 @@ public class SmtpTransport extends Transport {
             Map<String, String> extensions = sendHello(localHost);
 
             m8bitEncodingAllowed = extensions.containsKey("8BITMIME");
-
+            mEnhancedStatusCodesProvided = extensions.containsKey("ENHANCEDSTATUSCODES");
 
             if (mConnectionSecurity == ConnectionSecurity.STARTTLS_REQUIRED) {
                 if (extensions.containsKey("STARTTLS")) {
-                    executeSimpleCommand("STARTTLS");
+                    executeCommand("STARTTLS");
 
                     mSocket = mTrustedSocketFactory.createSocket(
                             mSocket,
@@ -488,10 +490,10 @@ public class SmtpTransport extends Transport {
      * @throws MessagingException
      *          In case of a malformed response.
      */
-    private Map<String,String> sendHello(String host) throws IOException, MessagingException {
+    private Map<String, String> sendHello(String host) throws IOException, MessagingException {
         Map<String, String> extensions = new HashMap<String, String>();
         try {
-            List<String> results = executeSimpleCommand("EHLO " + host);
+            List<String> results = executeCommand("EHLO %s", host).results;
             // Remove the EHLO greeting response
             results.remove(0);
             for (String result : results) {
@@ -504,7 +506,7 @@ public class SmtpTransport extends Transport {
             }
 
             try {
-                executeSimpleCommand("HELO " + host);
+                executeCommand("HELO %s", host);
             } catch (NegativeSmtpReplyException e2) {
                 Log.w(LOG_TAG, "Server doesn't support the HELO command. Continuing anyway.");
             }
@@ -563,12 +565,18 @@ public class SmtpTransport extends Transport {
         boolean entireMessageSent = false;
         Address[] from = message.getFrom();
         try {
-            executeSimpleCommand("MAIL FROM:" + "<" + from[0].getAddress() + ">"
+            String fromAddress = from[0].getAddress();
-                    + (m8bitEncodingAllowed ? " BODY=8BITMIME" : ""));
+            if (m8bitEncodingAllowed) {
-            for (String address : addresses) {
+                executeCommand("MAIL FROM:<%s> BODY=8BITMIME", fromAddress);
-                executeSimpleCommand("RCPT TO:" + "<" + address + ">");
+            } else {
+                executeCommand("MAIL FROM:<%s>", fromAddress);
             }
-            executeSimpleCommand("DATA");
+
+            for (String address : addresses) {
+                executeCommand("RCPT TO:<%s>", address);
+            }
+
+            executeCommand("DATA");
 
             EOLConvertingOutputStream msgOut = new EOLConvertingOutputStream(
                     new LineWrapOutputStream(new SmtpDataStuffing(mOut), 1000));
@@ -577,7 +585,7 @@ public class SmtpTransport extends Transport {
             msgOut.endWithCrLfAndFlush();
 
             entireMessageSent = true; // After the "\r\n." is attempted, we may have sent the message
-            executeSimpleCommand(".");
+            executeCommand(".");
         } catch (NegativeSmtpReplyException e) {
             throw e;
         } catch (Exception e) {
@@ -594,25 +602,13 @@ public class SmtpTransport extends Transport {
     @Override
     public void close() {
         try {
-            executeSimpleCommand("QUIT");
+            executeCommand("QUIT");
-        } catch (Exception e) {
-
-        }
-        try {
-            mIn.close();
-        } catch (Exception e) {
-
-        }
-        try {
-            mOut.close();
-        } catch (Exception e) {
-
-        }
-        try {
-            mSocket.close();
         } catch (Exception e) {
 
         }
+        IOUtils.closeQuietly(mIn);
+        IOUtils.closeQuietly(mOut);
+        IOUtils.closeQuietly(mSocket);
         mIn = null;
         mOut = null;
         mSocket = null;
@@ -660,76 +656,31 @@ public class SmtpTransport extends Transport {
         mOut.flush();
     }
 
-    private void checkLine(String line) throws MessagingException {
-        int length = line.length();
-        if (length < 1) {
-            throw new MessagingException("SMTP response is 0 length");
-        }
-
-        char c = line.charAt(0);
-        if ((c == '4') || (c == '5')) {
-            int replyCode = -1;
-            String message = line;
-            if (length >= 3) {
-                try {
-                    replyCode = Integer.parseInt(line.substring(0, 3));
-                } catch (NumberFormatException e) { /* ignore */ }
-
-                if (length > 4) {
-                    message = line.substring(4);
-                } else {
-                    message = "";
-                }
-            }
-
-            throw new NegativeSmtpReplyException(replyCode, message);
-        }
-
-    }
-    @Deprecated
-    private List<String> executeSimpleCommand(String command) throws IOException, MessagingException {
-        return executeSimpleCommand(command, false);
-    }
-
-    /**
-     * TODO:  All responses should be checked to confirm that they start with a valid
-     * reply code, and that the reply code is appropriate for the command being executed.
-     * That means it should either be a 2xx code (generally) or a 3xx code in special cases
-     * (e.g., DATA & AUTH LOGIN commands).  Reply codes should be made available as part of
-     * the returned object.
-     *
-     * This should be done using the non-deprecated API below.
-     */
-    @Deprecated
-    private List<String> executeSimpleCommand(String command, boolean sensitive)
-    throws IOException, MessagingException {
-        List<String> results = new ArrayList<>();
-        if (command != null) {
-            writeLine(command, sensitive);
-        }
-
-        String line = readCommandResponseLine(results);
-
-        // Check if the reply code indicates an error.
-        checkLine(line);
-
-        return results;
-    }
-
     private static class CommandResponse {
 
         private final int replyCode;
-        private final String message;
+        private final List<String> results;
 
-        public CommandResponse(int replyCode, String message) {
+        public CommandResponse(int replyCode, List<String> results) {
             this.replyCode = replyCode;
-            this.message = message;
+            this.results = results;
         }
     }
 
-    private CommandResponse executeSimpleCommandWithResponse(String command, boolean sensitive) throws IOException, MessagingException {
+    private CommandResponse executeSensitiveCommand(String format, Object... args)
+            throws IOException, MessagingException {
+        return executeCommand(true, format, args);
+    }
+
+    private CommandResponse executeCommand(String format, Object... args) throws IOException, MessagingException {
+        return executeCommand(false, format, args);
+    }
+
+    private CommandResponse executeCommand(boolean sensitive, String format, Object... args)
+            throws IOException, MessagingException {
         List<String> results = new ArrayList<>();
-        if (command != null) {
+        if (format != null) {
+            String command = String.format(Locale.ROOT, format, args);
             writeLine(command, sensitive);
         }
 
@@ -741,25 +692,45 @@ public class SmtpTransport extends Transport {
         }
 
         int replyCode = -1;
-        String message = line;
         if (length >= 3) {
             try {
                 replyCode = Integer.parseInt(line.substring(0, 3));
             } catch (NumberFormatException e) { /* ignore */ }
+        }
 
-            if (length > 4) {
+        char replyCodeCategory = line.charAt(0);
-                message = line.substring(4);
+        boolean isReplyCodeErrorCategory = (replyCodeCategory == '4') || (replyCodeCategory == '5');
+        if (isReplyCodeErrorCategory) {
+            if (mEnhancedStatusCodesProvided) {
+                throw buildEnhancedNegativeSmtpReplyException(replyCode, results);
             } else {
-                message = "";
+                String replyText = TextUtils.join(" ", results);
+                throw new NegativeSmtpReplyException(replyCode, replyText);
             }
         }
 
-        char c = line.charAt(0);
+        return new CommandResponse(replyCode, results);
-        if ((c == '4') || (c == '5')) {
+    }
-            throw new NegativeSmtpReplyException(replyCode, message);
+
+    private MessagingException buildEnhancedNegativeSmtpReplyException(int replyCode, List<String> results) {
+        StatusCodeClass statusCodeClass = null;
+        StatusCodeSubject statusCodeSubject = null;
+        StatusCodeDetail statusCodeDetail = null;
+
+        String message = "";
+        for (String resultLine : results) {
+            message += resultLine.split(" ", 2)[1] + " ";
+        }
+        if (results.size() > 0) {
+            String[] statusCodeParts = results.get(0).split(" ", 2)[0].split("\\.");
+
+            statusCodeClass = StatusCodeClass.parse(statusCodeParts[0]);
+            statusCodeSubject = StatusCodeSubject.parse(statusCodeParts[1]);
+            statusCodeDetail = StatusCodeDetail.parse(statusCodeSubject, statusCodeParts[2]);
         }
 
-        return new CommandResponse(replyCode, message);
+        return new EnhancedNegativeSmtpReplyException(replyCode, statusCodeClass, statusCodeSubject, statusCodeDetail,
+                message.trim());
     }
 
 
@@ -805,9 +776,9 @@ public class SmtpTransport extends Transport {
     private void saslAuthLogin(String username, String password) throws MessagingException,
         AuthenticationFailedException, IOException {
         try {
-            executeSimpleCommand("AUTH LOGIN");
+            executeCommand("AUTH LOGIN");
-            executeSimpleCommand(Base64.encode(username), true);
+            executeSensitiveCommand(Base64.encode(username));
-            executeSimpleCommand(Base64.encode(password), true);
+            executeSensitiveCommand(Base64.encode(password));
         } catch (NegativeSmtpReplyException exception) {
             if (exception.getReplyCode() == SMTP_AUTHENTICATION_FAILURE_ERROR_CODE) {
                 // Authentication credentials invalid
@@ -823,7 +794,7 @@ public class SmtpTransport extends Transport {
         AuthenticationFailedException, IOException {
         String data = Base64.encode("\000" + username + "\000" + password);
         try {
-            executeSimpleCommand("AUTH PLAIN " + data, true);
+            executeSensitiveCommand("AUTH PLAIN %s", data);
         } catch (NegativeSmtpReplyException exception) {
             if (exception.getReplyCode() == SMTP_AUTHENTICATION_FAILURE_ERROR_CODE) {
                 // Authentication credentials invalid
@@ -838,7 +809,7 @@ public class SmtpTransport extends Transport {
     private void saslAuthCramMD5(String username, String password) throws MessagingException,
         AuthenticationFailedException, IOException {
 
-        List<String> respList = executeSimpleCommand("AUTH CRAM-MD5");
+        List<String> respList = executeCommand("AUTH CRAM-MD5").results;
         if (respList.size() != 1) {
             throw new MessagingException("Unable to negotiate CRAM-MD5");
         }
@@ -847,7 +818,7 @@ public class SmtpTransport extends Transport {
         String b64CRAMString = Authentication.computeCramMd5(mUsername, mPassword, b64Nonce);
 
         try {
-            executeSimpleCommand(b64CRAMString, true);
+            executeSensitiveCommand(b64CRAMString);
         } catch (NegativeSmtpReplyException exception) {
             if (exception.getReplyCode() == SMTP_AUTHENTICATION_FAILURE_ERROR_CODE) {
                 // Authentication credentials invalid
@@ -911,52 +882,23 @@ public class SmtpTransport extends Transport {
     private void attemptXoauth2(String username) throws MessagingException, IOException {
         String token = oauthTokenProvider.getToken(username, OAuth2TokenProvider.OAUTH2_TIMEOUT);
         String authString = Authentication.computeXoauth(username, token);
-        CommandResponse response = executeSimpleCommandWithResponse("AUTH XOAUTH2 " + authString, true);
+        CommandResponse response = executeSensitiveCommand("AUTH XOAUTH2 %s", authString);
 
         if (response.replyCode == SMTP_CONTINUE_REQUEST) {
-            retryXoauthWithNewToken = XOAuth2ChallengeParser.shouldRetry(response.message, mHost);
+            String replyText = TextUtils.join("", response.results);
+            retryXoauthWithNewToken = XOAuth2ChallengeParser.shouldRetry(replyText, mHost);
 
             //Per Google spec, respond to challenge with empty response
-            executeSimpleCommandWithResponse("", false);
+            executeCommand("");
         }
     }
 
     private void saslAuthExternal(String username) throws MessagingException, IOException {
-        executeSimpleCommand(
+        executeCommand("AUTH EXTERNAL %s", Base64.encode(username));
-                String.format("AUTH EXTERNAL %s",
-                        Base64.encode(username)), false);
     }
 
     @VisibleForTesting
     protected String getCanonicalHostName(InetAddress localAddress) {
         return localAddress.getCanonicalHostName();
     }
-
-    /**
-     * Exception that is thrown when the server sends a negative reply (reply codes 4xx or 5xx).
-     */
-    static class NegativeSmtpReplyException extends MessagingException {
-        private static final long serialVersionUID = 8696043577357897135L;
-
-        private final int mReplyCode;
-        private final String mReplyText;
-
-        public NegativeSmtpReplyException(int replyCode, String replyText) {
-            super("Negative SMTP reply: " + replyCode + " " + replyText, isPermanentSmtpError(replyCode));
-            mReplyCode = replyCode;
-            mReplyText = replyText;
-        }
-
-        private static boolean isPermanentSmtpError(int replyCode) {
-            return replyCode >= 500 && replyCode <= 599;
-        }
-
-        public int getReplyCode() {
-            return mReplyCode;
-        }
-
-        public String getReplyText() {
-            return mReplyText;
-        }
-    }
 }

k9mail-library/src/main/java/com/fsck/k9/mail/transport/smtp/StatusCodeClass.java

@@ -0,0 +1,26 @@
+package com.fsck.k9.mail.transport.smtp;
+
+
+enum StatusCodeClass {
+    SUCCESS(2),
+    PERSISTENT_TRANSIENT_FAILURE(4),
+    PERMANENT_FAILURE(5);
+
+
+    private final int codeClass;
+
+
+    static StatusCodeClass parse(String statusCodeClassString) {
+        int value = Integer.parseInt(statusCodeClassString);
+        for (StatusCodeClass classEnum : StatusCodeClass.values()) {
+            if (classEnum.codeClass == value) {
+                return classEnum;
+            }
+        }
+        return  null;
+    }
+
+    StatusCodeClass(int codeClass) {
+        this.codeClass = codeClass;
+    }
+}

k9mail-library/src/main/java/com/fsck/k9/mail/transport/smtp/StatusCodeDetail.java

@@ -0,0 +1,80 @@
+package com.fsck.k9.mail.transport.smtp;
+
+
+enum StatusCodeDetail {
+    UNDEFINED(StatusCodeSubject.UNDEFINED, 0),
+    OTHER_ADDRESS_STATUS(StatusCodeSubject.ADDRESSING, 0),
+    BAD_DESTINATION_MAILBOX_ADDRESS(StatusCodeSubject.ADDRESSING, 1),
+    BAD_DESTINATION_SYSTEM_ADDRESS(StatusCodeSubject.ADDRESSING, 2),
+    BAD_DESTINATION_MAILBOX_ADDRESS_SYNTAX(StatusCodeSubject.ADDRESSING, 3),
+    DESTINATION_MAILBOX_ADDRESS_AMBIGUOUS(StatusCodeSubject.ADDRESSING, 4),
+    DESTINATION_ADDRESS_VALID(StatusCodeSubject.ADDRESSING, 5),
+    DESTINATION_MAILBOX_MOVED(StatusCodeSubject.ADDRESSING, 6),
+    BAD_SENDER_MAILBOX_SYNTAX(StatusCodeSubject.ADDRESSING, 7),
+    BAD_SENDER_SYSTEM_ADDRESS(StatusCodeSubject.ADDRESSING, 8),
+
+    OTHER_MAILBOX_STATUS(StatusCodeSubject.MAILBOX,0),
+    MAILBOX_DISABLED(StatusCodeSubject.MAILBOX,1),
+    MAILBOX_FULL(StatusCodeSubject.MAILBOX,2),
+    MESSAGE_LENGTH_EXCEEDED(StatusCodeSubject.MAILBOX,3),
+    MAILING_LIST_EXPANSION_PROBLEM(StatusCodeSubject.MAILBOX,4),
+
+    OTHER_MAIL_SYSTEM_STATUS(StatusCodeSubject.MAIL_SYSTEM,0),
+    MAIL_SYSTEM_FULL(StatusCodeSubject.MAIL_SYSTEM,1),
+    SYSTEM_NOT_ACCEPTING_MESSAGES(StatusCodeSubject.MAIL_SYSTEM,2),
+    SYSTEM_INCAPABLE_OF_FEATURE(StatusCodeSubject.MAIL_SYSTEM,3),
+    MESSAGE_TOO_BIG(StatusCodeSubject.MAIL_SYSTEM,4),
+    SYSTEM_INCORRECTLY_CONFIGURED(StatusCodeSubject.MAIL_SYSTEM,5),
+
+    OTHER_NETWORK_ROUTING(StatusCodeSubject.NETWORK_ROUTING,0),
+    NO_ANSWER_FROM_HOST(StatusCodeSubject.NETWORK_ROUTING,1),
+    BAD_CONNECTION(StatusCodeSubject.NETWORK_ROUTING,2),
+    DIRECTORY_SERVER_FAILURE(StatusCodeSubject.NETWORK_ROUTING,3),
+    UNABLE_TO_ROUTE(StatusCodeSubject.NETWORK_ROUTING,4),
+    MAIL_SYSTEM_CONGESTION(StatusCodeSubject.NETWORK_ROUTING,5),
+    ROUTING_LOOP_DETECTED(StatusCodeSubject.NETWORK_ROUTING,6),
+    DELIVERY_TIME_EXPIRED(StatusCodeSubject.NETWORK_ROUTING,7),
+
+    OTHER_MAIL_DELIVERY_PROTOCOL(StatusCodeSubject.MAIL_DELIVERY_PROTOCOL,0),
+    INVALID_COMMAND(StatusCodeSubject.MAIL_DELIVERY_PROTOCOL,1),
+    SYNTAX_ERROR(StatusCodeSubject.MAIL_DELIVERY_PROTOCOL,2),
+    TOO_MANY_RECIPIENTS(StatusCodeSubject.MAIL_DELIVERY_PROTOCOL,3),
+    INVALID_COMMAND_ARGUMENTS(StatusCodeSubject.MAIL_DELIVERY_PROTOCOL,4),
+    WRONG_PROTOCOL_VERSION(StatusCodeSubject.MAIL_DELIVERY_PROTOCOL,5),
+
+    OTHER_MESSAGE_CONTENT_OR_MEDIA(StatusCodeSubject.MESSAGE_CONTENT_OR_MEDIA,0),
+    MEDIA_NOT_SUPPORTED(StatusCodeSubject.MESSAGE_CONTENT_OR_MEDIA,1),
+    CONVERSION_REQUIRED_AND_PROHIBITED(StatusCodeSubject.MESSAGE_CONTENT_OR_MEDIA,2),
+    CONVERSION_REQUIRED_BUT_UNSUPPORTED(StatusCodeSubject.MESSAGE_CONTENT_OR_MEDIA,3),
+    CONVERSION_WITH_LOSS_PERFORMED(StatusCodeSubject.MESSAGE_CONTENT_OR_MEDIA,4),
+    CONVERSION_FAILED(StatusCodeSubject.MESSAGE_CONTENT_OR_MEDIA,5),
+
+    OTHER_SECURITY_OR_POLICY_STATUS(StatusCodeSubject.SECURITY_OR_POLICY_STATUS, 0),
+    DELIVERY_NOT_AUTHORIZED(StatusCodeSubject.SECURITY_OR_POLICY_STATUS, 1),
+    MAILING_LIST_EXPANSION_PROHIBITED(StatusCodeSubject.SECURITY_OR_POLICY_STATUS, 2),
+    SECURITY_CONVERSION_REQUIRED(StatusCodeSubject.SECURITY_OR_POLICY_STATUS, 3),
+    SECURITY_FEATURES_UNSUPPORTED(StatusCodeSubject.SECURITY_OR_POLICY_STATUS, 4),
+    CRYPTOGRAPHIC_FAILURE(StatusCodeSubject.SECURITY_OR_POLICY_STATUS, 5),
+    CRYPTOGRAPHIC_ALGORITHM_UNSUPPORTED(StatusCodeSubject.SECURITY_OR_POLICY_STATUS, 6),
+    MESSAGE_INTEGRITY_FAILURE(StatusCodeSubject.SECURITY_OR_POLICY_STATUS, 7);
+
+
+    private final StatusCodeSubject subject;
+    private final int detail;
+
+
+    public static StatusCodeDetail parse(StatusCodeSubject statusCodeSubject, String statusCodeDetailString) {
+        int value = Integer.parseInt(statusCodeDetailString);
+        for (StatusCodeDetail detailEnum : StatusCodeDetail.values()) {
+            if (detailEnum.subject == statusCodeSubject && detailEnum.detail == value) {
+                return detailEnum;
+            }
+        }
+        return null;
+    }
+
+    StatusCodeDetail(StatusCodeSubject subject, int detail) {
+        this.subject = subject;
+        this.detail = detail;
+    }
+}

k9mail-library/src/main/java/com/fsck/k9/mail/transport/smtp/StatusCodeSubject.java

@@ -0,0 +1,31 @@
+package com.fsck.k9.mail.transport.smtp;
+
+
+enum StatusCodeSubject {
+    UNDEFINED(0),
+    ADDRESSING(1),
+    MAILBOX(2),
+    MAIL_SYSTEM(3),
+    NETWORK_ROUTING(4),
+    MAIL_DELIVERY_PROTOCOL(5),
+    MESSAGE_CONTENT_OR_MEDIA(6),
+    SECURITY_OR_POLICY_STATUS(7);
+
+
+    private final int codeSubject;
+
+
+    static StatusCodeSubject parse(String statusCodeSubjectString) {
+        int value = Integer.parseInt(statusCodeSubjectString);
+        for (StatusCodeSubject classEnum : StatusCodeSubject.values()) {
+            if (classEnum.codeSubject == value) {
+                return classEnum;
+            }
+        }
+        return null;
+    }
+
+    StatusCodeSubject(int codeSubject) {
+        this.codeSubject = codeSubject;
+    }
+}

k9mail-library/src/test/java/com/fsck/k9/mail/transport/smtp/SmtpTransportTest.java

@@ -1,4 +1,4 @@
-package com.fsck.k9.mail.transport;
+package com.fsck.k9.mail.transport.smtp;
 
 
 import java.io.IOException;
@@ -26,7 +26,6 @@ import org.junit.Before;
 import org.junit.Test;
 import org.junit.runner.RunWith;
 import org.mockito.InOrder;
-import org.robolectric.annotation.Config;
 
 import static junit.framework.Assert.assertTrue;
 import static junit.framework.Assert.fail;
@@ -227,7 +226,8 @@ public class SmtpTransportTest {
             fail("Exception expected");
         } catch (AuthenticationFailedException e) {
             assertEquals(
-                    "Negative SMTP reply: 535 5.7.1 http://support.google.com/mail/bin/answer.py?answer=14257 hx9sm5317360pbc.68",
+                    "5.7.1 Username and Password not accepted. Learn more at " +
+                    "5.7.1 http://support.google.com/mail/bin/answer.py?answer=14257 hx9sm5317360pbc.68",
                     e.getMessage());
         }
 
@@ -343,7 +343,8 @@ public class SmtpTransportTest {
             fail("Exception expected");
         } catch (AuthenticationFailedException e) {
             assertEquals(
-                "Negative SMTP reply: 535 5.7.1 http://support.google.com/mail/bin/answer.py?answer=14257 hx9sm5317360pbc.68",
+                "5.7.1 Username and Password not accepted. Learn more at " +
+                "5.7.1 http://support.google.com/mail/bin/answer.py?answer=14257 hx9sm5317360pbc.68",
                 e.getMessage());
         }
 
@@ -374,7 +375,6 @@ public class SmtpTransportTest {
         server.verifyInteractionCompleted();
     }
 
-
     @Test
     public void open_withoutXoauth2Extension_shouldThrow() throws Exception {
         MockSmtpServer server = new MockSmtpServer();
@@ -497,6 +497,63 @@ public class SmtpTransportTest {
         server.verifyInteractionCompleted();
     }
 
+    @Test
+    public void open_withSupportWithEnhancedStatusCodesOnAuthFailure_shouldThrowEncodedMessage()
+            throws Exception {
+        MockSmtpServer server = new MockSmtpServer();
+        server.output("220 localhost Simple Mail Transfer Service Ready");
+        server.expect("EHLO localhost");
+        server.output("250-localhost Hello client.localhost");
+        server.output("250-ENHANCEDSTATUSCODES");
+        server.output("250 AUTH XOAUTH2");
+        server.expect("AUTH XOAUTH2 dXNlcj11c2VyAWF1dGg9QmVhcmVyIG9sZFRva2VuAQE=");
+        server.output("334 " + XOAuth2ChallengeParserTest.STATUS_401_RESPONSE);
+        server.expect("");
+        server.output("535-5.7.1 Username and Password not accepted. Learn more at");
+        server.output("535 5.7.1 http://support.google.com/mail/bin/answer.py?answer=14257 hx9sm5317360pbc.68");
+        server.expect("QUIT");
+        server.output("221 BYE");
+        SmtpTransport transport = startServerAndCreateSmtpTransport(server, AuthType.XOAUTH2, ConnectionSecurity.NONE);
+
+        try {
+            transport.open();
+            fail("Exception expected");
+        } catch (AuthenticationFailedException e) {
+            assertEquals(
+                    "Username and Password not accepted. Learn more at http://support.google.com/mail/bin/answer.py?answer=14257 hx9sm5317360pbc.68",
+                    e.getMessage());
+        }
+
+        InOrder inOrder = inOrder(oAuth2TokenProvider);
+        inOrder.verify(oAuth2TokenProvider).getToken(eq(USERNAME), anyInt());
+        inOrder.verify(oAuth2TokenProvider).invalidateToken(USERNAME);
+        server.verifyConnectionClosed();
+        server.verifyInteractionCompleted();
+    }
+
+    @Test
+    public void open_withManyExtensions_shouldParseAll() throws Exception {
+        MockSmtpServer server = new MockSmtpServer();
+        server.output("220 smtp.gmail.com ESMTP x25sm19117693wrx.27 - gsmtp");
+        server.expect("EHLO localhost");
+        server.output("250-smtp.gmail.com at your service, [86.147.34.216]");
+        server.output("250-SIZE 35882577");
+        server.output("250-8BITMIME");
+        server.output("250-AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH");
+        server.output("250-ENHANCEDSTATUSCODES");
+        server.output("250-PIPELINING");
+        server.output("250-CHUNKING");
+        server.output("250 SMTPUTF8");
+        server.expect("AUTH XOAUTH2 dXNlcj11c2VyAWF1dGg9QmVhcmVyIG9sZFRva2VuAQE=");
+        server.output("235 2.7.0 Authentication successful");
+        SmtpTransport transport = startServerAndCreateSmtpTransport(server, AuthType.XOAUTH2, ConnectionSecurity.NONE);
+
+        transport.open();
+
+        server.verifyConnectionStillOpen();
+        server.verifyInteractionCompleted();
+    }
+
     @Test
     public void sendMessage_withoutAddressToSendTo_shouldNotOpenConnection() throws Exception {
         MimeMessage message = new MimeMessage();
@@ -556,6 +613,30 @@ public class SmtpTransportTest {
         server.verifyInteractionCompleted();
     }
 
+    @Test
+    public void sendMessage_with8BitEncodingExtensionNotCaseSensitive() throws Exception {
+        Message message = getDefaultMessage();
+        MockSmtpServer server = createServerAndSetupForPlainAuthentication("8bitmime");
+        server.expect("MAIL FROM:<user@localhost> BODY=8BITMIME");
+        server.output("250 OK");
+        server.expect("RCPT TO:<user2@localhost>");
+        server.output("250 OK");
+        server.expect("DATA");
+        server.output("354 End data with <CR><LF>.<CR><LF>");
+        server.expect("[message data]");
+        server.expect(".");
+        server.output("250 OK: queued as 12345");
+        server.expect("QUIT");
+        server.output("221 BYE");
+        server.closeConnection();
+        SmtpTransport transport = startServerAndCreateSmtpTransport(server);
+
+        transport.sendMessage(message);
+
+        server.verifyConnectionClosed();
+        server.verifyInteractionCompleted();
+    }
+
     @Test
     public void sendMessage_withMessageTooLarge_shouldThrow() throws Exception {
         Message message = getDefaultMessageBuilder()
@@ -598,7 +679,7 @@ public class SmtpTransportTest {
         try {
             transport.sendMessage(message);
             fail("Expected exception");
-        } catch (SmtpTransport.NegativeSmtpReplyException e) {
+        } catch (NegativeSmtpReplyException e) {
             assertEquals(421, e.getReplyCode());
             assertEquals("4.7.0 Temporary system problem", e.getReplyText());
         }

k9mail-library/src/test/java/com/fsck/k9/mail/transport/smtp/SmtpTransportUriTest.java

@@ -1,4 +1,4 @@
-package com.fsck.k9.mail.transport;
+package com.fsck.k9.mail.transport.smtp;
 
 import android.annotation.SuppressLint;
 
@@ -6,6 +6,7 @@ import com.fsck.k9.mail.AuthType;
 import com.fsck.k9.mail.ConnectionSecurity;
 import com.fsck.k9.mail.ServerSettings;
 
+import com.fsck.k9.mail.transport.smtp.SmtpTransport;
 import org.junit.Test;
 
 import static org.junit.Assert.assertEquals;