21 files changed, 323 insertions, 22 deletions
diff --git a/src/async/imap/MCIMAPAppendMessageOperation.cpp b/src/async/imap/MCIMAPAppendMessageOperation.cpp
index 23eaaea0..69ed5c5f 100644
--- a/src/async/imap/MCIMAPAppendMessageOperation.cpp
+++ b/src/async/imap/MCIMAPAppendMessageOperation.cpp
@@ -16,6 +16,7 @@ using namespace mailcore;
 IMAPAppendMessageOperation::IMAPAppendMessageOperation()
 {
     mMessageData = NULL;
+    mMessageFilepath = NULL;
     mFlags = MessageFlagNone;
     mCustomFlags = NULL;
     mDate = (time_t) -1;
@@ -25,6 +26,7 @@ IMAPAppendMessageOperation::IMAPAppendMessageOperation()
 IMAPAppendMessageOperation::~IMAPAppendMessageOperation()
 {
     MC_SAFE_RELEASE(mMessageData);
+    MC_SAFE_RELEASE(mMessageFilepath);
     MC_SAFE_RELEASE(mCustomFlags);
 }
 
@@ -38,6 +40,16 @@ Data * IMAPAppendMessageOperation::messageData()
     return mMessageData;
 }
 
+void IMAPAppendMessageOperation::setMessageFilepath(String * path)
+{
+    MC_SAFE_REPLACE_RETAIN(String, mMessageFilepath, path);
+}
+
+String * IMAPAppendMessageOperation::messageFilepath()
+{
+    return mMessageFilepath;
+}
+
 void IMAPAppendMessageOperation::setFlags(MessageFlag flags)
 {
     mFlags = flags;
@@ -76,7 +88,12 @@ uint32_t IMAPAppendMessageOperation::createdUID()
 void IMAPAppendMessageOperation::main()
 {
     ErrorCode error;
-    session()->session()->appendMessageWithCustomFlagsAndDate(folder(), mMessageData, mFlags, mCustomFlags, mDate, this, &mCreatedUID, &error);
+    if (mMessageFilepath != NULL) {
+        session()->session()->appendMessageWithCustomFlagsAndDate(folder(), mMessageFilepath, mFlags, mCustomFlags, mDate, this, &mCreatedUID, &error);
+    }
+    else {
+        session()->session()->appendMessageWithCustomFlagsAndDate(folder(), mMessageData, mFlags, mCustomFlags, mDate, this, &mCreatedUID, &error);
+    }
     setError(error);
 }
 
diff --git a/src/async/imap/MCIMAPAppendMessageOperation.h b/src/async/imap/MCIMAPAppendMessageOperation.h
index ca3033a6..f711c988 100644
--- a/src/async/imap/MCIMAPAppendMessageOperation.h
+++ b/src/async/imap/MCIMAPAppendMessageOperation.h
@@ -24,7 +24,10 @@ namespace mailcore {
         
         virtual void setMessageData(Data * messageData);
         virtual Data * messageData();
-        
+
+        virtual void setMessageFilepath(String * path);
+        virtual String * messageFilepath();
+
         virtual void setFlags(MessageFlag flags);
         virtual MessageFlag flags();
         
@@ -41,6 +44,7 @@ namespace mailcore {
         
     private:
         Data * mMessageData;
+        String * mMessageFilepath;
         MessageFlag mFlags;
         Array * mCustomFlags;
         time_t mDate;
diff --git a/src/async/imap/MCIMAPAsyncSession.cpp b/src/async/imap/MCIMAPAsyncSession.cpp
index 7f00d105..676d9bc5 100755
--- a/src/async/imap/MCIMAPAsyncSession.cpp
+++ b/src/async/imap/MCIMAPAsyncSession.cpp
@@ -443,6 +443,18 @@ IMAPAppendMessageOperation * IMAPAsyncSession::appendMessageOperation(String * f
     return op;
 }
 
+IMAPAppendMessageOperation * IMAPAsyncSession::appendMessageOperation(String * folder, String * messagePath, MessageFlag flags, Array * customFlags)
+{
+    IMAPAppendMessageOperation * op = new IMAPAppendMessageOperation();
+    op->setMainSession(this);
+    op->setFolder(folder);
+    op->setMessageFilepath(messagePath);
+    op->setFlags(flags);
+    op->setCustomFlags(customFlags);
+    op->autorelease();
+    return op;
+}
+
 IMAPCopyMessagesOperation * IMAPAsyncSession::copyMessagesOperation(String * folder, IndexSet * uids, String * destFolder)
 {
     IMAPCopyMessagesOperation * op = new IMAPCopyMessagesOperation();
diff --git a/src/async/imap/MCIMAPAsyncSession.h b/src/async/imap/MCIMAPAsyncSession.h
index bbffacbd..b92d8017 100755
--- a/src/async/imap/MCIMAPAsyncSession.h
+++ b/src/async/imap/MCIMAPAsyncSession.h
@@ -120,7 +120,8 @@ namespace mailcore {
         virtual IMAPOperation * unsubscribeFolderOperation(String * folder);
         
         virtual IMAPAppendMessageOperation * appendMessageOperation(String * folder, Data * messageData, MessageFlag flags, Array * customFlags = NULL);
-        
+        virtual IMAPAppendMessageOperation * appendMessageOperation(String * folder, String * messagePath, MessageFlag flags, Array * customFlags = NULL);
+
         virtual IMAPCopyMessagesOperation * copyMessagesOperation(String * folder, IndexSet * uids, String * destFolder);
         virtual IMAPMoveMessagesOperation * moveMessagesOperation(String * folder, IndexSet * uids, String * destFolder);
         
diff --git a/src/async/smtp/MCSMTPAsyncSession.cpp b/src/async/smtp/MCSMTPAsyncSession.cpp
index d2f645da..46b25184 100644
--- a/src/async/smtp/MCSMTPAsyncSession.cpp
+++ b/src/async/smtp/MCSMTPAsyncSession.cpp
@@ -240,6 +240,17 @@ SMTPOperation * SMTPAsyncSession::sendMessageOperation(Address * from, Array * r
     return (SMTPOperation *) op->autorelease();
 }
 
+SMTPOperation * SMTPAsyncSession::sendMessageOperation(Address * from, Array * recipients,
+                                                       String * filename)
+{
+    SMTPSendWithDataOperation * op = new SMTPSendWithDataOperation();
+    op->setSession(this);
+    op->setMessageFilepath(filename);
+    op->setFrom(from);
+    op->setRecipients(recipients);
+    return (SMTPOperation *) op->autorelease();
+}
+
 SMTPOperation * SMTPAsyncSession::checkAccountOperation(Address * from)
 {
     SMTPCheckAccountOperation * op = new SMTPCheckAccountOperation();
diff --git a/src/async/smtp/MCSMTPAsyncSession.h b/src/async/smtp/MCSMTPAsyncSession.h
index 90849797..961df6ef 100644
--- a/src/async/smtp/MCSMTPAsyncSession.h
+++ b/src/async/smtp/MCSMTPAsyncSession.h
@@ -68,6 +68,8 @@ namespace mailcore {
         virtual SMTPOperation * sendMessageOperation(Data * messageData);
         virtual SMTPOperation * sendMessageOperation(Address * from, Array * recipients,
                                                      Data * messageData);
+        virtual SMTPOperation * sendMessageOperation(Address * from, Array * recipients,
+                                                     String * filename);
         virtual SMTPOperation * checkAccountOperation(Address * from);
         
         virtual SMTPOperation * noopOperation();
diff --git a/src/async/smtp/MCSMTPSendWithDataOperation.cpp b/src/async/smtp/MCSMTPSendWithDataOperation.cpp
index 03f6a530..4561b5d8 100644
--- a/src/async/smtp/MCSMTPSendWithDataOperation.cpp
+++ b/src/async/smtp/MCSMTPSendWithDataOperation.cpp
@@ -16,6 +16,7 @@ using namespace mailcore;
 SMTPSendWithDataOperation::SMTPSendWithDataOperation()
 {
     mMessageData = NULL;
+    mMessageFilepath = NULL;
     mFrom = NULL;
     mRecipients = NULL;
 }
@@ -24,6 +25,7 @@ SMTPSendWithDataOperation::~SMTPSendWithDataOperation()
 {
     MC_SAFE_RELEASE(mFrom);
     MC_SAFE_RELEASE(mRecipients);
+    MC_SAFE_RELEASE(mMessageFilepath);
     MC_SAFE_RELEASE(mMessageData);
 }
 
@@ -37,6 +39,16 @@ Data * SMTPSendWithDataOperation::messageData()
     return mMessageData;
 }
 
+void SMTPSendWithDataOperation::setMessageFilepath(String * path)
+{
+    MC_SAFE_REPLACE_RETAIN(String, mMessageFilepath, path);
+}
+
+String * SMTPSendWithDataOperation::messageFilepath()
+{
+    return mMessageFilepath;
+}
+
 void SMTPSendWithDataOperation::setFrom(Address * from)
 {
     MC_SAFE_REPLACE_COPY(Address, mFrom, from);
@@ -60,6 +72,10 @@ Array * SMTPSendWithDataOperation::recipients()
 void SMTPSendWithDataOperation::main()
 {
     ErrorCode error;
+    if (mMessageFilepath != NULL) {
+        session()->session()->sendMessage(mFrom, mRecipients, mMessageFilepath, this, &error);
+    }
+    else
     if ((mFrom != NULL) && (mRecipients != NULL)) {
         session()->session()->sendMessage(mFrom, mRecipients, mMessageData, this, &error);
     }
diff --git a/src/async/smtp/MCSMTPSendWithDataOperation.h b/src/async/smtp/MCSMTPSendWithDataOperation.h
index a8ee2515..768adda9 100644
--- a/src/async/smtp/MCSMTPSendWithDataOperation.h
+++ b/src/async/smtp/MCSMTPSendWithDataOperation.h
@@ -31,15 +31,18 @@ namespace mailcore {
         
         virtual void setMessageData(Data * data);
         virtual Data * messageData();
-        
+
+        virtual void setMessageFilepath(String * path);
+        virtual String * messageFilepath();
+
     public: // subclass behavior
         virtual void main();
         
     private:
         Data * mMessageData;
+        String * mMessageFilepath;
         Array * mRecipients;
         Address * mFrom;
-        
     };
     
 }
diff --git a/src/core/imap/MCIMAPSession.cpp b/src/core/imap/MCIMAPSession.cpp
index 96d34b73..4e92e97f 100755
--- a/src/core/imap/MCIMAPSession.cpp
+++ b/src/core/imap/MCIMAPSession.cpp
@@ -1655,6 +1655,18 @@ void IMAPSession::appendMessageWithCustomFlagsAndDate(String * folder, Data * me
     * pError = ErrorNone;
 }
 
+void IMAPSession::appendMessageWithCustomFlagsAndDate(String * folder, String * messagePath, MessageFlag flags, Array * customFlags, time_t date,
+                                                      IMAPProgressCallback * progressCallback, uint32_t * createdUID, ErrorCode * pError)
+{
+    Data * messageData = Data::dataWithContentsOfFile(messagePath);
+    if (!messageData) {
+        * pError = ErrorFile;
+        return;
+    }
+
+    return appendMessageWithCustomFlagsAndDate(folder, messageData, flags, customFlags, date, progressCallback, createdUID, pError);
+}
+
 void IMAPSession::copyMessages(String * folder, IndexSet * uidSet, String * destFolder,
      HashMap ** pUidMapping, ErrorCode * pError)
 {
diff --git a/src/core/imap/MCIMAPSession.h b/src/core/imap/MCIMAPSession.h
index c122e546..578350ac 100755
--- a/src/core/imap/MCIMAPSession.h
+++ b/src/core/imap/MCIMAPSession.h
@@ -85,7 +85,9 @@ namespace mailcore {
                                    IMAPProgressCallback * progressCallback, uint32_t * createdUID, ErrorCode * pError);
         virtual void appendMessageWithCustomFlagsAndDate(String * folder, Data * messageData, MessageFlag flags, Array * customFlags, time_t date,
                                                          IMAPProgressCallback * progressCallback, uint32_t * createdUID, ErrorCode * pError);
-        
+        virtual void appendMessageWithCustomFlagsAndDate(String * folder, String * messagePath, MessageFlag flags, Array * customFlags, time_t date,
+                                                         IMAPProgressCallback * progressCallback, uint32_t * createdUID, ErrorCode * pError);
+
         virtual void copyMessages(String * folder, IndexSet * uidSet, String * destFolder,
                                   HashMap ** pUidMapping, ErrorCode * pError);
         
diff --git a/src/core/rfc822/MCMessageBuilder.cpp b/src/core/rfc822/MCMessageBuilder.cpp
index a98cefd1..b3a95249 100644
--- a/src/core/rfc822/MCMessageBuilder.cpp
+++ b/src/core/rfc822/MCMessageBuilder.cpp
@@ -810,6 +810,31 @@ Data * MessageBuilder::dataForEncryption()
     return dataAndFilterBccAndForEncryption(false, true);
 }
 
+ErrorCode MessageBuilder::writeToFile(String * filename)
+{
+    FILE * f = fopen(filename->fileSystemRepresentation(), "wb");
+    if (f == NULL) {
+        return ErrorFile;
+    }
+
+    ErrorCode error = ErrorNone;
+    struct mailmime * mime = mimeAndFilterBccAndForEncryption(false, false);
+
+    int col = 0;
+    int r = mailmime_write_file(f, &col, mime);
+    if (r != MAILIMF_NO_ERROR) {
+        error = ErrorFile;
+    }
+
+    mailmime_free(mime);
+
+    if (fclose(f) != 0) {
+        error = ErrorFile;
+    }
+
+    return error;
+}
+
 String * MessageBuilder::htmlRendering(HTMLRendererTemplateCallback * htmlCallback)
 {
     MessageParser * message = MessageParser::messageParserWithData(data());
diff --git a/src/core/rfc822/MCMessageBuilder.h b/src/core/rfc822/MCMessageBuilder.h
index f03bd09a..3d26ac59 100644
--- a/src/core/rfc822/MCMessageBuilder.h
+++ b/src/core/rfc822/MCMessageBuilder.h
@@ -40,7 +40,10 @@ namespace mailcore {
         
         virtual Data * data();
         virtual Data * dataForEncryption();
-        
+
+        // Store builded message to file.
+        virtual ErrorCode writeToFile(String * filename);
+
         virtual String * htmlRendering(HTMLRendererTemplateCallback * htmlCallback = NULL);
         virtual String * htmlBodyRendering();
         
diff --git a/src/core/smtp/MCSMTPSession.cpp b/src/core/smtp/MCSMTPSession.cpp
index d0711c65..8bcaefff 100644
--- a/src/core/smtp/MCSMTPSession.cpp
+++ b/src/core/smtp/MCSMTPSession.cpp
@@ -617,7 +617,7 @@ void SMTPSession::sendMessage(Address * from, Array * recipients, Data * message
     }
     
     messageData = dataWithFilteredBcc(messageData);
-    
+
     mProgressCallback = callback;
     bodyProgress(0, messageData->length());
     
@@ -717,13 +717,28 @@ void SMTPSession::sendMessage(Address * from, Array * recipients, Data * message
     mProgressCallback = NULL;
 }
 
+void SMTPSession::sendMessage(Address * from, Array * recipients, String * messagePath,
+                              SMTPProgressCallback * callback, ErrorCode * pError)
+{
+    Data * messageData = Data::dataWithContentsOfFile(messagePath);
+    if (!messageData) {
+        * pError = ErrorFile;
+        return;
+    }
+
+    return sendMessage(from, recipients, messageData, callback, pError);
+}
+
+static void mmapStringDeallocator(char * bytes, unsigned int length) {
+    mmap_string_unref(bytes);
+}
+
 Data * SMTPSession::dataWithFilteredBcc(Data * data)
 {
     int r;
     size_t idx;
     struct mailimf_message * msg;
-    MMAPString * str;
-    
+
     idx = 0;
     r = mailimf_message_parse(data->bytes(), data->length(), &idx, &msg);
     if (r != MAILIMF_NO_ERROR) {
@@ -734,15 +749,16 @@ Data * SMTPSession::dataWithFilteredBcc(Data * data)
     int col = 0;
 
     int hasRecipient = 0;
-    str = mmap_string_new("");
+    bool bccWasActuallyRemoved = false;
     for(clistiter * cur = clist_begin(fields->fld_list) ; cur != NULL ; cur = clist_next(cur)) {
         struct mailimf_field * field = (struct mailimf_field *) clist_content(cur);
         if (field->fld_type == MAILIMF_FIELD_BCC) {
             mailimf_field_free(field);
             clist_delete(fields->fld_list, cur);
+            bccWasActuallyRemoved = true;
             break;
         }
-        else if ((field->fld_type == MAILIMF_FIELD_TO) || (field->fld_type == MAILIMF_FIELD_CC) || (field->fld_type == MAILIMF_FIELD_BCC)) {
+        else if ((field->fld_type == MAILIMF_FIELD_TO) || (field->fld_type == MAILIMF_FIELD_CC)) {
             hasRecipient = 1;
         }
     }
@@ -754,13 +770,24 @@ Data * SMTPSession::dataWithFilteredBcc(Data * data)
         struct mailimf_field * field = mailimf_field_new(MAILIMF_FIELD_TO, NULL, NULL, NULL, NULL, NULL, NULL, NULL, NULL, NULL, NULL, NULL, NULL, toField, NULL, NULL, NULL, NULL, NULL, NULL, NULL, NULL, NULL);
         mailimf_fields_add(fields, field);
     }
-    mailimf_fields_write_mem(str, &col, fields);
-    mmap_string_append(str, "\n");
-    mmap_string_append_len(str, msg->msg_body->bd_text, msg->msg_body->bd_size);
-    
-    Data * result = Data::dataWithBytes(str->str, (unsigned int) str->len);
-    
-    mmap_string_free(str);
+
+    Data * result;
+    if (!hasRecipient || bccWasActuallyRemoved) {
+        MMAPString * str = mmap_string_new("");
+        mailimf_fields_write_mem(str, &col, fields);
+        mmap_string_append(str, "\n");
+        mmap_string_append_len(str, msg->msg_body->bd_text, msg->msg_body->bd_size);
+
+        mmap_string_ref(str);
+
+        result = Data::data();
+        result->takeBytesOwnership(str->str, (unsigned int) str->len, mmapStringDeallocator);
+    }
+    else {
+        // filter Bcc and modify To: only if necessary.
+        result = data;
+    }
+
     mailimf_message_free(msg);
     
     return result;
diff --git a/src/core/smtp/MCSMTPSession.h b/src/core/smtp/MCSMTPSession.h
index 05571bfb..64ff30d0 100644
--- a/src/core/smtp/MCSMTPSession.h
+++ b/src/core/smtp/MCSMTPSession.h
@@ -60,7 +60,9 @@ namespace mailcore {
         virtual void sendMessage(Data * messageData, SMTPProgressCallback * callback, ErrorCode * pError);
         virtual void sendMessage(Address * from, Array * /* Address */ recipients, Data * messageData,
                                  SMTPProgressCallback * callback, ErrorCode * pError);
-        
+        virtual void sendMessage(Address * from, Array * /* Address */ recipients, String * messagePath,
+                                 SMTPProgressCallback * callback, ErrorCode * pError);
+
         virtual void setConnectionLogger(ConnectionLogger * logger);
         virtual ConnectionLogger * connectionLogger();
         
diff --git a/src/objc/imap/MCOIMAPSession.h b/src/objc/imap/MCOIMAPSession.h
index bab3be7f..6fd5f76e 100755
--- a/src/objc/imap/MCOIMAPSession.h
+++ b/src/objc/imap/MCOIMAPSession.h
@@ -305,6 +305,24 @@
                                                         customFlags:(NSArray *)customFlags;
 
 /**
+ Returns an operation to add a message with custom flags to a folder.
+
+     MCOIMAPOperation * op = [session appendMessageOperationWithFolder:@"Sent Mail"
+                                                        contentsAtPath:rfc822DataFilename
+                                                                 flags:MCOMessageFlagNone
+                                                           customFlags:@[@"$CNS-Greeting-On"]];
+     [op start:^(NSError * __nullable error, uint32_t createdUID) {
+       if (error == nil) {
+         NSLog(@"created message with UID %lu", (unsigned long) createdUID);
+       }
+     }];
+ */
+- (MCOIMAPAppendMessageOperation *)appendMessageOperationWithFolder:(NSString *)folder
+                                                     contentsAtPath:(NSString *)path
+                                                              flags:(MCOMessageFlag)flags
+                                                        customFlags:(NSArray *)customFlags;
+
+/**
  Returns an operation to copy messages to a folder.
 
      MCOIMAPCopyMessagesOperation * op = [session copyMessagesOperationWithFolder:@"INBOX"
diff --git a/src/objc/imap/MCOIMAPSession.mm b/src/objc/imap/MCOIMAPSession.mm
index 32dd1119..c245cdc3 100755
--- a/src/objc/imap/MCOIMAPSession.mm
+++ b/src/objc/imap/MCOIMAPSession.mm
@@ -264,6 +264,18 @@ MCO_OBJC_SYNTHESIZE_SCALAR(dispatch_queue_t, dispatch_queue_t, setDispatchQueue,
     return MCO_TO_OBJC_OP(coreOp);
 }
 
+- (MCOIMAPAppendMessageOperation *)appendMessageOperationWithFolder:(NSString *)folder
+                                                     contentsAtPath:(NSString *)path
+                                                              flags:(MCOMessageFlag)flags
+                                                        customFlags:(NSArray *)customFlags
+{
+    IMAPAppendMessageOperation * coreOp = MCO_NATIVE_INSTANCE->appendMessageOperation([folder mco_mcString],
+                                                                                      MCO_FROM_OBJC(String, path),
+                                                                                      (MessageFlag) flags,
+                                                                                      MCO_FROM_OBJC(Array, customFlags));
+    return MCO_TO_OBJC_OP(coreOp);
+}
+
 - (MCOIMAPCopyMessagesOperation *)copyMessagesOperationWithFolder:(NSString *)folder
                                                              uids:(MCOIndexSet *)uids
                                                        destFolder:(NSString *)destFolder
diff --git a/src/objc/rfc822/MCOMessageBuilder.h b/src/objc/rfc822/MCOMessageBuilder.h
index 1663d6f7..fbebb7f6 100644
--- a/src/objc/rfc822/MCOMessageBuilder.h
+++ b/src/objc/rfc822/MCOMessageBuilder.h
@@ -61,6 +61,9 @@
 /** RFC 822 formatted message for encryption.*/
 - (NSData *) dataForEncryption;
 
+/** Store RFC 822 formatted message to file. */
+- (BOOL) writeToFile:(NSString *)filename error:(NSError **)error;
+
 /**
  Returns an OpenPGP signed message with a given signature.
  The signature needs to be computed on the data returned by -dataForEncryption
diff --git a/src/objc/rfc822/MCOMessageBuilder.mm b/src/objc/rfc822/MCOMessageBuilder.mm
index 84cc37f2..31ebc742 100644
--- a/src/objc/rfc822/MCOMessageBuilder.mm
+++ b/src/objc/rfc822/MCOMessageBuilder.mm
@@ -70,6 +70,15 @@ MCO_OBJC_SYNTHESIZE_STRING(setBoundaryPrefix, boundaryPrefix)
     return MCO_OBJC_BRIDGE_GET(dataForEncryption);
 }
 
+- (BOOL) writeToFile:(NSString *)filename error:(NSError **)error
+{
+    mailcore::ErrorCode errorCode = MCO_NATIVE_INSTANCE->writeToFile(MCO_FROM_OBJC(mailcore::String, filename));
+    if (error) {
+        *error = [NSError mco_errorWithErrorCode:errorCode];
+    }
+    return errorCode == mailcore::ErrorNone;
+}
+
 - (NSString *) htmlRenderingWithDelegate:(id <MCOHTMLRendererDelegate>)delegate
 {
     MCOAbstractMessageRendererCallback * htmlRenderCallback = new MCOAbstractMessageRendererCallback(self, delegate, NULL);
diff --git a/src/objc/smtp/MCOSMTPSession.h b/src/objc/smtp/MCOSMTPSession.h
index 31055335..84d6949d 100644
--- a/src/objc/smtp/MCOSMTPSession.h
+++ b/src/objc/smtp/MCOSMTPSession.h
@@ -154,6 +154,24 @@
                                             from:(MCOAddress *)from
                                       recipients:(NSArray *)recipients;
 
+
+/**
+ Returns an operation that will send the message from the given file through SMTP.
+ It will use the sender and recipient set from the parameters.
+ It will also filter out Bcc from the content of the message.
+
+ MCOSMTPOperation * op = [session sendOperationWithContentsOfFile:rfc822DataFilename
+                                                             from:[MCOAddress addressWithMailbox:@"hoa@etpan.org"]
+                                                       recipients:[NSArray arrayWithObject:
+                                                                   [MCOAddress addressWithMailbox:@"laura@etpan.org"]]];
+ [op start:^(NSError * __nullable error) {
+ ...
+ }];
+ */
+- (MCOSMTPSendOperation *) sendOperationWithContentsOfFile:(NSString *)path
+                                                      from:(MCOAddress *)from
+                                                recipients:(NSArray *)recipients;
+
 /**
  Returns an operation that will check whether the SMTP account is valid.
 
diff --git a/src/objc/smtp/MCOSMTPSession.mm b/src/objc/smtp/MCOSMTPSession.mm
index 9bcbd48e..9406a719 100644
--- a/src/objc/smtp/MCOSMTPSession.mm
+++ b/src/objc/smtp/MCOSMTPSession.mm
@@ -170,6 +170,19 @@ MCO_OBJC_SYNTHESIZE_SCALAR(dispatch_queue_t, dispatch_queue_t, setDispatchQueue,
     return result;
 }
 
+- (MCOSMTPSendOperation *) sendOperationWithContentsOfFile:(NSString *)path
+                                                      from:(MCOAddress *)from
+                                                recipients:(NSArray *)recipients
+{
+    mailcore::SMTPOperation * coreOp =
+    MCO_NATIVE_INSTANCE->sendMessageOperation(MCO_FROM_OBJC(Address, from),
+                                              MCO_FROM_OBJC(Array, recipients),
+                                              MCO_FROM_OBJC(String, path));
+    MCOSMTPSendOperation * result = [[[MCOSMTPSendOperation alloc] initWithMCOperation:coreOp] autorelease];
+    [result setSession:self];
+    return result;
+}
+
 - (MCOSMTPOperation *) checkAccountOperationWithFrom:(MCOAddress *)from
 {
     mailcore::SMTPOperation *coreOp = MCO_NATIVE_INSTANCE->checkAccountOperation(MCO_FROM_OBJC(mailcore::Address, from));
diff --git a/tests/test-all.cpp b/tests/test-all.cpp
index 02a4081c..c3e25ada 100644
--- a/tests/test-all.cpp
+++ b/tests/test-all.cpp
@@ -63,6 +63,16 @@ class TestCallback : public mailcore::Object, public mailcore::OperationCallback
     }
 };
 
+static mailcore::String * temporaryFilenameForTest()
+{
+    char tempfile[] = "/tmp/mailcore2-test-XXXXXX";
+    char * result = mktemp(tempfile);
+    if (result == NULL) {
+        return NULL;
+    }
+    return mailcore::String::stringWithFileSystemRepresentation(tempfile);
+}
+
 static mailcore::Data * testMessageBuilder()
 {
     mailcore::Address * address = new mailcore::Address();
@@ -96,7 +106,12 @@ static mailcore::Data * testMessageBuilder()
     mailcore::Data * data = msg->data();
     
     MCLog("%s", data->bytes());
-    
+
+    mailcore::String *filename = temporaryFilenameForTest();
+    msg->writeToFile(filename);
+    mailcore::Data *fileData = mailcore::Data::dataWithContentsOfFile(filename);
+    MCAssert(data->isEqual(fileData));
+
     mailcore::MessageBuilder * msg2 = new mailcore::MessageBuilder(msg);
     mailcore::String *htmlBody = msg->htmlBody();
     mailcore::String *htmlBody2 = msg2->htmlBody();
@@ -104,7 +119,8 @@ static mailcore::Data * testMessageBuilder()
     
     msg->release();
     msg2->release();
-    
+    unlink(filename->fileSystemRepresentation());
+
     return data;
 }
 
@@ -200,6 +216,49 @@ static void testSMTP(mailcore::Data * data)
     smtp->release();
 }
 
+static void parseAddressesFromRfc822(mailcore::String * filename, mailcore::Array ** pRecipients, mailcore::Address ** pFrom)
+{
+    mailcore::MessageParser * parser = mailcore::MessageParser::messageParserWithContentsOfFile(filename);
+
+    mailcore::Array * recipients = mailcore::Array::array();
+    if (parser->header()->to() != NULL) {
+        recipients->addObjectsFromArray(parser->header()->to());
+    }
+    if (parser->header()->cc() != NULL) {
+        recipients->addObjectsFromArray(parser->header()->cc());
+    }
+    if (parser->header()->bcc() != NULL) {
+        recipients->addObjectsFromArray(parser->header()->bcc());
+    }
+    *pRecipients = recipients;
+    *pFrom = parser->header()->from();
+}
+
+static void testSendingMessageFromFileViaSMTP(mailcore::Data * data)
+{
+    mailcore::SMTPSession * smtp;
+    mailcore::ErrorCode error;
+
+    mailcore::String * filename = temporaryFilenameForTest();
+    data->writeToFile(filename);
+
+    smtp = new mailcore::SMTPSession();
+
+    smtp->setHostname(MCSTR("smtp.gmail.com"));
+    smtp->setPort(25);
+    smtp->setUsername(email);
+    smtp->setPassword(password);
+    smtp->setConnectionType(mailcore::ConnectionTypeStartTLS);
+
+    mailcore::Array * recipients;
+    mailcore::Address * from;
+    parseAddressesFromRfc822(filename, &recipients, &from);
+
+    smtp->sendMessage(from, recipients, filename, NULL, &error);
+
+    smtp->release();
+}
+
 static void testPOP()
 {
     mailcore::POPSession * session;
@@ -291,6 +350,36 @@ static void testAsyncSMTP(mailcore::Data * data)
     //smtp->release();
 }
 
+static void testAsyncSendMessageFromFileViaSMTP(mailcore::Data * data)
+{
+    mailcore::SMTPAsyncSession * smtp;
+    TestSMTPCallback * callback = new TestSMTPCallback();
+
+    mailcore::String * filename = temporaryFilenameForTest();
+    data->writeToFile(filename);
+
+    mailcore::Array * recipients;
+    mailcore::Address * from;
+    parseAddressesFromRfc822(filename, &recipients, &from);
+
+    smtp = new mailcore::SMTPAsyncSession();
+
+    smtp->setHostname(MCSTR("smtp.gmail.com"));
+    smtp->setPort(25);
+    smtp->setUsername(email);
+    smtp->setPassword(password);
+    smtp->setConnectionType(mailcore::ConnectionTypeStartTLS);
+
+    mailcore::SMTPOperation * op = smtp->sendMessageOperation(from, recipients, filename);
+    op->setSmtpCallback(callback);
+    op->setCallback(callback);
+    op->start();
+
+    mainLoop();
+
+    //smtp->release();
+}
+
 class TestIMAPCallback : public mailcore::Object, public mailcore::OperationCallback, public mailcore::IMAPOperationCallback {
     virtual void operationFinished(mailcore::Operation * op)
     {
@@ -411,12 +500,14 @@ void testAll()
     //mailcore::Data * data = testMessageBuilder();
     //testMessageParser(data);
     //testSMTP(data);
+    //testSendingMessageFromFileViaSMTP(data);
     //testIMAP();
     //testIMAPMove();
     //testIMAPCapability();
     //testPOP();
     //testNNTP();
     //testAsyncSMTP(data);
+    //testAsyncSendMessageFromFileViaSMTP(data);
     //testAsyncIMAP();
     //testAsyncPOP();
     //testAddresses();