I am trying to upload a profile image to twitter using their API. I found some good examples on the web on how to format the URLRequest, however I just can't seem to get this to work. Any help would be appreciated. The URL that I am using from Twitter API is http://twitter.com/account/update_profile_image.json -(void)uploadImageForAccount:(NSURL *)theURL intUserName:(NSString *)_userName initPassWord:(NSString *)_passWord image:(NSData *)image{ userName = [_userName retain]; passWord = [_passWord retain]; UIApplication *app = [UIApplication sharedApplication]; app.networkActivityIndicatorVisible = YES; requestedData = [[NSMutableData alloc] initWithLength:0]; NSMutableURLRequest *theRequest = [NSMutableURLRequest requestWithURL:theURL cachePolicy:NSURLRequestReloadIgnoringLocalCacheData timeoutInterval:60]; [theRequest setHTTPMethod:@"POST"]; NSString *stringBoundary = [NSString stringWithString:@"0xKhTmLbOuNdArY"]; NSString *contentType = [NSString stringWithFormat:@"multipart/form-data; boundary=%@", stringBoundary]; [theRequest addValue:contentType forHTTPHeaderField:@"Content-Type"]; // Credentials NSString *creds = [NSString stringWithFormat:@"%@:%@", userName, passWord]; [theRequest addValue:[NSString stringWithFormat:@"Basic %@",[self base64encode:creds]] forHTTPHeaderField:@"Authorization"]; NSMutableData *postBody = [NSMutableData data]; [postBody appendData:[[NSString stringWithFormat:@"\r\n\r\n--%@\r\n", stringBoundary] dataUsingEncoding:NSUTF8StringEncoding]]; [postBody appendData:[[NSString stringWithString:@"Content-Disposition: form-data; name=\"source\"\r\n\r\n"] dataUsingEncoding:NSUTF8StringEncoding]]; [postBody appendData:[[NSString stringWithString:@"canary"] dataUsingEncoding:NSUTF8StringEncoding]]; NSString *mimeType = mimeType = @"image/jpeg"; [postBody appendData:[[NSString stringWithFormat:@"\r\n--%@\r\n",stringBoundary] dataUsingEncoding:NSUTF8StringEncoding]]; [postBody appendData:[[NSString stringWithFormat:@"Content-Disposition: form-data; name=\"media\"; filename=\"%@\"\r\n", @"TNImage.jpeg"] dataUsingEncoding:NSUTF8StringEncoding]]; [postBody appendData:[[NSString stringWithFormat:@"Content-Type: %@\r\n", mimeType] dataUsingEncoding:NSUTF8StringEncoding]]; [postBody appendData:[[NSString stringWithString:@"Content-Transfer-Encoding: binary\r\n\r\n"] dataUsingEncoding:NSUTF8StringEncoding]]; [postBody appendData:image]; [postBody appendData:[[NSString stringWithFormat:@"\r\n--%@\r\n",stringBoundary] dataUsingEncoding:NSUTF8StringEncoding]]; [theRequest setHTTPBody:postBody]; NSURLConnection *connection = [[NSURLConnection alloc] initWithRequest:theRequest delegate:self startImmediately:YES]; if(DEBUG) NSLog(@"Connection = %@",[connection description]); if (connection == nil) { if(DEBUG) NSLog(@"Connection was Nil"); } }