Mail multipart alternative vs multipart mixed

Question

When creating email messages you are supposed to set the Content-Type to multipart alternative when sending HTML and TEXT or multipart mixed when sending TEXT and attachments   So what do you do if you want to send HTML  Text  and attachments  Use both

User · Answer

Use multipart mixed with the first part as multipart alternative and subsequent parts for the attachments  In turn  use text plain and text html parts within the multipart alternative part   A capable email client should then recognise the multipart alternative part and display the text part or html part as necessary  It should also show all of the subsequent parts as attachment parts   The important thing to note here is that  in multipart MIME messages  it is perfectly valid to have parts within parts  In theory  that nesting can extend to any depth  Any reasonably capable email client should then be able to recursively process all of the message parts

User · Answer

Mixed Subtype     The  mixed  subtype of  multipart  is intended for use when the body   parts are independent and need to be bundled in a particular order    Any  multipart  subtypes that an implementation does not recognize   must be treated as being of subtype  mixed     Alternative Subtype     The  multipart alternative  type is syntactically identical to    multipart mixed   but the semantics are different  In particular    each of the body parts is an  alternative  version of the same   information   Source

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Building on Iain s example  I had a similar need to compose these emails with separate plaintext  HTML and multiple attachments  but using PHP   Since we are using Amazon SES to send emails with attachments  the API currently requires you to build the email from scratch using the sendRawEmail      function     After much investigation  and greater than normal frustration   the problem was solved and the PHP source code posted so that it may help others experiencing a similar problem   Hope this help someone out - the troop of monkeys I forced to work on this problem are now exhausted   PHP Source Code for sending emails with attachments using Amazon SES    lt  php  require once  AWSSDKforPHP aws phar     use Aws Ses SesClient          SESUtils is a tool to make it easier to work with Amazon Simple Email Service    Features     A client to prepare emails for use with sending attachments or not        There is no warranty - use this code at your own risk        author sbossen with assistance from Michael Deal    http   righthandedmonkey com       Update  Error checking and new params input array provided by Michael Deal    Update2  Corrected for allowing to send multiple attachments and plain text html body      Ref  Http   stackoverflow com questions 3902455 smtp-multipart-alternative-vs-multipart-mixed      class SESUtils        const version    1 0       const AWS KEY    YOUR-KEY       const AWS SEC    YOUR-SECRET       const AWS REGION    us-east-1       const MAX ATTACHMENT NAME LEN   60                  Usage           params   array             to    gt   email1 gmail com              subject    gt   Some subject              message    gt    lt strong gt Some email body lt  strong gt               from    gt   sender verifiedbyaws               OPTIONAL            replyTo    gt   reply to gmail com               OPTIONAL            files    gt  array              1   gt  array                  name    gt   filename1                   filepath    gt    path to file1 txt                   mime    gt   application octet-stream                             2   gt  array                  name    gt   filename2                   filepath    gt    path to file2 txt                   mime    gt   application octet-stream                                                res   SESUtils  sendMail  params           NOTE  When sending a single file  omit the key  ie  the  1   gt            or use 0   gt  array      - otherwise the file will come out garbled        ie  use             files    gt  array                0   gt  array   name    gt   filename    filepath    gt   path to file txt                  mime    gt   application octet-stream                  For the  to  parameter  you can send multiple recipiants with an array            to    gt  array  email1 gmail com    other msn com          use  res- gt success to check if it was successful        use  res- gt message id to check later with Amazon for further processing        use  res- gt result text to look for error text if the task was not successful                 param array  params - array of parameters for the email         return  ResultHelper             public static function sendMail  params              to   self  getParam  params   to   true            subject   self  getParam  params   subject   true            body   self  getParam  params   message   true            from   self  getParam  params   from   true            replyTo   self  getParam  params   replyTo             files   self  getParam  params   files              res   new ResultHelper                get the client ready          client   SesClient  factory array                       key    gt  self  AWS KEY                       secret    gt  self  AWS SEC                       region    gt  self  AWS REGION                         build the message         if  is array  to                  to str   rtrim implode       to                   else                to str    to                      msg    To   to str n            msg     From   from n            if   replyTo                 msg     Reply-To   replyTo n                         in case you have funny characters in the subject          subject   mb encode mimeheader  subject   UTF-8             msg     Subject   subject n            msg     MIME-Version  1 0 n            msg     Content-Type  multipart mixed  n            boundary   uniqid   Part   time    true     random unique string          boundary2   uniqid   Part2   time    true     random unique string          msg      boundary    boundary   n            msg      n               now the actual body          msg     -- boundary n              since we are sending text and html emails with multiple attachments           we must use a combination of mixed and alternative boundaries           hence the use of boundary and boundary2          msg     Content-Type  multipart alternative  n            msg      boundary    boundary2   n            msg      n            msg     -- boundary2 n               first  the plain text          msg     Content-Type  text plain  charset utf-8 n            msg     Content-Transfer-Encoding  7bit n            msg      n            msg    strip tags  body     remove any HTML tags          msg      n               now  the html text          msg     -- boundary2 n            msg     Content-Type  text html  charset utf-8 n            msg     Content-Transfer-Encoding  7bit n            msg      n            msg     body            msg      n            msg     -- boundary2-- n               add attachments         if  is array  files                  count   count  files               foreach   files as  file                     msg      n                    msg     -- boundary n                    msg     Content-Transfer-Encoding  base64 n                    clean filename   self  clean filename  file  name    self  MAX ATTACHMENT NAME LEN                    msg     Content-Type    file  mime     name  clean filename  n                    msg     Content-Disposition  attachment  filename  clean filename  n                    msg      n                    msg    base64 encode file get contents  file  filepath                       msg      n-- boundary                                close email              msg     -- n                         now send the email out         try                ses result    client- gt sendRawEmail                      array                   RawMessage    gt  array                       Data    gt  base64 encode  msg                                           array                   Source    gt   from                   Destinations    gt   to str                                                  if   ses result                     res- gt message id    ses result- gt get  MessageId                  else                    res- gt success   false                   res- gt result text    Amazon SES did not return a MessageId                           catch  Exception  e                 res- gt success   false               res- gt result text    e- gt getMessage                          - To   to str  Sender   from  Subject   subject                     return  res             private static function getParam  params   param   required   false             value   isset  params  param      params  param    null          if   required  amp  amp  empty  value                 throw new Exception      param    parameter is required               else               return  value                               Clean filename function - to get a file friendly              public static function clean filename  str   limit   0   replace array     delimiter  -             if   empty  replace                   str   str replace  array  replace        str                       clean   iconv  UTF-8    ASCII  TRANSLIT    str            clean   preg replace     a-zA-Z0-9       -          clean            clean   preg replace        -       -    clean            if   limit  gt  0                  don t truncate file extension              arr   explode       clean                size   count  arr                base                    ext                   if   size  gt  0                    for   i   0   i  lt   size   i                          if   i  lt   size - 1      if it s not the last item  add to  bn                          base     arr  i                             if next one isn t last  add a dot                         if   i  lt   size - 2                               base                               else                           if   i  gt  0                               ext                                 ext     arr  i                                                                      bn size   mb strlen  base                ex size   mb strlen  ext                bn new   mb substr  base  0   limit -  ex size                  doing again in case extension is long              clean   mb substr  bn new  ext  0   limit                      return  clean            class ResultHelper        public  success   true      public  result text           public  message id             gt

User · Answer

Here is the best   Multipart mixed mime message with attachments and inline images  And image  https   www qcode co uk images mime-nesting-structure png  From  from qcode co uk To  to  qcode co uk Subject  Example Email MIME-Version  1 0 Content-Type  multipart mixed  boundary  MixedBoundaryString   --MixedBoundaryString Content-Type  multipart related  boundary  RelatedBoundaryString   --RelatedBoundaryString Content-Type  multipart alternative  boundary  AlternativeBoundaryString   --AlternativeBoundaryString Content-Type  text plain charset  utf-8  Content-Transfer-Encoding  quoted-printable  This is the plain text part of the email   --AlternativeBoundaryString Content-Type  text html charset  utf-8  Content-Transfer-Encoding  quoted-printable   lt html gt     lt body gt  0D      lt img src 3D 22cid masthead png 40qcode co uk 22 width 800 height 3D80    5C gt  0D      lt p gt This is the html part of the email  lt  p gt  0D      lt img src 3D 22cid logo png 40qcode co uk 22 width 200 height 3D60  5C   gt  0D    lt  body gt  0D  lt  html gt  0D  --AlternativeBoundaryString--  --RelatedBoundaryString Content-Type  image jpgeg name  logo png  Content-Transfer-Encoding  base64 Content-Disposition  inline filename  logo png  Content-ID   lt logo png qcode co uk gt   amtsb2hiaXVvbHJueXZzNXQ2XHVmdGd5d2VoYmFmaGpremxidTh2b2hydHVqd255aHVpbnRyZnhu dWkgb2l1b3NydGhpdXRvZ2hqdWlyb2h5dWd0aXJlaHN1aWhndXNpaHhidnVqZmtkeG5qaG5iZ3Vy         a25qbW9nNXRwbF0nemVycHpvemlnc3k5aDZqcm9wdHo7amlodDhpOTA4N3U5Nnkwb2tqMm9sd3An LGZ2cDBbZWRzcm85eWo1Zmtsc2xrZ3g   --RelatedBoundaryString Content-Type  image jpgeg name  masthead png  Content-Transfer-Encoding  base64 Content-Disposition  inline filename  masthead png  Content-ID   lt masthead png qcode co uk gt   aXR4ZGh5Yjd1OHk3MzQ4eXFndzhpYW9wO2tibHB6c2tqOTgwNXE0aW9qYWJ6aXBqOTBpcjl2MC1t dGlmOTA0cW05dGkwbWk0OXQwYVttaXZvcnBhXGtsbGo7emt2c2pkZnI7Z2lwb2F1amdpNTh1NDlh         eXN6dWdoeXhiNzhuZzdnaHQ3eW9zemlqb2FqZWt0cmZ1eXZnamhka3JmdDg3aXV2dWd5aGVidXdz dhyuhehe76YTGSFGA   --RelatedBoundaryString--  --MixedBoundaryString Content-Type  application pdf name  Invoice 1 pdf  Content-Transfer-Encoding  base64 Content-Disposition  attachment filename  Invoice 1 pdf   aGZqZGtsZ3poZHVpeWZoemd2dXNoamRibngganZodWpyYWRuIHVqO0hmSjtyRVVPIEZSO05SVURF SEx1aWhudWpoZ3h1XGh1c2loZWRma25kamlsXHpodXZpZmhkcnVsaGpnZmtsaGVqZ2xod2plZmdq         a2psajY1ZWxqanNveHV5ZXJ3NTQzYXRnZnJhZXdhcmV0eXRia2xhanNueXVpNjRvNWllc3l1c2lw dWg4NTA0  --MixedBoundaryString Content-Type  application pdf name  SpecialOffer pdf  Content-Transfer-Encoding  base64 Content-Disposition  attachment filename  SpecialOffer pdf   aXBvY21odWl0dnI1dWk4OXdzNHU5NTgwcDN3YTt1OTQwc3U4NTk1dTg0dTV5OGlncHE1dW4zOTgw cS0zNHU4NTk0eWI4OTcwdjg5MHE4cHV0O3BvYTt6dWI7dWlvenZ1em9pdW51dDlvdTg5YnE4N3Z3         OTViOHk5cDV3dTh5bnB3dWZ2OHQ5dTh2cHVpO2p2Ymd1eTg5MGg3ajY4bjZ2ODl1ZGlvcjQ1amts dfnhgjdfihn   --MixedBoundaryString--      Schema multipart related alternative  Header  From  email  To  email  MIME-Version  1 0  Content-Type  multipart mixed  boundary  boundary1   Message body  multipart mixed --boundary1  --boundary1     multipart related --boundary2      --boundary2         multipart alternative --boundary3          --boundary3          text plain          --boundary3          text html          --boundary3--      --boundary2          Inline image      --boundary2          Inline image      --boundary2--  --boundary1      Attachment1  --boundary1  Attachment2  --boundary1  Attachment3  --boundary1--

User · Answer

I hit this issue  This architecture  from Lain s answer  worked for me   Here is the solution in Python     mixed   alternative   text related   html inline image inline image   attachment attachment    Here is the main email creation function    def create message with attachment      sender  to  subject  msgHtml  msgPlain  attachmentFile          Create a message for an email       Args        sender  Email address of the sender        to  Email address of the receiver        subject  The subject of the email message        message text  The text of the email message        file  The path to the file to be attached       Returns        An object containing a base64url encoded email object              message   MIMEMultipart  mixed       message  to     to     message  from     sender     message  subject     subject      message alternative   MIMEMultipart  alternative       message related   MIMEMultipart  related        message related attach MIMEText msgHtml   html        message alternative attach MIMEText msgPlain   plain        message alternative attach message related       message attach message alternative       print  create message with attachment  file    attachmentFile     content type  encoding   mimetypes guess type attachmentFile       if content type is None or encoding is not None          content type    application octet-stream      main type  sub type   content type split      1      if main type     text           fp   open attachmentFile   rb           msg   MIMEText fp read     subtype sub type          fp close       elif main type     image           fp   open attachmentFile   rb           msg   MIMEImage fp read     subtype sub type          fp close       elif main type     audio           fp   open attachmentFile   rb           msg   MIMEAudio fp read     subtype sub type          fp close       else          fp   open attachmentFile   rb           msg   MIMEBase main type  sub type          msg set payload fp read            fp close       filename   os path basename attachmentFile      msg add header  Content-Disposition    attachment   filename filename      message attach msg       return   raw   base64 urlsafe b64encode message as string       Here is the full code for sending an email containing html text attachment   import httplib2 import os import oauth2client from oauth2client import client  tools import base64 from email mime multipart import MIMEMultipart from email mime text import MIMEText from apiclient import errors  discovery import mimetypes from email mime image import MIMEImage from email mime audio import MIMEAudio from email mime base import MIMEBase  SCOPES    https   www googleapis com auth gmail send  CLIENT SECRET FILE1    client secret json  location   os path realpath      os path join os getcwd    os path dirname   file      CLIENT SECRET FILE   os path join location  CLIENT SECRET FILE1  APPLICATION NAME    Gmail API Python Send Email   def get credentials        home dir   os path expanduser          credential dir   os path join home dir    credentials       if not os path exists credential dir           os makedirs credential dir      credential path   os path join credential dir                                      gmail-python-email-send json       store   oauth2client file Storage credential path      credentials   store get       if not credentials or credentials invalid          flow   client flow from clientsecrets CLIENT SECRET FILE  SCOPES          flow user agent   APPLICATION NAME         credentials   tools run flow flow  store          print  Storing credentials to     credential path     return credentials  def SendMessageWithAttachment sender  to  subject  msgHtml  msgPlain  attachmentFile       credentials   get credentials       http   credentials authorize httplib2 Http        service   discovery build  gmail    v1   http http      message1   create message with attachment sender  to  subject  msgHtml  msgPlain  attachmentFile      SendMessageInternal service   me   message1   def SendMessageInternal service  user id  message       try          message    service users   messages   send userId user id  body message  execute            print  Message Id   s    message  id           return message     except errors HttpError  error          print  An error occurred   s    error         return  error   def create message with attachment      sender  to  subject  msgHtml  msgPlain  attachmentFile          Create a message for an email       Args        sender  Email address of the sender        to  Email address of the receiver        subject  The subject of the email message        message text  The text of the email message        file  The path to the file to be attached       Returns        An object containing a base64url encoded email object              message   MIMEMultipart  mixed       message  to     to     message  from     sender     message  subject     subject      message alternative   MIMEMultipart  alternative       message related   MIMEMultipart  related        message related attach MIMEText msgHtml   html        message alternative attach MIMEText msgPlain   plain        message alternative attach message related       message attach message alternative       print  create message with attachment  file    attachmentFile     content type  encoding   mimetypes guess type attachmentFile       if content type is None or encoding is not None          content type    application octet-stream      main type  sub type   content type split      1      if main type     text           fp   open attachmentFile   rb           msg   MIMEText fp read     subtype sub type          fp close       elif main type     image           fp   open attachmentFile   rb           msg   MIMEImage fp read     subtype sub type          fp close       elif main type     audio           fp   open attachmentFile   rb           msg   MIMEAudio fp read     subtype sub type          fp close       else          fp   open attachmentFile   rb           msg   MIMEBase main type  sub type          msg set payload fp read            fp close       filename   os path basename attachmentFile      msg add header  Content-Disposition    attachment   filename filename      message attach msg       return   raw   base64 urlsafe b64encode message as string       def main        to    to address com      sender    from address com      subject    subject      msgHtml    Hi lt br  gt Html Email      msgPlain    Hi nPlain Email      attachment     path to file pdf      SendMessageWithAttachment sender  to  subject  msgHtml  msgPlain  attachment   if   name         main         main

User · Answer

Messages have content  Content can be text  html  a DataHandler or a Multipart  and there can only be one content  Multiparts only have BodyParts but can have more than one  BodyParts  like Messages  can have content which has already been described   A message with HTML  text and an a attachment can be viewed hierarchically like this   message   mainMultipart  content for message  subType  mixed       - gt htmlAndTextBodyPart  bodyPart1 for mainMultipart        - gt htmlAndTextMultipart  content for htmlAndTextBodyPart  subType  alternative           - gt textBodyPart  bodyPart2 for the htmlAndTextMultipart            - gt text  content for textBodyPart          - gt htmlBodyPart  bodyPart1 for htmlAndTextMultipart            - gt html  content for htmlBodyPart      - gt fileBodyPart1  bodyPart2 for the mainMultipart        - gt FileDataHandler  content for fileBodyPart1     And the code to build such a message          the parent or main part if you will     Multipart mainMultipart   new MimeMultipart  mixed            this will hold text and html and tells the client there are 2 versions of the message  html and text   presumably text        being the alternative to html     Multipart htmlAndTextMultipart   new MimeMultipart  alternative            set text     MimeBodyPart textBodyPart   new MimeBodyPart        textBodyPart setText text       htmlAndTextMultipart addBodyPart textBodyPart           set html  set this last per rfc1341 which states last   best      MimeBodyPart htmlBodyPart   new MimeBodyPart        htmlBodyPart setContent html   text html  charset utf-8        htmlAndTextMultipart addBodyPart htmlBodyPart           stuff the multipart into a bodypart and add the bodyPart to the mainMultipart     MimeBodyPart htmlAndTextBodyPart   new MimeBodyPart        htmlAndTextBodyPart setContent htmlAndTextMultipart       mainMultipart addBodyPart htmlAndTextBodyPart           attach file body parts directly to the mainMultipart     MimeBodyPart filePart   new MimeBodyPart        FileDataSource fds   new FileDataSource   path to some file txt        filePart setDataHandler new DataHandler fds        filePart setFileName fds getName         mainMultipart addBodyPart filePart           set message content     message setContent mainMultipart

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I hit this challenge today and I found these answers useful but not quite explicit enough for me    Edit  Just found the Apache Commons Email that wraps this up nicely  meaning you don t need to know below   If your requirement is an email with    text and html versions html version has embedded  inline  images attachments   The only structure I found that works with Gmail Outlook iPad is    mixed   alternative   text  related   html inline image inline image   attachment attachment    And the code is   import javax activation DataHandler  import javax activation DataSource  import javax activation URLDataSource  import javax mail BodyPart  import javax mail MessagingException  import javax mail Multipart  import javax mail internet MimeBodyPart  import javax mail internet MimeMultipart  import java net URL  import java util HashMap  import java util List  import java util UUID  import java util regex Matcher  import java util regex Pattern          Created by StrongMan on 25 05 14      public class MailContentBuilder        private static final Pattern COMPILED PATTERN SRC URL SINGLE   Pattern compile  src              Pattern CASE INSENSITIVE       private static final Pattern COMPILED PATTERN SRC URL DOUBLE   Pattern compile  src                 Pattern CASE INSENSITIVE                   Build an email message                The HTML may reference the embedded image  messageHtmlInline  using the filename  Any path portion is ignored to make my life easier        e g  If you pass in the image C  Temp dog jpg you can use  lt img src  dog jpg   gt  or  lt img src  C  Temp dog jpg   gt  and both will work                param messageText         param messageHtml         param messageHtmlInline         param attachments         return         throws MessagingException             public Multipart build String messageText  String messageHtml  List lt URL gt  messageHtmlInline  List lt URL gt  attachments  throws MessagingException           final Multipart mpMixed   new MimeMultipart  mixed                             alternative             final Multipart mpMixedAlternative   newChild mpMixed   alternative                                     Note  MUST RENDER HTML LAST otherwise iPad mail client only renders the last image and no email                 addTextVersion mpMixedAlternative messageText                   addHtmlVersion mpMixedAlternative messageHtml  messageHtmlInline                                attachments             addAttachments mpMixed attachments                        msg setText message   utf-8              msg setContent message  text html  charset utf-8            return mpMixed             private Multipart newChild Multipart parent  String alternative  throws MessagingException           MimeMultipart child    new MimeMultipart alternative           final MimeBodyPart mbp   new MimeBodyPart            parent addBodyPart mbp           mbp setContent child           return child             private void addTextVersion Multipart mpRelatedAlternative  String messageText  throws MessagingException           final MimeBodyPart textPart   new MimeBodyPart            textPart setContent messageText   text plain            mpRelatedAlternative addBodyPart textPart              private void addHtmlVersion Multipart parent  String messageHtml  List lt URL gt  embeded  throws MessagingException              HTML version         final Multipart mpRelated   newChild parent  related                Html         final MimeBodyPart htmlPart   new MimeBodyPart            HashMap lt String String gt  cids   new HashMap lt String  String gt             htmlPart setContent replaceUrlWithCids messageHtml cids    text html            mpRelated addBodyPart htmlPart               Inline images         addImagesInline mpRelated  embeded  cids              private void addImagesInline Multipart parent  List lt URL gt  embeded  HashMap lt String String gt  cids  throws MessagingException           if  embeded    null                        for  URL img   embeded                                final MimeBodyPart htmlPartImg   new MimeBodyPart                    DataSource htmlPartImgDs   new URLDataSource img                   htmlPartImg setDataHandler new DataHandler htmlPartImgDs                    String fileName   img getFile                    fileName   getFileName fileName                   String newFileName   cids get fileName                   boolean imageNotReferencedInHtml   newFileName    null                  if  imageNotReferencedInHtml  continue                     Gmail requires the cid have  lt  gt  around it                 htmlPartImg setHeader  Content-ID     lt   newFileName   gt                     htmlPartImg setDisposition BodyPart INLINE                   parent addBodyPart htmlPartImg                                      private void addAttachments Multipart parent  List lt URL gt  attachments  throws MessagingException           if  attachments    null                        for  URL attachment   attachments                                final MimeBodyPart mbpAttachment   new MimeBodyPart                    DataSource htmlPartImgDs   new URLDataSource attachment                   mbpAttachment setDataHandler new DataHandler htmlPartImgDs                    String fileName   attachment getFile                    fileName   getFileName fileName                   mbpAttachment setDisposition BodyPart ATTACHMENT                   mbpAttachment setFileName fileName                   parent addBodyPart mbpAttachment                                      public String replaceUrlWithCids String html  HashMap lt String String gt  cids                html   replaceUrlWithCids html  COMPILED PATTERN SRC URL SINGLE   src  cid  cid    cids           html   replaceUrlWithCids html  COMPILED PATTERN SRC URL DOUBLE   src   cid  cid     cids           return html             private String replaceUrlWithCids String html  Pattern pattern  String replacement  HashMap lt String String gt  cids            Matcher matcherCssUrl   pattern matcher html           StringBuffer sb   new StringBuffer            while  matcherCssUrl find                          String fileName   matcherCssUrl group 1                  Disregarding file path  so don t clash your filenames              fileName   getFileName fileName                  A cid must start with   and be globally unique             String cid         UUID randomUUID   toString           fileName              if  cids containsKey fileName                   cid   cids get fileName               else                 cids put fileName cid               matcherCssUrl appendReplacement sb replacement replace   cid  cid                      matcherCssUrl appendTail sb           html   sb toString            return html             private String getFileName String fileName            if  fileName contains                   fileName   fileName substring fileName lastIndexOf      1           return fileName            And an example of using it with from Gmail         Created by StrongMan on 25 05 14      import com sun mail smtp SMTPTransport   import java net URL  import java security Security  import java util    import java util regex Matcher  import java util regex Pattern  import javax activation DataHandler  import javax activation DataSource  import javax activation URLDataSource  import javax mail    import javax mail internet               http   stackoverflow com questions 14744197 best-practices-sending-javamail-mime-multipart-emails-and-gmail    http   stackoverflow com questions 3902455 smtp-multipart-alternative-vs-multipart-mixed              author doraemon     public class GoogleMail         private GoogleMail                           Send email using GMail SMTP server                 param username GMail username         param password GMail password         param recipientEmail TO recipient         param title title of the message         param messageText message to be sent         throws AddressException if the email address parse failed         throws MessagingException if the connection is dead or not in the connected state or if the message is not a MimeMessage             public static void Send final String username  final String password  String recipientEmail  String title  String messageText  String messageHtml  List lt URL gt  messageHtmlInline  List lt URL gt  attachments  throws AddressException  MessagingException           GoogleMail Send username  password  recipientEmail      title  messageText  messageHtml  messageHtmlInline attachments                         Send email using GMail SMTP server                 param username GMail username         param password GMail password         param recipientEmail TO recipient         param ccEmail CC recipient  Can be empty if there is no CC recipient         param title title of the message         param messageText message to be sent         throws AddressException if the email address parse failed         throws MessagingException if the connection is dead or not in the connected state or if the message is not a MimeMessage             public static void Send final String username  final String password  String recipientEmail  String ccEmail  String title  String messageText  String messageHtml  List lt URL gt  messageHtmlInline  List lt URL gt  attachments  throws AddressException  MessagingException           Security addProvider new com sun net ssl internal ssl Provider             final String SSL FACTORY    javax net ssl SSLSocketFactory               Get a Properties object         Properties props   System getProperties            props setProperty  mail smtps host    smtp gmail com            props setProperty  mail smtp socketFactory class   SSL FACTORY           props setProperty  mail smtp socketFactory fallback    false            props setProperty  mail smtp port    465            props setProperty  mail smtp socketFactory port    465            props setProperty  mail smtps auth    true                        If set to false  the QUIT command is sent and the connection is immediately closed  If set         to true  the default   causes the transport to wait for the response to the QUIT command           ref     http   java sun com products javamail javadocs com sun mail smtp package-summary html                 http   forum java sun com thread jspa threadID 5205249                 smtpsend java - demo program from javamail                    props put  mail smtps quitwait    false             Session session   Session getInstance props  null               -- Create a new message --         final MimeMessage msg   new MimeMessage session               -- Set the FROM and TO fields --         msg setFrom new InternetAddress username     gmail com             msg setRecipients Message RecipientType TO  InternetAddress parse recipientEmail  false             if  ccEmail length    gt  0                msg setRecipients Message RecipientType CC  InternetAddress parse ccEmail  false                       msg setSubject title               mixed         MailContentBuilder mailContentBuilder   new MailContentBuilder            final Multipart mpMixed   mailContentBuilder build messageText  messageHtml  messageHtmlInline  attachments           msg setContent mpMixed           msg setSentDate new Date              SMTPTransport t    SMTPTransport session getTransport  smtps             t connect  smtp gmail com   username  password           t sendMessage msg  msg getAllRecipients             t close

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Great Answer Lain   There were a couple things I did to make this work in a broader set of devices  At the end I will list the clients I tested on    I added a new build constructor that did not contain the parameter attachments and did not use MimeMultipart  mixed    There is no need for mixed if you are sending only inline images   public Multipart build String messageText  String messageHtml  List lt URL gt  messageHtmlInline  throws MessagingException        final Multipart mpAlternative   new MimeMultipart  alternative                      Note  MUST RENDER HTML LAST otherwise iPad mail client only renders              the last image and no email             addTextVersion mpAlternative messageText               addHtmlVersion mpAlternative messageHtml  messageHtmlInline              return mpAlternative     In addTextVersion method I added charset when adding content this probably could should be passed in  but I just added it statically   textPart setContent messageText   text plain    to textPart setContent messageText   text plain  charset UTF-8     The last item was adding to the addImagesInline method  I added setting the image filename to the header by the following code  If you don t do this then at least on Android default mail client it will have inline images that have a name of Unknown and will not automatically download them and present in email   for  URL img   embeded        final MimeBodyPart htmlPartImg   new MimeBodyPart        DataSource htmlPartImgDs   new URLDataSource img       htmlPartImg setDataHandler new DataHandler htmlPartImgDs        String fileName   img getFile        fileName   getFileName fileName       String newFileName   cids get fileName       boolean imageNotReferencedInHtml   newFileName    null      if  imageNotReferencedInHtml  continue      htmlPartImg setHeader  Content-ID     lt   newFileName   gt         htmlPartImg setDisposition BodyPart INLINE         htmlPartImg setFileName newFileName         parent addBodyPart htmlPartImg        So finally  this is the list of clients I tested on  Outlook 2010   Outlook Web App       Internet Explorer 11       Firefox       Chrome   Outlook using Apple   s native app   Email going through Gmail -    Browser mail client        Internet Explorer 11        Firefox        Chrome    Android default mail client    osx IPhone default mail client    Gmail mail client on Android    Gmail mail client on IPhone  Email going through Yahoo -   Browser mail client      Internet Explorer 11      Firefox      Chrome    Android default mail client    osx IPhone default mail client   Hope that helps anyone else

[email] Mail multipart/alternative vs multipart/mixed

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