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How to send inline pictures to gmail users?

Posted on 2014-12-18
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Last Modified: 2015-01-01
I have a school that sends out email to the parent body.  Until recently, there were no problems with sending the to gmail and the gmail users were able to view the pictures inline.
But now the gmail users see blanks with in the email and the users cannot load those pictures manually.
I have a gmail account and enabled show pictures and it does not work.
Other email programs I am able to see the pictures.
So what has to be done at the school for that to happen?
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Question by:jplatovsky
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by:Joe Winograd, EE MVE
Joe Winograd, EE MVE earned 334 total points
ID: 40508596
This is a well-known problem with Gmail that comes and goes. Here are some threads that discuss it:

http://www.benchmarkemail.com/help-FAQ/answer/Why-are-the-images-in-my-email-not-showing-up-in-Gmail
https://www.campaignmonitor.com/blog/post/4137/image-cache-display-issues-in-gmail
http://support2.constantcontact.com/articles/FAQ/3271
https://productforums.google.com/forum/#!topic/gmail/JIsy4p3ZOcU

I have not found a single solution yet that solves it in all cases. One thing that works sometimes (but not always) is to simply log off and then log back on again. Another idea (mentioned in the ConstantContact article) is to disable HTTPS, but not everyone is comfortable doing that (and in some cases may still not be the answer). Regards, Joe
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by:jplatovsky
ID: 40509199
I tried everything you have suggested and still no good.  Is it possible that the school needs to do something for their email server to be trusted?
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by:Joe Winograd, EE MVE
ID: 40509458
> Is it possible that the school needs to do something for their email server to be trusted?

Maybe, but I don't know for sure. One obvious thing to check is the certificate for their email server — is it valid?

It's true that Gmail now serves all images through Google's own secure proxy servers, so there may be a need for other servers to establish a trusted relationship with the Gmail servers, so that Gmail can get the images in the first place (and bring them into their secure proxy servers). Here's an interesting article that discusses it: Google Uses a Proxy to Load Gmail Images. It's from a year ago, but AFAIK, it's still the way Gmail does it.

I can't explain why this just started happening to you recently, unless it's either a glitch on the Gmail end or the school's email server certificate recently expired. Regards, Joe
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by:dgrafx
ID: 40509491
What I have done from time to time is to send the email with the image tag in the HTML SOURCE of the email.

Hello World,<br>
Check out the latest picture!<br>
<img src="http://www.somesite.com/flyers/pic12.png"><br>
Thank you,<br>
Your School ...

That will display pretty much without fail on gmail clients.
And NOTE that this is the html source.

Now one thing I don't know is are you able to edit the html source of the email?
Or are you just pulling up gmail in your browser and composing that way?

Couple questions
1. what are you composing emails with?
2. what language are you running on your server? i.e. php, asp, coldfusion, .net ???
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by:jplatovsky
ID: 40517587
It is a Java / java scripts based system.
I have tried the Alt solution, I have tried mixing text with it.  
How do the other email systems work?  Like constant contact?
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by:Joe Winograd, EE MVE
ID: 40517603
Did you check the certificate?
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by:dgrafx
ID: 40517690
OK so you guys are on a Java system.
Here is an article showing how to send email in a Java environment: http://www.tutorialspoint.com/java/java_sending_email.htm
Note that I'm not saying you need to do this - I am showing you "how other email systems work".
Typically we don't just pull up Gmail and send out email. It is one aspect of the entire application.

1. behind the scenes the email aspect of the web application is built by programmers.
It is they who you should consult with for modifications / ideas etc.
again typically the recipients are stored in a database and tagged with a mailing list setting so that you can have multiple mailing lists and recipients can belong to multiple lists.
anyway ...

2. on the front end the person who types the email is usually typing into a rich text editor on a "compose email" form in your web application. (this email is frequently stored in a database as well. but there are so many optional features that take us way off scope so I won't get into that.)
when a person wants to add images to the email then the "rich text compose email" app allows you to select an image from your "image library" and inserts it at the cursor position. a popular editor is TinyMce - http://www.tinymce.com/.
It's important to understand that from the user view point you are not seeing what is really happening to the source when you are typing or styling or adding a new line. what I posted earlier is what is actually being entered.
at the tinymce link look at the example at the top of the page - the far right icon is for inserting images - try it out and then under the tools menu select source code to show the html that is behind the scenes of what is in the editor window.
TinyMce is not complete by itself though - you need your programmers to tie it into your web application.
The first thing is to tell it to include the full website address in your image tags so they can be viewed anywhere - this is not a big issue - it's on the config page.

The bottom line is that you can use inline images without much of a problem but you need to be setup properly to have this type of control over your emails.
Don't let this intimidate you if you are not certain about some of the things I said. Just consult with your devs and you'll see that it's a lot easier than it may sound!

good luck ...
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by:jplatovsky
ID: 40518030
ok. Let me narrow the issue.
Joe:  What certificate?
Dgrafx:   2 things
1) We use Imail Server to be our email server.
2) Here is a simple code that we use in HTML for the email that goes out
<html>
      <body>
            <div align="center">
                  <p>
                        <img src="http://byqueens.org/resources/picturebackground.jpg" style="height: 400px; width: 400px;" /></p>
                  <p>
                        <font face="Comic Sans MS" size="4">Here's a view of <a href="http://byqueens.org/resources/welcome_to_byq.wmv">BYQ</a>.</font></p>
            </div>
            <p>
                   </p>
      </body>
</html>
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by:Joe Winograd, EE MVE
ID: 40518038
> Joe:  What certificate?

The certificate for the school's email server, as mentioned in this post <http:#a40509458>.
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by:jplatovsky
ID: 40518468
The Imail Server has its' own.  All mail goes through to all the email systems.  It is just the inline pictures that are not being viewed in gmail.  It works fine with Yahoo, AOL, Hotmail, etc. But not gmail.
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by:Joe Winograd, EE MVE
ID: 40518548
> It works fine with Yahoo, AOL, Hotmail, etc. But not gmail.

I understand that, which is why I suggested the certificate issue. I don't know how the other mail services work (they may be different from Gmail), but Gmail serves all images through Google's own secure proxy servers. So what I'm saying is that maybe (I don't know for sure) other servers need to establish a trusted relationship with the Gmail servers so that Gmail can bring the images into their own secure proxy servers. I mentioned this article earlier that discusses it: Google Uses a Proxy to Load Gmail Images.

This would explain why it just started happening to you recently, i.e., if the school's mail server certificate recently expired, then it would not be able to establish a trusted relationship with the Gmail servers. So Gmail may be willing to send the text, but not "dangerous" content, like images. Regards, Joe
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by:jplatovsky
ID: 40518621
So I went through the email server logs and found that SSL is enforce and for AOL this is the entry:  Verifying SSL settings for host 173.194.195.26 and for GMAIL this is the entry: STARTTLS successfully negotiated for host 64.12.88.163
Don't know why SSL would be for AOL and goes through and TLS is for GMAIL
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by:Joe Winograd, EE MVE
ID: 40518656
SSL and TLS are essentially the same thing, with TLS being the new name — it supersedes SSL. When SSL reached version 3.1, it became TLS version 1.0. That's why you'll often see it referred to as SSL/TLS. Here's an MSDN article that discusses it:
http://msdn.microsoft.com/en-us/library/windows/desktop/aa380515%28v=vs.85%29.aspx

If you do a web search for "difference between ssl and tls", you'll get more details.

My guess (and that's all it is) is that AOL still calls it SSL because AOL is a bit long in the tooth and/or because the term was coined by Netscape, which was acquired by AOL.

Interesting to note that earlier this year (on 20-March), Gmail switched to using HTTPS (SSL/TLS) ALWAYS! Since 2010, it has been the default, but now it is always used. Here's a Google blog post that discusses it:
http://gmailblog.blogspot.com/2014/03/staying-at-forefront-of-email-security.html

Regards, Joe
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by:dgrafx
dgrafx earned 166 total points
ID: 40518690
To jump in here ...

1. jplatovsky - it looks like you are essentially doing what I suggested so I don't have more to say other than I have not experienced this issue or had this issue reported to me at companies I've worked at.

2. joe winograd - tls is NOT ssl - and when ssl evolved it wasn't renamed to tls - and that's not what the msdn article says either - just fyi ...

jplatovsky
you could always send mail using tls instead of ssl and see if your problem persists or not.
consult with your "server guys" to see what your server software version supports

here is a link for you to read: https://luxsci.com/blog/ssl-versus-tls-whats-the-difference.html

good luck ...
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by:Joe Winograd, EE MVE
ID: 40518729
> joe winograd - tls is NOT ssl - and when ssl evolved it wasn't renamed to tls - and that's not what the msdn article says either - just fyi ...

Everything I've read read says that SSL evolved into TLS and that, essentially, SSL 3.1 became TLS 1.0. But since I was not involved in the development of either and have not looked under the covers of them, I only know what I've read about them, which could certainly be wrong. So I'm happy to defer to your knowledge on these protocols, which could certainly be more informed than what I've read on the web. I do know that some email clients lump them together, such as the latest version of Thunderbird (31.3.0):

Thunderbird SSL-TLS
But, again, happy to defer to your deeper knowledge on this. Thanks for sending the link — I'll take a look at it. Regards, Joe
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by:jplatovsky
ID: 40518756
So getting back to Joe:
So if my server successfully negotiated with GMAIL using TLS what else do I need to do?
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by:Joe Winograd, EE MVE
ID: 40518780
If it connected successfully via TLS, all should be well. In this case, I don't think that server communication is the problem.

Something we haven't discussed yet — the browser. What browser are you using to access Gmail? Whatever it is, try something else — Chrome, Firefox, IE, Opera, Safari, etc. Try a few — do they all have the same problem with images? Regards, Joe
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by:jplatovsky
ID: 40520498
one third of the emails are going to gmail.  All have the same problem.  Not a browser issue.
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Joe Winograd, EE MVE earned 334 total points
ID: 40520503
> one third of the emails are going to gmail

I don't mean where they're going. I mean what browser are you using to access the Gmail? Or are you using an email client to do it, like Outlook or Thunderbird? If you're using, for example, IE to access the Gmail, then try Chrome or Firefox. In other words, you said in your first post, "I have a gmail account and enabled show pictures and it does not work." With what browser do you get that behavior? Do you get the same behavior when accessing that Gmail in all browsers? And how about if you access that Gmail via an email client, like Thunderbird?
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by:jplatovsky
ID: 40526773
Unfortunately there was no solution
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