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Outlook.com (hotmail) blocking images from alt-port or non fqdn src


Morning all,

So I have a strange issue with Outlook.com, former hotmail.com...

I am working on a project to supply businesses with micro servers (raspberry pi) which I have setup as apache servers, and installed an HTML/PHP/BASH program that allows the user to create html email campaigns and send them to groups of contacts. The program/hardware works perfectly.

Except:

Emails received by outlook clients do not receive the images (just place-holders).

I have figured out though testing that the images are blocked because the src="non-fqdn" - in other words, I am using the IP of the client without registering a domain - because that is over complicated and they are NOT hosting a website. So there should be no reason for an fqdn.

If this problem can be solved, don't read further!!!

BTW Every other MUA renders the images perfectly :-(

So I am re thinking a way around this, and figured I would host the images on my own domain, however; the clients raspberry pis will need to be able to upload the images on a server within my domain, so for security reasons, I have setup a stand-alone headless server for just that purpose, and aligned it to port 8080. Problem solved right? NO!

Outlook still bloody blocks them. WHY!!!!

Here is an example to explain my problem.

Consider the following IMG codes which would be in the email html:

Eg. 1
<img src="http://fqdn.com/images/example.jpg" width="30%" align="center">

Eg. 2
<img src="http://fqdn.com:8080/images/example.jpg" width="30%" align="center">

Eg. 3
<img src="http://IP/images/example.jpg" width="30%" align="center">

In Eg.1 The image is rendered perfectly. In Eg.2 & 3 The images are blocked.

Note: fqdn in both 1 and 2 are the same.

Please help me :-) Months of work about to be shit canned...

Tim


Solution

  • Well, there is no freaking answer to this... In the end I have set up a section of my company domain to host the images, on port 80 with fqdn. The remote servers upload the images over key-auth sftp, jailed to their own directories within the www/ and user shells set to /bin/rssh to limit access to sftp only.

    I hope this is secure enough. I also hope one day microsft hops into the 21st century...