Ensuring that your email isn’t considered spam and Office365

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Since I started noticing some of my mail messages bouncing back as spam I’ve been trying to correct the issue.  The biggest problem when you start getting bouncebacks is that you really don’t know how many message are being rejected.   Most companies won’t generate a bounceback.  Their philosophy is that its better to reject the mail and not let the spammers know that they got rejected.

So I’ve taken a number of steps and made a few changes to the my Office365 environment to ensure that my mail is getting out or that I at least know that my mail is considered  spam so I can fix it.

So here is my advice to you:

  1. Don’t use Images in your Signature – I use a QR code and a Company logo.  Better SPAM filters use a scoring system to flag messages as spam.  The existence of images could be considered spam and therefore your messages may be rejected.
  2. Don’t use URL shorteners in your Signature or email body – URL shortners allow you to hide the ugly URL’s and provide a simple shorter string.  These are seen as URL redirection.  To a spam filter they are seen as away of obfuscating  your intent.  To a spam filter you may be taking the intended recipient to a bad website.
  3. Try to use simple text.  HTML content increases your score.  Add everything together and you maybe considered spam.

When my messages were being rejected  I stated that the Office365 servers were considered SPAM servers.  Well that was true and not true.  Office365 will check every message going out of the service.  They themselves will score your message and make some intelligent decisions on it.  If your message is considered outbound spam, office365 makes a routing decision.  Its decision is intended to reduce the impact of outbound spam on legitimate emails.  So it routes the message through a series of high risk routers.  So these routers can potentially be flagged as spam producers but they don’t impact what are considered legitimate mail routers.  So my mail message, in its simplicity, was routed through one of these highrisk server.

Office365 provides  you with a a number of things that you can do to reduce the chance of being considered spam.   All of these can be done in the ECP administration client.  I’ll give specific details in the next blog entry but here are the choices that you can make.

  1. Use a smarthost.  This allows you to route mail through a separate service.
  2. Create a connector to the client – you can add your client as a smarthost.  This means that any message that goes to a specific client will use a specific connector and therefore not be considered spam by office365.
  3. Get a notification from Office365 on what mail it considers spam.  At least if you know your mail is considered spam you can take steps to fix it.
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