We have developed some CRM software which allows the users (our clients) to send emails to their clients (both individually and as a bulk email-out).

The emails are sent via our email server, but with the user's email set as the From address.

All emails are injected with an image tagged with a unique id that updates the database when the email is opened (assuming the image is downloaded).

ie img src='https://ourdomain.com/emailOpenedImage.jsp?id=0cb5a87f-3a35-11e0-8f64-11ac2edfd58d'/

We have taken the following steps to assist in ensuring that the messages are delivered:

  1. Throttling - the queue is paused every 200 messages.
  2. Reverse DNS - We have the IP address of the server registered to a domain.

We are also looking at the following, and I'm wondering if they will help.

  1. Domain toggling - if we send an email to say jon@hotmail.com, make sure the next few emails don't go to hotmail.com
  2. Changing the Sender Header - the From header and Reply-To Header will be set to, say, "John Smith (johnsmith@hotmail.com)" while the Sender Header will be set to "John Smith(johnsmith=hotmail.com@mymailserverdomain.com)". Thus the email appears as "on behalf of".

So in a nutshell, given our situation, will Domain Toggling and Changing the Sender Header help (or hinder?) the chances of emails making it to the inbox?

And is there anything else we should be doing?

Any advice is much appreciated.

  • 2
    It's interesting that you've used the spam tag because the more I read the more convinced I am that what you are describing is indeed a spam generator. Feb 25 '11 at 3:49
  • 1
    @John: ever heard of a newsletter? Order confirmation? Password reminder? Catalog? Groupon? not every mass email system is malicious.
    – gravyface
    Feb 25 '11 at 4:04
  • @gravyface Thanks. What our clients send out is indeed relatively innocent material, and sent to mailings lists of up to 1000 current clients.
    – Ben Cook
    Feb 25 '11 at 4:14
  • @John it sounds to me more like an email marketing management solution (i.e. not spam).
    – Wesley
    Feb 25 '11 at 5:10
  • Curious, why would you not use a system like PostageApp or MailChimp to send out your transactional and/or bulk email? Better deliverability and none of the headache.
    – JonLim
    Feb 25 '11 at 16:26
  • Setup SPF records
  • Use DKIM
  • Have a simple, highly-visible unsubscribe option
  • lose the tracking image; just because the image was loaded, it doesn't mean they read it (preview pane, pre-fetch, etc. etc.), and it'll get blocked by 90% of clients out there anyways.
  • don't send too many emails.
  • most important tip: if it looks like spam, reads like spam, and acts like spam, it probably is spam, so don't send it.
  • Thanks for that. We do also inject an unsubscribe option which flags the client as do not mail in the database. Assuming the tracking images won't do any harm, I will keep them, as I am more concerned with knowing that our emails are actually getting delivered. I understand the limitations, but some information is better than none :)
    – Ben Cook
    Feb 25 '11 at 4:16
  • Just trying to get some clarity around SPF. Would this require each user to approve our emailserver against their specific email address? Is there a web portal to achieve this?
    – Ben Cook
    Feb 25 '11 at 4:24
  • @Ben, each domain, not each user. That's done in DNS. If they don't do it you can be assured that even a rudimentary spam filter will block those message. Feb 25 '11 at 8:14

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