Bulk email through exchange?

[lsi]

I have a customer that is hell-bent on sending newsletters to their customers through exchange distribution lists and they keep getting blacklisted. I have set them up with Constant Contact and trained them on how to send out newsletters with it but they want to use Exchange because it's so easy to manage the lists from there and they want to be able to do everything in Outlook. Is there an appliance or 3rd party software I can put on their exchange server that can handle email batching or bulk email so that they can send out their newsletters without getting blacklisted? How are other companies doing this?

 

[YeOldeStonecat]

It's not Exchanges fault....is their ISP or whatever SMTP outbound service they are using. Their static (hopefully) public IP address is not assigned a high reputation. There could be other factors that contribute to being blacklisted faster...have they gotten setup with a PTR with their ISP? Do that have a .TXT record in their DNS stating the domain is safe to send e-mail from their static IP? Have you run their MX record through the MXToolbox scanner and resolved any/all issues it points out?

 

[lsi]

Right now they are using a relay service called Exchange Defender but I am thinking about moving them over to MX Logic. I'm wondering if that will fix their issues? It does look like the spf record does not exist. The biggest problem we've been having is that certain ISPs are blocking emails with a maximum number of recipients. For example AOL will block emails that are addressed to more than 50 recipients in the header even if only 3 of the addresses are aol emails. So I'm not sure if there is some sort of batching software to split those up?

 

[YeOldeStonecat]

Honestly IMO the best thing to do is have them make the leap and do it right.
Anti-SPAM rules are always changing/evolving. If you spend hours and hours coming up with some bandaid/bubblegum/paperclip and duct tape approach...and get it working for a few months....until some recipients now start dropping mail from them, or it gets black listed again...

Unsure about MXLogic...no interest in them since McCrapee took them over.

Have 'em check out SendGrid
https://sendgrid.com/docs/Glossary/bulk_email_service.html

 

[Markverhyden]

I had a long conversation with Appriver about this type of situation. Most, if not all, of the major mail providers, meaning SMTP as well as IMAP/POP, do not tolerate bulk emails. Like @YeOldeStonecat said do it right. Get a proper bulk emailing service. They do not send batches of email with a bazzillion BCC's in each email. One email at a time with one address. I've got one customer who sends about 40k emails once a week. He is using MaxBulk Mailer through his own email server on a fixed IP address. Speaking of which a fixed IP is absolutely essential.

I also tested MaxBulk using Mandrill, which worked very well.

 

[TenYardFight]

Sendgrid or their competitor Mandrill is made for this. Still way harder than Constant Contact or Mailchimp. I know I am not tellling your anything you don't know, but running thru Constant Contact is so easy and so feature rich...I would tell them to get bent if they refused.

 

[fencepost]

Even simpler, tell them that you've given them your best advice - that for bulk email, you use a service designed for that.

If they insist on doing it otherwise, you can help them or not but make it clear to them that ANY time you spend is billable even if it would normally be covered under some sort of service plan.

 

[putz]

Using a reputable third party bulk email service would be my suggestion.

Bulk newsletters and advertisement emails from your on-premise email server dont mix. We have a few customers like the one you describe. They are typically sales and brokers that need to advertise pricing info multiple times a day to a large amount of customers. We have told them repeatedly to stop using their business email to do this, because eventually they end up on block lists. They are also using MXLogic.

You can only control part of the problem on your end. Many recipients may be using gmail, hotmail, outlook, or other large hosted email providers. These providers are always monitoring their email traffic and it only takes one bad keyword, phrase, link, etc, in your email to trigger something on their end. Or if they are horrible at updating their bulk lists, and they send to invalid senders, even that can trigger a block. Multiply that by however many recipients are on the same provider and eventually you get added to a blocklist either by the recipients email provider or by a third party. Most blocklists are IP but some are domain based too.

Using a more reputable mail filtering service helps but only to some degree. We've also recommended things like constant contact but they never want to switch. But they complain all day when their emails get rejected and don't make it to customers. One thing i have thought of doing is setting up another SMTP server on the network with something like postfix with a different domain that they would use for bulk email and 1:1 NAT it with a different public IP, at least that way if it gets blocked, they can still correspond with other customers normally with their regular email addresses. Luckily it hasnt come to anything like that yet.