Remember the days when you could get a customer-service rep on the phone…or even better, just walk into one of their offices and deal face-to-face?

Them days is long gone.

It’s perfectly logical from a business dollars-&-cents perspective, though. For service businesses primarily, employee cost is the biggest category of costs by far. Lowering them pays off big in terms of enhanced profits and the capital to self-finance company growth.

And so we get the inevitable. Closing branch offices and centalizing because of lower costs of communication. Then we got those horrendous voicemail-hell, answering-system trees, which the Urban Dictionary defines as:

When accessing a voice mail phone answering system, one becomes lost, going down the wrong path or getting stuck in a loop, unable to get pertinent information or leave a message with the appropriate party.

Those have actually become better in the last decade with voice recognition and AI tech. Some are downright good when they prompt you to just say what you’re trying to do and they place you in the right, or close to the right, place.

Then you have trouble or support tickets. Now, I deal with a few companies and their support is fantastic. Quick and pertinent. And often, chat is available and that usually provides me a way to sort of casually get an issue resolved right on the spot and I can be doing other things whilst the guy or gal is off investigating.

But this story is about when it goes awful. Read on.

…Back in April of 2021 when I converted this blog to a member’s site, I knew I needed to use my newsletter list as a primary tool for building memberships. At the time, it was 4,500 subscribers or so, now about 6,000. The problem was, Mailchimp was my provider and they are super expensive. So, I looked for alternatives and the CRM I use, FluentCRM, also has an add-on, FluentSMTP (the sending of email to people in the customer relationship management (CRM) database that has integrations with various email services.

I had to do a double take. Just a paper napkin analysis would save hundreds of dollars per month by using Amazon Simple Email Service (SES), part of their AWS suite of services. So now, I send upwards of 150,000 emails per month and the cost averages about 10 bucks with AmazonSES. It would be hundreds with Mailchimp.

The tradeoff is that for that money, Mailchimp is invested in making sure your emails get into inboxes, and not spam folders. Moreover, they will monitor bounces. Most bounces are legit. The recipient has abandoned the email address, cancelled it, or hasn’t done housekeeping and the box is full.

By contrast, AmazonSES is bare bones. They just send the email. What happens on the recipient side in terms of junk folders and bounces is on you. You have to maintain and guard your own sender reputation. And I did, no problem. That is, until a couple of months ago when all of the Microsoft property email services (hotmail, outlook, live, MSN, etc.) started bouncing hundreds of emails, all with this troubling message:

Bounced Reason: smtp; 550 5.7.1 Unfortunately, messages from [23.251.242.9] weren’t sent. Please contact your Internet service provider since part of their network is on our block list (S3150). You can also refer your provider to http://mail.live.com/mail/troubleshooting.aspx#errors. [AM7EUR06FT023.eop-eur06.prod.protection.outlook.com] @ 2022-08-14 23:20:49

A bit of a distinction is in order. Your SPAM / Junk management works in a couple of ways. If you use a service like Gmail, it has its own pretty-damn-good filtering. There are rarely any false positives when I scroll through before emptying the folder. If you use an email client direct to an ISP that does not have this filtering, then most email client applications have some ability to filter obvious SPAM. And, of course, you can use both. I use Gmail with its filtering, but I fetch email from Gmail with my Apple Mail client. Double protection; and it works damn well. Almost nothing gets through, and false positives are rare.

Aside: if you like getting my emails and don’t want them in your SPAM folder, then add my 2 addresses to both the web portal of the service (gmail, hotmail, outlook, live, msn, yahoo, etc etc) and also to the contacts in your email client if you use one.

• RN [*] FREETHEANIMAL [*] COM
• RNIKOLEY [*] GMAIL [*] COM

(I trust you know what the bracketed asterisks translate to.)

…Bounces are an entirely different thing in this context; for, it’s not because of a dead email address, it’s because they are ‘protecting’ you.

It is the stark tendency of big tech now—in all of its manifestations—to treat everyone like their children and mommy knows best…what’s good and especially, what’s bad for you. See, by bouncing the emails, they don’t even get to your service or email client to eventually be evaluated by the SPAM tech, or by you personally.

They are the quintessential overbearing parent, now. And what happens? Nobody learns anything…just like the kids ill-suited to live in society…where they continually touch social hot stoves—or can’t change a flat tire—because they never had the opportunity to gain their own experiences and learn lessons from mistakes or ignorance.

Yesterday, I finally resolved to see if I could do something about it and after a bit of Googling, learned that there’s a place to request “mitigation”—their word for ceasing to block emails you send to recipients using their services. So I submitted and to their credit, they are very responsive, impressively so.

Dear Richard Nikoley

Please note that your ticket number is in the subject line of this mail.

23.251.242.9

Note: Errors are unlikely, however, if an error is indicated, please resubmit the specific IP or IP range.

Thank you,

Outlook.com Deliverability Support

It was quickly followed up by this.

Dear Richard Nikoley

We have completed reviewing the IP(s) you submitted. The following table contains the results of our investigation.

Not qualified for mitigation
23.251.242.9
Our investigation has determined that the above IP(s) do not qualify for mitigation.

Please ensure your emails comply with the Outlook.com policies, practices and guidelines found here: http://mail.live.com/mail/policies.aspx.

To have Deliverability Support investigate further, please reply to this email with a detailed description of the problem you are having, including specific error messages, and an agent will contact you.

Regardless of the deliverability status, Outlook.com recommends that all senders join two free programs that provide visibility into the Outlook.com traffic on your sending IP(s), the sending IP reputation with Outlook.com and the Outlook.com user complaint rates.

Junk Email Reporting program (JMRP) When an Outlook.com user marks an email as “junk”, senders enrolled in this program get a copy of the mail forwarded to the email address of their choice. It allows senders to see which mails are being marked as junk and to identify mail traffic you did not intend to send. To join, please visit

https://sendersupport.olc.protection.outlook.com/snds/JMRP.aspx

Smart Network Data Services program (SNDS). This program allows you to monitor the ‘health’ and reputation of your registered IPs by providing data about traffic such as mail volume and complaint rates seen originating from your IPs. To register, please visit .

There is no silver bullet to maintaining or improving good IP reputation, but these programs help you proactively manage your email eco-system to help better ensure deliverability to Outlook.com users.

Thank you,

Outlook.com Deliverability Support

Emphasis mine

So I took the opportunity to write a detailed description so that support would investigate further.

Thank you for your help in resolving this.

As background, I have written a blog for 19 years (and have published over 5,000 posts). About 10 years ago I decided to create a newsletter and began collecting the subscriptions via the blog. I used Mailchimp for many years with zero problems.

Then I heard about the FluentCRM plugin and FluentSMTP with its integration with AmazonSES. The price difference between SES and Mailchimp is radical. So in about April 2021 I switched everything over. No problems until just a couple of months ago when I began getting some, not all, emails to Microsoft properties (outlook, hotmail, live, msn, etc.) bouncing. A screen clip:

(too much personal info to publish here; it simply shows that all the bounces are from the various Microsoft email provider properties)

All of the error messages read the same:

“Bounced Reason: smtp; 550 5.7.1 Unfortunately, messages from [23.251.242.9] weren’t sent. Please contact your Internet service provider since part of their network is on our block list (S3150). You can also refer your provider to http://mail.live.com/mail/troubleshooting.aspx#errors. [AM7EUR06FT023.eop-eur06.prod.protection.outlook.com] @ 2022-08-14 23:20:49”

I’ve attached a PDF of the sorts of emails I send out.

Please let me know if there is any other information I can provide.

Then I get a quick reply and that’s when I get perturbed.

My name is Salma and I work with the Outlook.com Deliverability Support Team.

We have investigated your deliverability issue regarding IP’s (23.251.242.9). At the current time, these IPs are not eligible for mitigation.

We are concerned with a pattern of irregular mail traffic originating from your IPs. While this could be benign, sudden changes in email sending volume can be the result of a server or network compromise or the result of compromised user accounts.

It takes time to improve IP reputation and careful vigilance of your email systems which includes monitoring the information you can receive from server logs and programs such as JMRP and/or SNDS to help identify potential issues, such as compromised servers or accounts, spikes in sending overall volume etc. There is no silver bullet, unfortunately, to improve or maintain IP reputation.

While we cannot offer mitigation at this time, please note that our technologies designed to prevent unwanted mail are not static and will respond to changes in sending practices over time. In addition to the best practices we have already recommended, here are some specific recommendations for you to consider:

· Review outbound mail logs – It’s recommended that you have network and email admins review server logs for anomalies and verify all of the email sending is intentional. Be aware that not all compromises immediately result in a high volume of mail. Some attacks may be more subtle, and may only periodically send mail from infected mail servers. Therefore, careful log review may be necessary to detect and address potential compromise issues. As a best practice, set up monitoring on outbound sending volume to ensure that sudden, unexpected peaks are quickly identified and reviewed.

· Security review of sending servers – In addition, it’s recommended you ensure all sending servers are up-to-date with the latest security patches, updates, etc. and that security and anti-virus scans are regularly executed against all sending servers.

· Implement Sending Limits – It’s a recommended best practice to enforce sending limits on your domain accounts; this is a simple method to prevent users who may be compromised from sending bulk emails and helps better protect the reputation of your IPs.

In addition, Microsoft has several programs which can assist you with identifying and monitoring potential issues, such as compromised servers, outdated mailing lists, etc. Joining these programs does not mean you are whitelisted from Outlook.com. Here are some specific recommendations for you to consider:

· Actively monitor your junk mail reports – The free JMRP program (http://mail.live.com/mail/services.aspx) provides reports on junk email reported by Outlook.com customers for your IP addresses. This helpful feedback mechanism allows you to ensure that mails being sent on your IPs are not resulting in negative feedback that could impact your sending IP reputation. Being vigilant about users who mark your e-mail as unwanted (or junk) or the types of messages that are being marked as unwanted (or junk) can help you identify unintended mail traffic, modify future campaigns and keep mailing lists updated with only interested consumers. You can Enroll at
https://postmaster.live.com/snds/JMRP.aspx?wa=wsignin1.0

· Actively Monitor IP Traffic – Consider joining the Smart Network Data Services program (SNDS). This free program provides data about traffic seen originating from your registered IPs, such as mail volume and complaint rates. The data is built from the log files of the inbound mail machines and other servers at Outlook.com and Microsoft and represents factual information about the traffic from your mail servers to Outlook.com users. For more information about this free program refer to https://postmaster.live.com/snds/FAQ.aspx. To register, please go to https://sendersupport.olc.protection.outlook.com/snds/​

Sincerely,
Salma
Outlook.com Deliverability Support

Fucking yawn yawn yawn…put me to fucking sleep. So I get measured snarky in my reply. Good thing I wasn’t drinking emotion from a bottle.

Well, it’s AmazonSES, I doubt they are “compromised.”

It is a shared server, though. Still, Amazon.

You big companies crack me up, and that’s why so many of us hate and loathe you. Your emails smell of bots and canned text, and most of them, someone like me could write them before they show up in my inbox.

Mostly, you all deflect and play the blame-others game…in this case, Amazon, with the ridiculous nonsense that they may be compromised and don’t know it, and that I don’t know what I’m doing after running client/server in my own company for 20 years.

Could not possibly be that you have it wrong.

And what do you know? It fucking paid off. Just an hour and a half later:

My name is Tanzeem and I work with the Outlook.com Sender Support Team.

We have implemented mitigation for your IP (23.251.242.9) and this process may take 24 – 48 hours to replicate completely throughout our system.

Sincerely,

Tanzeem

Outlook.com Deliverability Support

And as is my business-born habit, I never gloat in any way when this sort of thing [rarely] happens. Rather, I was thankful and conciliatory.

Best practices.

So in the wider context of things, you have to be persistent nowadays. It reminds me of when I originally set up AmazonSES on their Northern California servers in April of 2021. Once you get it all configured, you are informed that you’re in The Sandbox, which means your sending limit is 200 emails per day, at a rate of 1 email per second. They invite you to submit a request to increase those limits and they give you a list of information you need to provide, which I did.

In short order I received a rejection, which had the odor of a canned, bot-based auto-reply. Incredibly, the reason for the rejection was that I had not provided the required info. So I replied, specifying that indeed I had and quoted it. Later, I received a reply from an ostensible human being, granting me a green light with a sending limit of 50,000 per day at a rate of 14 emails per second.

…My backup plan here, which I had already set in motion, was to duplicate my configuration on AmazonSES’ Northern Virginia servers, which would have a different IP address than the one being blocked by Microsoft, et al.

In left-hand, right-hand fashion, they put me in the sandbox again, so I jumped through the hoops, adding that I’d already been sending hundreds of thousands of emails from their N Cal servers over the last year and a half. And guess what? I got an auto-bot rejection that was verbatim to the one I’d received way back when.

This time, however, I guess it was auto-escalated and in not too long, I got a preemptive follow-up granting me the full access.

…So, the moral of the story? Persist, keep the faith, be reasonable, check emotion and snark to measured levels…and if/when it works out, be gracious.

Anyone have similar stories to share in comments?