Do I need a "high-reputation" service?

pizzafoundry · 23 Apr 2022, 08:36 AM

One of my clients runs a service where some of the emails he sends to his customers are of such a highly critical nature that if a particular message does not arrive by a certain time, he may be liable for fines in the tens of thousands of dollars.

He's currently hosted at In Motion Hosting, and recently has had several bounces saying his messages will be delayed 24 hours, which is unacceptable. These bounces come with the "451 4.7.500 Server busy. Please try again later" error code. Researching that seems to indicate that it is the result of the Microsoft Office 365 service, more specifically from their anti-spam filters. So these bounces are caused by the remote end and the fact they're using the Microsoft email cloud, apparently.

The In Motion Hosting mail server is not blacklisted but Microsoft doesn't just allow those emails through every time for some reason. And In Motion tells me their email service is not intended for high-critical emails, they're primarily a web hosting company so I "may want to look elsewhere". Great.

So I need to find what I'm calling a "high-reputation" service which I can run the client's domain name on, and which can be run IMAP and SMTP using Outlook clients. Is there such a thing? Or another solution? Bounces of any kind are just unacceptable, though I realize the email system is not 100%. However, he has had occasions where even after multiple retries, he was simply unable to get an email delivered, and it was a critical one that caused a bit of a ruckus. He's let me know he's not in the mood for any more of that.

So I'm just looking to improve the odds of delivery I suppose. Any ideas?

eno

pjroutledge · 23 Apr 2022, 10:54 AM

Quote:

Originally Posted by pizzafoundry

One of my clients runs a service where some of the emails he sends to his customers are of such a highly critical nature that if a particular message does not arrive by a certain time, he may be liable for fines in the tens of thousands of dollars.

To be frank, I think your client may have failed to conduct a proper risk analysis for his service.
Email, by design, cannot be guaranteed to be delivered, let alone delivered within a specified timeframe.

digp · 23 Apr 2022, 09:57 PM

No such thing.

Closest perhaps you could come to is:

Use Gmail workplace or MS 365 email AND ask the recipient to whitelist (add to safe senders or similar) the sender's email addresses.

Fax is usually used for the scenario you describe.

ioneja · 24 Apr 2022, 01:39 AM

Can confirm both digp's and pjroutledge's advice in general. Any time I have a mission critical communication with a client, I call them on the phone and talk with them human to human and confirm they have everything. I wouldn't even *personally* trust fax anymore either BTW since so much of it is virtual and sits in buffers on servers with email notifications, so these days a "fax" has much the same potential for lag. Unless you know for a fact your client has a hard wired fax machine.

The best advice you give your client is what pjroutledge said about them conducting a proper risk analysis.

Good luck.

digp · 24 Apr 2022, 04:58 AM

ioneja is right. I forgot real fax machines don't really exist anymore.

FredOnline · 24 Apr 2022, 06:30 PM

Quote:

Originally Posted by digp

ask the recipient to whitelist (add to safe senders or similar) the sender's email addresses

Perhaps, also consider a provider that has 'read receipt' and/or 'delivery status notification' as an option when sending e-mails.

I know that read receipts can be ignored by the receiver, but the delivery status notification should still work - at least it does for me, when I just tested sending to my Gmail account from a personal domain using Roundcube.

jarland · 26 Apr 2022, 12:06 AM

My pride and joy is getting emails where they're supposed to be and I wouldn't feel comfortable at all making the kinds of promises required. In a situation like that I feel like an Office 365 account is the best way to go. They can get blocked elsewhere, they can and do have outages, but if you constantly need to deliver letters quickly inside of a burning building I do recommend being inside of the building.

And when you have to point out that your vendor had a problem, for some reason people really love for that vendor to be Microsoft. It's the whole "nobody ever got fired for using IBM" thing, pure marketing but if it works on people then it does it's job.

TenFour · 26 Apr 2022, 12:26 AM

It doesn't matter what service is used to send the emails because what service is receiving the emails is equally as important. Unless this person has control over both ends--sending and delivery--there is no guarantee of delivery using email. Even when you do control both ends stuff just happens, like the Internet being out at the delivery end of things. Note how the IRS and certain companies will send snail mail reminders of certain things even if you have signed up for e-delivery.

ioneja · 26 Apr 2022, 01:24 AM

Technically, I would trust jarland's own Mxroute service over Microsoft any day of the week, and I'm not a customer of Mxroute. Jarland is passionate about protecting his deliverability, by all accounts here in the forum, and that's a good thing for a situation like your client. Again, I'm not a customer, so I can only go by what I've read in the forum.

On the other hand, even though Microsoft has lousy deliverability sometimes, even within itself, and even within the same organization on the same domain, I definitely see jarland's point, and he's right about "nobody ever got fired for using IBM." So if you HAVE to use email (which again, your client really needs to do a proper risk analysis like pjroutledge suggested), then as jarland mentioned, Microsoft might be an option. Cheers.

alexu2007 · 28 Apr 2022, 08:31 PM

You may try consider this:

For every major ESP use a smtp server from their trusted network.

For example, for email addreses that use Gmail (regular Gmail accounts or Google Workspace with their own domains) just use the gmail smtp (you will need a regular gmail or google workspace).

For email addresses that use Microsoft Outlook / Office servers, you should send the emails from an outlook.com smtp (you will need a regular outlook.com email account or a business plan that allows you a custom domain).

For email addresses that use Amazon servers you should send the emails from an aws smtp server (simple mail service or amazon workmail).

For other email addresses that use other email service providers, just use a major smtp provider, for example MailChannels.

However, the email has many weaknesses regarding the success of delivery and should be not used for such critical missions. You should take into consideration other methods of sending push alerts, that can be traced and confirm the delivery.

alexu2007 · 28 Apr 2022, 08:39 PM

Another idea that will solve all email delivery problems:

your client should sign up for Google Workplace or similar service from Microsoft. Create email accounts for every customer in the same Google Workplace account and request that the customers should use that email accounts if they want to be sure that the emails will never fail reaching the destination.

Sending the emails from a Google Workspace account to other accounts from the same oranization hosted at Google Workspace will give you the best deliverability rate.

However this is expensive, it will cost around 6$ for every customer.

23 Apr 2022, 08:36 AM	#1
pizzafoundry Junior Member Join Date: Apr 2022 Posts: 1	Do I need a "high-reputation" service? One of my clients runs a service where some of the emails he sends to his customers are of such a highly critical nature that if a particular message does not arrive by a certain time, he may be liable for fines in the tens of thousands of dollars. He's currently hosted at In Motion Hosting, and recently has had several bounces saying his messages will be delayed 24 hours, which is unacceptable. These bounces come with the "451 4.7.500 Server busy. Please try again later" error code. Researching that seems to indicate that it is the result of the Microsoft Office 365 service, more specifically from their anti-spam filters. So these bounces are caused by the remote end and the fact they're using the Microsoft email cloud, apparently. The In Motion Hosting mail server is not blacklisted but Microsoft doesn't just allow those emails through every time for some reason. And In Motion tells me their email service is not intended for high-critical emails, they're primarily a web hosting company so I "may want to look elsewhere". Great. So I need to find what I'm calling a "high-reputation" service which I can run the client's domain name on, and which can be run IMAP and SMTP using Outlook clients. Is there such a thing? Or another solution? Bounces of any kind are just unacceptable, though I realize the email system is not 100%. However, he has had occasions where even after multiple retries, he was simply unable to get an email delivered, and it was a critical one that caused a bit of a ruckus. He's let me know he's not in the mood for any more of that. So I'm just looking to improve the odds of delivery I suppose. Any ideas? eno

26 Apr 2022, 12:06 AM	#7
jarland Essential Contributor Join Date: Apr 2014 Posts: 399 Representative of: MXRoute.com	My pride and joy is getting emails where they're supposed to be and I wouldn't feel comfortable at all making the kinds of promises required. In a situation like that I feel like an Office 365 account is the best way to go. They can get blocked elsewhere, they can and do have outages, but if you constantly need to deliver letters quickly inside of a burning building I do recommend being inside of the building. And when you have to point out that your vendor had a problem, for some reason people really love for that vendor to be Microsoft. It's the whole "nobody ever got fired for using IBM" thing, pure marketing but if it works on people then it does it's job. Last edited by jarland : 26 Apr 2022 at 12:14 AM.

23 Apr 2022, 09:57 PM	#3
digp Master of the @ Join Date: May 2003 Posts: 1,320	No such thing. Closest perhaps you could come to is: Use Gmail workplace or MS 365 email AND ask the recipient to whitelist (add to safe senders or similar) the sender's email addresses. Fax is usually used for the scenario you describe.

24 Apr 2022, 01:39 AM	#4
ioneja Cornerstone of the Community Join Date: Jul 2011 Posts: 713	Can confirm both digp's and pjroutledge's advice in general. Any time I have a mission critical communication with a client, I call them on the phone and talk with them human to human and confirm they have everything. I wouldn't even personally trust fax anymore either BTW since so much of it is virtual and sits in buffers on servers with email notifications, so these days a "fax" has much the same potential for lag. Unless you know for a fact your client has a hard wired fax machine. The best advice you give your client is what pjroutledge said about them conducting a proper risk analysis. Good luck.

24 Apr 2022, 04:58 AM	#5
digp Master of the @ Join Date: May 2003 Posts: 1,320	ioneja is right. I forgot real fax machines don't really exist anymore.

26 Apr 2022, 12:26 AM	#8
TenFour Master of the @ Join Date: Feb 2017 Location: USA Posts: 1,722	It doesn't matter what service is used to send the emails because what service is receiving the emails is equally as important. Unless this person has control over both ends--sending and delivery--there is no guarantee of delivery using email. Even when you do control both ends stuff just happens, like the Internet being out at the delivery end of things. Note how the IRS and certain companies will send snail mail reminders of certain things even if you have signed up for e-delivery.

26 Apr 2022, 01:24 AM	#9
ioneja Cornerstone of the Community Join Date: Jul 2011 Posts: 713	Technically, I would trust jarland's own Mxroute service over Microsoft any day of the week, and I'm not a customer of Mxroute. Jarland is passionate about protecting his deliverability, by all accounts here in the forum, and that's a good thing for a situation like your client. Again, I'm not a customer, so I can only go by what I've read in the forum. On the other hand, even though Microsoft has lousy deliverability sometimes, even within itself, and even within the same organization on the same domain, I definitely see jarland's point, and he's right about "nobody ever got fired for using IBM." So if you HAVE to use email (which again, your client really needs to do a proper risk analysis like pjroutledge suggested), then as jarland mentioned, Microsoft might be an option. Cheers.

28 Apr 2022, 08:31 PM	#10
alexu2007 Essential Contributor Join Date: Aug 2007 Posts: 287	You may try consider this: For every major ESP use a smtp server from their trusted network. For example, for email addreses that use Gmail (regular Gmail accounts or Google Workspace with their own domains) just use the gmail smtp (you will need a regular gmail or google workspace). For email addresses that use Microsoft Outlook / Office servers, you should send the emails from an outlook.com smtp (you will need a regular outlook.com email account or a business plan that allows you a custom domain). For email addresses that use Amazon servers you should send the emails from an aws smtp server (simple mail service or amazon workmail). For other email addresses that use other email service providers, just use a major smtp provider, for example MailChannels. However, the email has many weaknesses regarding the success of delivery and should be not used for such critical missions. You should take into consideration other methods of sending push alerts, that can be traced and confirm the delivery.

28 Apr 2022, 08:39 PM	#11
alexu2007 Essential Contributor Join Date: Aug 2007 Posts: 287	Another idea that will solve all email delivery problems: your client should sign up for Google Workplace or similar service from Microsoft. Create email accounts for every customer in the same Google Workplace account and request that the customers should use that email accounts if they want to be sure that the emails will never fail reaching the destination. Sending the emails from a Google Workspace account to other accounts from the same oranization hosted at Google Workspace will give you the best deliverability rate. However this is expensive, it will cost around 6$ for every customer.