How do you sell email hosting in your business?
Problem reported by Brian Bjerring-Jensen - VonBjerring GmbH - 10/17/2025 at 10:01 AM
Submitted
I am looking for USP's for selling Smartermail email compared to Office365...

Is it privacy or your support or functionality?
Nathan Replied
I guess it has to be privacy / data residency, functionality wise you are not going to beat 365 (Exo / Teams / OneDrive) with Smartermail. Similarly, even the economics of offering large 25/50/100GB mailboxes with SM is a tough when compared to MS pricing versus the cost of the infrastructure.

It will be interesting to see what others think.
Richard Laliberte Replied
I can say we have lost clients in the past due to mailbox sizes, as we can't keep up with the pricing MS can offer. We've also lost clients because oddly enough we seem to routinely get spam blocked by Microsoft servers (which is funny because they are the only ones that ever block our mail server). Privacy / data residency is also a hit an miss, as many clients have switch to Microsoft on-prem.

2 items that have worked for us, 1) Support. if you get locked out of your account, good luck with MS, were at least we can get you back in, and 2) more recently we've started to focus heavily on the mailing list feature of SM, even integrating it into our CMS. We've found it's MUCH more cost effective than some mainstream brands, although we do have issues with LARGE volume sends with our current systems.

We are hoping the new Market Place will bring in some new fresh plugin's to SM once the open source community really gets involved, but so far we are a bit under-whelmed... 

Hopefully others can share some selling points that have worked for them.
Douglas Foster Replied
I am not a hosting system operator, but I have been managing our SmarterMail environment for more than a decade, and watching Microsoft since Windows 1.   I will offer some observations, but others will have to judge which ones are safe to use as a selling strategy. 
 
Microsoft dominates by bundling and bundle pricing.  An early attempt was bundling Internet Explorer into Windows 95, in an attempt to wipe out the market for other browsers.   They lost that battle, but they have one most every battle since.   They wiped out WordPerfect and Lotus 1-2-3 by bundling Word and Excel.   They dominated on-premise email by superseding standards-based IMAP with proprietary MAPI, EWS, and EAS.   The user interface was superior to once-dominant IBM PROFS and provided synchronization features that could not be obtained on Unix/Linux system.    So they get credit for anticipating a market need and addressing it, but the consequence of that success is that customers become dependent on that vendor.

Microsoft is continuing that process with the other products that have been discussed here.   Teams integration and bundle pricing has effectively pulled customers away from remote support solutions that have been around much longer.  Notably, Teams must be installed on a local PC for the support person to obtain remote control.  Once installed Teams launches every time a user logs in to that device.

Microsoft also dominates by applying coercion to existing customers.    Nobody wanted WindowsME, Windows Vista, or Windows8 based on features, but Microsoft decided that these would be what everybody must buy.   When that process failed to force upgrades at the speed that they wanted, Microsoft use end-of-support to solve their problem.   When Microsoft decided that they wanted to own cloud computing, they used pricing to force customers away from on-premise Exchange and onto Office365.   It was only possible because customer had already become dependent on the Exchange.

We have also seen the coercion applied with Outlook.  The first coercion was exposed when Outlook forced us to use Autodiscover to configure their protocols.  Then they used Autodiscover to silently connect to their servers.   For everyone that does not use Office365, this is a malicious act which sends confidential information to Microsoft without permission.   But the point is (probably) not to steal your credentials, it is to eavesdrop on your data, presumably to feed their A.I. Model   The current extension of this coercion is “New” Outlook.   It is installed automatically by Windows Update, and displaces old Outlook by default.  If used, it forces traffic through Microsoft servers without permission and without notification.

Then there is the quality of the Office365 environment.   One evidence is the way that Office365 uses ARC data to report security issues in email messages.   A credentialled login is reported with a Received record claiming a MAPI connection from a server to itself, and an initial ARC set that asserts SPF PASS, DKIM PASS, and DMARC PASS even when those assertions are actually false.   More importantly, Office365 accepts uncredentialled SMTP connections.  It uses an ARC set to report actual results for SPF, DKIM, and DMARC, but thereafter proceeds as if the connection has been validated.  It will happily apply a DKIM signature to an unauthenticated message, so that the recipient is duped into believing that the message originated without impersonation.

The quality of the environment is also indicated by the obvious spam that arrives to my system, even though it carries message headers indicating that the message was carefully checked by their spam filter yet allowed to proceed.

More subtly, it shows up in DNS timeouts, which are exposed by DMARC reports.  I have been told on an IETF forum that Microsoft had a known problem with DNS timeouts, but more than a year later, it does not appear to be fixed..

Eric Tykwinski Replied
This isn't trying to cause controversy, but one of my biggest complaints about SmarterTools new CI/CD development process is that I can't afford a bug.  Literally every outage or bug is just a company leaving to O365, since an outage on Microsoft is just considered acceptable, but with smaller providers it's considered a time to move.  This latest issue with Outlook (https://portal.smartertools.com/community/a97532/outlook-mapi-connections-breaking.aspx) which I don't even think has anything to do with SmarteMail per se, can cause turnover.  Having to edit a desktop registry is considered taboo, so doing this and creating a new profile is a death sentence when talking to MSPs.  How can SmarterTools predict issues on Office upgrades is definitely not possible, but they could at least set major version upgrades, ie LTS to at least quarterly updates and I would be happy.
J. LaDow Replied
Good luck on LTS -- I've been begging for an LTS channel for two years now - and others here for MUCH LONGER.

Issues with upgrades that were buggy already cost me customers once - not getting bitten by that again.

MailEnable survivor / convert --

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