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How is the LINUX version of SmarterMail? I am thinking of switching all my MAPI/Outlook users...
Problem reported by dean brown - 1/30/2025 at 10:53 AM
Submitted
d
Not a Smartermail issue, but maybe some one can help out. 
I have a program that sends email from a web server (IIS). It sends through the email server (with SSL, user email and password), but the email header shows it comes from the web server ip address, not the email server address. Mail is delivered to some accounts, but gmail rejects it outright (not even in spam or can be whitelisted). I've tried various DNS config's, but still no luck. 
Top of the header:

Return-Path: <formsubmit@boardgamesforsale.org>
Received: from www (UnknownHost [205.210.140.24]) by mx1.netsell.com with SMTP
    (version=TLS\Tls12
    cipher=Aes256 bits=256);
   Wed, 29 Jan 2025 17:05:49 -0500
Authentication-Results: smtp.mx1.netsell.com; auth=passed (login)
Zach Sylvester Replied
2/3/2025 at 7:30 AM
Employee Post
Hello, 

Thanks for reaching out. I’ve been running SmarterMail on Linux for personal use, and it’s been working well despite limited resources (1 GB RAM, 2 GB swap, 2 CPUs). I primarily use IMAP, WebDAV, and webmail, hosted on Hetzner’s Oregon servers. From what I’ve heard, SmarterMail on Linux performs just as reliably as on Windows. I recommend spinning up a test server and doing a trial migration to see how it handles your data. Below are some of my daily RAM usage averages. 

Kind Regards, 

Zach Sylvester

Software Developer
SmarterTools Inc.
Gabriele Maoret - SERSIS Replied
2/3/2025 at 7:46 AM
Hi Zach!

Thanks for the info, but my goal is to understand how the Linux version of SmarterMail behaves with a REAL production environment where there are HUNDREDS of MAPI users (with MS Outlook) and EAS users (various smartphones)...

For me IMAP is not a problem...

...and a test environment can be a good test to see if the actual data is converted correctly, but NOT to understand how it behaves with hundreds of real MAPI/EAS users...

EDIT: I edited the first post to clarify...
Gabriele Maoret - Head of SysAdmins and CISO at SERSIS
Currently manages 6 SmarterMail installations (1 in the cloud for SERSIS which provides services to a few hundred third-party email domains + 5 on-premise for customers who prefer to have their mail server in-house)
Linda Pagillo Replied
2/3/2025 at 2:08 PM
We also have a Unix server running with SmarterMail and we love it. No problems so far. We are not currently using MAPI/EWS or EAS,
Linda Pagillo
Mail's Best Friend
Email: linda.pagillo@mailsbestfriend.com
Web: www.mailsbestfriend.com
Authorized SmarterTools Reseller
Authorized Message Sniffer Reseller
 
Gabriele Maoret - SERSIS Replied
2/22/2025 at 2:39 AM
Is there really no one who uses the linux version and has a large number of MAPI users with MS Outlook?
Gabriele Maoret - Head of SysAdmins and CISO at SERSIS
Currently manages 6 SmarterMail installations (1 in the cloud for SERSIS which provides services to a few hundred third-party email domains + 5 on-premise for customers who prefer to have their mail server in-house)
Zach Sylvester Replied
2/24/2025 at 7:40 AM
Employee Post
Hey Gabriele, 

There are quite a few but I don't think they are active community members. 

Kind Regards, 

Zach Sylvester

Software Developer
SmarterTools Inc.
Gabriele Maoret - SERSIS Replied
2/24/2025 at 10:33 AM
Oh, OK! 
However, it's a pity that we can't hear their impressions...
Gabriele Maoret - Head of SysAdmins and CISO at SERSIS
Currently manages 6 SmarterMail installations (1 in the cloud for SERSIS which provides services to a few hundred third-party email domains + 5 on-premise for customers who prefer to have their mail server in-house)
Brantz Replied
3/18/2025 at 3:25 PM
I just tried my first migration attempt from Smartermail on windows to Ubuntu and had some problems I haven't been able to resolve, so I've gone back to Windows for now.

Here's what I did:
- Followed the instructions to download and install SmarterMail Build 9182 on Ubuntu 24.04.2
- Followed the instructions to delete JSON files and move the folders and files over to the Linux system per:
migrating-smartermail-to-linux documentation. 
- Note: The instructions have a small error var Lib smartermail where "Lib" should be "lib". Not a big deal but perhaps should be fixed in the documentation.
- When I started the service and went to the Smartermail UI I was prompted to create an admin password, but I was never directed to an "OS Conversion page" as was indicated in the documentation. 

I tried the manual entry of the interface/convert-status page and got the following:
    No Active Conversions
    No conversion needed. You can proceed to login to webmail.

When I login to the server, it does not show any domains.

Any suggestions?  Thanks.
Kyle Kerst Replied
3/18/2025 at 3:40 PM
Employee Post
Hi Brantz! SmarterMail coming up with the setup wizard page (asking you to create an admin password) indicates SmarterMail didn't find the existing JSON configuration files at the system level, or wasn't able to access them due to a permissions issue or something similar. Those system level configuration files are kept under /etc/smartermail and if your existing JSONs weren't there at startup time we would have created new blank ones resulting in that wizard popping up on startup. Did you place the old config files there prior to starting the SmarterMail service on the linux side? If so, does the user you are running the service as have read/write access to that directory and the files inside of it?
Kyle Kerst
Lead Internal Network/System Administrator
SmarterTools Inc.
Brantz Replied
3/18/2025 at 4:08 PM
Now that I read that section about moving the JSON files, it doesn't say where to move them FROM on the the windows side - are they in SmarterTools\Smartermail\service\settings? If so, are there any others to move over? Thanks.
Matt Petty Replied
3/18/2025 at 4:34 PM
Employee Post
The stuff in that folder (program files...service\settings) should be moved into /etc/smartermail
The folders in C:\SmarterMail\ move into the /var/lib/smartermail/ folder

Hopefully this fixes your conversion not seeing these json files (and thus treating it like a fresh install)
Matt Petty
Senior Software Developer
SmarterTools Inc.
Kyle Kerst Replied
3/18/2025 at 4:57 PM
Employee Post
Yep! As @Matt Petty pointed out those are the two locations: 

- In Windows we store system under Program Files (x86)\SmarterTools\SmarterMail\Service\Settings and those will go into /etc/smartermail. 
- In Windows we store the data under the C:\SmarterMail\ folder by default and those end up in /var/lib/smartermail.
Kyle Kerst
Lead Internal Network/System Administrator
SmarterTools Inc.
M
Mars _ Replied
3/19/2025 at 3:43 AM
I love the linux version of SmarterMail - we are running some instances without any problems (migrated from Windows, detach+attach).
They are running fast and stable and in contrary to the windows version the update process on linux is very fast.
But no high volume - but I can imagine that also 100+ users would be no problem.
N
Nick Jansen Replied
3/19/2025 at 8:35 AM
We don't have hundreds of users (we have less than 100) nor do we use every feature SmarterMail offers (probably not close to it even), but we have been using SmarterMail Enterprise on Ubuntu Server since about when SmarterMail for Linux was first released (and are currently on SM Build 9182 and Ubuntu version 24.04.2). We converted from the Windows version, and the conversion process and pretty much everything after has been very smooth for us. We have a mix of MAPI, EAS, and IMAP/SMTP users (mostly MAPI).
Brantz Replied
3/19/2025 at 10:12 AM
Thanks @Matt & @Kyle, that helped a lot - I got everything over and the set-up wizard ran fine this time. I think the only problem I have left is securing the internal web server. The email server side is fine with SMTP TLS testing fine and I can get at WebMail with HTTP, but I can't see how to secure the built-in SM web server for HTTPS. When I look at bindings there is no HTTPS option. Can you please point me to that in the docs, or if it isn't there please let me know how to do it?  Thanks much!
Kyle Kerst Replied
3/19/2025 at 11:57 AM
Employee Post
That's great to hear @Brantz, happy to help! The SSL setup is done within SmarterMail itself in Settings>SSL Certificates and you should be able to upload your own certificates (if you don't want to generate them) in the Certificates tab. I don't believe there is a way to modify the bindings for the internal web server directly, so you'd need to set it up behind a reverse proxy for that like Apache or NGINX. 
Kyle Kerst
Lead Internal Network/System Administrator
SmarterTools Inc.
Brantz Replied
3/19/2025 at 12:48 PM
Actually, the built-in web server seems to be working fine now providing HTTPS. Not sure what happened other than a reboot. The SSL Certificate and settings came over with the migration and works for the email server, auto renewing from Let's Encrypt. It appears that SM uses Kestrel for the built in WebMail and I guess it's picking up the same certificate after all, so this was easier than I thought.  Thanks again for the support!
Matt Petty Replied
3/19/2025 at 3:24 PM
Employee Post
Glad to hear the success stories!

P.S. If you choose to use the "built-in" webserver during the installer on linux we'll bind to port 80 and 443 instead of the usual 17017, so the reverse proxy is only necessary if you aren't using the built in server.
(technically we're always using Kestrel, but "built-in" just changes the default ports and sets up the SSL certs to be served through Kestrel)
Found the performance with Kestrel to be VERY good.
Matt Petty
Senior Software Developer
SmarterTools Inc.
Brantz Replied
3/25/2025 at 11:29 AM
A quick note to the community that when I tried running SmarterMail build 9182 for Linux on Ubuntu 24.04.2 or Debian 12.10.0 under VMware ESXi 6.5.0 on older hosts (ProLiant DL380 G7 with Intel Xeon E5620) it would run for a while and then crash the VM. Note that Linux itself was stable and it was only when the SM service / ASP.NET was started that the VM would crash. When I migrated the workload to newer compute nodes (i5 & i3) that are running the newer VMware ESXi, 7.0.1 as hosts, it ran just fine. Also, note that the same version of SmarterMail was running very stable on Windows 2019 Server on the older ProLiant hardware & ESXi before migrating to Linux, so it is something about the service on Linux with the older hardware that was causing the issue. Since then, I have upgraded to build 9210 and everything is still running fine on the newer hosts. Hope that helps someone!

Brantz
Difference in hardware versions on vm tools?
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