SMTP Relay

[StephenPink]

Hi all,

 

With the Basic Authentication deprecation, we have a number of systems/applications that still don't support Modern Authentication. Microsoft's own SMTP Relay server is a bit hit-and-miss these days (having been deprecated since Server 2012 R2 I believe) so was wondering what alternative SMTP Relay software people were using? Obviously one that does support Modern Authentication, and preferably free?

 

Thanks,

Stephen

[colly72]

Have you looked here:

 

https://learn.microsoft.com/en-us/exchange/mail-flow-best-practices/how-to-set-up-a-multifunction-device-or-application-to-send-email-using-microsoft-365-or-office-365

[StephenPink]

Thanks - yes I have. In fact, that's where PaperCut directs you from their support article on the deprecation of Basic Auth, and advises the SMTP Relay option. Cheers

[TechMonkey]

As far as I am aware, using SMTP AUTH still works, with the right changes made, so just using that. Got rid of anon smtp ages ago, so apart from updating a couple of couples everything carries on regardless.

[HPlum78]

Yeah SMTP was dropped in 2012 and was initially for those thar remember removed from 2016 but MS gave it back as to many organisations needed it. I use it for a host of applications and have never hit an issue (running on Server 2019) but that said looking at the following https://www.hmailserver.com/

[free780]

If you have the budget you can use mailgun or similar to send mail as long as your app/service supports authentication.

[highsky]

Proxmox mail gateway?

Not tested yet.

[StephenPink]

Thanks all, will double check built-in SMTP on Server 2022 and see how it goes - will also have a look at that hmailserver, that rings a bell anyway actually.

 

As far as I am aware, using SMTP AUTH still works, with the right changes made, so just using that. Got rid of anon smtp ages ago, so apart from updating a couple of couples everything carries on regardless.

I thought SMTP AUTH still used Basic Authentication though so is going to stop working?

[FN-GM]

I am also looking for an SMTP relay (for other reasons - we can’t expose our servers directly to the internet) So far the windows options haven’t been great. I was considering something on Linux but going to look at the other suggestions here.

 

Thanks all, will double check built-in SMTP on Server 2022 and see how it goes -

 

Don’t waste your time with 2022 SMTP features. It doesn’t work. You won’t be able to edit the config. You will get an error. It works fine in Server 2019 - we used it in the last company.

 

For our purpose the built in option doesn’t have enough features. I need to direct to different upstream servers depending on the message type.

Edited November 7, 2022 by FN-GM

[CHiLL]

I had the SMTP relay working without issues up to and including on Server 2019. However, it simply doesn't work on Server 2022. I'm now using HMailServer as an alternative and it's been fine.

[TechMonkey]

I thought SMTP AUTH still used Basic Authentication though so is going to stop working?

 

My understanding is that if you are using SMTP Auth it isn't turned off, if you aren't MS will disable it but you can re-enable it. SMTP Auth will be the next thing to be gotten rid of, but as it is so ubiquitous MS made the decision to phase that out later.