SMTP with Microsoft 365

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matteu

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Jul 9, 2017
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Hello @SteveITS
and thanks for your answer.
Unfortunately this will not be possible :(
Proxmox doesn t have on the roadmap to integrate modern authentication for the notification ?
I know for veeam I use it.
 
I took the instructions in the OP post and used Claude to setup a O365 email proxy on one of my Linux systems... this way all of my devices on my home network can send email using my O365 via the proxy on Linux. I can now eliminate the Gmail account I originally setup just for this feature.
 
In the past, I've used the primary MX server for a destination SMTP server. It's worked for me - but YMMV when it comes to your own delivery.

I assume you're using your own domain - so you can do a `dig mx <yourdomain>` to find the primary MX server.

It might be hit and miss - depending on your connectivity, who your ISP is, if you're in a dynamic IP pool for your ISP, etc etc - but it costs nothing to try :)
 
matteu said:
Is it possible to get the configuration I need to apply for SMTP to work with M365 without basic authentication enabled ?
Click to expand...
Yes. But sometimes M365 is a PITA. But first things first.

- Are we talking about a business or private account?
- Is SMTP even allowed? You can block that by policy. You can also disable it as a user setting. Go to outlook.com and check for the user, go to admin.microsoft.com and check policies.
- They can't do SSL on port 465. You have to do STARTTLS on port 587
- Proxmox does not support modern auth? Use App Passwords instead. Go to you user settings, security and create an App Password. That thing alone changed places many times in the last few years. It is a mess. I would like to give you the official MS link to AppPasswords for private accounts https://go.microsoft.com/fwlink/?linkid=2274139 or the one for company https://support.microsoft.com/en-us...app-passwords-for-your-work-or-school-account, but that is probably also broken like most stuff for MS.
 
Hi,

IsThisThingOn said:
Use App Passwords instead.
Click to expand...
It's not working anymore, M365 enforced OAUTH authentication (or at least it's what we have seen with business accounts with our clients).

Since then we either use OAUTH or a SMTP relay (create with proxmox mail gateway).

Best regards,
 
@janus57
It's for professional setup so M365 enterprise account and not personnal one
You can use OAUTH natively with proxmox to send mail ? It's what I would like but I totally ignore how to
 
Hi,

No we use simple SMTP through our SMTP relay, as far as i know pve or pbs don't have OAUTH setting.

Best regards,
 
janus57 said:
Hi,

No we use simple SMTP through our SMTP relay, as far as i know pve or pbs don't have OAUTH setting.

Best regards,
Click to expand...
Thanks for your answer.
That means the only way today for it to work is to get an SMTP relay... Or just not use SMTP notifications !
 
janus57 said:
It's not working anymore, M365 enforced OAUTH authentication (or at least it's what we have seen with business accounts with our clients).
Click to expand...
Works for me on my business accounts (yes, accounts as in multiple).
Not saying that I don't believe you, MS is a clusterfuck, could be a gradual rollout, could be some obtuse setting, the list goes on.
Some applications don't work well with 587, that is why I also got a throwaway gmail account.
 
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