Intermittent Pushmail Problem

[Peso]

Hello everyone,

I am seeking some advice as I’ve hit my knowledge ceiling.
I have three HDRs, which send me a Pushmail each everyday. One morning two weeks ago they stopped.
I had made no changes. But got saw this on the log.
ssmtp: Cannot open smtp-mail.outlook.com:587

I have tried re-entering the email address details. Tried an alternative smtp for Microsoft of smtp.office365.com.

No matter what I do the same behaviour follows. Some mornings some boxes manage to send to email while others not. On two days everyone emailed me as usual. The next day no one.
From the settings menu where you put in the smtp details you can send a test email. Also here sometimes it goes, sometimes not, on all boxes. When it fails to go the Webif-error log gives the same error as above, just a bit longer
Runtime Error: /opt/webif/plugin/ssmtpmail/sendtestmail.jim:54: ssmtp: Cannot open smtp-mail.outlook.com:587

Can anyone speculate what’s going on?

Thank you for reading this.

 

[prpr]

"Cannot open" covers a multiple of things and is pretty much useless as error messages go.
It could be DNS problems, server problems, or connectivity problems to one (or more) of the many servers hiding behind that address.
Or it could be something wrong with your device, local network or ISP connection of course.
It might also be the time of the month/phase of the moon.

 

[Dino]

Saw this which concerns 3rd party mail client access to outlook- the reported timescales don't match and it doesn't imply intermittent problems but maybe attempts to fix the outlook IMAP are causing collateral.

Microsoft's Outlook IMAP login issue is affecting several third-party email clients

For the past few days, an issue with Microsoft's Outlook service is affecting numerous third-party email clients. It results in problems when authenticating accounts and exchanging emails.

www.neowin.net

I'd try setting up an account on a different provider - gmail or something and reconfiguring the HDR.

 

[Dino]

According to microsoft answers the IMAP problem is fixed. So not that.

 

[Peso]

Thank you Dino for the thought.
I agree trying a none MS email address will be a good next step.

 

[Peso]

Dino was probably right.
Hadn’t got round to trying a new email, but for the last 5 days all Pushmail from my three HDRs have been sent with out issues.

 

[Peso]

It’s done it again! OK it’s been 3 years…

No Pushmail for 3 days from all 3 devices via outlook.com.
Tried a gmail address, but also get nothing. Not even showing as sent from the email account.
Attached the Pushmail log. Doesn’t mention a problem.
Could it be to do with this OAith2/Modern Auth?

 

[Dino]

Could be several things, including authorisation.
Hard to diagnose with the tools available and information provided.

I gave up trying to interface obsolete clients to email providers a couple of years ago.
The workaround I have is to use an email relay on the LAN.
My relay runs on a NAS, but might be possible on a pi or similar.
Technically obsolete clients (the HDR and other old tech) can happily send mail locally to the NAS using their limited capability.
The NAS forwards them to a provider using current methods.

 

[Peso]

Technically obsolete clients (the HDR and other old tech) can happily send mail locally to the NAS using their limited capability.

That’s very interesting.
It just so happens I got a NAS this year. Ostensibly for backing up the families photos from their phones. But I keep finding other useful uses for it.

Could you please point me in the direction of what I need to do get my HDRs to email the NAS. I take it the NAS can offer it’s version of smtp-mail.outlook.com:587.

 

[Dino]

I'd imagine what you need to do varies between products. What brand of NAS do you have?

If your NAS is set up for mail notifications of monthly reports etc. then the NAS is working as a regular client with your provider.
This is fairly standard. You need something extra to allow the old tech to piggy back on this set up.
On a Synology the extra functionality is provided by 'SMTP relay' which is part of their Mail Server bundle.

I experimented for a day or so on a pi (with partial success) before I thought of using the NAS.

 

[Peso]

What brand of NAS do you have?

Hello Dino

I have a Synology. It supports mail server, not the MailPlus.
I had a quick go myself, but got lost. All the guides I found are based on wanting external access.

In the smtp settings for the hostname, given its internal only, I assume you can you use anythingyoulike.com
But then what username do you put before the @anythingyoulike.com on the HDR?
I enable the TLS, as that’s what I’ve always used.

Do Aliases get me a username@ to send too? But Aliases list every user but root as invalid!

Only when and if you have time, any pointers would be greatly appreciated.

 

[Dino]

I started from the point of having the NAS set up as a client sending status notifications via a real world mail service to other email accounts.
I assume you have that working. If not, get it working with whatever current security protocols your real world mail server demands before moving on. Using the NAS to relay mails from the HDR builds on this.

Your query is a bit scattergun and I'm not sure which screens on the NAS or the HDR you are on to but I've tried to guess.

In the smtp settings for the hostname, given its internal only, I assume you can you use anythingyoulike.com

Do you mean 'Hostname (FQDN)' in Synology Mail Server -> SMTP ?
If so, then yes it can be anythingyoulike.com, if you mean hostname in the HDR ssmtp plug-in settings leave it blank, the NAS will not care.

For simplicity, set up a new user account on the NAS. You can restrict permissions to access the Synology Mail Server only if you like - call it say 'mailuser'.

On the HDR, under the ssmtp plug-in settings, the outgoing mail server and port is set to the (fixed) LAN IP address of the NAS followed by :25 so something like
192.168.5.100:25 - obviously changing the IP address to suit your set up
The SMTP server user name is 'mailuser' or whatever you set up on the NAS.
The SMTP server user password is whatever you set when setting up the account on the NAS
The From email address must match the account that the NAS uses to access the real world mail server for the status emails.

I enable the TLS, as that’s what I’ve always used.

Do you mean on the HDR ?, If so, it's not strictly necessary. In my case the idea is that the old tech on the LAN can be really simple behind the NAS, but your requirement may not be the same.

Do Aliases get me a username@ to send too? But Aliases list every user but root as invalid!

Are you referring to the Alias section in the Synology Mail Server configuration ? If so, leave well alone, use the account you've set up on the NAS as described above.
The important bits are in the SMTP relay sub-section. This will be set to access the same real world Web server with all the authentication required.

 

[Peso]

Big thank you Dino for guide. Really appreciate the effort. I can report 50% success.
Total success in getting emails from the HDR to the NAS. Hooray! I can see them in the Mail Log on the NAS.
Sending them out over the internet however, so far is eluding me.

I have an email account on the NAS for notifications. When creating it I was given a Microsoft login box to complete I remember.
The SMTP Relay box in the mail server only requires me to put in the same details I had in the HDR before it stopped. Have tried an outlook and gmail email in the SMTP relay box.
The attached image is all I'm given to to enter the real world email provider to use. Some site suggest outlook.office365.com as the smtp address, so tried that too.
Test emails from the NAS control centre over the same email provider work.

One question to clarify, the ""From" email address" on the HDR, when you say "account" do you mean "myemail@outlook.com" if that the the email address you sending mails via?

 

[Dino]

Big thank you Dino

You're welcome, happy to try to help.

I can see them in the Mail Log on the NAS.

That's good, what status is reported ?

I have an email account on the NAS for notifications.

Test emails from the NAS control centre over the same email provider work.

That's what I've called the 'real world account' for want of a better description.

One question to clarify, the ""From" email address" on the HDR, when you say "account" do you mean "myemail@outlook.com" if that the the email address you sending mails via?

Information related to the real world account is used in three places on this set up.

1) The account that the NAS uses to send notifications (requires username, server name/port/protocols, password)
Found under Contol Panel -> Notifications - Email Tab.

2) The SMTP Relay set up on the NAS (requires username, server name/port/protocols, password)
Found under Synology Mail Server, click the 'SMTP' section, then click 'SMTP relay'

3) The "From" field of the HDR (requires username only)
Found under 'Settings' -> ssmtpmail Plug-in Settings
The other fields here relate to using the NAS mail server.
If the mails that the HDR originate appear to come from anywhere other than the real world account it can cause problems.

The SMTP Relay box in the mail server only requires me to put in the same details I had in the HDR before it stopped. Have tried an outlook and gmail email in the SMTP relay box.
The attached image is all I'm given to to enter the real world email provider to use. Some site suggest outlook.office365.com as the smtp address, so tried that too.

Well that's a bit confusing to me. You need a working real world account that the NAS can use. That's why the one it uses for 'Notifications' may be a good choice.
Whatever the HDR used before is not relevant in this set up (unless the HDR and the NAS were using the same real world account)
In theory you can use any email server you have an account on, but some mail services are picky about being accessed by machine account.
Can't comment on gmail, outlook or office365.com.

If you have a real world account which works for NAS Notifications it should be good for Relay as well.
It may be better to focus on that rather than just trying servers.

 

[Peso]

Hello again

That's good, what status is reported ?

"resent". It keeps trying.
Above Mail Log is Queue. Emails are in there with a description of SASL Authentication Failed.

1) The account that the NAS uses to send notifications (requires username, server name/port/protocols, password)
Found under Contol Panel -> Notifications - Email Tab.

I looked here again. To set an email for Notifications you can choose outlook/gmail/custom smtp. If I select outlook a little browser windows opens connected to microsoft for you to put your password in. Then it works, test email sent.
If you choose custom and put the outlook smtp details in yourself and make a test it says
Test mail failed to send. Please check your settings and try again. 535 5.7.139 Authentication unsuccessful, basic authentication is disabled. [FR2P281CA0039.DEUP281.PROD.OUTLOOK.COM 2024-10-04T16:52:23.355Z 08DCE3D3E845681F]

I assume the Modern Authorisation thingy implemented by my chosen email providers is the stumbling block. Need to get a new email provider for Relay SMTP, or to use directly on the HDR's.

From another angle, if I can get the HDR's pushmails to the NAS, how can I read them from the NAS?

 

[Peso]

From another angle, if I can get the HDR's pushmails to the NAS, how can I read them from the NAS?

Answered that myself with Mail Station. I can read the HDR generated emails through that. I'll see how cumbersome it is to use via web browser (so 1990's), before signing up for another email.
Thanks a ton again Dino.

 

[Dino]

Sorry I hadn't twigged you were using the pull downs for the Notifications set up
I'd never needed the pull downs and so didn't realise there was a pop up behind them.
Matching the SMTP relay settings to what I used in Custom Server Settings for Notifications just worked (for my provider - gmx).

The suggestion is that when setting up an outlook account the pop up is doing some work beyond what's possible in the custom screen, if so, I think you may be right.

A cursory search suggests a gmail account might still be a option - something they call an 'app password' and/or turning off 2 step verification on the account (if they still let you) may work. Yahoo might be an option.