HELP: FMS stopped being able to send emails, no idea why. LA say its not them :o(

[TwistedHelixis]

Until recently, FMS was able to send emails for things like BACS payments etc.

 

At first I thought it must be a settings issue in G suite as Google are making some changes to how apps can send emails, but I have realised they are not making those changes until next month (February).I have checked every setting I can think of, disabled the server firewall, re entered the correct email account details etc.

 

Luckily I look after a few other primary schools, so as another test I used the email settings from another school where FMS is able to send emails, but I still get the error 'connection to the specified mail server failed.

 

Our internet connection, filtering and firewall are all run by our LA, so I logged a job with them. They have come back and said it can't be an issue their side.

 

So what do I do next?

[Edu-IT]

Are the other schools on the same ISP?

[mavhc]

Can you just open a telnet connection to the mail server on the port you're using?

[timbo343]

To completely rule out the ISP and your onsite equipment, are you able to tether your phone to a test machine at all to bypass your ISP, this will tell you if the issue is on the mailbox.

 

Just today i have been converting the service mailboxes that have the less secure apps option enabled to use 2fa and configure the App Password option. Things so far have been successful in the change as i didnt want to get caught out.

[jthompson]

FYI, the Google changes you're referring to are happening in February next year (2021), not this year).

[TwistedHelixis]

Are the other schools on the same ISP?

Yes

 

Can you just open a telnet connection to the mail server on the port you're using?

When I run, 'telnet smtp.gmail.com 587' it does connect. Is there a way of checking the account can actually send emails using telnet?

 

To completely rule out the ISP and your onsite equipment, are you able to tether your phone to a test machine at all to bypass your ISP, this will tell you if the issue is on the mailbox

I am assuming it's the FMS running on the main server that actually sends out the email on behalf of the client, so probably not.

 

Just today i have been converting the service mailboxes that have the less secure apps option enabled to use 2fa and configure the App Password option. Things so far have been successful in the change as i didnt want to get caught out.

I did test this but still got the same error.

[TwistedHelixis]

So could I use outlook (desktop) to try and connect to the gmail account and then test for sending emails. If this would work (never used outlook) I could test from my laptop, both in school and outside.

 

Would Outlook be a good test?

 

Or is there another app / software for connecting to an email account.

[timbo343]

Yes

 

 

When I run, 'telnet smtp.gmail.com 587' it does connect. Is there a way of checking the account can actually send emails using telnet?

 

 

I am assuming it's the FMS running on the main server that actually sends out the email on behalf of the client, so probably not.

 

 

I did test this but still got the same error.

 

To test the account could you use an MFD or spiceworks or papercut or bromcom (if you use it) to test the mailbox via port 587. You just need an application that uses SMTP to send email for a test.

 

Could it be the firewall on the server?

[jthompson]

Some AV systems might intervene and block something if it reckons it looks like a mass-mailer worm.