SMTP connector stopped working after broadband upgrade

Soldato
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You can't use modem mode with static IP's on Virgin. It only works with a dynamic IP.

With 5 static IP's the hitron IP remains as 192.168.0.1 unless you change it.

Hmmm ok then, must have been duff info from Virgin! Scrap that lightbulb moment then! Is there anything I need to change in the Hitron? I notice it still has the option to open ports etc or does it bypass all of the settings in there?
 
Soldato
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Also for your telnet test you should be doing:

telnet mydomain.mail.protection.outlook.com 25

Also is there any reason why you don't use option 1 on this guide as it's a lot easier and you don't need to use the connector:

https://docs.microsoft.com/en-us/ex...e-or-application-to-send-email-using-office-3

The telnet on mydomain 25 appears to work but still wont send the emails! I'll check with 587 and 465.

I originally tried option 1 when I set this up years ago but it wouldnt work. Ive just tried it again and it comes back with an error code 554.
 
Soldato
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I assume you've done a 'Message Trace' just to see if mail in going through the connector (and out)?

And are the FROM/REPLY legit and working addresses (be it a mailbox or a distribution group) within your domain/O365 tenant?
I don't believe it's a requirement for O365 SMTP relay/connector but I've always done it (typically a distribution group) so you get bounce-backs etc.

The telnet on mydomain 25 appears to work but still wont send the emails!

If you haven't, run through this telnet tutorial, https://docs.microsoft.com/en-us/exchange/mail-flow/test-smtp-with-telnet?view=exchserver-2019, as it should send an actual email rather than just testing the connection to the connector.
Test with sending mail to 'inside' (domain/O365 tenant mailboxes) and 'outside' (like Gmail etc; we've had/have problems sending mail to Hotmail through a O365 connector/SMTP relay).

....with an error code 554.

What's generating the '554' error?
As that typically suggests either the TO/FROM header is malformed, so i'd be looking at the application or device that is sending the email and making sure the settings there are correct. Certainly also worth testing the connector with a mail app or another device though.
 
Soldato
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I assume you've done a 'Message Trace' just to see if mail in going through the connector (and out)?

I dont think I can use a message trace as the software doesnt seem to be able connect to O365? Ive checked the error log in the software and it says the following - Could not send: Unaccepted server reply from command RCPT TP: [email protected] NOTIFY=NEVER (error code is 550)

And are the FROM/REPLY legit and working addresses (be it a mailbox or a distribution group) within your domain/O365 tenant?
I don't believe it's a requirement for O365 SMTP relay/connector but I've always done it (typically a distribution group) so you get bounce-backs etc.

It was previously set up as a distribution list email when it worked but to rule that out as an issue I set it up with my own email and get the same error for both.

If you haven't, run through this telnet tutorial, https://docs.microsoft.com/en-us/exchange/mail-flow/test-smtp-with-telnet?view=exchserver-2019, as it should send an actual email rather than just testing the connection to the connector.
Test with sending mail to 'inside' (domain/O365 tenant mailboxes) and 'outside' (like Gmail etc; we've had/have problems sending mail to Hotmail through a O365 connector/SMTP relay).

I'll look at that now thanks.

What's generating the '554' error?

As that typically suggests either the TO/FROM header is malformed, so i'd be looking at the application or device that is sending the email and making sure the settings there are correct. Certainly also worth testing the connector with a mail app or another device though.

Its the error from the software when trying to send an email using option 1
 
Soldato
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If you haven't, run through this telnet tutorial, https://docs.microsoft.com/en-us/exchange/mail-flow/test-smtp-with-telnet?view=exchserver-2019, as it should send an actual email rather than just testing the connection to the connector.
Test with sending mail to 'inside' (domain/O365 tenant mailboxes) and 'outside' (like Gmail etc; we've had/have problems sending mail to Hotmail through a O365 connector/SMTP relay).

Started reading this and noticed it says there is a tool that you can try - https://testconnectivity.microsoft.com/? so thought I would give it a try and used the Outbound SMTP Test. A few things passed the test but it failed on Real Time Black Hole List? Here is what it says:

Performing Real-Time Black Hole List (RBL) Test
The RBL test failed. Your IP address was found on one or more block lists.

Minus.gif
Additional Details
Elapsed Time: 12509 ms.

Minus.gif
Test Steps

Success.png
Checking Block List "SpamHaus Block List (SBL)"
The address isn't on the block list.

Plus.gif
Additional Details
Success.png
Checking Block List "SpamHaus Exploits Block List (XBL)"
The address isn't on the block list.

Plus.gif
Additional Details
Warning.png
Checking Block List "SpamHaus Policy Block List (PBL)"
The test passed with some warnings encountered. Please expand the additional details.

Minus.gif
Additional Details

An unexpected status code was received from RBL: 11
Elapsed Time: 31 ms.
Success.png
Checking Block List "SpamCop Block List"
The address isn't on the block list.

Plus.gif
Additional Details
Success.png
Checking Block List "NJABL.ORG Block List"
The address isn't on the block list.

Plus.gif
Additional Details
Error.png
Checking Block List "SORBS Block List"
The IP address was found on block list.

Minus.gif
Additional Details

The IP address x.x.x.146 was found on the block list.
Status code: 10
Elapsed Time: 1223 ms.
Success.png
Checking Block List "MSRBL Combined Block List"
The address isn't on the block list.

Plus.gif
Additional Details
Success.png
Checking Block List "UCEPROTECT Level 1 Block List"
The address isn't on the block list.

Plus.gif
Additional Details

Might that be the problem?
 
Soldato
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Could not send: Unaccepted server reply from command RCPT TP: [email protected] NOTIFY=NEVER (error code is 550)

I could be wrong, as this is stretching my knowledge of mail/SMTP etc, but that error message doesn't make sense as i would have thought a '550' error would correlate to a 'Recipient not found', 'Recipient address rejected', 'Sender address rejected' type error message rather than 'Unaccepted server reply'.
Similarly, i believe 'RCTP TO' ('TP' was an error?) type errors would give you a '510' error code.

Is there anything else (that's related) in the application's logs when it attempts to connect and send mail via the connector? Does it show the SMTP host and TO/FROM addresses (just to make sure those are correct)?

I'll look at that now thanks.

Definitely do the telnet test above as it should give you some insight to what the issue is

Also have you tried removing the connector and using 'Direct Send'/Option 2? As arguably you don't need to use a connector/SMTP relay if you're sending mail to internal addresses.

Started reading this and noticed it says there is a tool that you can try - https://testconnectivity.microsoft.com/? so thought I would give it a try and used the Outbound SMTP Test. A few things passed the test but it failed on Real Time Black Hole List?

You're using O365 as your SMTP relay, so this shouldn't affect that. This would only be a potential problem if you ran the mail server locally, eg - using your .146 address to send mail.
 
Soldato
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Definitely do the telnet test above as it should give you some insight to what the issue is

I ran through the telnet test and it turned out Microsoft has blocked the IP and it needed to be verified by visiting https://sender.office.com/ 30 minutes later and everything is working as it should be again.

Many thanks for yours and @pcfarrar help with this, I would never have sorted it otherwise.
 
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