Gmail Rejected For Invalid Message ID When Sending From SMTP

[Auguy]

Here is the rejection I'm getting.

Failed Recipient: Somebody@gmail.com
Reason: Remote host said: 550 5.7.1 [68.70.182.60] Messages missing a valid messageId header are not
5.7.1 accepted. m24-20020aed27d8000000b0031ed8c203f3si7715036qtg.266 - gsmtp

-- The header and top 20 lines of the message follows --

Received: from DESKTOP-EHED324 (UnknownHost [12.200.88.186]) by sm1.Company1.net with SMTP
(version=TLS\Tls
cipher=Aes256 bits=256);
Wed, 20 Jul 2022 14:34:49 -0400
Message-ID: <5c671334-91a1-4896-951d-52bd6ca50653>
MIME-Version: 1.0
From: "Company2" <sales@CompanyName.com>
To: Somebody@gmail.com
Date: 20 Jul 2022 14:33:32 -0400
Subject: Contract
Content-Type: multipart/mixed; boundary=--boundary_1_39386abc-11ab-448f-b2fc-f0ffd50e5e77

I have tried

      Dim objGuid As Guid = New Guid()
      objGuid = Guid.NewGuid()
      Dim MessageID As String = "<" & objGuid.ToString() & "@CompanyName.com" & ">"
      message.Headers.Add("Message-ID", MessageID)

But it still gets rejected by g mail recipients, others are OK.
Do I need something else in the Header for g mail?
I've looked for how to generate a valid message ID for g mail, but haven't found anything that describes exactly how to create a valid one.



Auguy
Sylvania/Toledo Ohio

 

[Ericrep]

Hello

I've the same problem, did you find a solution ?

I've also found nothing on how to create a valid message id....

thanks

best regards

 

[strongm]

I'd suspect a DKIM misconfiguration.

Since I don't know what software your SMTP gateway is running, here is some info about DKIM from Microsoft and Google:

https://docs.microsoft.com/en-us/mi...o-validate-outbound-email?view=o365-worldwide

https://support.google.com/a/answer/174124?hl=en

 

[Auguy]

Ericep,
The code I posted may be working.
Still testing.
One email I sent went thru to the g mail account, but they got a warning about coming from a third party (or something like that).
I can live with that, but the client may not be happy.

Stromngm,
Their internet and email provider is using Smartmail.
Supposedly they have DKIM configured correctly.
I will pass the links on to them.
They also told me the issue is that Smartmail does not automatically add a header for mail sent thru SMTP.
They also said that Smartmail was looking into making a change about this.

Thanks to both of you.

Auguy
Sylvania/Toledo Ohio

 

[strongm]

>Supposedly they have DKIM configured correctly.

Fair enough - although I'd have then expected to see a [tt]DKIM-Signature[/tt] header in the bounced message.

 

[Ericrep]

hi,
i will try this
thanks you

 

[strongm]

Out of interest, did you get this resolved?

 

[Auguy]

This code seems to work, but some of the recipients get a warning about third party emails or something like that. But a least they are going thru.

Dim objGuid As Guid = New Guid()
      objGuid = Guid.NewGuid()
      Dim MessageID As String = "<" & objGuid.ToString() & "@CompanyName.com" & ">"
      message.Headers.Add("Message-ID", MessageID)

Auguy
Sylvania/Toledo Ohio

 

[strongm]

Odd - that's the exact same code you reported did NOT work in your original post

 

[Auguy]

I think that was operator error on my client's end.
Working with a "NON computer literate user and I think they clicked on their live program and not the test one I sent them.


Auguy
Sylvania/Toledo Ohio

 

[Stephen_]

The problem may be related to the "@CompanyName.com" part of your code as the initial example is missing an @<something>, which required for a valid message-ID.
This may not be the reason Gmail rejected the message -there seems to be a general problem in this area since early August- , but it may be related.