Emails sent to gmail account undeliverable

[#1]

Hi Steve,

Do you have STARTTLS port set to 587 and SMTP authentication enabled? Full details Here.

Also what is the bounceback you receive? Feel free to copy and paste it here, redacting email addresses etc. 

[#2]

Possibly as relevant, is the SMTP server configuration set up use authentication (same as incoming server)?

[#3]

I have checked the SMTP settings and they are:
Port 587
STARTTLS
Password Normal.

This is the bounce message from gmail but I have just changed the Gmail email address so I don't get spammed.
The gmail email address is a known good one. It's also the same message to other gmail accounts.
Thanks

This is an automatically generated Delivery Status Notification.

Delivery to the following recipients failed permanently:

* fred@gmail.com

Reason: A message that you sent to the following recipient could not be delivered due to a permanent error. ** The remote server ?? responded with: ** fred@gmail.com ??:?? This message was created automatically by mail delivery software on the server .



Reporting-MTA: dns; avasout-peh-002 [212.159.14.18]
Received-From-MTA: dns; [192.168.0.6] [195.213.194.240]
Arrival-Date: Thu, 11 Aug 2022 14:17:45 +0100


Final-recipient: rfc822; fred@gmail.com
Diagnostic-Code: smtp; 550-5.7.26 This message does not pass authentication checks (SPF and DKIM both

Last-attempt-Date: Thu, 11 Aug 2022 14:17:45 +0100

[#4]

Exactly the same as my situation 

[#5]

@fleckney

What’s the sender’s address? That message suggests Gmail does not like the sender details - nothing to do with the receipt address. Gmail has got this space wrong before.

[#6]

@Townman
The senders address has always been the same for years. Nothing has changed at the senders end. I believe it's something to do with a change at Gmail.

The senders email address is the same as everyone else that has a plusnet email address.

name@username.plus.com

Thanks for trying to help.

[#7]

"Delivery to the following recipients failed permanently:

* fred@gmail.com

Reason: A message that you sent to the following recipient could not be delivered due to a permanent error. ** The remote server ?? responded with: ** fred@gmail.com ??:?? This message was created automatically by mail delivery software on the server .



Reporting-MTA: dns; avasout-peh-002 [212.159.14.18]
Received-From-MTA: dns; [192.168.0.6] [195.213.194.240]
Arrival-Date: Thu, 11 Aug 2022 14:17:45 +0100


Final-recipient: rfc822; fred@gmail.com
Diagnostic-Code: smtp; 550-5.7.26 This message does not pass authentication checks (SPF and DKIM both"

===============================================================

My observation is that the NDR appears to have been generated by a PN server. If google is rejecting the message then perhaps the rejection by the google server should be part of the NDR.

The last bit of the error (Final-recipient: rfc822; fred@gmail.com
Diagnostic-Code: smtp; 550-5.7.26 This message does not pass authentication checks (SPF and DKIM both)) is an improvement on the errors (identical bar the last two lines) I occassionally see when e-mailing another Plusnet customer.

[#8]

"Do you have STARTTLS port set to 587 and SMTP authentication enabled?"

If that were not correctly set then surely the receiving SMTP server would reject the message and the client software would report an immediate error, rather than accepting the message and then generating a NDR?

[#9]

@greygit

Thank you for trying to help.
I am not mega technical but all the settings on Thunderbird are, and have always been correct as I posted previously.
It's a shame this forum doesn't thread the replies to a post. It would be easier to see my original comment and previous help offered by people rather than people just seeing the last post and commenting.

I have no Idea about or how to fix an NDR, PN, SPF or DKIM.

I just want to put the normal information in to Thunderbird for sending and Receiving emails for a Plusnet email account.
Why does every email sent via Plusnet to anyone who is not a gmail address receive it?
Why is the email sent via Plusnet to a gmail address rejected?

Perhaps Plusnet could setup an account on Thunderbird and work out why it's not working and offer a solution. That would be really helpful to me and others having the same problem. Thank you

[#10]

---

@greygit wrote:

"Do you have STARTTLS port set to 587 and SMTP authentication enabled?"

If that were not correctly set then surely the receiving SMTP server would reject the message and the client software would report an immediate error, rather than accepting the message and then generating a NDR?

---

No not at all.

If a user is connected to the Plusnet network, then authentication on the SMTP server is not mandatory.  However, in such circumstances, the email is sent as "not authenticated" and the REMOTE SMTP server (Gmail's) might use that as a reason to decline receipt of the email from Plusnet - that is a stage AFTER email submission was accepted.

This whole scenario is way past accepting message submission.

[#11]

---

@fleckney wrote:
The senders email address is the same as everyone else that has a plusnet email address.
name@username.plus.com

---

That is not entirely true.

1. Some "Plusnet" email users have their own domain names and use that as the sending address (as do I)
2. Many "Plusnet" email addresses are legacy product email addresses which are run on very different configurations

SPF, DKIM et al are all related to what is to the right of the @ symbol in the address - regardless of actual mailbox / service.  For example, I can access my "Plusnet" email as both me@mydomain.co.uk and me@myaccount.plus.com - to all intents and purposes they are one and the same ... until one looks at anti-spam measures - then they become entirely different.

The last time Gmail fouled up in this space, the situation looked like this...

• Sending to any Gmail address using me@mydomain.co.uk worked without issue
• Sending to any BUSINESS Gmail address using me@myaccount.plus.com worked without issue
• Sending to fred@googlemail.com address using me@myaccount.plus.com worked without issue
• Sending to fred@gmail.com (the same email account) address using me@myaccount.plus.com experienced sever delays, but was delivered eventually (possibly days later)

That is why precision is so important - not being precise can lead to incorrect conclusions / advice being offered.

The fact that the SENDING address has been the same for years, is no assurance that Gmail has not changed the way their systems behave.  The last time we saw issues like this, sending email to other email providers remained unchanged.

[#12]

Thank you for taking the time to try and help me.

To Recap. Thunderbird is set for Port 587, STARTTLS Authentication.

Example not the real senders address:
steve@donkey.plus.com
There is some webspace with the plusnet account but it's not being used. If I use the example above and go to www.donkey.plus.com you can see the webspace.

If an email is sent to a gmail address via the plusnet webmail page online, it does Not get rejected and gets to the person intended.

Only via the Thunderbird email client do the gmail addressed emails get rejected.

I read somewhere on the internet others having the excact same problem.

One person said they had cured there problem by changing the from email address.
Example: This was originally the email address: steve@donkey.plus.com change it to donkey@plus.com
They said some technical stuff about it that I didn't understand. I tried it and I couldn't send emails so I changed it back.

Does this mean anything and could it be something to do with the problem?

Thank you

[#13]

I also found this...
Could I change something in Thunderbird (TB) for it to work with the Plusnet account?

Thank you

https://support.mozilla.org/lt/questions/1369698

[#14]

If an email is sent to a gmail address via the plusnet webmail page online, it does Not get rejected and gets to the person intended.

Only via the Thunderbird email client do the gmail addressed emails get rejected.

@fleckney that definitely seems like Thunderbird is set to use a different From: address to that used by webmail.

Try sending yourself an email from both Thunderbird and webmail and see if the From: address is correct ( name@<username>.plus.com ) in both cases

[#15]

Brilliant idea..
Thank you for trying to help me.
I think you might be on to something now.

I can't get on the computer to change anything at the moment but I have checked the webmail sent address against the ones received at a NON Gmail address.

From Thunderbird it's being sent with the correct email address. (Example not real address) steve@donkey.plus.com

From Plusnet Webmail it's being sent with the Plusnet Username as the person?
example donkey@donkey.plus.com

I will change the email address to the same as the webmail sent email address and see if they get through when I get a chance.

Thank you