emails bouncing from Gmail accounts.

[pipexdinosaur]

Dear support,

My emails are consistently being bounced back from gmail with a warning "550-5.7.26 This mail is unauthenticated, which poses a security risk" . Its been ongoing for weeks and don't *think* it is anything at my end. I have a legacy pipex email address, no idea if this is relevent or not. Thanks.

[pipexdinosaur]

Thanks, I will try and get something set-up with Speednames.

I tried again using ***@dial.pipex.com as return address (ie no mention anywhere of my speednames domain) and still bouncing with same message so looks like I will have to give up on sending to gmail addresses from pipex / talktalk with outlook.

[Gondola]

Secure mail via Speednames for your personal hosted email service:

Webmail: https://webmail.speednames.uk/#/login

Email client settings:

Server Host Names: mailc50.megamailservers.eu
Username: Email Address
Password: Email password - can be obtained through Mail Manager
Incoming Port Numbers: 993(IMAP) or 995(POP)

Outgoing SMTP Port Number: 465
Authentication: Password
Outgoing server authentication should be enabled; using the same settings as your incoming server
SSL/TLS: Enabled

[pipexdinosaur]

thanks again for your reply, I didn't send a photo as it was quicker but believe I transcribed the settings accurately. Speednames host my domain so maybe having them host my email is the solution I seek.

I will go back and check again with settings modified to only pipex addy as first time round it still bounced.

[Gondola]

Unexpectedly, the bounceback is via an Amazon web services IP address used for hosting services.  Is that where your personal domain is hosted? Suggests you're sending from a personal domain email address not from a TalkTalk email address.

Gmail is rejecting the incoming email as unauthenticated. Gmail does use strict authentication checking that some other mail services do not bother with.

You've not shown me screenshots of the actual setup you're using with Outlook. If Outlook was sending from a pipex email address and therefore the Return-Path was a pipex email address then the mail would be fully authenticated by TalkTalk. TalkTalk does not authenticate the sending from personal domain email addresses. The Reply-To is not relevant when checking for authentication.

If you wish to send from a personal domain email address then you must use the smtp servers provided by the email hosting service in order to get authentication.  To help with this aspect I'd need to know your personal domain.

[pipexdinosaur]

Hi,

Thanks.

So, I modify outgoing server inputting password and checked it worked to a non gmail address - it does, just like it did with 'using same settings as incoming server'

From outlook I tried using the ***@dial.pipex.com address as 'reply to' (the other reply email address is a domain I own so I believe valid), yet it still bounces.

The error code message is;

"Reporting-MTA: dns; cm3nec [10.103.251.3]
Received-From-MTA: dns; LAPTOPG8I8PNAD [35.176.41.238]
Arrival-Date: Mon, 19 Jun 2023 12:49:01 +0100

Final-recipient: rfc822; @****@gmail.com
Diagnostic-Code: smtp; 550-5.7.26 This mail is unauthenticated, which poses a security risk to the

Last-attempt-Date: Mon, 19 Jun 2023 12:49:02 +0100 "

Note : the error message is truncated, stopping at 'the' exactly as above.

I had actually expected that using the webmail email address as reply to would have worked, even if it wouldn't have worked for me with outlook.

[Gondola]

The outgoing server smtp.talktalk.net via port 587 and encryption STARTTLS requires authentication. The authentication is by Username as the full email address and Password is the email password. So, rather than use the same settings as incoming set up the requires authentication with the pipex email and password.

What happens at the Gmail end is that Gmail should check the Return-Path email address for the TalkTalk SPF file and for DKIM signing and the TalkTalk DMARC policy. The Return-Path email address should be valid and it's normally the Pipex sending email address. The Reply-To email address isn't normally checked but should be a valid address. Send from the master Pipex email address if that's not already in place.

You've proved that sending from webmail works ok so Gmail isn't blocking your email address. I assume Gmail is rejecting on the basis of failed authentication. Fully authenticated mail sending should override normal IP address blocks unless Gmail has your IP address blocked by Gmail recipients for spam. If still seeing an error message back from Gmail then let us know what that message is.

[pipexdinosaur]

Hi,

No, I still need help, just up to my eyeballs and only just getting round to it...

Outlook is most recent MS 365 version

incoming : username ****@dial.pipex.com. server :  pop.talktalk.net  port 995 (note I have an alias points to this). I have no problem receiving.

outgoing : smtp.talktalk.net  port 587, requires auth, use same settings as incoming. Note my email reply setting is to an alias email addy that points to the ***@dial.pipex.com address

Something in there is causing gmail (only) to throw a loop and block sent mail

Thanks!

[Gondola]

Not heard back so assume you've updated the software or settings and no longer need help.

[Gondola]

Which version of Outlook and what incoming and outgoing server settings are you using? Screenshot the settings, image edit to obscure the first part of your email address and upload here using the camera icon above this reply area. I'll take a look and advise.

[pipexdinosaur]

Hi, thanks for reply, confirm works direct from webmail. I use Outlook and from their doesn't work.

[Gondola]

Sign in to webmail to prove that you can send fully authenticated pipex mail from TalkTalk to Gmail.