FREENETNAME outgoing email has stopped working Oct 2020

[#1]

Outgoing e-mails failed at start of October 2020; my last e-mail send was on 30 Sept

Incoming e-mails are still fine, but outgoing e-mails now come back with "Your email server rejected your login".

I'm using Outlook & Win10 and the settings on the account still has the SMTP server set to smtpmail.freenetname.co.uk, the outgoing mail is still set as "My outgoing server (smtp) requires authentication" and "Use same settings as my incoming email server".

I have tried deleting the outlook account and recreated it but the "Test account settings" says POP3 incoming is fine but for outgoing it comes back with "Your email server rejected your login".

Any clues?

Regards,

Steve

[#2]

Hi Steve,

A warm welcome to the forums.

The fact that you can still receive emails points away from your password being wrong or having been changed to address security issues (the email account having been compromised).  Given that this is a legacy email account, there is a fair possibility that you are not using Plusnet as your ISP and that your current IP address is suspect.

Email clients are usually not very good at discerning the reason for connections to SMTP severs being rejected.  The following will enable you to obtain a much clearer insight as to why the connection is being rejected.

Test SMTP authentication

Email programs often report username / password error for issues not actually related to those being wrong, but for other connectivity issues. Such can be very frustrating when you are convinced that they are correct. Testing SMTP authentication through a command line interface can deliver a more precise error message. The following describes how to do this using TELNET.

This is not difficult, but you need the following resources which might be unfamiliar...

1. TELNET - this might need installing as an additional option, for Windows see enabling TELNET.
2. A code64 encoder / decoder such as this.

You can use TELNET to communicate direct with the SMTP server as follows...

Open the code64 encoder in a web browser and leave ready for use in the following steps.

Launch a windows command line window (DOS window) - press windows-key+R - type CMD into the run box - click OK

Enter...

telnet relay.plus.net 587

Press enter. Note if you use one of the other brand email services, use the appropriate SMTP server name for that brand. In response to SMTP server I'm here message, say 'HELLO'...

EHLO relay.plus.net

The SMTP server will then report what it can do after which tell the server you wish to authenticate...

AUTH login

The server should return the following, which is a base64 encoded string that requires your username:

334 VXNlcm5hbWU6

Use the code64 encoder to encode your username and paste it into the telnet window and press enter. For example:

bXl1c2VybmFtZQ==

The server should return the following, which is a base64 encoded string that requires your password:

334 UGFzc3dvcmQ6

Paste the base64 encoded password for the username. For example:

bXlwYXNzd29yZA==

The server will then report success or failure, any failure message should clearly indicate the reason for the failure. If the reason for the failure is not clear, please report back the message.

Close the SMTP / TELNET session by entering

quit

The session should look something similar to the below wherein your input is in bold...

220 avasout03 smtp relay.plus.net
EHLO relay.plus.net
250-avasout03 hello [your IP address], pleased to meet you
250-HELP
250-AUTH LOGIN PLAIN
250-SIZE 104857600
250-PIPELINING
250-8BITMIME
250-STARTTLS
250 OK
AUTH LOGIN
334 VXNlcm5hbWU6
bXl1c2VybmFtZQ==
334 UGFzc3dvcmQ6
bXlwYXNzd29yZA==
235 ... authentication succeeded
quit
221 avasout03 smtp closing connection
Connection to host lost.

Here are some examples of failure responses...

535 ...authentication rejected [as username / password is wrong]
535 ...authentication rejected as source IP has a poor reputation

[#3]

Many thanks; I started to do this (I think the EHLO should be HELO) but before I could get the encoding sorted my e-mails were all back working.  I hadn't changed anything, and the stacked up e-mails just got sent!  It was fine for a couple of days then died again (same symptoms) then OK the day after that.  This has continued, working for a few days and then it fails again for a day or two. Receiving e-mails has always worked fine, it is just the sending.

It looks like something on smtpmail.freenetname.co.uk keeps getting changed and then someone resets it; so who "owns" smtpmail.freenetname.co.uk?  Is it Plusnet or Microsoft, and what do I ask them to do to re-enable the sending of e-mails?

[#4]

It’s more likely that the dynamic IP address allocated is blackballed.

Otherwise there is ongoing reservations about the behaviour of email from that IP address. I have seen the fixed IP address at a local pub go on / off blacklisting over a week or so. It was that experience which lead to the documentation of the test.

I will check out your observation.

[#5]

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@SteveNoyes wrote:

I started to do this (I think the EHLO should be HELO)

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It would appear that these are interchangeable!

I think in the past I have seen "HELO" used, but the resource I referenced used "EHLO" - I just ran a test and both elicited the same response.