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FREENETNAME outgoing email has stopped working Oct 2020

Posts: 1
Registered: 3 weeks ago

FREENETNAME outgoing email has stopped working Oct 2020

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, 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?



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Posts: 16,327
Thanks: 6,625
Fixes: 56
Registered: ‎22-08-2007

Re: FREENETNAME outgoing email has stopped working Oct 2020

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


telnet 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'...


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:


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:


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


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

220 avasout03 smtp
250-avasout03 hello [your IP address], pleased to meet you
250-SIZE 104857600
250 OK
334 VXNlcm5hbWU6
334 UGFzc3dvcmQ6
235 ... authentication succeeded
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