topic Re: Free-online: Can’t send e-mail via “Outlook” in Email

Free-online: Can’t send e-mail via “Outlook”

Anonimouse — Sat, 06 May 2023 20:15:48 GMT

I have a “Free-online” account and until recently I could send and receive e-mail via “Outlook” for “Windows 10” without any problems.

Now, when I try to send e-mail, my username and password are rejected by the SMTP server. I haven’t changed any settings.

Is it possible to fix this problem please?

Re: Free-online: Can’t send e-mail via “Outlook”

Townman — Mon, 08 May 2023 08:29:16 GMT

Can you send emails via the Webmail interface?

Are you still a Plusnet broadband user?

If yes, is the device accessing the internet using your Plusnet connection, without the involvement of a VPN?

Have you changed the password on the mail account recently?

Re: Free-online: Can’t send e-mail via “Outlook”

Anonimouse — Mon, 08 May 2023 19:48:42 GMT

Thanks for your reply.

Yes, I can send emails via the webmail interface.

I am not a Plusnet broadband user.

I haven't changed the password on the mail account.

Re: Free-online: Can’t send e-mail via “Outlook”

Townman — Mon, 08 May 2023 20:50:31 GMT

You might get a clearer indication of the issue, by running this SMTP access test...

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...

TELNET - this might need installing as an additional option, for Windows see enabling TELNET.
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
535 Too many SMTP auth failures. Please try again later.

Re: Free-online: Can’t send e-mail via “Outlook”

Anonimouse — Wed, 10 May 2023 20:45:34 GMT

Thanks for your reply and details of the SMTP access test. Unfortunately I don't feel able to attempt this, as it is beyond my level of expertise.

Re: Free-online: Can’t send e-mail via “Outlook”

Townman — Wed, 10 May 2023 22:13:36 GMT

It is not as hard as you might think. It was written carefully to be easy to follow. No expertise beyond reading required.

Re: Free-online: Can’t send e-mail via “Outlook”

Townman — Wed, 31 May 2023 15:28:01 GMT

@Anonimouse

Can you please re-visit / re-test this please?