enter password try again

[#1]

Win10 Thunderbird.  Attempts to send messages produce the attached screen message.  I have tried every password I ever remember using to no avail.   This started sporadically a few weeks ago but is now appearing every time.  I can send messages via webmail but it's a cut & paste faladdle.

[#2]

Typically email clients squeal "password error" for any and every difficulty in connecting to the SMTP server, from simple timeouts through to real password errors.  Thereby fiddling with passwords might not actually fix anything.

Are you connected direct to the Plusnet network here, a 3/4/5G mobile network or a third party ISP connection? Non-Plusnet connections can present their own issues.

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
535 Too many SMTP auth failures. Please try again later.

[#3]

Thank you for this.. Big boys stuff.  I'll check back when I've worked through the steps.  Excellent.

[#4]

Floundering somewhat.  Command line all to readily and rapidly reverts to "connection lost".  Got as far as attached cmd screen but no further.  Possibly my own ineptitude. 

[#5]

That connection lost is down to the telnet session to the SMTP server timing out in the absence of input from you.  You just need to bash through the steps with gusto!