couple of things to check:

Is the smtp server using the correct 'username'?

'Tools' > 'Account Settings' > 'Outgoing Server(SMTP)' or right click onmail account name in folder Pane and select : 'Settings' then click on 'Outgoing Server(SMTP)'

It will show you a list of all your outgoing servers. select the smtp server that the mail account is using. The 'Username' should say your full email address. Use the 'Edit' button if you need to manually alter anything. confirm: Is the smtp server showing a correct username email address?

Do you use an anti-virus software to scan outgoing mail ? If yes, then stop scanning outgoing mail. What anti-virus / firewall product are you using?

Please post this info: In thunderbird Help > Troubleshooting Information click on 'copy text to clipboard' button In this forum question, right click in a 'Post a Reply' box and select 'Paste'. you can remove al the info on fonts and printers, but nothing else.

Hi Toad-Hall

Thank you for the response.

All Outgoing Server [SMTP] settings are correct as per ISP configuration. Anti-virus scan software, Adblock, was disabled.

The problem persists in that, on 'Send' for an outgoing email I am asked to enter the password. On doing so it the system continually loops, asking To Enter New Password.

I have other mailboxes within the Thunderbird setup, these are no longer downloading messages, but they can be seen via my ISP webmail account. No messages can be sent.

My ISP cannot help because they are unfamiliar with Thunderbird.

Is there perhaps a DHE (Diffie–Hellman) key exchange conflict as explained at http://springwolf.com/2015/ssl-not-working-for-thunderbird-38-1-0/?

Query One Copy: Thunderbird will not send outgoing emails, returning the following message in the Error Console

Error: An error occurred during a connection to imap.slingshot.co.nz:993. SSL received a record that exceeded the maximum permissible length.(Error code: ssl_error_rx_record_too_long)

Reply One Copy: couple of things to check:

Is the smtp server using the correct 'username'?

'Tools' > 'Account Settings' > 'Outgoing Server(SMTP)' or right click onmail account name in folder Pane and select : 'Settings' then click on 'Outgoing Server(SMTP)'

It will show you a list of all your outgoing servers. select the smtp server that the mail account is using. The 'Username' should say your full email address. Use the 'Edit' button if you need to manually alter anything. confirm: Is the smtp server showing a correct username email address?

Do you use an anti-virus software to scan outgoing mail ? If yes, then stop scanning outgoing mail. What anti-virus / firewall product are you using?

Your ISP needs to fix their SSL certificates, is what that error says to me.

Until they get their act together I suggest you use their settings for no SSL. https://help.slingshot.co.nz/Email/44644701/How-to-set-up-Slingshot-email-on-your-computer-or-device.htm

FYIlink to 80 support topics for this error.

Matt, in consultation with ISP support the fiddling with account settings only made things worse, Thunderbird now constantly loops with messages: 1.] Entry of password results in authentication failed. 2.] Enter new password

   and so on.

The password is correct as it was reset in conjunction with the ISP support. The support person recommended I uninstall/reinstall Thunderbird, which I have started to do.

In doing backup compression of the Thunderbird folder in AppData\Roaming\Thunderbird. The message is, 'Compression cannot be performed, path to file or directory too long.'

For the compression path problem I shall post that as a separate issue for help.

Matt Posted 9/29/15 8:39 PM

Your ISP needs to fix their SSL certificates, is what that error says to me.

Until they get their act together I suggest you use their settings for no SSL. https://help.slingshot.co.nz/Email/44644701/How-to-set-up-Slingshot-email-on-your-computer-or-device.htm

FYIlink to 80 support topics for this error.

Toad-Hall Posted 9/29/15 5:28 AM Toad-Hall

couple of things to check:

Is the smtp server using the correct 'username'?

'Tools' > 'Account Settings' > 'Outgoing Server(SMTP)' or right click onmail account name in folder Pane and select : 'Settings' then click on 'Outgoing Server(SMTP)'

It will show you a list of all your outgoing servers. select the smtp server that the mail account is using. The 'Username' should say your full email address. Use the 'Edit' button if you need to manually alter anything. confirm: Is the smtp server showing a correct username email address?

Do you use an anti-virus software to scan outgoing mail ? If yes, then stop scanning outgoing mail. What anti-virus / firewall product are you using?

Victor4087 Posted 9/28/15 9:13 PM Thunderbird will not send outgoing emails, returning the following message in the Error Console

Error: An error occurred during a connection to imap.slingshot.co.nz:993. SSL received a record that exceeded the maximum permissible length.(Error code: ssl_error_rx_record_too_long)

Apparently your ISPs support people have no idea about SSL. This is not at all uncommon. Theirs is broken. Umtil they fix it SSL connections will simply not work. This is not something you can fix in Thunderbird. No amount of fiddling with setting and resetting of passwords can cure an issue with your ISPs mail servers. They can tell you from now until they are blue in the face that they support SSL. The truth is they do not.

It is Highly probable that the issue is caused by Thunderbird tightening it's SSL system in response to this. https://weakdh.org/ But that does not excuse your ISP.

So for the time being your will need to change your port to 143 and turn off SSL in the account setting.

The error message you are getting is based on the fact that windows can not have a path to a file, including it's name of more than 255 characters. You have managed to have more than that in the path of at least one file. Thunderbird would not be able to access a folder that had more than 255 characters, so it must be in one of those mozeml files that are only used by windows search, or you would be seeing other side effects.

It is clear your support person knows basically nothing about Thunderbird or they would not be encouraging you to reinstall it. It will achieve nothing useful in the vast majority of cases. Microsoft use the registry for everything and uninstalling removes things from the registry. Settings can be reset by reinstalling. Thunderbird stores your settings in your profile. So uninstalling and reinstalling only replaces the program files.