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So how do you use email? What software on what devices or just webmail?
What's your email domain - the bit after the @ in the email address for example, talktalk.net tiscali.co.uk lineone.net or some other?
And when your email doesn't send do you see an error message and if so what is the full error message with the TT code as that can help to identify the issue.
I've updated my profile with some information.
I have a Tiscali.co.uk e-mail address.
Currently using Windows 10 with Outlook 2016.
The problem is very intermittent, somedays I can send e-mails ok, other days it keeps requestion the SMPT password and when I enter it just presents the same dilogue box again and again as if it has not registered the password I enter.
The TT608 error is a block on sending that's triggered when multiple concurrent logins are detected from different locations. It's a hacker protection function that's being triggered. But there have been an unusually high number of such reports so I'm beginning to conclude that the TT608 error code may now also be used if the count of wrong password attempts or weak password usage passes a certain threshold.
Outlook does seem to be implicated in these cases and Outlook does suffer from corruption of data including passwords and therefore could result in multiple attempts with wrong passwords. Often re-entering the Outlook account password on request and saving that password gives a fix. Removing the account from Outlook and re-adding again gives a fix because that requires a password to be entered. Forcing a password change by changing a tiscali smtp server to a talktalk smtp server (both authenticate each other as permitted senders) again seems to give a fix because that forces the user to enter the password. But if the email admins are applying this TT608 usage to the tiscali SMTP server as a way of limiting tiscali spam from vulnerable mailboxes its a workaround that doesn't force the genuine user to upgrade the password.
So, this could be the almost normal Outlook corruption scenario and or a hacker protection issue with counting the usage of wrong or weak passwords.
What's your take on your password strength? How secure do you think your password is? Enter the password (or a similarity to it if worried about security) into this secure website: https://howsecureismypassword.net/
If a computer would take thousands of years to crack the password you're probably ok... I prefer to see 'millions of years' for extra confidence.