Last last year, a client called and said Microsoft Outlook Express was prompting for their user name and password.  Normally, it automatically  starts and no credentials are entered. They use this program for their business email. Everything they do is tied to their email.  When it has a problem, their business stops.

Part of the problem is their computer still ran Windows Vista which has been retired from Microsoft updates.  My client has since got a new Windows 10 computer which I set up for them and their email has worked fine for six months.

But for this blog I will explain part of my troubleshooting methodology on their old vista computer and Outlook Express. My client entered their username and password and clicked ok but it wouldn’t go away.  I connected remotely and tried the same thing and got the same result. I restarted Outlook express and it was ok this time! Their email worked for two days and then I got a call with the same problem. They couldn’t access their email with Outlook Express.  I connected to his PC via Teamviewer. On the screen was a :windows security” box “Login to mail.comcast.net”. I tried their username and pw which failed. I played around with different settings in the email client and failed. I tried logging into his account via my Linux computer Linux via Firefox and it worked. I know it isn’t his login credentials. So went back to his computer. I went into windows mail settings Tools-Accounts- and changed some settings with no success. I got it to work by closing and opening Outlook Express.

Two days later my client calls with the same problem – the same windows mail login box was there. I cleared it and shut down Win mail and restarted and this time it Did not help. My client said he was on phone with his email/internet provider for  over an hour without any help. I restarted his computer and no help. I tried entering his credentials and no help. Now will try logging in from internet web browser to see if his password has changed.  I changed the password on the internet provider’s web site to what it used to be  I clicked on forgot pw. The error hes getting is “-ERR[AUTH] Plaintext authentication disallowed on non-secure (SSL/TLS) connection Port 110. Secure SSL. ” maybe I need to change port incom I opened the Tools-Accounts- Advanced- i clicked this server requires secure con SSL. I got his email messages to pour in to inbox by checking the boxes “This server requires a sec con SSL” on both incoming and outgoing. This action changed the Out port to 25 and in port to 995. I noticed he has 7200 messages in his inbox, 1835 in Sent, 5783 in deleted. i don’t know if this is the problem.  i do know the more messages in your email account, the more likely problems will arise.  So we deleted many of the unneeded messages and my client continued using their email. 

As I mentioned earlier, my client has a new Windows 10 computer and his email hasn’t had any problems so far.  As you can see, having an out-dated operating system and lots of messages in your email client can cause intermittent problems for yourself.