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I am posting this in the hope that it may help others.
Background: My wife and I have identical laptops running Vista and Windows Mail. About a month ago, I added an account to my computer that used the new pop3 servers, and continued to use BOTH the incoming and pop servers successfully so far. However, my wife made no changes and finally began having trouble a few days ago. The "incoming" server kept asking for her to sign-in with her password, but would not accept the sign-in. It just repeatedly asked for her to sign-in again and again. While the incoming server occassionally asks me for a sign-in, simply hitting "cancel" and then "send and receive" again has always succeeded without ever signing-in again.
The problem(s): I added another account to my wife's e-mail using the new pop3 settings, just as I had done on my own computer. It did not work. EVENTUALLY, with the help of a Verizon tech on the phone, I noticed that the "Logon using secure password authentication" box was checked. I knew better than this and THOUGHT that I had unchecked it. However, when I hit "apply" for the new parameters on the "Advanced" tab screen, for some unknown reason, the SMTP port had switched back to 25 from 465 and became highlighted. I fixed THAT and checked THAT screen for other changes, then hit "apply" again and it seemed to take everything. What I did NOT do was recheck the other pages/screens of that new account for changes that I did not expect, so it MAY be that the SPA box was rechecked on the "Servers" screen when the SMTP port was inexplicablyy changed on the "Advanced" screen. SO, that is lesson #1: recheck everything after hitting "apply."
With that fixed, my wife's new e-mail account would receive, but not send e-mails. That is something that I have read about on this forum, so I wanted to check it while the Verizon tech was still on the line. We futzed with it for quite a while, and he finally gave-up, saying to talk to Microsoft about it. He said that there must be some difference between my computer and my wife's to make them act differently with the same settings - perhaps a corrupted file. After hanging-up, I tried rebooting my wife's computer and sending a new test message. For the first time in 6 test messages, the computer asked for a sign-in as soon as I hit "send" on the individual message screen. It was then that I realized my wife had her system set to send e-mails immediately and mine is set to wait for me to push the "send/receive" button. When I changed her setting to wait for the "send/receive" button, everything started working correctly. Prior to that, I had NOT seen any attempt to send the e-mails immediately, and they had appeared to go to her "out" folder, with the number "1" appearing next to it and the message residing in it. When I selected the new account with the drop-down menu of the "send/receive" button, it made the number of unsent e-mails in her out folder indicate nothing (empty) instead on "1", but upon opening the "out" folder, the unsent e-mail was still there. I don't understand exactly what changed, but, lesson #2: if you have similar problems getting the new security settings to allow you to send e-mails, try (a) unchecking "send immediately" in the "send" tab under "options" (and probably any other such automatic send feature, such as the "send and receive meassges at startup" box under the "general" tab of "options"); and (b) try restarting your computer.
I might have avoided these issues if I had simply changed the existing account instead of adding an account and manually selecting which one to use. However, when something is working, I hate to mess with it until I have its replacement working and tested.
And a final lesson #3: My wife's computer has completely stopped working with the old "incoming" servers, whiile mine continues to work fine with the same settings. We have the same model computers with the same software running through the same LAN using the same IP through the same modum. Apparently we are reaching different servers of the old "incoming" type. So, that remains a wild card in the debugging process that neither the user nor the Verizon tech can directly investigate.