Windows 10: Windows Live Mail keeps asking for my password when sending an email

AdHoc,
Assuming your Win 7 default browser is Internet Explorer.
Clear your browser cache.........
Open your IE > click Tools > click Internet Options > under Browsing History, click Delete > make sure the top 4 entries are checked > click Delete.

What is your default browser ?

For your future reference.......
Clear your web browser's cache, cookies, and history
https://kb.iu.edu/d/ahic

AdHoc said:

Firefox

See the post above yours. Post # 14. It has a link of how to clear FF browser cache.
It's under the heading Desktop browsers.

AdHoc said:

Thanks David. I know how to clear the Firefox cache, I just fail to see how this is directly linked to WLM’s inability to connect to the Outlook SMTP server successfully. It feels like two very separate things.

Allow me to speculate................

1. You did a Windows Essentials Repair but you said it did not fix the problem.
My speculation : you did not restart the computer afterwards.

2. After you did the IE cache clear up, you said "it works now".
My speculation : you had restarted the computer after that.

My point is : Repairing Windows Essentials 2012 will work after a reboot.

I notice that there was no response to your problem in Seven Forums. 148 Views and no Replies. We used to have a lot of experts in Mail. Sad to see that they have disappeared.

Anyway, a week as gone by. I wonder if your old problem has reappeared, or you are A-OK........ so far.