I am beginning to frequently get a message that an email could not be sent and to retry or cancel but all settings are correct and it usually sends a 2nd time

Have been using Thunderbird for years and it has worked just fine. Have not made any changes to any of the settings. My boyfriend also used T'bird for years but last year it stopped sending messages and he finally had to stop using it. My T/bird is beginning to act the way his did. I will write a message and press send and then a window will open saying the message couldn't be sent and to retry or cancel. Usually a retry will work. Sometimes I get a message asking me to enter my password (I don't even think I have one or if I do I don't know what it is because I have never logged in to send email). So I'm worried that my T/bird program is beginning to fail like his did. I don't want to lose the use of the program and all my saved emails and addresses, mail groups, etc. My OS is Windows 7.

That sounds exactly like an issue that has plagued McAfee users for around a year.
Try disabling email scanning in your anti virus program.

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