I wish I had a coin for every time someone posts "It keeps asking for my password, but doesn't accept it. I know it's correct, because I verified it" I would be a rich man. Now lets get down to it. You are asked for a password because the connection failed and the error reporting system is somewhat brain dead, it assumes the password is the problem. 20 years ago it probably was. Now it is rarely the cause of a connection failure. Lets start with if you account is with Google,Yahoo or outlook/hotmail et. al. (There are other that use oauth, but those are the big three) and you are asked for a password your authentication method is wrong. They do not use a password. If this issue occurs immediately post an update it is almost always a problem with the installed third party antivirus. They do an excellent job over all of putting folk off the use of mail clients by messing up the connection process. Disabling the antivirus will generally cure the issue, but some like Norton do not disable themselves when they say they do so problems persist. The only way to honestly test is with a wired internet connection in the operating systems safe mode with networking. if you can connect in that operating system state it indicates that other software loaded in a normal startup is the problem. This will include the antivirus program but may include other software. If you have a VPN, disable it and see if that is the problem. VPNs generally have a poor history of working well with email. Some do not even allow communication on the ports used by email and some providers rall7y do not like them resulting in connection issues.