We could work on the lost ones with a lot more info, but eMail requirements have stiffened as far as security...
Cant create re add Mail
James Walker1 User level:Level 1 (129 points)
Mar 1, 2019 10:39 AM in response to if240
I was having this problem trying to add a mail (not gmail) account just for Notes. In my ~/Library/Keychains folder, I found a subfolder with a long hexadecimal and hyphens name. I deleted that subfolder, logged out, and logged back in. I was then able to add the account, without having lost any passwords from my keychains.
If you get a corrupted message...
Naw, not damaged, it's just that you have an old copy already in Applications, there are 2 cures...
Disconnect from the Internet & set the Date back to 2014, then you can run the Install MacsOS High Sierra App in Applications, so expired Certificates are not expired.
Or... trash the Install MacsOS High Sierra.app in Applications, empty trash & restart, then a new copy of a more recent version can be downloaded…new loc
Mac's Mail App is not as modern as iOS's Mail app, Many eMail providers now require a separate App Password different from your eMail password…
If it's an IMAP account, delete it in Sys Prefs Internet Accounts then use "Other" instead of gMail choice to add it.
Most likely biggest factor is using Other in Mail setup, then using a Browser that doesn’t have gMail PW stored init to get the App PW.
It might just need an App Password separate from the gMail password…
https://support.google.com/a/answer/9003945?hl=en#apple-mail&zippy=%2Cset-up-gmail-with-mail-on-a-mac
https://discussions.apple.com/thread/254920541?answerId=259158920022#259158920022
https://support.google.com/mail/answer/185833?hl=en-GB
Apple Mail won't sign in to Google account - Apple Community
my iMac has OS Yosemite 10.10.5 Does this… - Apple Community
my iMac has OS Yosemite 10.10.5 Does this… - Apple Community
gmail on mail Version 11.5 (3445.9.1) - Apple Community
gmail on mail Version 11.5 (3445.9.1) - Apple Community
Note from PrestoWebDesign…
https://discussions.apple.com/thread/253701684?answerId=257151754022#257151754022
Trying to add Gmail account to Apple Mail… - Apple Community
https://blog.google/technology/safety-security/the-beginning-of-the-end-of-the-password/
Possible gMail fix…
Apple Mail App Not Functioning - Apple Community
iMac says Connection Insecure. Failed to … - Apple Community
https://discussions.apple.com/thread/254659965?answerId=258757070022#258757070022
Also Mac's Mail App is not as modern as iOS's Mail app, Many eMail providers now require a separate App Password different from your eMail password…
Then you may need Ways to securely access AOL Mail…
https://help.aol.com/articles/allow-apps-that-use-less-secure-sign-in
Or it may just need an App Password...
https://support.google.com/mail/answer/185833?hl=en-GB
Yahoo has gone to this too...
https://help.yahoo.com/kb/access-yahoo-mail-third-party-apps-sln15241.html
Yahoo cure…
https://discussions.apple.com/thread/254879377?answerId=259375262022#259375262022
Yahoo App password…
Generate and manage third-party app passwords
Some older, third-party email apps (that do not use our Yahoo branded sign in page) require you to enter a single password for login credentials. To access your Yahoo Mail account on these apps, you'll need to generate and use an app password. An app password is a long, randomly generated code that gives a non-Yahoo app permission to access your Yahoo account. You’ll only need to provide this code once to sign in to your third-party email app.
https://help.yahoo.com/kb/access-yahoo-mail-third-party-apps-sln15241.html
Most likely biggest factor is using Other in Mail setup, then using a Browser that doesn’t have Yahoo PW stored init to get the App PW.
https://discussions.apple.com/thread/255004776