Q: “I seem to be having a lot of trouble emailing people who have Yahoo and AOL accounts. They are either getting my emails in their junk folder or not at all. Sometimes I’m not getting an indication the email was not undelivered and other times I get various delivery or delay notices.”
A: Several months ago (roughly October 2019) security updates were apparently made to Yahoo’s and AOL’s servers. From that time some there have been intermittent problems sending email to any Yahoo or AOL email addresses. We did a test with a personal Yahoo account and discovered that nearly always emails from the server (that you are on) went to the Yahoo or AOL recipient’s spam folder. Unfortunately, folks don’t always think to look there. Since we at CharlesWorks have no access into Yahoo or AOL servers, the recipient must go into their spam folder in their web mail (logging into their account in a web browser) and mark your message(s) as NOT SPAM or NOT JUNK or NOT BULK or whatever their choice is along those lines. Once we did that in our test, emails always went right to the Yahoo inbox. We also found that having multiple links within the body of email sent to yahoo.com or aol.com addresses also sometimes triggered an overzealous spam warning. If this is someone you intend to email frequently, please have them add your email to their Yahoo or AOL contact list. This appears to help with ensuring emails always got to where they needed to go.