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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 we have heard many indicating there have been intermittent problems sending email to any Yahoo or AOL email addresses.

CharlesWorks did a test sending email to a personal Yahoo account using CharlesWorks mail servers and discovered that nearly always emails from the server (that you are most likely on) went to the Yahoo or AOL recipient’s spam folder. Unfortunately, folks don’t always think to look there – or only occasionally check it.

We at CharlesWorks have zero access into Yahoo or AOL servers. The recipient (the email address you are writing to at Yahoo or AOL) must go into their spam folder using their web mail (which entails 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 (what these are called sometimes change as Yahoo and AOL email programs are updated).

Once we did that process in our test, emails always went right to the Yahoo inbox. We also discovered that having multiple links within the body of an email sent to yahoo.com or aol.com addresses also could trigger 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.

Another factor in this is that many of the CharlesWorks clients who have consistently had this problem occasionally use their email accounts to send bulk mailings to prospective or current customers. All it takes is for one single spam complaint from a Yahoo or AOL address to mark your email address as a spammer on those systems. It is much wiser to use Constant Contact (which offers a free trial) or some such bulk email provider to avoid making your emails inaccessible. We recommend Constant Contact because it appears to have the highest delivery rate.

Finally, here is what appears to be a solution. CharlesWorks is a Microsoft Partner. We can hook you up with what’s called a Microsoft hosted exchange email account. As it turns out, Microsoft owns both Yahoo and AOL so it’s no wonder that emails are always delivered among those three. We charge $5.99 per email account. It is a robust account with 50 gigabytes of space (that’s 10 times as much space as offered with our web services). It’s also faster and much easier to use on phones and so forth with the free Outlook app for Android and iPhones. It also has a calendar functionality so you can use your calendar from anywhere you can get internet. Call our office and ask about this.

CharlesWorks