Terry got a new Mac for an early Christmas present and is waiting awhile to reinstall stuff. Leo says that's a good idea. It's much better to only install new programs as needed. Every program he installs is a potential security risk, so he should install as little as possible.
Elise uses Apple Mail with her Gmail account and whenever she saves a draft email, it disappears. Rich thinks the culprit may be a corruption in the Apple Mail program itself. He recommends that she look in Gmail in her browser to verify is the draft emails are still there. They probably are. Then she can reset or rebuild Apple Mail. She may need to delete her email account from the app and then add it again.
Brian wants to know how he can use tags to stay organized on his email. Leo says that tags are great for searching and it makes it really simple to stay organized. Gmail can tag messages. Mailtags has been around for years and it works great. Leo used it a long time ago and it works in Apple Mail, which can be a challenge because Apple changes Mail with just about every version of macOS. It's also great for photos. Google Photos is great for tagging as well.
Karlo has a cookie business, and when people order cookies and pay by Paypal, he has to use Outlook to get notifications. Leo says that Go Daddy's interface will support other email interfaces, regardless of what they may say. Outlook itself is a modern system and would work, but it's not the only game in town. He can also use Gmail. There's also Thunderbird, Windows Live Mail, and the Apple Mail app on Mac.
David bought a used Mac Mini and he is trying to set up his Apple Mailbox. It's not moving the messages over fast enough, though. Leo says that David is trying to store hundreds of thousands of messages and that just takes time to download them. Why do that when he can keep them in the cloud? Also, the new Apple Mail has to reindex the mail and that takes time. This is why Leo is against this proprietary mail format. He prefers open source options like Thunderbird or with GMail.
Cindy has two email addresses: One for business, and one for personal. Her Apple mail program always confuses business and personal, though. Leo says that most email programs have a setting for delegation, which would allow her to delegate which email she'll want to reply from. She should go into the composing settings of Apple Mail and she'll be able to select which message address she wants to send from. She should also make sure she has outgoing mail servers for both accounts and that's in the "Accounts" section.
LaVerne updated to OS X El Capitan and now her email account has been wiped clean. Leo says that doesn't mean the email is missing. The messages are probably still on the server. It just means that since LaVerne is using Apple Mail and linked it to GMail, El Capitan probably missed a step in linking the old email. Other El Capitan users have reported similar problems.
Jeff has about 50,000 email addresses and he wants to know if there's a script or app that can pull emails and send them information. Leo says that it depends on where the data is. Jeff says it's in Apple Mail. Leo says the best thing to do is export the data into a text file format. Once that's done, he can use scripting language like Pearl, Python or Ruby to search for the email and make a master list of them.
Kenny wants to know if there's any easy way to sync Microsoft Outlook with Apple Mail? Leo says that if the email is handled via IMAP, then all that email is on the server. So if it's on an IMAP server, both Apple Mail and Outlook will access it in the same place. It may not get everything, though. If it doesn't then he'll have to export all of his mail and import it into Apple Mail.