Julia is having problems with Windows Live Mail, which is rejecting her Gmail. Leo says that Julia needs to check her settings to make sure the server settings are properly configured. Make sure that IMAP is enabled in GMail's settings. She could also use POP, but Leo says that IMAP is better. GMail will also give her step by step instructions to set it up as well. Leo recommends turning on two factor authentication. There may be an app specific password she'll need once she turns that on, though.
Pat has four macs in various locations and wants to know if they will all be synced with iCloud like DropBox does. Leo says yes and no. It will sync, but not via a folder. The key is all the same Macs running the same shared Apple ID. Can she go work on different macs simultaneously? Leo says that could be problematic. To do team operations, a good third party app is GitHub.
Bill has a Windows desktop and a MacBook Pro and he wants to sync them together with email. He uses POP3. Leo says to stop using that, and use IMAP instead. IMAP is the best way to go because it doesn't take his email off the server. POP3 downloads email and then deletes it from the server. So Bill should go with IMAP and then he can have a central location for all of his email that's accessible from any device.
The way your email client is set up on your phone or tablet can determine how email is handled on your desktop as well. For instance, you may find that after downloading all of your email to your phone, the email disappears on your desktop. This behavior can be changed by either using IMAP (Internet Message Access Protocol) or POP3 (Post Office Protocol version 3).
Greg hears that POP 3 is going to be obsolete and that he should go with and IMAP through Microsoft Exchange for an extra cost. Is that true? Leo says that it is, but he recommends going with Gmail instead. He could also buy the Google Apps account, and they do a great job with organization and spam filtering. IMAP will also work better with iOS devices. Leo also says he can shop around and get a better deal on IMAP. But Leo uses Gmail.
Alan would like to delete all the emails at once on his iPhone. Leo says if that email is on an IMAP server, then the messages are on the server and not on his phone.
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.
Frank is ready to finally get rid of AOL and wants to know what's a better alternative; especially for email. Leo likes Gmail because he can sync all of his devices thanks to the IMAP email protocol which keeps all email at the server level. Frank can just use the webmail version or he can use an email client like Outlook. Mozilla has one called Thunderbird.
Don has been having trouble getting his email through Windows Live Mail. Some of it shows up on his Galaxy S4, but not all of it. He's learned that POP3 won't give him email on both devices. Leo says that's true, and the problem could be how Don added his account to his Galaxy S4. Don says it's a Gmail account, though. Leo says Gmail and Live mail are two different services and that explains why Don isn't getting all his email. He's only getting his Gmail.
Mary is having trouble getting her email. Leo says her email may be configured incorrectly. It may also be getting blocked from her antivirus software suite. Norton 360 is a perfect example. Leo suggests using POP3 as opposed to IMAP to see if that works. She can also try using port 9954 for incoming, and 465 for outgoing mail. That can bypass any blocking from the ISP. Here's a technote from Cox on how to fix it.