While I used to use webmail, I now use Postbox via IMAP. Here is what I do so that everything is up to date. If you aren’t a Google G Suite user, this will also work for a Gmail account (see below). For reasons explained below, I use Address Book for my contacts, but not Google Contacts. We use Google G Suite ourselves, but also set it up for a lot of clients along with their business websites, so I get to see quite a bit of it in action. If you haven’t come across it before, Google G Suite lets you use a Gmail account with your own domain – plus a whole bunch of other resources as part of a single account (Google Calendar and Google Docs being the main ones of interest). I use Google G Suite (formerly Google Apps) for my mail and calendar. Here is my current way of managing information across iMac, Macbook Pro, iPad and iPhone. I’m a long time Mac user, have paid my MobileMe dues and tried all sorts of other tricks over time. Once you have a desktop at work, a laptop for out and about as well as a tablet and phone, well, it just gets complicated. Keeping mail, address book and calendar up to date across different computers can be surprisingly difficult.
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