Mastering Outlook and Google two-way calendar syncing

It’s easy enough to display a Google calendar in Outlook, but getting them to stay in sync requires jumping through some hoops. Here’s help.

Microsoft Outlook is a complex, multifunctional software package, jam-packed with options and features. So, it's somewhat surprising that the calendaring function in Outlook 365/Outlook 2016 for Windows has almost no facility for two-way syncing with anything other than another Exchange-supported Outlook calendar.

The Outlook client can open several types of calendars, and it does an excellent job of displaying an overlay view of multiple calendars. The problem many users face is syncing those calendars for updates, especially bidirectionally. Changes made in Google Calendar, for example, may update in Outlook. But changes you make with Outlook will not be reflected in your Google calendars.

Here's my real-world need: My wife and I maintain Google calendars for various purposes, but one primary calendar is the family calendar that keeps track of school events, appointments, practices, exams and so on for our children and ourselves. I frequently need to be able to see both my work calendar and my personal calendars side-by-side, so I can check for conflicts. Do I need to leave work right at 5:00 to ferry a child to soccer practice? If so, don't set up that 4:30 meeting. I could duplicate my personal calendar events onto my work calendar, making them "private," but that's frankly just not a good idea — and most companies frown on it.

I've been testing both free and paid solutions to this problem for several years. Despite claims from some products that they can achieve reliable bidirectional syncing, most of them don't. For a time, Google offered a free service that worked most of the time, but it discontinued it several years ago. I found one paid product that worked, but the company discontinued the service. Another commercial product worked most of the time but stopped working occasionally, and support was surly and ineffective.

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