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I've added a calendar to my work Outlook with all of work holidays. And though it shows the second calendar next to my primary, if I schedule anything for a day that is filled on the internet calendar it will show "no conflicts".

Is there any way to get Outlook to see those events as blocking?

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up vote 1 down vote accepted

If you want to continue using the Internet calendars as subscriptions (automatically updating), don't want to install additional software, or the Google calendar is not your Google account's primary calendar, no.

If you don't mind installing additional software and the calendar is your Google account's primary, you can use Google Calendar Sync. It can be configured for one-way sync either way (Outlook -> Google or Google -> Outlook), or it can do two-way (Outlook <-> Google).

If that's not an option and the calendar is static ("2012 US Holidays"), or you don't mind reloading the calendar on a regular basis, Microsoft provides a step-by-step walkthrough for importing a "Calendar Snapshot" into Outlook. Following those directions, it still won't appear as a "busy" event, but you can now move things between the two (note that I think you can copy from subscribed calendars, too, but I don't have Outlook in front of me to test, and Microsoft seems to be implying that you cannot). From the last time I did this, I believe it may prompt you to add these directly to your existing calendar, too...but I could be wrong. If it does, that would be the most straightforward way not using Google Calendar Sync to make Google appointments appear "busy" in Outlook.

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