Canvas due dates not syncing with Outlook calendar

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I'm an instructor, and I want to be able to tell my students to sync their Canvas calendar with their Outlook calendar so that they'll only have to use one calendar. I tried syncing my own, to see how it works, and I'm running into a problem.

The bigger problem first: all the due dates aren't syncing. I can see all the due dates when I look at the calendar in Canvas, but only some of them show up when I look at the calendar in Outlook. (It seems like, for the assignments that were created as quizzes within Canvas, the ones that I can see are the ones that I'd copied from another course, but I'm not certain that's the pattern.) Also, for WebAssign assignments that have been linked with Canvas, and to which I assigned due dates, they don't transfer to the Outlook calendar at all. I also post a new module each Monday, Wednesday, and Friday, and I add those to the calendar in Canvas as all-day events, and those don't transfer over to Outlook, either.

Also, this isn't something working wrong, exactly, but it would be nice if there was an easy way to take the due dates and add them to Outlook as all-day appointments, so that they'd display at the top of the page in the week view in Outlook. The week view seems to be the most common way for people to use the Outlook calendar, and assignments that are due at 11:59 PM are basically invisible when viewed that way, since you have to scroll all the way to the bottom of the page to see them.

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