Yup I can tell what system you are coming from in the video which is super cute! Love it! I had to laugh at @kona response and I would add to that DO NOT USE SAFARI! LOL! The built in browsers (IE/Edge/Safari) are problematic because the browser updates are reliant on operating system updates which some people do not do on regular basis. This is even an issue on campus. We are on Win7 and when you open IE, it aggressive tells you to update your browser which won't be done til we move to Win10.
The biggest issue we had when we first migrated was the migration process itself. We were coming from WebCT/BlackCT and this process worked very well in Canvas so we allowed people to do it on their own. We make a poor assumption that people would take our advice about reorganizing their courses to fit Canvas. Many NEVER did so we still have many course sites still look like a quasi WebCT homepage. This was an error on our part so if I had to do a migration all over again I would probably control the migration process a little more such as cleaning up a course before releasing it to the instructor.
The other issue we had during the migration process we had was the instructor's understanding of how integrated the assignments are with other tools in the course (Syllabus, calendar, and grades). WebCT had very limited integration between tools so this was a hard concept for our instructors to learn.
Our most common current issues are very similar to the ones Kona listed. Publishing courses and content is the number one issue following closely by students finding bad links in a course.
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