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Hi Matthew,
By checking the escalated case, I notice that the engineer has provided the following troubleshooting steps and is waiting for a response. Feel free to email him back with any update and we'll assist you further according to your situation.
- Install Windows updates. Make sure your machine is up to update.
- Add the SharePoint Online site to the “Local intranet” site of IE:
a. Click the setting icon of IE => click Internet options:
b. Click the Security tab => Local intranet => Sites
c. Click “Advanced” => Input your SharePoint site URL => click Add button
- Clean the IE cache and close IE. Reopen an IE window to test whether the “Open in explorer” function works.
Thanks for working with us.
Lingyu Sun