Open with Explorer on SharePoint Online

If you've been around SharePoint and Office 365 for a while, you've likely run into issues opening a document library in Windows Explorer. The most recent flavor of SharePoint Online gives this very unhelpful  and grammatically questionable error:
"We're having trouble opening this library in File Explorer. learn more.

Syncing this library will give you better experience."

There are some thing you can try on the client end to help with this:
Make sure the WebClient service is enabled and started.
Also, put * in your Trusted Sites in Internet Explorer.

If this still dos not solve your issue, this may be a network routing issue. At my current client, this is a common issue with Office 365 because their IP addresses keep changing for their online services. Also, their network has multiple paths to the Internet. The return route doesn't always seem to match the outgoing route. This kills things like WebDAV and the One Drive for Business synchronization tool.

To resolve this, I configured the proxy infrastructure to bypass the SharePoint Online traffic and use a direct connection instead.


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