This may help:

[Alex5-crypto]

          This may help:

https://support.getoutline.org/s/article/Error-Messages?language=en_US
The steps may vary based on your Windows operating system version, but we’ve provided general steps for how to uninstall the TAP adapter and Outline and then reinstall Outline.
Uninstall the TAP adapter for Outline.
Go to “Device Managers”, then look under “Network Adapters”
Find the “TAP-Windows Adapter V9” file or the TAP adapter associated with Outline
Uninstall or delete this adapter. Keep in mind that this could affect other VPN apps that you have installed.
Uninstall Outline
Go into “Programs & Features”, then go to “Uninstall Program”
Find the Outline app and uninstall Outline
Download the latest version of Outline from getoutline.org and re-install it on your Windows device. The new installation should install a new TAP adapter for you.

As for me, I haven't uninstalled the TAP adapter. I have just updated it. Then I uninstalled the Outline Client and installed the latest version. It works.

Originally posted by @ogreogles in Jigsaw-Code/outline-server#1431 (comment)