Fiddler's update check will always fail by default because you've disabled TLS/1.0 support on your server and Fiddler's now-very-outdated TLS config only enables TLS/1.0 by default. The user must manually go into Tools > Fiddler Options > HTTPS and change the Supported protocols string to <client>;tls1.2 to fix this problem (and to also fix problems with the Composer and any other Fiddler features that do not pass through traffic through a client that supports later TLS.

This is tracked by oAcceptedServerHTTPSProtocols in Config.cs.