I can confirm there is indeed bug, although in my case /ch10/ is also bugged.

{"apps":{"http":{"servers":{"srv0":{"automatic_https":{"skip":["localhost"]},"listen":[":5001"],"routes":[{"handle":[{"handler":"subroute","routes":[{"handle":[{"handler":"headers","response":{"deferred":true,"delete":["Server"]}}]},{"handle":[{"handler":"subroute","routes":[{"handle":[{"handler":"rewrite","strip_path_prefix":"/ch10"}]},{"group":"group19","handle":[{"handler":"rewrite","uri":"/MyCh10{http.request.uri}"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch10/*"]}]},{"handle":[{"handler":"subroute","routes":[{"handle":[{"handler":"rewrite","strip_path_prefix":"/ch20"}]},{"group":"group39","handle":[{"handler":"rewrite","uri":"/MyCh20{http.request.uri}"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch20/*"]}]},{"handle":[{"handler":"subroute","routes":[{"group":"group0","handle":[{"handler":"rewrite","uri":"/MyCh1/video.m3u8"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch1/"]}]},{"handle":[{"handler":"subroute","routes":[{"handle":[{"handler":"rewrite","strip_path_prefix":"/ch1"}]},{"group":"group1","handle":[{"handler":"rewrite","uri":"/MyCh1{http.request.uri}"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch1/*"]}]},{"handle":[{"handler":"subroute","routes":[{"group":"group2","handle":[{"handler":"rewrite","uri":"/MyCh2/video.m3u8"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch2/"]}]},{"handle":[{"handler":"subroute","routes":[{"handle":[{"handler":"rewrite","strip_path_prefix":"/ch2"}]},{"group":"group3","handle":[{"handler":"rewrite","uri":"/MyCh2{http.request.uri}"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch2/*"]}]},{"handle":[{"handler":"subroute","routes":[{"group":"group4","handle":[{"handler":"rewrite","uri":"/MyCh3/video.m3u8"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch3/"]}]},{"handle":[{"handler":"subroute","routes":[{"handle":[{"handler":"rewrite","strip_path_prefix":"/ch3"}]},{"group":"group5","handle":[{"handler":"rewrite","uri":"/MyCh3{http.request.uri}"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch3/*"]}]},{"handle":[{"handler":"subroute","routes":[{"group":"group6","handle":[{"handler":"rewrite","uri":"/MyCh4/video.m3u8"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch4/"]}]},{"handle":[{"handler":"subroute","routes":[{"handle":[{"handler":"rewrite","strip_path_prefix":"/ch4"}]},{"group":"group7","handle":[{"handler":"rewrite","uri":"/MyCh4{http.request.uri}"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch4/*"]}]},{"handle":[{"handler":"subroute","routes":[{"group":"group20","handle":[{"handler":"rewrite","uri":"/MyCh11/video.m3u8"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch11/"]}]},{"handle":[{"handler":"subroute","routes":[{"handle":[{"handler":"rewrite","strip_path_prefix":"/ch11"}]},{"group":"group21","handle":[{"handler":"rewrite","uri":"/MyCh11{http.request.uri}"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch11/*"]}]},{"handle":[{"handler":"subroute","routes":[{"group":"group22","handle":[{"handler":"rewrite","uri":"/MyCh12/video.m3u8"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch12/"]}]},{"handle":[{"handler":"subroute","routes":[{"handle":[{"handler":"rewrite","strip_path_prefix":"/ch12"}]},{"group":"group23","handle":[{"handler":"rewrite","uri":"/MyCh12{http.request.uri}"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch12/*"]}]},{"handle":[{"handler":"subroute","routes":[{"group":"group24","handle":[{"handler":"rewrite","uri":"/MyCh13/video.m3u8"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch13/"]}]},{"handle":[{"handler":"subroute","routes":[{"handle":[{"handler":"rewrite","strip_path_prefix":"/ch13"}]},{"group":"group25","handle":[{"handler":"rewrite","uri":"/MyCh13{http.request.uri}"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch13/*"]}]},{"handle":[{"handler":"subroute","routes":[{"group":"group8","handle":[{"handler":"rewrite","uri":"/MyCh5/video.m3u8"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch5/"]}]},{"handle":[{"handler":"subroute","routes":[{"handle":[{"handler":"rewrite","strip_path_prefix":"/ch5"}]},{"group":"group9","handle":[{"handler":"rewrite","uri":"/MyCh5{http.request.uri}"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch5/*"]}]},{"handle":[{"handler":"subroute","routes":[{"group":"group10","handle":[{"handler":"rewrite","uri":"/MyCh6/video.m3u8"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch6/"]}]},{"handle":[{"handler":"subroute","routes":[{"handle":[{"handler":"rewrite","strip_path_prefix":"/ch6"}]},{"group":"group11","handle":[{"handler":"rewrite","uri":"/MyCh6{http.request.uri}"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch6/*"]}]},{"handle":[{"handler":"subroute","routes":[{"group":"group26","handle":[{"handler":"rewrite","uri":"/MyCh14/video.m3u8"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch14/"]}]},{"handle":[{"handler":"subroute","routes":[{"handle":[{"handler":"rewrite","strip_path_prefix":"/ch14"}]},{"group":"group27","handle":[{"handler":"rewrite","uri":"/MyCh14{http.request.uri}"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch14/*"]}]},{"handle":[{"handler":"subroute","routes":[{"group":"group28","handle":[{"handler":"rewrite","uri":"/MyCh15/video.m3u8"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch15/"]}]},{"handle":[{"handler":"subroute","routes":[{"handle":[{"handler":"rewrite","strip_path_prefix":"/ch15"}]},{"group":"group29","handle":[{"handler":"rewrite","uri":"/MyCh15{http.request.uri}"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch15/*"]}]},{"handle":[{"handler":"subroute","routes":[{"group":"group12","handle":[{"handler":"rewrite","uri":"/MyCh7/video.m3u8"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch7/"]}]},{"handle":[{"handler":"subroute","routes":[{"handle":[{"handler":"rewrite","strip_path_prefix":"/ch7"}]},{"group":"group13","handle":[{"handler":"rewrite","uri":"/MyCh7{http.request.uri}"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch7/*"]}]},{"handle":[{"handler":"subroute","routes":[{"group":"group14","handle":[{"handler":"rewrite","uri":"/MyCh8/video.m3u8"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch8/"]}]},{"handle":[{"handler":"subroute","routes":[{"handle":[{"handler":"rewrite","strip_path_prefix":"/ch8"}]},{"group":"group15","handle":[{"handler":"rewrite","uri":"/MyCh8{http.request.uri}"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch8/*"]}]},{"handle":[{"handler":"subroute","routes":[{"group":"group16","handle":[{"handler":"rewrite","uri":"/MyCh9/video.m3u8"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch9/"]}]},{"handle":[{"handler":"subroute","routes":[{"handle":[{"handler":"rewrite","strip_path_prefix":"/ch9"}]},{"group":"group17","handle":[{"handler":"rewrite","uri":"/MyCh9{http.request.uri}"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch9/*"]}]},{"handle":[{"handler":"subroute","routes":[{"group":"group30","handle":[{"handler":"rewrite","uri":"/MyCh16/video.m3u8"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch16/"]}]},{"handle":[{"handler":"subroute","routes":[{"handle":[{"handler":"rewrite","strip_path_prefix":"/ch16"}]},{"group":"group31","handle":[{"handler":"rewrite","uri":"/MyCh16{http.request.uri}"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch16/*"]}]},{"handle":[{"handler":"subroute","routes":[{"group":"group18","handle":[{"handler":"rewrite","uri":"/MyCh10/video.m3u8"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch10/"]}]},{"handle":[{"handler":"subroute","routes":[{"group":"group32","handle":[{"handler":"rewrite","uri":"/MyCh17/video.m3u8"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch17/"]}]},{"handle":[{"handler":"subroute","routes":[{"handle":[{"handler":"rewrite","strip_path_prefix":"/ch17"}]},{"group":"group33","handle":[{"handler":"rewrite","uri":"/MyCh17{http.request.uri}"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch17/*"]}]},{"handle":[{"handler":"subroute","routes":[{"group":"group34","handle":[{"handler":"rewrite","uri":"/MyCh18/video.m3u8"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch18/"]}]},{"handle":[{"handler":"subroute","routes":[{"handle":[{"handler":"rewrite","strip_path_prefix":"/ch18"}]},{"group":"group35","handle":[{"handler":"rewrite","uri":"/MyCh18{http.request.uri}"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch18/*"]}]},{"handle":[{"handler":"subroute","routes":[{"group":"group36","handle":[{"handler":"rewrite","uri":"/MyCh19/video.m3u8"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch19/"]}]},{"handle":[{"handler":"subroute","routes":[{"handle":[{"handler":"rewrite","strip_path_prefix":"/ch19"}]},{"group":"group37","handle":[{"handler":"rewrite","uri":"/MyCh19{http.request.uri}"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch19/*"]}]},{"handle":[{"handler":"subroute","routes":[{"group":"group40","handle":[{"handler":"rewrite","uri":"/MyCh21/video.m3u8"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch21/"]}]},{"handle":[{"handler":"subroute","routes":[{"handle":[{"handler":"rewrite","strip_path_prefix":"/ch21"}]},{"group":"group41","handle":[{"handler":"rewrite","uri":"/MyCh21{http.request.uri}"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch21/*"]}]},{"handle":[{"handler":"subroute","routes":[{"group":"group38","handle":[{"handler":"rewrite","uri":"/MyCh20/video.m3u8"}]},{"handle":[{"handler":"reverse_proxy","upstreams":[{"dial":"127.0.0.1:5002"}]}]}]}],"match":[{"path":["/ch20/"]}]}]}],"match":[{"host":["localhost"]}],"terminal":true}]}}},"pki":{"certificate_authorities":{"local":{"install_trust":false}}},"tls":{"automation":{"policies":[{"issuers":[{"module":"internal"}]}]}}},"logging":{"logs":{"default":{"level":"DEBUG"}}}}

Using jq it's easy to see several paths are out of place.

I created a pr.

@fa1rid Can you try xcaddy build fix-route-sort to see if it's fixed?

Uh oh!

Routes Bug #7012

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