docker context remote ssh not working in host to > non-rootfull remote setup

Description

when both host and remote have rootfull setup in place it works as expected: https://docs.docker.com/engine/install/linux-postinstall/#manage-docker-as-a-non-root-user meaning running commands without sudo while they are running as superuser anyway.

when the host is not rootfull seems to work but the behaviour is erratic sometimes askpassword prompt happens and no connection is made.

seems the only way it consistently works is when both host and remote are rootfull without sudo commands.

Reproduce

without rootfull using sudo commands:

# sudo docker create context --docker host=ssh://user@ip testremote
testremote
Successfully created context "testremote"
# sudo docker context use testremote
testremote
Current context is now "testremote"
# sudo docker ps
Cannot connect to the Docker daemon at http://docker.example.com. Is the docker daemon running?

if remote is non rootfull it works as expected, the daemon is running but requires sudo in the remote then fails.

Expected behavior

maybe prompt again for sudo password or allow sudo password in remote

docker version

Client: Docker Engine - Community
 Version:           23.0.0
 API version:       1.42
 Go version:        go1.19.5
 Git commit:        e92dd87
 Built:             Wed Feb  1 17:47:38 2023
 OS/Arch:           linux/amd64
 Context:           default

Server: Docker Engine - Community
 Engine:
  Version:          23.0.0
  API version:      1.42 (minimum version 1.12)
  Go version:       go1.19.5
  Git commit:       d7573ab
  Built:            Wed Feb  1 17:44:45 2023
  OS/Arch:          linux/amd64
  Experimental:     false
 containerd:
  Version:          1.6.16
  GitCommit:        31aa4358a36870b21a992d3ad2bef29e1d693bec
 runc:
  Version:          1.1.4
  GitCommit:        v1.1.4-0-g5fd4c4d
 docker-init:
  Version:          0.19.0
  GitCommit:        de40ad0

docker info

Client:
 Context:    default
 Debug Mode: false
 Plugins:
  buildx: Docker Buildx (Docker Inc.)
    Version:  v0.10.2
    Path:     /usr/libexec/docker/cli-plugins/docker-buildx
  compose: Docker Compose (Docker Inc.)
    Version:  v2.15.1
    Path:     /usr/libexec/docker/cli-plugins/docker-compose
  scan: Docker Scan (Docker Inc.)
    Version:  v0.23.0
    Path:     /usr/libexec/docker/cli-plugins/docker-scan

Server:
 Containers: 11
  Running: 8
  Paused: 0
  Stopped: 3
 Images: 9
 Server Version: 23.0.0
 Storage Driver: overlay2
  Backing Filesystem: btrfs
  Supports d_type: true
  Using metacopy: false
  Native Overlay Diff: true
  userxattr: false
 Logging Driver: json-file
 Cgroup Driver: systemd
 Cgroup Version: 2
 Plugins:
  Volume: local
  Network: bridge host ipvlan macvlan null overlay
  Log: awslogs fluentd gcplogs gelf journald json-file local logentries splunk syslog
 Swarm: inactive
 Runtimes: io.containerd.runc.v2 runc
 Default Runtime: runc
 Init Binary: docker-init
 containerd version: 31aa4358a36870b21a992d3ad2bef29e1d693bec
 runc version: v1.1.4-0-g5fd4c4d
 init version: de40ad0
 Security Options:
  seccomp
   Profile: builtin
  cgroupns
 Kernel Version: 6.1.9-200.fc37.x86_64
 Operating System: Fedora Linux 37 (Workstation Edition)
 OSType: linux
 Architecture: x86_64
 CPUs: 16
 Total Memory: 30.96GiB
 Name: # removed by user
 ID: # removed by user
 Docker Root Dir: /var/lib/docker
 Debug Mode: false
 Registry: https://index.docker.io/v1/
 Experimental: false
 Insecure Registries:
  127.0.0.0/8
 Live Restore Enabled: false

Additional Info

if this is the desired behaviors it should be documented that context use over ssh does not work with sudo commands in remote

Start by reproducing the reported docker context create, docker context use, and docker ps commands with host and remote rootless/rootful combinations. Trace the Docker CLI's SSH context path and sudo handling; done means the remote daemon connects reliably or the supported limitation is documented.