I see there's an error about tty command not found?
17:14:46.759569 tramp-wait-for-regexp (6) # sh: tty: command not found "" tramp_exit_status 0 ///a8f473ab7528e4f6fa765c1a88e32326#$ 17:14:46.759605 tramp-get-connection-property (7) # process-buffer *eshell*; cache used: t 17:14:46.759630 tramp-get-connection-property (7) # process-buffer *eshell*; cache used: t 17:14:46.759702 tramp-send-command-and-read (1) # Wrong type argument: "Wrong type argument", "stringp nil" sh: tty: command not found "" 17:14:46.759723 tramp-set-connection-property (7) # remote-tty nil I think that's from tramp-open-connection-setup-interactive-shell, this part particularly: ;; Set `remote-tty' process property. (let ((tty (tramp-send-command-and-read vec "echo \\\"`tty`\\\"" 'noerror))) (unless (string-empty-p tty) (process-put proc 'remote-tty tty) (tramp-set-connection-property proc "remote-tty" tty))) Here is another relevant log output for connecting to alpine: 17:14:46.762109 tramp-send-command (6) # cd /root/ && exec <<'713f3ba2fe251156a2bf6b9635a2bb49' env PS1\=/docker\:alpine3173\:/root/\ \#\$\ INSIDE_EMACS\=30.0.50\,eshell\,tramp\:2.7.0-pre LINES\=51 COLUMNS\=235 OLDPWD\=/docker\:4a3b345bbb1c\:/root PATH\=/bin\:/usr/bin\:/sbin\:/usr/sbin\:/usr/local/bin PWD\=/docker\:alpine3173\:/root /bin/sh ( whoami ) </dev/tty 713f3ba2fe251156a2bf6b9635a2bb49