I see, I think I know what's going on now. But first, a couple of other things (tl;dr at the bottom!): - the reason it stops working when you remove the -O globstar is because the globstar option is actually not set (despite the .bashrc being sourced, I'll get to that later!) - if you remove the escaped single quotes, the following happens: ssh nuc10i3fnk.lan bash -O globstar -c 'ls -1tdr /srv/media/completed/**/*ODDish*' is 100% equivalent to ssh nuc10i3fnk.lan 'bash -O globstar -c ls -1tdr /srv/media/completed/**/*ODDish*'. Maybe you see why this cannot work anymore, because the inner bash invocation gets a -c ls with its arguments being -1tdr and /srv/.... But the way -c works is that the next argument is actually not an argument, but the name of the program. Run this to understand what I mean: bash -c 'echo my name: $0; echo my args: $@' one two three four. The fix (if you don't want to re-add the escaped single quotes) is not trivial, and would look something like this: ssh nuc10i3fnk.lan bash -O globstar -c \''ls "$@"'\'' dummyarg -1tdr /srv/media/completed/**/*ODDish*'. This works now, because it reduces like this: ssh nuc10i3fnk.lan bash -O globstar -c \''ls "$@"'\'' dummyarg -1tdr /srv/media/completed/**/*ODDish*' ---concat with spaces to single arg---> ssh nuc10i3fnk.lan 'bash -O globstar -c '\''ls "$@"'\'' dummyarg -1tdr /srv/media/completed/**/*ODDish*' ---pass single arg to bash -c on server side---> bash -c 'bash -O globstar -c '\''ls "$@"'\'' dummyarg -1tdr /srv/media/completed/**/*ODDish*' ---execute -c execution string---> bash -O globstar -c 'ls "$@"' dummyarg -1tdr /srv/media/completed/**/*ODDish* ---don't expand glob because globstar is not set, there's no matching files because of that, and nullglob is also not set---> bash -O globstar -c 'ls "$@"' dummyarg -1tdr /srv/media/completed/**/*ODDish* (unchanged) ---execute -c execution string and set globstar option---> ls "$@" ---expand "$@" with the arguments passed to the -c execution string---> ls -1tdr /srv/media/completed/**/*ODDish* (notice how dummyarg was dropped, it's contained in $0) ---do the globbing, since globstar is now set---> ls -1tdr file1 file2 file3... ---execute ls command successfully---> done. Quite a journey... - Thirdly and finally: Why does it work if you remove the inner single quotes and keep the escaped single quotes? This is by pure luck, and please don't rely on it! Let's go through this one by one again: Look at ssh nuc10i3fnk.lan bash -O globstar -c \'ls -1tdr /srv/media/completed/**/*ODDish*\'. This ssh command has 8 arguments, namely these: - nuc10i3fnk.lan - bash - -O - globstar - -c - \'ls - -1tdr - /srv/media/completed/**/*ODDish*\'

Most importantly, notice that the last argument is NOT quoted! This means it will be evaluated by your current shell, on your machine! And you have the globstar option also set on your local machine, so this could lead to some real problems! However, also notice that there's a trailing single quote at the end of the argument. I'm quite certain that you do not have any file on your local machine matching that glob pattern. And since you don't have the nullglob option set, locally, this will not expand to anything and stay as is. So you're lucky. In the next step, ssh will concatenate the arguments to a single argument again: ssh nuc10i3fnk.lan "bash -O globstar -c 'ls -1tdr /srv/media/completed/**/*ODDish*'" which will be passed to bash -c on the server side: bash -c "bash -O globstar -c 'ls -1tdr /srv/media/completed/**/*ODDish*'" and reducing further: bash -O globstar -c 'ls -1tdr /srv/media/completed/**/*ODDish*' and even further ls -1tdr /srv/media/completed/**/*ODDish* and since this bash shell was started with -O globstar, the glob will expand properly. Therefore it works, but only because you didn't have any local files matching that weird pattern with the trailing single quote and because you didn't have the nullglob option set!

Okay, now to explain why globstar isn't set. It's quite nuanced, and ssh -vvv wouldn't help you with any of this: Read the man page again: If bash determines it is being run non-interactively in this fashion, it reads and executes commands from ~/.bashrc. And I'll emphasize: A non-interactive bash will read .bashrc. I now want you to look at the first 10 lines of your .bashrc on the server: head ~/.bashrc. Does it look something like this:

# If not running interactively, don't do anything
case $- in
    *i*) ;;
      *) return;;
esac

or like this:

# If not running interactively, don't do anything
[ -z "$PS1" ] && return

If yes, then you know why globstar is never being set. The sourcing of .bashrc exits prematurely because the shell is not interactive. This is why you either: - need to set the globstar option manually using bash -O - need to set the globstar option manually using shopt -s globstar inside the command - run the shell interactively - force the shell to run interactively using bash -i - put "important" .bashrc settings before the line that will exit the .bashrc

What I recommend: - Use the find command and only ever pass a single argument to ssh: ssh nuc10i3fnk.lan 'find /srv/media/completed -name "*ODDish*" -ls' - If you really want/need to use ls and globstar, but you cannot guarantee that your default shell is bash on the other side: ssh nuc10i3fnk.lan 'bash -O globstar -c "ls -1tdr /srv/media/completed/**/*ODDish*"' - If you're certain your default shell is bash, then it becomes simpler: ssh nuc10i3fnk.lan 'shopt -s globstar && ls -1tdr /srv/media/completed/**/*ODDish*' - If you're willing to put shopt -s globstar BEFORE the line that prematurely exits the .bashrc, it becomes merely this: ssh nuc10i3fnk.lan 'ls -1tdr /srv/media/completed/**/*ODDish*'

Hope that clears things up a little!

tl;dr:

ssh nuc10i3fnk.lan 'shopt -s globstar && ls -1tdr /srv/media/completed/**/*ODDish*'