You don't use
-e as per this page:
Also, FYI, there is a lot of ambiguity between config, settings and pipelines.
"settings" is your logstash.yml. <- this can't be reloaded automatically
Pipelines can be reloaded automatically. These are your .conf files but are referred to as your config files when talking about auto-reloading.
You need to mount your pipelines directory in a docker volume so you can edit them on the host. When you save the config, the docker image sees the change and reloads logstash's config.
You could try something like this:
docker run -it \
--name logstash \
-v $LOCAL_PIPELINE:$REMOTE_PIPELINE \
-v $LOCAL_CONFIG:$REMOTE_CONFIG \
-p 5044:5045 \
-p 514:5144 \