Yes, order important.
Sure, need use alphabetical ordering.

If we talk about drop-in functionality. Then need separate drop-in types

1. created by admins - permanent drop-in, example enabled/disabled modules;
2. runtime drop-in - temporal drop-in, example listeners configured using cloud providers tools.

Say may be defined configuration key include_dropin {wildcard}
Then kamailio looks dropins in folders /etc/kamailio/kamailio.cfg.d and /run/kamailio/kamailio.cfg.d.
List of dropin folders maybe configurable on predefined.
Example

### Loading modules drop-in ###
include_dropin *-modules.cfg

### Loading interface listeners ###
include_dropin *-listeners.cfg

In example above on file system may exist files

/etc/kamailio/kamailio.cfg.d/10-jasson-modules.cfg
/etc/kamailio/kamailio.cfg.d/20-db_postgres-modules.cfg
/run/kamailio/kamailio.cfg.d/10-amazon-listeners.cfg

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