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I haven’t pursued this issue since I posted it here. For now, I’ve just worked around it (there is no work around that’s as nice as “it just working”, which is what I hoped tagged rules would do).
i’m having the same exact problem and it is definitely not the expected behavior.
in addition, new when you add a droplet to your firewall by using tags and then assign that tag to a new droplet, the firewall will not apply to the newly tagged droplet as it should.
conversely, destroying a droplet that has been tagged for a firewall will not remove that droplet from the firewall and you will be left with orphan droplets when you view the firewall. i believe what is actually happening here is that the firewalls and rules that you set up are being assigned their various droplets only at the time that the firewall or firewall rule is saved.
see: [https://www.digitalocean.com/community/tutorials/an-introduction-to-digitalocean-cloud-firewalls]
where it says:
Any Droplet or Load Balancer already tagged will be allowed to establish a connection, and new or existing Droplets will be allowed as soon as they are tagged.
i’ll open a case.