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In this case, Pulumi sends the delete API request which succeeds. AWS then spends 5 minutes failing to delete the SG. There's not much that Pulumi can do, unfortunately...

If you import the ENI and associate them correctly, then Pulumi will know that the deletion will fail and tell you before even sending the API request.

Yeah that’s correct.. AWS spends time trying to do stuff it can’t do. Ha. Except in console when trying to delete the SG it is an immediate response, so assumed the cli or however pulumi does it would also get the same error response and not keep trying?

Don't know about that. I know Pulumi (or maybe the TF bridge?) handles similar situations better, so there may be something Pulumi can do to make it better. Maybe you could raise an issue in GitHub about it?