@Perk, I'm trying to understand your network connectivity situation. The

<https://pkg.osquery.io/rpm/GPG>

URI is accessible from most locations? I can confirm that I can resolve

<http://pkg.osquery.io|pkg.osquery.io>

and connect over 443 and that file does exist. From the text you pasted it looks like the timeout is connecting over TCP to

(<http://pkg.osquery.io|pkg.osquery.io>)|2600:9000:21f2:7400:16:f64e:ee40:93a1|:443

. Is there any reason the two regions you mentioned would be blocking those connections? There are no network access controls on the S3 bucket where that file is hosted.