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I created a very basic workflow (literally the API url and a GUID) to gather the latest O365 IPs from their Endpoints service. It works fine on desktop/designer, but I get a "Couldn't connect to server (tool ID: 2)" error when running it on the Gallery. Does this suggest my company's firewall is blocking connections, or is the Download tool not compatible with Gallery?
Both of your suspicions could be correct, the server admins can choose to block tools like run command and the download tool but the error suggests that your server is blocked from connecting to that URL (probably firewall)
As @colorado970 are you able to remote into your Alteryx server and run the workflow in designer? This will give you a definitive answer.