I'd like to get the SO community opinion on automated deployments to external clients. We develop software that we wrap in an install shield and ship it to customers so that they install on their own servers. Most of these clients wants contain all of their data within their environments without punching any holes which makes automated deployments a little challenging.
The problem we're trying to solve is to get rid of install shield and writing Install-Script code which sucks and maintenance heavy and move towards a modern way to deploy software.
Azure and AWS is out of the question because it involves hosting data externally and our clients does not like that.
We've investigated Octopus Deploy so far and seems like a promising tool especially that they have a "Polling Tentacle" that does not require punching firewall holes.
Do you have any other suggestions? Ideas?
This largely depends on the relationship you have with your customers. Octopus Deploy is a good solution if you are responsible and trusted for scheduling and conducting deployments. Otherwise it will be difficult to persuade your customers to setup an Windows Service which polls an external endpoint waiting for commands.
Microsoft ClickOnce will a good option if your customers prefer you to provide a package for them to evaluate and deploy themselves.
Both options are mature with plenty of vendor and community support available.