I never see mention of Windows with Session Manager. I have a mixed infrastructure with a number of Windows (IIS) app servers running various things.<p>We currently connect via SSH to a bastionhost, then tunnel from there to various systems, which allows connecting to SSH (linux instances), RDP (Windows), or basically any other network services like Redis or a database. I ended up writing some scripts to automate all this, so as long as you have the right certificates and IAM permissions, you can connect with a single command -- for Windows instances, it even retrieves the randomized password from the EC2 API. The end result is for any EC2 instances you're instantly popped into a shell/RDP session without having to enter credentials.<p>I'd love to replace this with something better (eg Session Manager), but I've not seen how to do this for RDP, and haven't had the time to go experimenting on my own to see if it's even possible. If I can't 100% replace the bastionhosts, having two entirely different connection methods doesn't solve anything (and in fact makes it worse, because it's harder to use).