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I know people do that, what with cloud based VMs and all, but still... I don't get it.

It should be noted that AWS and other Cloud providers let you set up Security Groups containing specific IP addresses or ranges (i.e. just whitelist your static IP for SSH/RDS access).

It isn't as secure as a VPN (and not as convenient), but definitely a stop-gap if you don't want to pay for Client VPN.

It’s usually to run some old, proprietary software that only has a Windows version.

"Old, proprietary software" describes something like 80% of all the software keeping the modern world going.

Some of it is new software. South Korean love of ActiveX for example, a technology dead for at least 10 years. Still getting new stuff written.

On the contrary, most critical software is plenty new - things like MS Office. Still bound to Windows.

The remaining systems rely on truly custom software and should be either airgapped (so no RDP) or rewritten. I'm thinking industrial - they should've planned for this many years beforehand. There were instances back when Windows XP was the main driver.

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