When comparing ssh of Cygwin vs WinSSHTerm, the Slant community recommends ssh of Cygwin for most people. In the question“What are the best SSH clients for Windows?” ssh of Cygwin is ranked 14th while WinSSHTerm is ranked 15th. The most important reason people chose ssh of Cygwin is:
So you can have handy UI with tabs and other features. (For tab-like experience there is also GNU screen).
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Pros
Pro May be used with console emulators like Cmder
So you can have handy UI with tabs and other features. (For tab-like experience there is also GNU screen).
Pro Freeware
WinSSHTerm is free for anyone to use.
Pro Keyboard shortcuts
Keyboard shortcuts are especially valuable for professionals.
Pro Supports X Server
There is easy, automatic integration with X Server and starts/stops can take place with the launch/exit of WinSSHTerm.
Pro Supports file transfer
The user can start a WinSCP session inside WinSSHTerm, without the need to duplicate the session in WinSCP.
Pro Highly portable
The user can run WinSSHTerm from a USB drive on different computers.
Pro Ready for production use
There are no annoying bugs in WinSSHTerm. Navigation tools and keyboard shortcuts are a great time saver, especially if you have to manage multiple connections.
Cons
Con Like using Windows 95
Con Not a true terminal emulator
It's a PuTTY interface and it's mostly used to access remote machines through ssh, so it may not be very suitable for working on a local machine.