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I'm receiving the same error message when trying to connect Computer A, which is running Ubuntu, to Computer B, which is running Windows 10 with Cygwin and OpenSSH installed. When using the command ssh user@<IPaddress> on Computer A, it takes about 2 minutes before it returns the message 'ssh: connection to host port 22: connection timed out'. I have been able to ssh from Computer B to Computer A successfully.

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    That sounds more like a question for a Windows forum - have you checked your Windows firewall settings? – steeldriver Jul 10 '16 at 0:19
  • Is computer B's firewall configured to allow incoming packets on port 22? – Alcuin Arundel Jul 10 '16 at 0:20
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    Check the port 22 to be open on computerB from computerA with nmap -PN -p 22 ipComputerB. I guess your ssh service is not running, or if it's running, it may be blocked by windows defender (or another firewall). Also notice that 22 is the default ssh port, your cygwin may be using another port. – bistoco Jul 10 '16 at 0:21
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This problem may occur when: 1. Port 22 is closed. 2. Ssh is not installed on the machine.

Check whether ssh service is running or not on the machine to which you want to connect.

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