Chrome Version       : Google Chrome 62.0.3202.94
OS version               : System Version: OS X 10.10.5 (14F27), Kernel Version: Darwin 14.5.0

What steps will reproduce the problem?
(1) Log out all user sessions from Mac OS GUI
(2) Log in user via SSH only
(3) Run chrome from CLI via SSH with --headless flag, e.g making a screenshot command:
/Applications/Google\ Chrome.app/Contents/MacOS/Google\ Chrome --headless --disable-gpu --screenshot --window-size=1280,1696 https://www.chromestatus.com/

What is the expected result?
screenshot.png file is created

What happens instead?
Error report shows up, saying that connection to WindowServer cannot be established
(_RegisterApplication(), FAILED TO establish the default connection to the WindowServer, _CGSDefaultConnection() is NULL) and the process hangs.

Full output:
mac2:~ shots$ /Applications/Google\ Chrome.app/Contents/MacOS/Google\ Chrome --headless --disable-gpu --screenshot --window-size=1280,1696 https://www.chromestatus.com/
Nov 20 21:01:31 mac2 Google Chrome[65944] <Error>: Set a breakpoint at CGSLogError to catch errors as they are logged.
Nov 20 21:01:31 mac2 Google Chrome[65944] <Error>: This user is not allowed access to the window system right now.
_RegisterApplication(), FAILED TO establish the default connection to the WindowServer, _CGSDefaultConnection() is NULL.
Nov 20 21:01:31 mac2 Google Chrome[65944] <Warning>: CGSConnectionByID: 0 is not a valid connection ID.
Nov 20 21:01:31 mac2 Google Chrome[65944] <Warning>: CGSConnectionByID: 0 is not a valid connection ID.
Nov 20 21:01:31 mac2 Google Chrome[65944] <Warning>: CGSConnectionByID: 0 is not a valid connection ID.
Nov 20 21:01:31 mac2 Google Chrome[65944] <Warning>: CGSConnectionByID: 0 is not a valid connection ID.
Nov 20 21:01:31 mac2 Google Chrome[65944] <Warning>: CGSConnectionByID: 0 is not a valid connection ID.
Nov 20 21:01:31 mac2 Google Chrome[65944] <Warning>: Invalid Connection ID 0
Nov 20 21:01:31 mac2 Google Chrome[65944] <Warning>: CGSConnectionByID: 0 is not a valid connection ID.
Nov 20 21:01:31 mac2 Google Chrome[65944] <Warning>: CGSConnectionByID: 0 is not a valid connection ID.
Nov 20 21:01:31 mac2 Google Chrome[65944] <Warning>: CGSConnectionByID: 0 is not a valid connection ID.
Nov 20 21:01:31 mac2 Google Chrome[65944] <Warning>: CGSConnectionByID: 0 is not a valid connection ID.
Nov 20 21:01:31 mac2 Google Chrome[65944] <Warning>: CGSConnectionByID: 0 is not a valid connection ID.
Nov 20 21:01:31 mac2 Google Chrome[65953] <Error>: Set a breakpoint at CGSLogError to catch errors as they are logged.
Nov 20 21:01:31 mac2 Google Chrome[65953] <Error>: This user is not allowed access to the window system right now.
Nov 20 21:01:32 mac2 Google Chrome[65953] <Error>: CGContextConcatCTM: invalid context 0x0. This is a serious error. This application, or a library it uses, is using an invalid context  and is thereby contributing to an overall degradation of system stability and reliability. This notice is a courtesy: please fix this problem. It will become a fatal error in an upcoming update.
Nov 20 21:01:32 mac2 Google Chrome[65953] <Error>: CGContextConcatCTM: invalid context 0x0. This is a serious error. This application, or a library it uses, is using an invalid context  and is thereby contributing to an overall degradation of system stability and reliability. This notice is a courtesy: please fix this problem. It will become a fatal error in an upcoming update.
Nov 20 21:01:32 mac2 Google Chrome[65953] <Error>: CGContextGetCTM: invalid context 0x0. This is a serious error. This application, or a library it uses, is using an invalid context  and is thereby contributing to an overall degradation of system stability and reliability. This notice is a courtesy: please fix this problem. It will become a fatal error in an upcoming update.
Nov 20 21:01:32 mac2 Google Chrome[65953] <Error>: CGContextGetDefaultUserSpaceToDeviceSpaceTransform: invalid context 0x0. This is a serious error. This application, or a library it uses, is using an invalid context  and is thereby contributing to an overall degradation of system stability and reliability. This notice is a courtesy: please fix this problem. It will become a fatal error in an upcoming update.
Nov 20 21:01:32 mac2 Google Chrome[65953] <Error>: CGContextSaveGState: invalid context 0x0. This is a serious error. This application, or a library it uses, is using an invalid context  and is thereby contributing to an overall degradation of system stability and reliability. This notice is a courtesy: please fix this problem. It will become a fatal error in an upcoming update.
Nov 20 21:01:32 mac2 Google Chrome[65953] <Error>: CGContextConcatCTM: invalid context 0x0. This is a serious error. This application, or a library it uses, is using an invalid context  and is thereby contributing to an overall degradation of system stability and reliability. This notice is a courtesy: please fix this problem. It will become a fatal error in an upcoming update.
Nov 20 21:01:32 mac2 Google Chrome[65953] <Error>: CGContextGetAlpha: invalid context 0x0. This is a serious error. This application, or a library it uses, is using an invalid context  and is thereby contributing to an overall degradation of system stability and reliability. This notice is a courtesy: please fix this problem. It will become a fatal error in an upcoming update.
Nov 20 21:01:32 mac2 Google Chrome[65953] <Error>: CGContextRestoreGState: invalid context 0x0. This is a serious error. This application, or a library it uses, is using an invalid context  and is thereby contributing to an overall degradation of system stability and reliability. This notice is a courtesy: please fix this problem. It will become a fatal error in an upcoming update.



If user is logged-in in Mac OS GUI, everything works OK.