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On Windows x64, using Docker Toolbox and VirtualBox 6, when trying to create a new machine, it hangs for a long time at the "Waiting for an IP..." point, eventually timing out with this message:

Error creating machine: Error in driver during machine creation: Too many retries waiting for SSH to be available. Last error: Maximum number of retries (60) exceeded

enter image description here

I've got the paths to both VirtualBox and Docker Toolbox in my environment path.

I'm still wet behind the ears with Docker; anyone know what the issue is?

J. Scott Elblein
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2 Answers2

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Please see the issue I opened on both Docker and OpenSSH specifically dealing with this issue showing a full video reproduction of the issue, and the workaround including all the versions I tested:

https://github.com/docker/machine/issues/4483

https://github.com/PowerShell/Win32-OpenSSH/issues/1155

Before I posted this root cause and workaround/testing, I could find no reference to this ever being uncovered/reported and as far as I know, to date I cannot believe it is still not fixed.

Collin Chaffin
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Windows 10 version 1803 or higher ships with its own (beta) version of OpenSSH 7.7, a native port of the OpenSSH project. Unfortunately, that version seems to be incompatible with the latest Docker Machine, hence it fails to connect properly.

You can try to uninstall the OpenSSH client by navigating to Settings -> Apps -> Manage optional features (below Apps & features) and clicking on OpenSSH -> Uninstall.

Alternatively, you can remove C:\WINDOWS\System32\OpenSSH\ from the Windows PATH environment variable.

Source: Courtesy of Steve Cliff

IRQ
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    Thanks for the heads-up. I got a bit excited since it's the only real different answer I've seen so far in all my searching, but unfortunately, even after uninstalling Windows' OpenSSH and rebooting, the problem persists. – J. Scott Elblein Feb 02 '19 at 04:45