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vCenter – Unable to login with WinSCP

Hey all it has certainly been a while since I have posted anything, but I am back now and I have quite a few things in the pipeline including a walk through of my new home lab!! For now lets get down to business with being unable to login with WinSCP.

Today I wanted to cover an issue that has been plaguing me quite a bit the last few months. As I am sure you are all aware, VMware vSphere and ESX 6.7 has been out of support since October 2022. Back in August of 2022, my team members at the company I work for worked dilligently to upgrade all of the vCenters and ESXi hosts in out environment.

If you are not aware, upgrading a VCSA appliance from 6.7 to 7.0 involves deploying a new 7.0 appliance and migrating your settings from one to another. Our Friends at VMware have done an amazing job with building a wizard that does most of the work for you. Perhaps as part of my new lab I will try do a guide on the upgrade process as I am sure there are many companies out there who have yet to do the upgrade. In fact I might even go as far as upgrading to 8.0!! Tune in for more.

Back to the matter at hand, When you deploy a new vCenter one of the issues you may run into is not being able to log in with WinSCP. For those of you that do not know, WinSCP is a free application (donations are accepted and appreacated) that allows you to transfer files using the SCP protocol (among others) on a Windows PC and it gives you a nice graphical user interface. You can download a copy of WinSCP here. You can also download it using Chocolatey if that is your thing.

When you try to connect to vCenter using WinSCP you may get this message:

Host is not communicating for more than 15 seconds. If the problem repeats, try turning off ‘Optimize connection buffer size’.

This can be particularly annoying when you need to add or remove a file from vCenter and because like me you probably don’t add or remove files from vCenter all that often so most times you forget that this could be an issue.

To solve the issue you will need to log into vCenter using SSH as root and run this command:

chsh -s /bin/bash root

and press enter.

Once you have done this you can then retry connecting via WinSCP and the issue should be resolved. If you don’t have the root credentals, please check out this article to find out how you can get around that.

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