When uploading file to Datastore you receive: The operation failed for an undetermined reason.  Typically this problem occurs due to certificates that the browser does not trust….

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In most corporate environments you will be using an Internal or External Certificate Authority and so you will be looking to use that, however in my lab I haven’t set one up.

When you connect to your vCenter (I have tested with Chrome and IE) you receive: There is a problem with this websites security certificate

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Select Continue to this Website (not recommended)

Your vCenter page will load.  At the Bottom Right there is an option to Download trusted root CA certificates

NOTE: I only saw and tested this with vSphere 6.5 and with the VCSA – I have read this option is only available with VCSA and in 6+

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Select this and save the ZIP file

Open the file and navigate to the Certs folder – there will be a Linux, Mac and Windows folder – open the appropriate folder4

There are two files, we want the file ending in 0 (NOT r0)

Extract this file by dragging to an appropriate directory

Rename the file by changing the extension from .0 to .cer

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Open a Command Prompt with Administrator rights and select Yes at the Prompt6

Type: certmgr.msc

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And press Enter – this will bring up the Certificate Manager

Navigate to Trusted Root Certification Authorities and expand this

Right click on Certificates and select All Tasks > Import

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Select Next and Browse to the Certificate you just renamed and select Next

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Leave the Defaults and Finish

Select Yes at the Security Warning

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And you should see: Import Successful

Close your Browser and then Re-open and try to access vCenter again

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After this I was able to upload files to my datastores