Upload Files to VMware Datastore Fails

KB ID 0001777


Whilst attempting to upload an ISO into a VMware datastore this morning, I got this error;

VMware upload fails certificates

The operation failed for an undetermined reason. Typically this problem occurs due to certificates that the browser does not trust. If you are using self-signed or custom certificates, open the URL below in a new browser tab and accept the certificate, then retry the operation.


I’ve encountered this exact problem once before here: VMware: ISO Upload or Deploy OVA Fails ‘Undetermined Reason’ It happens because you do not trust the CA that signed the certificate that vSphere is using. Go back to the initial logon page and click ‘Download Trusted Root CA Certificates‘. Note: if you have a stupid browser that tries to open the file (I’m looking at you Microsoft Edge!) Then choose ‘Save target as’ and save the zip file containing the root CA Certificates.

vSphere Download certificatesOpen the Zip file and choose the Windows or Mac version and locate the file that has the CRT extension, (the other file is a certificate revocation list, and you don’t need this). Double click the certificate and choose ‘Install Certificate‘.

vSphere Download CA Certificate

Select ‘Local Machine‘.

vSphere Download Certificate to Local Machine

Select the option to choose which store to use and put it in ‘Trusted Root Certification Authorities‘  > Then complete the import wizard, (and ensure it says import successful). Then restart your browser, log back into vSphere and try again.

vSphere Download CA Cert to Trusted

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Author: PeteLong

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1 Comment

  1. Thanks for this. The same issue happened for me a few vCenter Server upgrades ago and my workaround was logging into an ESXi host directly and uploading the file through it’s UI. It’s one of those “annoying but not annoying enough to find a solution” problems that I kept putting off.

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