Error Uploading Files to Datastore or Deploying OVAs in vSphere 6.5

If you’ve deployed vCenter Server using self-signed certificates you may run into an issue when trying to upload files to a datastore or deploy an OVA file. The message is along the lines of:

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.

https://fqdn

If this does not resolve the problem, other possible solutions are shown in this KB article:

http://kb.vmware.com/kb/2147256

Window showing error received in vSphere 6.5 from trying to upload an ISO to a datastore through a web browser.

Fortunately, the fix for this is usually pretty simple. You just need to install the trusted root CA certificates from you vSphere install.

The Fix for Datastore Uploading Error in vSphere 6.5:

  1. Open a browser and navigate to the url of your vcenter server (e.g. https://vcenter.mydomain.com)
  2. Note the “Not Secure” message next to your url.
  3. At the getting started page, click the link in the bottom right labeled “Download trusted root CA certificates.” This will download a compressed zip archive, most likely labeled download.zip.
  4. Note the contents of the zip file, there should be security certificate .crt files.
  5. Extract the contents of the compressed zip file.
  6. Double-click on the security certificate file (or right click and click Install Certificate).
  7. The Certificate Import Wizard will launch. Select the radio button next to “Local Machine” under Store Location and click Next.
  8. Select the radio button next to “Place all certificates in the following store” and choose “Trusted Root Certification Authorities from the Browse… button and click Next.Click Finish to complete the import wizard.
  9. Restart your browser (in this example it is Chrome), navigate to the url of your vSphere Web Client, and verify that the SSL URL is now labeled “Secure”.
  10. You should now be able to upload files to your datastores or deploy an OVA file.

A note for Firefox users: In some versions you must add these security certificates within the browser options under Options -> Advanced -> Certification -> View Certificates -> Import.

If you still have problems uploading files and the error message is referencing the url of a specific host you may have other networking issues outside of vSphere. You might try logging into the web client of the ESXi host mentioned in the url and uploading the file as a workaround until you resolve the networking issue.

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