Uploading files through vSphere Client you receive the following error: "The operation failed for an undetermined reason"

Products

VMware vCenter Server VMware vSphere ESXi

Issue/Introduction

Initiating a file upload to either a content library or datastore, or attempting to deploy an OVF or OVA template, might result in the operation failing with an error:

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://target-ip

Environment

VMware vSphere ESXi 6.5
VMware vCenter Server 6.7.x
VMware vSphere ESXi 6.7
VMware vCenter Server 6.5.x
VMware vCenter Server 7.0.x
VMware vCenter Server 8.0.x

Resolution

Follow the solutions below as per the scenario.

Solution 1:

From a client system Web browser, go to the base URL of the vCenter Server system or the vCenter Server Virtual Appliance without appending port numbers or 'vsphere-client' extension.
For example:
https://vcenter.domain.com/
Enter the vCenter FQDN details on a Web browser.
Click the Download trusted root CA certificates link at the bottom of the grey box on the right and download the file.

Note: if there is a new tab with a lot of text by clicking on Download trusted root CA, open the same link on a different browser or do a right-click and select the option Save as...

Change the extension of the file to .zip. The file is a ZIP file of all root certificates and all CRLs in the VMware Endpoint Certificate Store (VECS).
Extract the contents of the ZIP file. The result is a .certs folder that contains two types of files. Files with a number as the extension (.0, .1, and so on) are root certificates. Files with an extension that starts with an r (.r0,. r1, and so on) are CRL files associated with a certificate.
Install the certificate files as trusted certificates by following the process that is appropriate for the operating system used.
For most Microsoft Windows systems, follow the instructions at Manage trusted root certificates.

Notes:

Firefox browser has its own trusted roots store and does not use the operating system store. If using Firefox, download the certificate as described above, and then select Settings > Privacy & Security for Certificates, and click View Certificates Tab to import.
Some datastores with special characters will not allow the downloads of files. In some cases, removing the special characters from the datastore name has allowed us to download. This is a rare problem, and the above solution is more likely.

Solution 2:

In some cases, the Serenity database becomes corrupt, reset Serenity DB to resolve the issue.

The impact of resetting the Serenity database is very tiny -- when connecting to the vCenter through the web client, it will take a few seconds longer than usual while the system rebuilds that database.

Follow the below steps:

- The below path is applicable for prior to vSphere 6.0 version appliance:
  # service vsphere-client stop
  rm -rf /etc/vmware-vsphere-client/SerenityDB/serenity/*
  # service vsphere-client start
- For vSphere 6.5.x and vSphere 6.7.x follow the below path
  # service-control --stop vsphere-client
  rm -rf /storage/vsphere-client/SerenityDB/serenity/*
  # service-control --start vsphere-client
- For vSphere 7.0 and above
  # service-control --stop vsphere-ui
  rm -rf /storage/vsphere-client/SerenityDB/serenity/*
  # service-control --start vsphere-ui
- In Windows:
  # cd <C:\Program Files\VMware\vCenter Server\bin>
  # service-control --stop vspherewebclientsvc
- Delete the contents of the folders below.
  <C:\programdata\vmware\vCenterServer\data\vSphere Web Client\SerenityDB\serenity>
  #service-control --start vspherewebclientsvc

Solution 3:

The "details" window of the failed file upload task may provide the name of an ESXi host the vCenter is having trouble trusting. The window may also provide instructions to resolve the trust issue by accessing the ESXi host vSphere client, only needing to accept the host certificate, proceeding to the login page.
- If an error related to HSTS is received when accessing the ESXi vSphere client, perform the following steps:
  - Clear client browser cookies for at least the specific ESXi host vSphere client webpage or clear all cookies.
- Once browser cookies are deleted, it should be possible to accept the ESXi vSphere client certificate and proceed to the login page.
- After proceeding to the ESXi login page, it is now possible to upload files from the vCenter vSphere client.

Additional Information

As a workaround, Continue uploading files from esxi host client.
If the issue persists despite the above resolutions, file a case with Broadcom Support and note this KB article ID (343447) in the problem description.
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