Hi @Denis_Chorbadzh ,

As you suggested, we've added stax2, woodstox jars, and integrated the libraries directory into plugin.zip.

Now we can see that the libraries folder getting extracted into /etc/vmware/vsphere-ui/vc-packages/vsphere-client-serenity/. Even with this change, we are still facing a timeout issue with our plugin. The org.springramework.orm unresolved dependency is still there but we're ignoring it as suggested and all the other dependencies are resolved/active.
At this stage, we are able to see plugin entry into /mob and "Failed" entry at Administration -> Client Plug-Ins. The vsphere_client_virgo.log shows an ERROR for deployment mentioning timeout but does not tell anything else.
Is there any other log to check or any debugging method to root cause the timeout issue? Please advice.

[2023-02-24T13:35:26.515Z] [INFO ] sdk-plugin-deployer-93 com.vmware.vise.plugin.status.LocalPluginStatusServiceImpl DEPLOYING: Deploying plugin package com.vcplugin.plugin:1.2.1.27 ...
[2023-02-24T13:35:26.516Z] [WARN ] sdk-plugin-deployer-93 com.vmware.vise.extensionfw.impl.PackageManifestParser Plugin version mismatch for com.vcplugin.plugin between the plugin registration info (1.2.1.27)
[2023-02-24T13:35:26.531Z] [INFO ] sdk-plugin-deployer-93 com.vmware.vise.extensionfw.impl.sandboxing.EsaBuilder Creating OSGi sandbox for package com.vcplugin.plugin with scope fullyIsolated
[2023-02-24T13:35:27.476Z] [INFO ] plugin-deploy13 com.vmware.vise.extensionfw.impl.PackagesDeployer Deploying plugin package 'com.vcplugin.plugin:1.2.1.27'.
[2023-02-24T13:35:27.476Z] [INFO ] plugin-deploy13 com.vmware.vise.extensionfw.impl.DeploymentEventLoggerImpl Event=PACKAGE_DEPLOY_BEGIN; Params=com.vcplugin.plugin, 1.2.1.27
[2023-02-24T13:45:26.841Z] [INFO ] plugin-discovery-bus-thread com.vmware.vise.vim.extension.PluginStatusTaskManager User: VSPHERE.LOCAL\vsphere-webclient-1c7d92d8-3b3b-4ec1-85ad-da68e934700d initiated plugin DOWNLOAD task for plugin com.vcplugin.plugin:1.2.1.27.
[2023-02-24T13:45:26.863Z] [INFO ] plugin-discovery-bus-thread com.vmware.vise.vim.extension.PluginStatusTaskManager User: VSPHERE.LOCAL\vsphere-webclient-1c7d92d8-3b3b-4ec1-85ad-da68e934700d initiated plugin DEPLOYMENT task for plugin com.vcplugin.plugin:1.2.1.27.
[2023-02-24T13:45:27.476Z] [ERROR] sdk-plugin-deployer-93 com.vmware.vise.extensionfw.impl.PackagesDeployer Package deployer timed out waiting for com.vcplugin.plugin:1.2.1.27;
[2023-02-24T13:45:27.489Z] [ERROR] sdk-plugin-deployer-93 com.vmware.vise.plugin.status.LocalPluginStatusServiceImpl DEPLOYMENT_FAILED: Error deploying plugin package com.vcplugin.plugin:1.2.1.27. Reason: Plugin deployment has timed out.
[2023-02-24T13:45:27.489Z] [INFO ] plugin-validation1 com.vmware.vise.extensionfw.impl.OsgiUsageValidationService Started validating com.vcplugin.plugin:1.2.1.27
[2023-02-24T13:45:27.489Z] [INFO ] plugin-validation1 com.vmware.vise.extensionfw.impl.OsgiUsageValidationService Begin VmwareNameMisuseCheck on com.vcplugin.plugin:1.2.1.27
[2023-02-24T13:45:27.490Z] [ERROR] plugin-deploy13 com.vmware.vise.extensionfw.impl.PackagesDeployer Error deploying one of more bundles for the plugin package /etc/vmware/vsphere-ui/vc-packages/vsphere-client-serenity/com.vcplugin.plugin-1.2.1.27 java.lang.InterruptedException: null
[2023-02-24T13:45:27.493Z] [INFO ] plugin-validation1 com.vmware.vise.extensionfw.impl.OsgiUsageValidationService End VmwareNameMisuseCheck on com.vcplugin.plugin:1.2.1.27
[2023-02-24T13:45:27.493Z] [INFO ] plugin-validation1 com.vmware.vise.extensionfw.impl.OsgiUsageValidationService Begin DynamicImportUsageCheck on com.vcplugin.plugin:1.2.1.27
[2023-02-24T13:45:27.493Z] [INFO ] plugin-validation1 com.vmware.vise.extensionfw.impl.OsgiUsageValidationService End DynamicImportUsageCheck on com.vcplugin.plugin:1.2.1.27
[2023-02-24T13:45:27.493Z] [INFO ] plugin-validation1 com.vmware.vise.extensionfw.impl.OsgiUsageValidationService Begin RequireBundleUsageCheck on com.vcplugin.plugin:1.2.1.27
[2023-02-24T13:45:27.493Z] [INFO ] plugin-validation1 com.vmware.vise.extensionfw.impl.OsgiUsageValidationService End RequireBundleUsageCheck on com.vcplugin.plugin:1.2.1.27
[2023-02-24T13:45:27.493Z] [INFO ] plugin-validation1 com.vmware.vise.extensionfw.impl.OsgiUsageValidationService Begin UnversionedPackageImportCheck on com.vcplugin.plugin:1.2.1.27
[2023-02-24T13:45:27.493Z] [ERROR] sdk-plugin-deployer-93 com.vmware.vise.vim.extension.VcExtensionManager Deployment of plugin package: 'com.vcplugin.plugin:1.2.1.27' registered in vCenter Server: 'VCSA80.test.com (a25c1537-d8c0-4ff4-bd69-09e97a946de0)' has failed. java.util.concurrent.CompletionException: com.vmware.vise.plugin.deploy.PluginDeploymentException: Deployment of plugin: 'com.vcplugin.plugin:1.2.1.27' in vCenter server: 'VCSA80.test.com (a25c1537-d8c0-4ff4-bd69-09e97a946de0)' failed!
Caused by: com.vmware.vise.plugin.deploy.PluginDeploymentException: Deployment of plugin: 'com.vcplugin.plugin:1.2.1.27' in vCenter server: 'VCSA80.test.com (a25c1537-d8c0-4ff4-bd69-09e97a946de0)' failed!
[2023-02-24T13:45:27.493Z] [INFO ] sdk-plugin-deployer-93 com.vmware.vise.plugin.registry.VcExtensionStateRegistry Updating entry: Plugin: 'com.vcplugin.plugin:1.2.1.27', State: 'FAILED_DEPLOY'
[2023-02-24T13:45:27.502Z] [INFO ] plugin-validation1 com.vmware.vise.extensionfw.impl.OsgiUsageValidationService End UnversionedPackageImportCheck on com.vcplugin.plugin:1.2.1.27
[2023-02-24T13:45:27.502Z] [INFO ] plugin-validation1 com.vmware.vise.extensionfw.impl.OsgiUsageValidationService Begin PluginPackageGlobalScopeCheck on com.vcplugin.plugin:1.2.1.27
[2023-02-24T13:45:27.502Z] [INFO ] plugin-validation1 com.vmware.vise.extensionfw.impl.OsgiUsageValidationService End PluginPackageGlobalScopeCheck on com.vcplugin.plugin:1.2.1.27
[2023-02-24T13:45:27.502Z] [INFO ] plugin-validation1 com.vmware.vise.extensionfw.impl.OsgiUsageValidationService Begin PluginDeploymentExceptionCheck on com.vcplugin.plugin:1.2.1.27
[2023-02-24T13:45:27.502Z] [INFO ] plugin-validation1 com.vmware.vise.extensionfw.impl.OsgiUsageValidationService End PluginDeploymentExceptionCheck on com.vcplugin.plugin:1.2.1.27
[2023-02-24T13:45:27.502Z] [INFO ] plugin-validation1 com.vmware.vise.extensionfw.impl.OsgiUsageValidationService Finished validating com.vcplugin.plugin:1.2.1.27
[2023-02-24T13:45:27.519Z] [WARN ] vice-extension-mngr-pool-144 com.vmware.vise.vim.extension.PluginStatusTaskManager Skip posting tasks for plugin package com.vcplugin.plugin:1.2.1.27: No task to update. This has no impact on plugin package deployment but is expected only during plugin development. In Production the plugin package should be registered as a vCenter extension.
[2023-02-24T13:45:27.519Z] [ERROR] plugin-deploy13 com.vmware.vise.plugin.status.LocalPluginStatusServiceImpl DEPLOYMENT_FAILED: Error deploying plugin package com.vcplugin.plugin:1.2.1.27. Reason: Deployment error. java.lang.InterruptedException: null
[2023-02-24T13:45:27.675Z] [ERROR] plugin-deploy13 com.vmware.vise.extensionfw.impl.DeploymentEventLoggerImpl Event=PACKAGE_DEPLOY_FAIL; Params=com.vcplugin.plugin, 1.2.1.27

The second thing is as mentioned in the document https://vdc-repo.vmware.com/vmwb-repository/dcr-public/77dd6491-bb96-47f3-8c2e-a5a4655f078b/b916bc3c... the libraries folder should be added in /usr/lib/vmware-vsphere-ui/plugin-packages/<Sample Plugin>. But we don't find any <Sample Plugin> package there.

Note: VCSA80.test.com is just for example. In our environment, it is FQDN and is resolvable.

Best Regards,

Shivam