We are on Jira 8.20.0 Server, self hosted, with all three installed
- Jira Core 8.20.0
- Jira Software 8.20.0
- Jira Service Managment 4.20.0

In our attempt to examine our migration to the could version, we where being blocked by the "Insights" (com.riadalabs.jira.plugins.insight: 9.1.2) plugin, and in order to check if we could move forward we went ahead and disabled it temporarily.
It seems that this is the core plugin form Service Desk, and after disabling this, our Service Desk projects as well as our customer portals where not available anymore. Furthermore we couldn't "enable" the plugin again, which showed a generic error, and no errors in the logs.
In our attempt to fix the problem we went ahead re-installed a fresh installation of our backup .tar.gz for 8.20.0, and the Insight plugin is enabled, as well as the three installations show that they are installed.
However, all the Service Desk Projects still acts as simple projects, our queues are gone, and portal urls display a 404 message. We can't even create a Service Desk project anymore.
In our logs during startup we are noticing this message which just times out
2022-01-06 23:21:59,542+0200 JIRA-Bootstrap INFO [c.a.plugin.util.WaitUntil] Plugins that have yet to be enabled: (17): [com.atlassian.servicedesk.servicedesk-knowledge-base-plugin, com.atlassian.servicedesk.servicedesk-reports-plugin, com.atlassian.servicedesk.approvals-plugin, com.atlassian.servicedesk.plugins.automation.servicedesk-automation-then-webhook-plugin, com.atlassian.servicedesk.public-rest-api, com.atlassian.servicedesk.servicedesk-variable-substitution-plugin, com.atlassian.jira.mobile.jira-mobile-rest, com.intenso.jira.plugins.jsd-extender, com.atlassian.servicedesk.plugins.automation.servicedesk-automation-modules-plugin, com.atlassian.servicedesk.servicedesk-lingo-integration-plugin, com.atlassian.servicedesk.incident-management-plugin, com.atlassian.servicedesk, com.atlassian.servicedesk.frontend-webpack-plugin, com.atlassian.servicedesk.project-ui, com.atlassian.servicedesk.plugins.servicedesk-search-plugin, com.atlassian.servicedesk.servicedesk-notifications-plugin, com.atlassian.servicedesk.servicedesk-canned-responses-plugin], 1 seconds remaining
And the modules are disabled in the "System > Manage Apps > Application components" with no way to enabled them.

This is what is available in the database
> select * from pluginstate ;
pluginkey | pluginenabled
-----------------------------------------------------------------------------------------+---------------
com.atlassian.jira.jira-view-issue-plugin | true
com.atlassian.jira.jira-projects-plugin | true
com.atlassian.jira.plugins.jira-importers-plugin | true
com.atlassian.jira.jira-issue-nav-components | true
com.atlassian.jira.plugins.workflow.sharing.jira-workflow-sharing-plugin | true
com.atlassian.jira-core-project-templates | true
com.atlassian.jira.project-templates-plugin | true
com.atlassian.jira.rest | true
com.atlassian.jira.plugins.jira-workflow-designer | true
com.atlassian.jira.jira-project-config-plugin | true
com.onresolve.jira.groovy.groovyrunner:jsd-canned-comment-loader | false
com.onresolve.jira.groovy.groovyrunner | true
com.atlassian.jira.jira-software-application | true
com.atlassian.jira.plugin.ext.bamboo | true
com.atlassian.jira.plugins.jira-bitbucket-connector-plugin | true
com.atlassian.jira.plugins.jira-development-integration-plugin | true
com.atlassian.jira.plugins.jira-software-plugin | true
com.atlassian.jira.plugins.jira-transition-triggers-plugin | true
com.atlassian.jirafisheyeplugin | true
com.atlassian.jpo | true
com.atlassian.teams | true
com.pyxis.greenhopper.jira | true
com.radiantminds.roadmaps-jira | true
com.atlassian.jira.plugins.workinghours | false
com.refinedwiki.jira.todos | true
com.atlassian.servicedesk.plugins.automation.servicedesk-automation-then-webhook-plugin | true
com.atlassian.servicedesk.public-rest-api | true
com.atlassian.servicedesk.plugins.servicedesk-search-plugin | true
com.atlassian.servicedesk.approvals-plugin | true
com.atlassian.servicedesk.servicedesk-notifications-plugin | true
com.atlassian.servicedesk.frontend-webpack-plugin | true
com.atlassian.servicedesk.project-ui | true
com.atlassian.servicedesk.servicedesk-knowledge-base-plugin | true
com.atlassian.servicedesk.servicedesk-canned-responses-plugin | true
com.atlassian.servicedesk.servicedesk-variable-substitution-plugin | true
com.atlassian.servicedesk.servicedesk-lingo-integration-plugin | true
com.atlassian.servicedesk.servicedesk-reports-plugin | true
com.atlassian.servicedesk.incident-management-plugin | true
com.atlassian.servicedesk.plugins.automation.servicedesk-automation-modules-plugin | true
com.atlassian.servicedesk | true
Finally, we also try upgrading to 8.21.0, which allows us to upgrade Service Desk to 4.21.0, however the problem still remains.
At the moment we are stuck, and are facing a real issue given we can't serve our customers in any way.