When updating from any of Jira version 8 to 9.4.4, the process will fail with errors similar to the one below visible on the Jira server.

Unable to start JIRA.

• Jira 9.4.4.
• SSO
• Error
• Update from any of Jira version 8 to 9.4.4

On the Jira documentation page, it is stated: 

• Download the latest version of the Okta Authenticator plugin, as this is reportedly fixed in version 3.1.9. Check Okta Jira Authenticator Version History for more details.
• Replace the plugin JAR and restart Jira.

On May 3rd 2023 version 3.2.2 was released that is compatible with Jira Core: 8.20.20, 9.4.4, 9.7.0 / Jira Software: 8.20.20, 9.4.4, 9.7.0 / Jira Service Management (formerly JIRA Service Desk): 4.20.20, 5.4.4, 5.7.0
 

JIRA authenticator 3.2.2 supports JIRA version 9.4.4. Please follow the same documentation page provided by Atlassian, but use the JAR file from the 4.2.2 version of the toolkit.

Another possible alternative solution is to use Jira's native support for SAML. Please contact Jira support for additional information.