Unable to flag an issue if you apply a context to the Flagged custom field

Issue Summary

The Flagged custom field is created after you first flag an issue in the Backlog. The field is not lock and allows editing. If you add a new context for the field with a new option, you won't be able to flag issues in any project associated with that new context. When attempting to do so, you'll receive a pop-up error in the UI to the effect of:

Invalid value '10100' passed for customfield 'Flagged'.

There are no errors logged to atlassian-jira.log or Catalina.out

Environment

Reproduced on Jira 7.6, 7.13, 8.4 on Linux.

Steps to Reproduce

1. Flag an issue on a backlog to create the Flagged custom field
2. Add a new context for the field, define an option and associate to a project:
   
3. Attempt to flag an issue on the backlog of the associated context
   

Expected Results

Issue should be flagged on the backlog.

Actual Results

Issue is not flagged & UI error thrown.

Notes

If this is expected behavior, the Flagged field should be locked to prevent editing of this nature.

Workaround

Currently there is no known workaround for this behavior. A workaround will be added here when available.