In our Jira (v4.4) we are using Greenhopper (v5.7.4), as such Greenhopper makes use of the Flagged custom field to mark Impediments, it is of type "Multi-Checkboxes".
Whilst transitioning from one state to another we are using a pre-installed Post Function to try a set the Flagged custom field. Specifically we are trying the 'Set field value from User Property value' post function.
To support this 'post function' we have tried adding a transition property called flagged with value Impediment and referencing it in the 'post function'.
This doesn't work.
Essentially 2 questions arise.
For a better explanation of the default flagging behaviour see Flagging Issues in Greenhopper, this is what we want to automate in our transition's 'post function'.
Resolved the Issue - for those that may be looking for a similar solution - here is what I discovered, hope it helps.
Contacting Atlassian the following was suggested:
To set the multi checkbox custom field via post-function is possible. First of all, you need to install JIRA suites utility plugin:
https://plugins.atlassian.com/plugin/details/5048 After that, in the workflow transition, add a "Update Issue Custom Field" post function with your custom field and put the flagged option (e.g. Impediment) written in the "Custom Field Value" field.
So using the suggested "Update Issue Custom Field" post function I chose the Flagged custom field and used the value 'Impediment' on its own. This worked.
For another transition that unmarked the impediment I used the "Clear Field Value Function" and simple chose the "Flagged" field. This also worked at clearing the Impediment.