I would like to create a custom field that behaves like assignee, called Tester, in that when it is displayed on the screen, it will have the users icon picture and will display unassigned if it is unassigned.
Currently, if a generic user picker is created, if no one is selected it does not display, and it does not display the users avatar.
tester Assignee.jpg
Unfortunately, that is how the user picker custom field works. You will have to write a plugin to expose a field similar to assignee but that will not be possible in Cloud.
Vote for this feature request: https://jira.atlassian.com/browse/JRA-33883. It is a step in the right direction.
It would definitely be nice to have parity between the behavior of the user picker in the Assignee and Reporter and the behavior of the custom field User Picker. Both the functionality to show the selected user's avatar as well as display the field even when it's not set (or set it to Unassigned like the user picker for the Assignee/Reporter fields... yet another difference in behavior).
I would create a more consistent user experience IMO. I was definitely disappointed the first time I added the User Picker custom field.
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