I created a custom field called Update free text. I have users submitting updates and dropping content into the field.
When I add the column to the custom field order for any selected filter, the column does not appear for some filters but does for others.
I believe that you're hitting a known bug, which report is available here. If this is the case, then you'll need to either manually select the Issue Types returned for your query, instead of "Any", or change the custom field context to be applicable on all issue types.
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