I use workflows with conditions to ensure a transition is not allowed if some extra data must be entered.
This works in terms that the transition button is not visible if it cannot be used, but how do I tell the user why they cannot do it?
The available options have pop-up help explaining what they do, perhaps if the unavailable options were shown, but disabled I could put something in the pop-up to help.
Perhaps I could display an annotated version of the workflow graph.
Even just a button to display a PDF.
It's not much, but assuming you have the free Jira Toolkit add-on, you can create a message custom field to show when viewing an issue. There's an article with an example of how the custom field works here: https://confluence.atlassian.com/jirakb/how-to-add-a-message-or-field-on-jira-create-issue-screen-759990667.html
A single custom field can show different messages for each project/issuetype combination by using different configuration contexts as shown in the article above. So don't feel like you need to create a separate custom field for every case.
You can also show/hide or adjust the contents of such a field based on issue conditions (who's viewing it, custom field values, issue status, etc) if you have additional add-ons like ScriptRunner, which can conditionally modify the attributes of a field in a variety of ways (the documentation for their Behaviours module goes into this).
Alternatively, you could drop conditions altogether for these cases and use validators. The transition is allowed to show, but can only successfully complete if validation passes (e.g., pop up a screen with all the fields required for that transition to be permitted, and validate that they've been filled appropriately). This may make it more clear to your users that there's a reason why the issue can't get to the desired status.
Whether validation is a good alternative depends on which validators are available on your instance and what needs to be able to block your transitions.
I cannot see me getting any more custom fields into the system, it is a large shared corporate resource and it is already weighed down.
It seems a shame for this thing to get to version 7 with no context sensitive help.
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