It could be one of the following 'simple' reasons...
1. Your workflow doesn't have a transition step for To-Do to In-Progress
2. The Jira project you are using with Greenhopper is not using the workflow above (Administrator | Your Project | Workflows)
3. The issue type you are trying to move to In-progress is not configured to use the workflow above (Administrator | Your Project | Workflows)
4. Your Rapid Board columns are not mapped to the statuses defined for In-progress in the workflow above (Agile | Rapid Board | Configure | Columns)
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