I am having the same problem as the other post with this name.
https://answers.atlassian.com/questions/6686/start-work-in-jira-and-activate-task-not-enabled-even-though-time-tracking-in-mylyn-is-on
I have followed all the steps and made sure my Status and Transition IDS are correct. I still get a greyed out "Start work in jira and activate task" button in my IDE.
Mylyn is set to allow time tracking as well as my JIRA account.
I am using onDemand. Is that the issue?
Here is my IDE settings for Mylyn
Here are my settings:
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