Usually we forget to associate work item before check-in files or the work item associating fail while check-in. Below are the steps to associate work item to changes set after check-in the files.
1. Keep change set id and go to Work Item, the one need to associate to change set.
2. Click on 'Link to' as shown in below image,
4. result will be as shown in below image. Save work item to complete the action.
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