Please look at the image below. We work with Jira Agile and sprints. We move issues through different columns in our work flow. But we ALWAYS forget to log how many hours we've worked on specific issues.
Is there any way to have Jira prompt me the "Log work" field when I move an issue between the fields "In progress" and "Ready for test"?
On
As a first step you need to create a custom screen with log work field on it, here you can find a documentation how to do it => DOCS
The second step would be to associate the screen with transition from 'In Progress' to 'Ready to Test'. To achieve this you need to go to Workflow configuration, (Projects > ProjectName (PKEY) > Administration > Workflows), edit the transition and configure your new screen as a transition screen. Remember to publish changes to workflow otherwise you will not see any result. Detail documentation here.
One way to achieve this would be to create a custom screen that contained only the log work field. Then associate that screen with the transition from 'In Progress' to 'Ready to Test'.
That way, when you transition an issue the custom screen will pop up. It would still be up to the individual to complete the field, but they would have no excuse for forgetting to do it.