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A typical use for this workflow condition is when you can reach a certain Status from several other Statuses (through the same Transition) and want to be able to return to the originating Status.
Consider the following partial workflow :

JIRA will allow you to create a single Transition from both Open and In Progress statuses to the Waiting for clarification status. But how do you create the transition (Provide info) back to Open and In Progress? And, more importantly, how do you make sure the issue is transitioned back to the originating status?
Here's the trick:

1. create two Provide info transitions, one from Waiting for clarification to Open, and another from Waiting for clarification to In Progress (just add a space at the end of the name of one of the two transitions so that JIRA doesn't complain about duplicate transition names).
2. on the first transition, add a Previous Status Condition to make the transition available only if the previous status was Open (don't forget to check the "Most recent status only" checkbox).
3. on the second transition, add a Previous Status Condition to make the transition available only if the previous status was In Progress (don't forget to check the "Most recent status only" checkbox).

And voilà! Your users will see only one transition from the Waiting for clarification status, and it will transition the ticket back to the originating status.
You can also restore the previous Assignee by saving it in a custom field during the Request clarification transition and then restoring it during the Provide info transition (see Copy Value From Other Field workflow function in JIRA Suite Utilities). Alternatively, you can use the Assign to last role member function described below to assign the issue to the last user in the Users role.