@rpearcy Hi, this is because the name of the request is the same and thus, the new data is overriding the existing data in the same file.
What you can do is Right click the collection >Edit > Tests
And change the request name to the following:
requestName: `${request.name || request.url}-${pm.info.iteration}`,
Like so:
Now, for every iteration a new file will be stored along with the corresponding iteration that you ran via the runner.