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I managed to reproduce your situation on my end.
I set the flaky test's On Error property to "Continue running" in the execution plan then it keeps going through the rest of the repetitions, however it also doesn't stop the current test. Anything after the Error message in that current item is still executed. If you are relying on the call to Log.Error to stop the current item, it looks like it won't do what you want.
I think TestComplete is doing exactly what it's told, so it's not necessarily a bug. TestComplete is just doing "Run this item until it fails, or until it's been run <count> times."
Maybe it would be worth creating a feature request for an option for the On Error property to have a new option for stopping the current iteration of the test and moving onto the next.
Here's where you can add a feature request:
https://community.smartbear.com/t5/TestComplete-Feature-Requests/idb-p/TestXCompleteFeatureRequests
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