This would work as you expect, mostly, in real trading. It will never work in simulation entirely right. That is partly because of some limitations of simulators and partly because the nature of the data the simulator is given.
RE works with events. 'New Bar' is an event but not fine-grained enough for the two (sequential) actions you want (actually 3 since there is a fill that must occur). A bar is made up of many ticks, and thus many events (sequentially), and so RE can process several actions within one bar. That's what you want. However, if your data feed is bars and RE is 'generating' ticks from bars, you still will not see quite the behavior you want. But you will be closer.
Things will work better when you move to ticks. Your understanding of the sequence of events will be much better if you include "OutputMessage" liberally in your code.