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Problem with Live Looping and Track Arm

Electric Raven

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So I got myself a MIDI Controller Keyboard. After fiddling around with the knobs and knob settings (unrelated) I've decided to try and set up loop recording. I somehow managed to edit the "Record" section to make it work, however, 90% of the time, it doesn't work. I have 2 MIDI inputs bound to VST tracks (Synth1 and Sketching Orchs, but it didn't matter which plugin I used).
I record the first section, wait out one or two loops, record the second section on the second instrument and after the loop starts again the second melody starts playing using the first instrument. After I stop the recording everything is fine again. Video Demonstration: 

I've tried:
- Changing everything in the "Record" tab
- 2 different keyboards
- Sending MIDI data using different MIDI Channels for each track rather than Omni
- Switching drivers from ASIO4ALLv2 to Fl Studio ASIO
- Changing the order of the tracks
- Recording directly into the tracks (Skipping the MIDI Inputs entirely).
- Finding references reading the manual

So... Any thoughts?
I'm using the latest version of Cakewalk.

Before posting this I decided to take another look. Turns out that this bug only happens if I start to play at the end of the loop (holding a key while the loop is going to it's beginning). If that happens (and that happens a lot to me), the whole recording that you are currently taking will inevitably play sound from the first instrument (after you're done recording, during the recording everything sounds fine).

Also found a bug (Is this a good place to put out bugs?):
The keybind for "Arm Recording" doesn't work if you start recording and then try to change it (it works in playback mode though).
"Allow Arm Changes During Playback/Record" is ticked and I can change the Track Arm using the mouse whether I am recording or simply playing back.

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