@Bearili We've seen this before with OBS. It could be a key timing issue.
Have you tried "direct key" mode on the Twiddler?
From Eric, the lead Twiddler engineer:
With a typical keyboard, you hold the key for a non-zero amount of time. On KeyDown, the key reports are sent to the host. Time passes. Depending on amount of time they key is held, additional repeat reports with the same information can be sent (side note: this is not the character repeat rate manifested on screen in a text editor, which the OS translates and has repeat delay controls for) on KeyUp an empty report is sent to the host.
With the Twiddler, when a chord starts to release, the KeyDown report is sent. The KeyUp (i.e. empty) report is sent immediately afterwards.
it's probable OBS's interpreter needs to the "key-held" time to have a longer duration. Likely because it is an application layer that receives events from a lower HID/Input later and it may appear and clear within an interval and their software may not be aware of (or if they do, acknowledge) those events