My guess is that your system is attempting to accelerate so quickly that the sensorless estimator can't lock onto the rotor and handle the transition from open-loop to closed-loop. When you are running using the sensor there is no open-loop period and so the motor is going to have the best possible response.
Have you confirmed using the Software Oscilloscope that your system is actually able to track your velocity profile? If you are trying to accelerate the motor faster than what it is capable of (given the system inertia and friction) you will see issues with the sensorless startup and wouldn't see those same issues when using a sensor.
When performing a sensorless startup you do not have full torque available. KMS will work with up to 50% load, and in some cases more, but it will struggle (like all sensorless estimators) with starting with 100% torque demand to meet a speed ramp.
Is there also a defined amount of time you have to take to ramp the motor to speed in sensorless control? If so what is that?
There is no defined time required to ramp up the motor when in sensorless. The startup failure occurs if the stall error or loss of sync error occurs during or just after (2x Stall Detect Time after transitioning from open to closed loop) the startup period. I would suspect that given your very fast acceleration, you are getting a stall error, but due to the proximity to the startup, it is showing up as a startup failure.
Also, what are the speed thresholds that the Estimator block takes over control. In the reference manual the estimator block looks to take over at 400 RPM?
The estimator will take over control based on the speed set in the Speed Threshold field on the Speed Control tab in Motor Manager. This will default to 10% of your rated speed.