Hello,
By enabling Route anomalies on my routes layer, I was able to identify a few issues lollipops. It seems that the one below has 4 points. Three with a measure of zero at the intersection of the loop and the stick and one with a measure of 573.56 m at the end of the stick. Please see the screen below.
According to the following link, the lollipop has to have only two calibration points to be calibrated correctly in roads and Highways.

Loop and lollipop routes—Roads and Highways Desktop | Documentation
I ran the calibrate point tool as per the article with the settings below but the lollipop route still appears as non - monotonic . What am I missing here ?

Thanks,
Ihab