Are you sure the cue points were set when Quantize was on? Otherwise it will not quantize..
Normally when i press "loop out", the song will play to the next beatgrid, before it jumps to the start of the loop. But sometimes when i press "loop out", the loop instantly jumps to the start of the loop, causing the beatgrids to get out of sync. The loop lenght is still quantized. After about a minute it will randomly work like normal again. The problem occour about every half hour. The problem also occour when i have sync turned on.
I use the the ddj-rb. I don't know if it is the controller or softaware that is causing the problem.
I use windows 10, and rekordbox 5.0.1.
The problem also occoured in rekordbox 4
Video of the problem: https://www.youtube.com/watch?v=3s1gipWlhLg
Video of how it normally behave (when there is no error): https://youtu.be/WfORArs37pc
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Are you sure the cue points were set when Quantize was on? Otherwise it will not quantize..
Check these settings in the preferences:

I have all the settings enabled. I have tried turning them on and off, but neither did it work. I don't think that the problem is caused by wrong settings, as the problem ocour randomly. Sometimes, the vinyl/pitch stop working while the problem with the loop occour. In that case i can fix both problems temporary, by turning one of the decks, but ONLY when the vinyl/pitch stop aint working. The error is really weird and everything is happening totally random. I have tried reisntalling rekordbox, but neither did it work.
@frederique I have turned on auto-cue.