How many entrants do you have the shows set to?

Minimum entrants is 1 and maximum is 20. I've tried setting the max to 10 but it didnt seem to change anything

I cannot say for random shows nor minimum. This is how I do it:

I have mine set to Disciplines only. Primary Discipline to be exact. Minimum number of entrants is 0 and Maximum is 30.

That set up has always worked out for me no problem. Just on occasion when I am entering my flat racers, sometimes Foundie or Local tier will have well over 30 entrants and I have to go in manually on the horses' page itself and change it to 100, even though some of these horses are tier II, the Enter All ((not the second version)) does not recognize this and just counts tier I as altogether and putting it to over 100 allows all my horses to be entered and it may be possible when you are entering your horses, those shows get filled up to your limits fast.

Try changing it up to how I have my way set up and see how it goes for a little bit?

Dusty has the right idea!

I'm 99% sure your issue emfermo is your min/max not being high enough.  I have my min set to 0, max set to 2000 (just so it never encounters the issue of being too low lol.) If you up your max entrants, it should work fine. I use random as well in mine and it works. I show almost exclusively eventing on all 3 accounts, so if you're doing eventing you're going to for sure need to up it from 10 or 20 max as I just...dump all mine in shows when I get a chance to play. I know a few players show specific disciplines (Driving, WP, Cutting, Eventing, SJ are all VERY common discs) so those commonly used ones are going to almost always have higher amounts of entries - even with multi shows a day. Just really depends on when certain people are on and actively showing! I will say, more entries doesn't necessarily mean you're not going to get good points/payout, it's not based on entries per say and everything goes by percentages so ultimately it doesn't matter if there's 10 entries or 1000 entries, don't let higher filled shows scare you from disc showing if you truly wanna disc show! 

IF you do chance your max to a higher number and it still throws an error, feel free to post a screenie of your settings and we can always look if it may be something else. For what it's worth, these are my personal settings on my accounts: https://ibb.co/1JHs8W2 

I keep my max at 20 and I usually dont have issues but sometimes on lower-tier horses I have to raise it to 50 to get all 10 entrants. I prefer lower entrants, but that's a personal preference. If you dont mind then I would put a higher number as well because sometimes they can get well into the hundreds. 

Thank you all for the suggestions!! I'll try them out and see if it fixes it :)

Jumping in on this thread a bit late... I recently purchased the Enter All button and am having an issue where it doesn't always use all of my horse's energy. Sometimes it does, but other times it leaves them with 20-40%. That's after I read this thread and set my entrants to min 0/max 2000.

What's different is I do have it set to enter halter shows as most of my horses do well there and I've found it to be the best and fastest way to level them up. I have my settings at 2 halter and 6 discipline. 

Any thoughts about why it tends to leave some energy on the table under these settings?