I've been having issues with Powerbeats Pro since day 1. I purchased my set about 2 months after launch and I purchased a second set about two weeks later for my fiancé.
My initial issues were getting the Powerbeats Pro to connect to my phone (iPhone XS Max) every time I put one in my ear, unlike my trusty Airpods, which always connect as soon as they go in an ear. In order to get the Beats to work, I would have slowly open/close/open the clamshell near my phone and it would then popup the graphic/widget showing everything was connected. Only then they would the earbuds function properly. (This only worked for a few weeks)
My fiancés Powerbeats Pro had issues out of the Gate connecting to her iPhone (iPhone X). She would get the Beats to connect, but after a few minutes of wearing them, one or both would stop working and she'd have to put them in the case and reset the connection by holding the reset button on the case and start the pairing process all over again each time she wanted to use them. The annoying part is this always happens when she is in the middle of a workout or on a walk away from the case, so she either abandons the headphones till her workout is completed or she listens to the one ear that is playing music until she is done. Luckily for her, these are the extent of her issues.
My issues on the other hand have escalated. Many on here complain about the left earbud, but my issue is primarily the right earbud. I will have the case on my counter and I will push down on both earbuds and verify on the power widget that each are charging and very carefully close the lid. Next morning I go to use them and the right one is either dead or where I left it charging the night before, i.e. 16%. Sometimes I will see on the widget the power jump from 16%(Red) to 47%(Green) then back to 16%(Red). Other times I will see the power go down rather than up while it shows its charging, or one earbud will stop charging while the other one charges and swap back and forth.
Recently I couldn't get the earbuds to properly pair to my phone, which I never unpaired after last use, but this is the life of a Powerbeats Pro owner. I go thru the daily case reset unpairing/repairing ritual, sometimes followed by the forget device ritual, which the last time I did this resulted in the case not even registering on my phone as a pairable device waiting to be discovered/paired. (i.e. no connection app and no indication in Bluetooth settings) No matter what I did, my phone or other devices could see my Powerbeats Pro. The case indicated it was trying to pair according to the light on it, but nothing launched the connection app. (FYI, I baby the case and these headphones, so it's not an issue from damage.) To fix this issue, I had to plug the case into my computer and connect to the Beats website for firmware updates, just to be told the firmware was already up to date and no new updates were available. Somehow this process did reset something, because I was finally greeted with the pairing screen (Connection App) on my phone as soon as I opened the case.
The most annoying thing I've yet to see anyone talk about has to do with the headphones being paired, but then somehow briefly unpairing, resulting in an earbud randomly going from full power to dead. For example, both earbuds will show 100% on the home screen widget when the case is open and also on the power widget, as they should, because they will usually be charging for more than 6 hours between each use. I will simply pull one earbud out (sometimes left first, sometimes right first) and place it in an ear, which will quickly be followed with the dreaded dead battery tone, rather than the happy connection tone. At this point I will place the earbud back in the case to join it's other brother, which the widget will now show 0% battery or very low battery on that specific earbud. Whenever this happens I will also need to repair the device otherwise it won't properly connect the one earbud that is still charged and working. (I will usually just abandon using the earbuds until they are both fully charged.) In my opinion, this issue has to be a software glitch, which makes the chip in the earbuds think it doesn't have battery and it forces them to shutdown until the case fully charges them again, because it only happens to whatever earbud I take out of the case first. I've had where I will check to see if the earbuds are properly connected and playing music, then I will put them back into the case to verify they still have the power first indicated, then I will proceed to get them back out a few minutes later, only to have this same issue happen with the first earbud that is removed from the case instantly showing 0%.
I purchased this product, because it was suppose to be built on Apples magical chip architecture for connecting to my iPhone with ease and I wanted beats magical sound and for the fact these earbuds were designed to stay in your ear while you workout. I love my Airpods, because they always work as intended, but if I workout with them, they fall out or have to be adjusted every 10 steps I take. The Powerbeats Pro can't even remember the device they are paired with most of the time, which is the least of their issues. I have a cheap $12.00 knockoff version which is Bluetooth and they have yet to randomly power off, loose connection or even fail to pair as soon as they are powered on and they stay functioning thru an entire workout session. It's just sad that these headphones have soo many issues given the price and name behind them.
I don't plan on purchasing anything else from Beats and I hope Apple adopts the "stay in head, sweat resistant, workout style headphone" going forward for their Airpod product line, because unlike Powerbeats Pro, Airpods actually work as advertised.