Witty Pi 4 mini, missing scheduled startups

Hi, I'm working on my first raspberry pi project with wittypi and a zero 2w, and it seems to be randomly missing scheduled startups. Recently I got a Voltaic Systems v25 battery and solar panel ( https://voltaicsystems.com/v25/) to hook up with the wittypi. Before this, I was just using a generic power bank that seemed to work fine, the only limit being the battery running out.

Now with this new system I'm having a hard time troubleshooting. There's no indication of anything going wrong in the logs (schedule for 5mins up every 20 mins):

[2025-02-01 20:20:20] Current Vout=4.77V, Iout=0.45A
[2025-02-01 20:20:20] System starts up because scheduled startup is due.
[2025-02-01 20:20:25] Schedule next shutdown at: 2025-02-01 20:25:00  
[2025-02-01 20:20:26] Schedule next startup at: 2025-02-01 20:40:00   <-- next startup at 20:40
USB mounted successfully
mkdir: cannot create directory ‘/media/data/images/2025-02-01’: File exists
[2025-02-01 20:22:03] Send out the SYS_UP signal via GPIO-17 pin.
[2025-02-01 20:22:03] Pending for incoming shutdown command...
[2025-02-01 20:24:58] Shutting down system because scheduled shutdown is due.
[2025-02-01 20:24:58] Halting all processes and then shutdown Raspberry Pi...  <-- doesn't startup until I press button much later
[xxxx-xx-xx xx:xx:xx] Witty Pi daemon (v4.21) is started.
[xxxx-xx-xx xx:xx:xx] System: Debian GNU/Linux 12 (bookworm), Kernel: Linux 6.6.31+rpt-rpi-v8, Arc>
[xxxx-xx-xx xx:xx:xx] Running on Raspberry Pi Zero 2 W Rev 1.0
[xxxx-xx-xx xx:xx:xx] RTC offset register has value 0x77
[xxxx-xx-xx xx:xx:xx] Seems RTC has good time, write RTC time into system
[xxxx-xx-xx xx:xx:xx] Writing RTC time to system...
[2025-02-01 21:02:40] Done 🙂
[2025-02-01 21:02:40] Firmware ID: 0x36
[2025-02-01 21:02:40] Firmware Revison: 0x05
[2025-02-01 21:02:40] Current Vout=4.71V, Iout=0.32A
[2025-02-01 21:02:40] System starts up because the button is clicked.

Once I press the button it starts up and will resume a normal schedule for a while. I haven't found any evidence of the battery losing power/connection at the critical startup time. I simply watch the startup time come and go and the Pi just pretends like nothing's happening.

My main questions at this point are:

1. To install the wittypi I used a kit from Adafruit where you can push in the header pins without soldering. I assumed that this was an alternative to soldering because it worked for so long but now I'm questioning if that is causing some sort of poor connection. This was before I realized you can buy a zero 2w with header already soldered.

2. I'm wondering if there's a possible workaround, such as being able to try multiple startups in a row or something? it's very fragile because if a single startup is missed, then the whole system breaks will never start up again automatically.

Any thoughts on my issue here would be greatly appreciated.