I have three MacBook Pros "MBP", two running High Sierra, one running Ventura. One of the High Sierra I carry with me to different work locations.
I have multiple iOS devices (iPhones, iPads, iPad Pro), and I carry two iPhone with me to different work locations. All my iOS devices are on the latest iOS (16.6)
I've been having this issue of the various devices forgetting WiFi password since about April or May 2023, around the time I upgraded my iCloud from the free 5G to the paying 2TB plan. But it could also have coincided with an iOS upgrade.
The issue has definitely nothing to do with my MacOS, since I didn't upgrade the MacOS at that time. Though I may have upgraded the Ventura; the High Sierra have been their latest versions.
Even when I don't move my MBP from site to site, after sleep or after restart, they will occasionally forget the password and I have to re-enter the WiFi password.
When I go to my my habitual work or home locations (I am a physician working at 5 different clinic locations), the MBP and the iPhones I carry with me will forget WiFi passwords, such I have to re-enter the password on each device before I can log into the clinic WiFi network. I need to connect to the clinics' network to use their network resources. Since each clinic has their own unique password, it can be quite frustrating.
Since Aug 1, Apple has reached out to me weekly, and I've helped them collect Analytics information from my iOS devices at the different sites - Analytics at the time the WiFi password was forgotten, and Analytics after the WiFi connects. I've sent them over 70 files (screenshots and Analytics) - totalling gigabytes of data. It's been a fairly time consuming process.
If any of you get contacted by Apple, try to collect data to submit to them. It's definitely an iCloud keychain problem, and they need to get to the bottom of this. What is seemingly an annoying problem now, could snowball into something bigger. Let's hope this issue is resolved ASAP.