I use a shell script to announce the time as described in this old-but-still-accurate forum topic.
In order for this to work, I have to open VoiceOver Utility and select the "Allow VoiceOver to be controlled with AppleScript" checkbox. This is no problem. It's a one-time change, and afterwards, the script runs when invoked with a Keyboard Commander keypress.
However, for multiple releases going back years including the most recent 12.5.1, upgrading causes this setting to malfunction. The checkbox is still checked, but the scripts can no longer be invoked by keyboard Commander. After each upgrade, I must open VoiceOver Utility, uncheck the checkbox, then check it again. After this, Keyboard Commander once again will execute my time script.
This is clearly a bug: after an upgrade, the checkbox is checked, but the setting is not active until I uncheck the box and check it again.
I've reported this to Apple. I've mentioned it in the blog post for each release where I experience it. It naggingly persists. Thus, I'm opening this forum topic to increase visibility.
Could the AppleVis editors consider opening this as a bug in the bug tracker database? Thanks.
Has been around at least since 11.1
I dug through some old posts to find out when I first mentioned the issue. I found a post where I reported a repeated experience of the issue after the 11.2 upgrade. So the issue has been present since at least 11.1.
Here's the 11.2 discussion. See my comment with title "Executing script from keyboard commander broke - again"
Being the squeaky wheel
This bug is still present immediately after upgrading to 12.6.
Strangely it seems to work…
Strangely it seems to work after a while. I use VOCR quite a bit and, in the latest beta, though it doesn't work after restart immediately, neither does the time callout command, it seems to work after a time... So not fixed, maybe patched?