New test install using pip on Debian 12.
python3 -m pip install weewx
This installed Pillow 10.0.0 which was just released (2023-07-01)
WeeWX dies with  unrecoverable exception in 
generator'weewx.imagegenerator.ImageGenerator'

Log:
Jul 01 17:44:05 rpi4dev python3[5337]: weewx[5337] INFO __main__: 
Initializing weewx version 5.0.0b5
Jul 01 17:44:05 rpi4dev python3[5337]: weewx[5337] INFO __main__: Using 
Python 3.11.2 (main, Mar 13 2023, 12:18:29) [GCC 12.2.0]
Jul 01 17:44:05 rpi4dev python3[5337]: weewx[5337] INFO __main__: Located 
at /home/panders/weewx-venv/bin/python3
Jul 01 17:44:05 rpi4dev python3[5337]: weewx[5337] INFO __main__: Platform 
Linux-6.1.0-9-arm64-aarch64-with-glibc2.36
Jul 01 17:44:05 rpi4dev python3[5337]: weewx[5337] INFO __main__: Locale is 
'en_US.UTF-8'
Jul 01 17:44:05 rpi4dev python3[5337]: weewx[5337] INFO __main__: Entry 
path: /home/panders/weewx-venv/lib/python3.11/site-packages/weewxd.py
Jul 01 17:44:05 rpi4dev python3[5337]: weewx[5337] INFO __main__: Using 
configuration file /home/panders/weewx-data/weewx.conf
Jul 01 17:44:05 rpi4dev python3[5337]: weewx[5337] INFO __main__: Debug is 0
Jul 01 17:44:05 rpi4dev python3[5337]: weewx[5337] INFO weewx.engine: 
Loading station type Simulator (weewx.drivers.simulator)
Jul 01 17:44:05 rpi4dev python3[5337]: weewx[5337] INFO weewx.engine: 
StdConvert target unit is 0x1
Jul 01 17:44:05 rpi4dev python3[5337]: weewx[5337] INFO weewx.wxservices: 
StdWXCalculate will use data binding wx_binding
Jul 01 17:44:05 rpi4dev python3[5337]: weewx[5337] INFO weewx.engine: 
Archive will use data binding wx_binding
Jul 01 17:44:05 rpi4dev python3[5337]: weewx[5337] INFO weewx.engine: 
Record generation will be attempted in 'hardware'
Jul 01 17:44:05 rpi4dev python3[5337]: weewx[5337] INFO weewx.engine: Using 
archive interval of 300 seconds (specified in weewx configuration)
Jul 01 17:44:05 rpi4dev python3[5337]: weewx[5337] INFO weewx.restx: 
StationRegistry: Registration not requested.
Jul 01 17:44:05 rpi4dev python3[5337]: weewx[5337] INFO weewx.restx: 
Wunderground: Posting not enabled.
Jul 01 17:44:05 rpi4dev python3[5337]: weewx[5337] INFO weewx.restx: 
PWSweather: Posting not enabled.
Jul 01 17:44:05 rpi4dev python3[5337]: weewx[5337] INFO weewx.restx: CWOP: 
Posting not enabled.
Jul 01 17:44:05 rpi4dev python3[5337]: weewx[5337] INFO weewx.restx: WOW: 
Posting not enabled.
Jul 01 17:44:05 rpi4dev python3[5337]: weewx[5337] INFO weewx.restx: 
AWEKAS: Posting not enabled.
Jul 01 17:44:05 rpi4dev python3[5337]: weewx[5337] INFO weewx.engine: 
'pyephem' detected, extended almanac data is available
Jul 01 17:44:05 rpi4dev python3[5337]: weewx[5337] INFO __main__: Starting 
up weewx version 5.0.0b5
Jul 01 17:44:05 rpi4dev python3[5337]: weewx[5337] INFO weewx.engine: Clock 
error is -0.10 seconds (positive is fast)
Jul 01 17:44:05 rpi4dev python3[5337]: weewx[5337] INFO weewx.engine: Using 
binding 'wx_binding' to database 'weewx.sdb'
Jul 01 17:44:05 rpi4dev python3[5337]: weewx[5337] INFO weewx.manager: 
Starting backfill of daily summaries
Jul 01 17:44:05 rpi4dev python3[5337]: weewx[5337] INFO weewx.manager: 
Daily summaries up to date
Jul 01 17:44:05 rpi4dev python3[5337]: weewx[5337] INFO weewx.engine: 
Starting main packet loop.
Jul 01 17:45:15 rpi4dev python3[5337]: weewx[5337] INFO weewx.manager: 
Added record 2023-07-01 17:45:00 EDT (1688247900) to database 'weewx.sdb'
Jul 01 17:45:15 rpi4dev python3[5337]: weewx[5337] INFO weewx.manager: 
Added record 2023-07-01 17:45:00 EDT (1688247900) to daily summary in 
'weewx.sdb'
Jul 01 17:45:17 rpi4dev python3[5337]: weewx[5337] INFO 
weewx.cheetahgenerator: Generated 8 files for report SeasonsReport in 1.78 
seconds
Jul 01 17:45:17 rpi4dev python3[5337]: weewx[5337] ERROR 
weewx.reportengine: Caught unrecoverable exception in generator 
'weewx.imagegenerator.ImageGenerator'
Jul 01 17:45:17 rpi4dev python3[5337]: weewx[5337] ERROR 
weewx.reportengine:         ****  module 'PIL.ImageFont' has no attribute 
'LAYOUT_BASIC'
Jul 01 17:45:17 rpi4dev python3[5337]: weewx[5337] ERROR 
weewx.reportengine:         ****  Traceback (most recent call last):
Jul 01 17:45:17 rpi4dev python3[5337]: weewx[5337] ERROR 
weewx.reportengine:         ****    File 
"/home/panders/weewx-venv/lib/python3.11/site-packages/weewx/reportengine.py", 
line 196, in run
Jul 01 17:45:17 rpi4dev python3[5337]: weewx[5337] ERROR 
weewx.reportengine:         ****      obj.start()
Jul 01 17:45:17 rpi4dev python3[5337]: weewx[5337] ERROR 
weewx.reportengine:         ****    File 
"/home/panders/weewx-venv/lib/python3.11/site-packages/weewx/reportengine.py", 
line 384, in start
Jul 01 17:45:17 rpi4dev python3[5337]: weewx[5337] ERROR 
weewx.reportengine:         ****      self.run()
Jul 01 17:45:17 rpi4dev python3[5337]: weewx[5337] ERROR 
weewx.reportengine:         ****    File 
"/home/panders/weewx-venv/lib/python3.11/site-packages/weewx/imagegenerator.py",
 
line 37, in run
Jul 01 17:45:17 rpi4dev python3[5337]: weewx[5337] ERROR 
weewx.reportengine:         ****      self.gen_images(self.gen_ts)
Jul 01 17:45:17 rpi4dev python3[5337]: weewx[5337] ERROR 
weewx.reportengine:         ****    File 
"/home/panders/weewx-venv/lib/python3.11/site-packages/weewx/imagegenerator.py",
 
line 109, in gen_images
Jul 01 17:45:17 rpi4dev python3[5337]: weewx[5337] ERROR 
weewx.reportengine:         ****      image = plot.render()
Jul 01 17:45:17 rpi4dev python3[5337]: weewx[5337] ERROR 
weewx.reportengine:         ****              ^^^^^^^^^^^^^
Jul 01 17:45:17 rpi4dev python3[5337]: weewx[5337] ERROR 
weewx.reportengine:         ****    File 
"/home/panders/weewx-venv/lib/python3.11/site-packages/weeplot/genplot.py", 
line 208, in render
Jul 01 17:45:17 rpi4dev python3[5337]: weewx[5337] ERROR 
weewx.reportengine:         ****      self._renderBottom(draw)
Jul 01 17:45:17 rpi4dev python3[5337]: weewx[5337] ERROR 
weewx.reportengine:         ****    File 
"/home/panders/weewx-venv/lib/python3.11/site-packages/weeplot/genplot.py", 
line 407, in _renderBottom
Jul 01 17:45:17 rpi4dev python3[5337]: weewx[5337] ERROR 
weewx.reportengine:         ****      bottom_label_font = 
weeplot.utilities.get_font_handle(self.bottom_label_font_path,
Jul 01 17:45:17 rpi4dev python3[5337]: weewx[5337] ERROR 
weewx.reportengine:         ****                         
 ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
Jul 01 17:45:17 rpi4dev python3[5337]: weewx[5337] ERROR 
weewx.reportengine:         ****    File 
"/home/panders/weewx-venv/lib/python3.11/site-packages/weeplot/utilities.py", 
line 581, in get_font_handle
Jul 01 17:45:17 rpi4dev python3[5337]: weewx[5337] ERROR 
weewx.reportengine:         ****      layout_engine=ImageFont.LAYOUT_BASIC, 
# See note 2 above
Jul 01 17:45:17 rpi4dev python3[5337]: weewx[5337] ERROR 
weewx.reportengine:         ****                    ^^^^^^^^^^^^^^^^^^^^^^
Jul 01 17:45:17 rpi4dev python3[5337]: weewx[5337] ERROR 
weewx.reportengine:         ****  AttributeError: module 'PIL.ImageFont' 
has no attribute 'LAYOUT_BASIC'
Jul 01 17:45:17 rpi4dev python3[5337]: weewx[5337] ERROR 
weewx.reportengine:         ****  Generator terminated
Jul 01 17:45:17 rpi4dev python3[5337]: weewx[5337] INFO weewx.reportengine: 
Copied 5 files to /var/www/html

Have another instance of WeeWX V5.0.0b5 running on Debian 12 which has 
Pillow9.5.0. 
If I pip uninstall Pillow 10.0.0
Then pip install Pillow==9.5.0 the problem is resolved.
Crazy you can't trust upstream packages to  not introducebreaking changes.

Paul

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