Comment 30 for bug 1891657

Trying again... After reading the linked systemd bug report, I changed /usr/lib/systemd/system/apport-autoreport.path from having PathExistsGlob to PathChangedGlob and ran sudo systemctl daemon-reload, and this seemed to fix the problem:

[Unit]
Description=Process error reports when automatic reporting is enabled (file watch)
ConditionPathExists=/var/lib/apport/autoreport

[Path]
PathChangedGlob=/var/crash/*.crash

[Install]
WantedBy=paths.target

Now journalctl -e shows:

Sep 23 18:00:35 xps15 whoopsie-upload-all[12306]: /var/crash/_opt_wine-devel_bin_wine-preloader.1000.cr>
Sep 23 18:00:35 xps15 whoopsie-upload-all[12306]: All reports processed
Sep 23 18:00:35 xps15 systemd[1]: apport-autoreport.service: Succeeded.
Sep 23 18:00:35 xps15 systemd[1]: Finished Process error reports when automatic reporting is enabled.