As reproducing it is actually pretty easy, with the benefit of hindsight:
~# systemd-run -P -p MountImages="/this/should/definitely/not/exist.img:/run/img2\:3:nosuid" false
Running as unit: run-u42.service
free(): double free detected in tcache 2
(! test -f /tmp/test-50-confext/etc/waldo )
fi
+# Sneak in a couple of expected-to-fail invocations to cover
+# https://github.com/systemd/systemd/issues/29610
+(! systemd-run -P -p MountImages="/this/should/definitely/not/exist.img:/run/img2\:3:nosuid" false)
+(! systemd-run -P -p ExtensionImages="/this/should/definitely/not/exist.img" false)
+(! systemd-run -P -p RootImage="/this/should/definitely/not/exist.img" false)
+(! systemd-run -P -p ExtensionDirectories="/foo/bar /foo/baz" false)
+
touch /testok