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According to the doc,
"In prudent mode, file compression is not supported nor allowed. (We can't have one JVM writing to a file while another JVM is compressing it.)".
so in the zip compression case, the prudent mode cannot be used.
also looked
LOGBACK-162, it talked about a different topic - cannot delete the old zip files if number of the archive files exceeds MaxHistory. In LOGBACK-879, it concerns about an issue: cannot delete the old files which have been zipped into a zip file. Those files are unzipped and original. After the compression, they need to be cleaned up.