Rollover does not occur for old files when short lived application is restarted. This issue is related to LBCORE-26.However, the solution implemented in LBCORE-26 works if the RollingFileAppender has the File property set. This is not always the case. For instance

<appender name="FILE" class="ch.qos.logback.core.rolling.RollingFileAppender">
<rollingPolicy class="ch.qos.logback.core.rolling.TimeBasedRollingPolicy">
<FileNamePattern>test.%d.log.zip</FileNamePattern>
</rollingPolicy>
<layout/>
</appender>
<root level="info">
<appender-ref ref="FILE"/>
</root>

Problem originally reported by Ch Pasha. See also http://www.qos.ch/pipermail/logback-user/2009-March/001030.html