I have something similar (using logback 1.0.7) but we use <cleanHistoryOnStart>true</cleanHistoryOnStart> and we have a.gz extension in the filenamePattern to try and force rollover/archive removal/compression.

That works overnight (but only compresses one previous file) but restarting the application mid-day DOES do a rollover, but doesn't trigger an archive/compress.

I will try to find a simpler (and more reproducible) use case, ours is quite complex as we are trying to fit logback into an existing logfile format/rollover policy.

    <appender name="FILE" class="ch.qos.logback.core.rolling.RollingFileAppender">
        <file></file>
        <rollingPolicy class="ch.qos.logback.core.rolling.TimeBasedRollingPolicy">
            <!-- daily rollover -->
            <fileNamePattern>${jetty.logs}/newssolr.log.%d{yyyyMMdd}_%d{HHmmss,aux}.gz</fileNamePattern>
            <!-- keep 5 days' worth of history -->
            <maxHistory>5</maxHistory>
            <cleanHistoryOnStart>true</cleanHistoryOnStart>

            <timeBasedFileNamingAndTriggeringPolicy
                class="ch.qos.logback.core.rolling.SizeAndTimeBasedFNATP">
                <!-- or whenever the file size reaches 100MB -->
                <maxFileSize>100MB</maxFileSize>
            </timeBasedFileNamingAndTriggeringPolicy>
        </rollingPolicy>
 
        <encoder>
            <pattern>%date %level [%thread] %logger{10} [%file:%line] %msg%n</pattern>
        </encoder>
    </appender>