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https://issues.apache.org/jira/browse/LOG4J2-2517?page=com.atlassian.jira.plugin.system.issuetabpanels:comment-tabpanel&focusedCommentId=16731679#comment-16731679
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Jon Hanson commented on LOG4J2-2517:
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I've just tried the project (with log4j2 2.11.1) on a macbook, and the 
behaviour seems intermittent. The first rerun it did roll the log file, on 
subsequent reruns it did not.

Regarding your erlier comment:
{quote}Re-reading your original issue description - Why would the log file time 
be after the JVM start-up time and if it is after the JVM startup time why 
would you want to roll it over?

The OnStartupTriggeringPoliciy's purpose is mainly to insure that each time you 
start up your application you use a different file then was used the previous 
time the application ran. If the file timestamp is newer than the JVM startup 
time then that already has to be true.
{quote}
I'm not sure how I can explain this any more clearly. It appears log4j2 is 
failing to roll the log file because by the time it checks the timestamp of the 
base file (logjam.log in my example) it has already re-opened that file for 
writing. This changes the file timestamp to a value that is later that the JVM 
startup time. If I put a breakpoint on the first line of the 
OnStartupTriggeringPolicy.initialize method and then check the log file 
timestamp before I execute that line, I can see the timestamp has changed to 
shortly before now.

> RollingFileManager OnStartupTriggeringPolicy never rolls the file on startup
> ----------------------------------------------------------------------------
>
>                 Key: LOG4J2-2517
>                 URL: https://issues.apache.org/jira/browse/LOG4J2-2517
>             Project: Log4j 2
>          Issue Type: Bug
>          Components: Appenders
>    Affects Versions: 2.11.1
>            Reporter: Jon Hanson
>            Priority: Minor
>         Attachments: log4j2.json, log4j2_debug.log
>
>
> I'm trying to get log4j2 (V2.11.1) to roll the existing log file at startup 
> before it starts logging into a new file. My config is atached to the jira. 
> I'm using a RollingFileManager with a OnStartupTriggeringPolicy with 
> minSize=0, which, according to the documentation should be sufficient.
> However what i'm finding is that at startup, the 
> {{OnStartupTriggeringPolicy}} class {{initialize}} method compares the 
> timestamp of the log file to the JVM startup, and if the log file time is 
> after the start-up time then it won't roll the file. If I step through the 
> code then I see that at the point that check is made the file time is always 
> after the JVM start time, because log4j2 appears to have already opened the 
> file for writing at that point.
> More info here:
> [https://stackoverflow.com/questions/53632091/log4j2-rollingfilemanager-onstartuptriggeringpolicy-never-rolls-the-file-on-star]
>  



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