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https://issues.apache.org/jira/browse/JAMES-3791?page=com.atlassian.jira.plugin.system.issuetabpanels:all-tabpanel
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Karsten Otto reopened JAMES-3791:
---------------------------------

Since I cherry-picked the solution for 3.7.x, I should also cherry-pick the 
addition.

> Remote Delivery sometimes uses wrong MAIL FROM address
> ------------------------------------------------------
>
>                 Key: JAMES-3791
>                 URL: https://issues.apache.org/jira/browse/JAMES-3791
>             Project: James Server
>          Issue Type: Bug
>          Components: Remote Delivery
>    Affects Versions: master, 3.7.0
>            Reporter: Karsten Otto
>            Priority: Major
>          Time Spent: 2h 10m
>  Remaining Estimate: 0h
>
> *Observed Issue:*
> When delivering a mail to a remote server, James sometimes under load uses 
> the wrong envelope sender (MAIL FROM). This creates a wrong Return-Path at 
> the recipients end, which among other things causes problems with DSN replies.
> *Analysis:*
> I traced this to MailDelivrerToHost.tryDeliveryToHost(), which shows in the 
> debug log a pattern like:
>  # Attempting delivery of ... from al...@example.org
>  # Mail sent successfully to ... from b...@example.org
> I also notice that getPropertiesForMail() modifies the shared SMTPSession by 
> putting the envelope sender into its properties. So this is likely a race 
> condition.
> *Possible Fixes:*
> I am not sure what the best fix for this would be:
>  # Make tryDeliveryToHost() synchronized (ugly)
>  # Use SMTPMessage.setEnvelopeSender() instead of SMTPSession properties
> Fix 2 is nicer as it preserves concurrency, but it requires that 
> mail.getMessage() is always an SMTPMessage (extends MimeMessage). I do not 
> know the James code base well enough to be certain of that.
> Any thoughts?



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