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https://issues.apache.org/jira/browse/JAMES-2519?page=com.atlassian.jira.plugin.system.issuetabpanels:all-tabpanel
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John Bester updated JAMES-2519:
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    Description: 
To get around issues where remote delivery does not work (relay denied), I have 
configured email clients to use the SMTP server directly and move sent items to 
James SENT folder. While this works, it does have a strange side effect. If you 
send an item to an external recipient and CC to a recipient in the domain 
handled by James, then multiple copies of the sent item ends up in SENT folder. 
While this might look like a email client problem, I would have expected this 
to have happened before switching to James. So, my guess is the following 
happens:

1. You send a message to external recipient and CC to internal recipient (email 
client uses external SMTP server)
 2. Email client copies mail to SENT folder 
 3. Fetchmail retrieves a copy from external POP3 server
 4. Fetchmail interprets "FROM" address and stores it in SENT folder of sender

Possible solution (if my interpretation is correct):
When fetchmail interprets the FROM address, it first checks whether a duplicate 
already exists before adding it to the SENT folder. The fields to use for 
checking whether or not it is in fact a duplicate might or might not be trivial.

  was:
To get around issues where remote delivery does not work (relay denied), I have 
configured email clients to use the SMTP server directly and move sent items to 
James SENT folder. While this works, it does have a strange side effect. If you 
send an item to an external recipient and CC to a recipient in the domain 
handled by James, then multiple copies of the sent item ends up in SENT folder. 
While this might look like a email client problem, I would have expected this 
to have happened before switching to James. So, my guess is the following 
happens:

1. You send a message to external recipient and CC to internal recipient (email 
client uses external SMTP server)
 2. Email client copies mail to SENT folder 
 3. Fetchmail retrieves a copy from external POP3 server
 4. Fetchmail interprets "FROM" address and stores it in SENT folder of sender


> Duplicate entries in sent items
> -------------------------------
>
>                 Key: JAMES-2519
>                 URL: https://issues.apache.org/jira/browse/JAMES-2519
>             Project: James Server
>          Issue Type: Bug
>          Components: Remote Delivery
>    Affects Versions: 3.0.1
>         Environment: Ubuntu 18.04 Server (James)
> Postgresql 10 (message store)
> Ubuntu 16.04 (Desktops) with Evolution (Email client)
>            Reporter: John Bester
>            Priority: Major
>
> To get around issues where remote delivery does not work (relay denied), I 
> have configured email clients to use the SMTP server directly and move sent 
> items to James SENT folder. While this works, it does have a strange side 
> effect. If you send an item to an external recipient and CC to a recipient in 
> the domain handled by James, then multiple copies of the sent item ends up in 
> SENT folder. While this might look like a email client problem, I would have 
> expected this to have happened before switching to James. So, my guess is the 
> following happens:
> 1. You send a message to external recipient and CC to internal recipient 
> (email client uses external SMTP server)
>  2. Email client copies mail to SENT folder 
>  3. Fetchmail retrieves a copy from external POP3 server
>  4. Fetchmail interprets "FROM" address and stores it in SENT folder of sender
> Possible solution (if my interpretation is correct):
> When fetchmail interprets the FROM address, it first checks whether a 
> duplicate already exists before adding it to the SENT folder. The fields to 
> use for checking whether or not it is in fact a duplicate might or might not 
> be trivial.



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