The Delete from Server setting only applies to POP accounts which don’t really 
synchronise with the server. If email is set up using the POP protocol all mail 
is downloaded and stored locally. If you use two devices you can set up your 
secondary device to not delete the message from the server so that you can 
still download the message on the primary device in case you want to archive it.
POP is an old protocol which was never really meant to be used in a world where 
people use computers, smartphones, tablets and so on. In that world you want 
your mail, contacts and calendars stored in the cloud on a server and set up 
your devices to access and sync with that masterset of data and that is where 
IMAP, Exchange Active Sync and full-blown Exchange comes in.
I know some people still like to use POP and I don’t want to start another 
discussion about the Pros and Cons of POP vs IMAP vs Exchange/Exchange Active 
Sync, but the fact is that POP does not handle multiple devices well. Yes, you 
can get your mail on two or three devices, but it does not sync back, i.e. if I 
reply to an email then that email shows as replied to on whichever device I use 
to reply and the message I sent is on that device, it does not show up on my 
other devices as well.

Regards,
Sieghard

From: [email protected] [mailto:[email protected]] On Behalf Of 
Thom Spittle
Sent: Thursday, April 7, 2016 9:55 AM
To: [email protected]
Subject: Re: iPhone, Outlook.com ail and Windows Live Mail?

Hi Jim, sometimes there is a setting that you need to change what to do with a 
deleted message.
And you needed to say something like delete from server.
I've never used your set up, but I have used an IMAP and that was a problem I 
was having as well. I hope this helps. Tom

Sent from my iPhone

On Apr 7, 2016, at 12:04 PM, Jim Portillo 
<[email protected]<mailto:[email protected]>> wrote:
Good morning,

Here’s hoping I can get an answer to something I might be doing wrong.

One of my students has his Outlook.com<http://outlook.com> account set up on 
his phone.  Now, he has a laptop and is learning to use Windows Live Mail.  I 
set up that same Outlook.com<http://outlook.com> account on his laptop with 
Windows Live Mail and used the iMap settings.  My thought was that it would 
sync across all devices.  However, when my student tries to delete a message on 
his phone, it still shows up on his computer.  When he deletes a message on his 
computer, it still shows up on his phone.  I thought iMap was supposed to sync.
If this is not a good solution, I’ll need to do something different.
Thanks much.
Jim


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