Shift Delete doesn't delete email from server

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M

MarkT

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Outlook version
Outlook 2019 64-bit
Email Account
Office 365 Exchange
I have a user with Windows 10, Office 2019, and Exchange 365. About 2-3 months ago she noticed her email no longer was in sync between Outlook and her iPhone. I have narrowed it down to this.
If you hit del or choose del from the toolbar on an email in Outlook it deletes from Exchange and thus from her phone.
If she hits shift-del (which she frequently does) it deletes from Outlook but does not del from Exchange and thus stays on her phone.
I tested this by opening Outlook on one screen and OWA on another and can see message stay in OWA with a shift-del but disappear with a normal del.
Never seen this one before..... Any ideas?
 
I thought I was repro'ing it but now it is working - I don't know if it was just a delay or if I kicked started it when I looked in the Deleted items folder in outlook. Testing on another account, it is a delay here - about a minute or so (i did not time it, but it was a fairly long time.)
 
All other users are working correctly as far as I know and hers was until 2-3 months ago. I have removed and reinstalled Office, re created her MAPI profile and made a new OST file.
 
Thank you Peter for your reply, maybe I didn't explain this clearly enough.
I can open Outlook on one monitor and Outlook Web Access on another monitor. (OWA shows what is on the server and the iPhone.)
I can hit delete on an inbox email in Outlook and within a few seconds watch it be removed from inbox on OWA and thus her iPhone.
If I hit shift+del on an inbox email in Outlook I see it removed in Outlook but it stays in OWA and thus stays on her phone.
 
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< gmail and deleted emails. | Outlook Email Body Text Disappears/Overlaps, Folders Switch Around when You Hover, Excel Opens Randomly and Runs in the Background - Profile Corrupt? >
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