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IOS13 Mail outlook.com duplicate sent items

This has bugged me with MacOS Mail for years, and with iOS13 Mail I now have the problem on the iphone (6s)

I have 4 email accoonts, one icloud account (no problems) and 3 Outlook.com accounts. All 3 now store duplicate sent items in the app.

They are not stored on the server sent folder, and only one copy is received by the recipient.

I have deleted the accounts and added back.

Thete is no setting on webmail to help me.

IOS 11 and 12 did not have this problem though MacOS have had it for years. Its no doubt a Microsoft glitch but only shows up in 13.

Any help, or others testing this would be appreciated.

iPhone 6s

Posted on Sep 21, 2019 10:10 AM

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Posted on Sep 25, 2019 8:33 AM

We are seeing this currently only with corporate mail and iPhone 8+ and older phones running v 13 and 13.1. We deleted the mail profile from 2 devices and reinstalled and the problem came back. We use Exchange 2016 on prem w/ Active Sync and Airwatch MDM.  If a user has an iphone with just personal mail we do not see the problem.   If we add a personal mail account to a corp phone with the double sent problem the personal mail account is fine. The double item is not presented in OWA or Outlook client.


Interestingly when you open the double sent items on the phone - one of the two will then disappear.  (it is always the first of the two that are showing on the phone that gets deleted).  Kind of like the message was staged for sending, and when actually sent in generated a second sent item entry.  Open that first one and it goes away…

 

Now, if you delete the item from Outlook or OWA first, it deletes the 2nd item showing as sent from the phone.  Now go to the first item of the double items sent on the phone and open it and it does not auto-magically delete... Not sure how that helps but at least wanted to put it out there...

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Sep 25, 2019 8:33 AM in response to LD150

We are seeing this currently only with corporate mail and iPhone 8+ and older phones running v 13 and 13.1. We deleted the mail profile from 2 devices and reinstalled and the problem came back. We use Exchange 2016 on prem w/ Active Sync and Airwatch MDM.  If a user has an iphone with just personal mail we do not see the problem.   If we add a personal mail account to a corp phone with the double sent problem the personal mail account is fine. The double item is not presented in OWA or Outlook client.


Interestingly when you open the double sent items on the phone - one of the two will then disappear.  (it is always the first of the two that are showing on the phone that gets deleted).  Kind of like the message was staged for sending, and when actually sent in generated a second sent item entry.  Open that first one and it goes away…

 

Now, if you delete the item from Outlook or OWA first, it deletes the 2nd item showing as sent from the phone.  Now go to the first item of the double items sent on the phone and open it and it does not auto-magically delete... Not sure how that helps but at least wanted to put it out there...

Oct 29, 2019 4:02 PM in response to hakanfrombath

What amazes me is that it took me three days and two bumps to get any response and despite my requesting help not one single member of any standing (i.e. above level 1) has contributed by testing it.

Yet I know that the higher levels have access to things like conference calls that can get this looked at.

If a support agent cannot escalate to third level support, who can?

In the mean time everyone should post a bug report at https://www.apple.com/feedback/

Oct 30, 2019 11:38 AM in response to JJSWW

Release 13.2 has fixed two and maybe three of the annoyances for me (at least so far). Note I rebooted the phone after applying the patch.


  1. When I forward a message, the original message thread is in tact AND 2. the icon indicator that the message was forwarded is synced and shows in Outlook! Tested on 5 forwards - curious if anyone else see this fixed now.


To note, if I Reply to a message however, the Outlook icon indicating a reply does not sync. I can see the indicator on the iPhone but it does not sync to Outlook.


  1. My phone is receiving pushes without having to swipe to request them.


Still double Sent Items, Still have to open an item twice on the phone to see it was sent, still have to delete an item twice on the phone for it to delete.


Have had one hand since the update but can't elaborate on the what or why.

Nov 15, 2019 3:54 AM in response to Malper

The whole thing seems like a problem wit Active Sync.

  • Hits O365, Outlook.com, and Hotmail.
  • Ghost message only resides on the phone.
  • Trash only empties on one side.
  • Read/unread doesn't carry over between iPhone and Exchange Online.
  • Folders are not updated properly


If you ask Microsoft, they say the truth is always OWA (or the online Exchange web interface), because there is no client and therefore no sync involved. Whenever you got problems, their first question (even from premier support) is "How does it look on OWA". Active sync was developed by Microsoft. The issue came up with iOS 13 and persists ever since.


With all of that in mind you might guess which side the issue is on.

Dec 10, 2019 10:38 AM in response to luvjazz_

Wahoo we waited long enough...


  • Fixes issues in Mail that may prevent downloading new messages
  • Addresses an issue that prevented deleting messages in Gmail accounts
  • Resolves issues that could cause incorrect characters to display in messages and duplication of sent messages in Exchange accounts


my battery is 17% lol need to charge before it will allow me to update. Best of luck everyone is this a very merry Christmas from Apple?

Oct 29, 2019 9:45 PM in response to LD150

Besides the double vision in the sent folder the other problem with iOS/exchange mail now is that it doesn’t refresh automatically unless you quit mail and come back to it… I can’t tell you how many emails my team has missed since the new iOS came out – simply because their mail is frozen two hours earlier and they did not notice.

Sep 24, 2019 4:50 PM in response to Michael 541

Same for me. 13.1 does not help. Still No Sender and No Subject.

i added a new email account, that was in my iPad, to my iPhone and the sender and subject worked OK. So it would seem that deleting the account and creating is again will work.


I am just about to buy a new iPhone 11 Pro Max. Any thoughts on migrating from my current iPhone? Will this solve the Sender Subject issue?

Sep 25, 2019 1:46 PM in response to sm_philly

"Interestingly when you open the double sent items on the phone - one of the two will then disappear.  (it is always the first of the two that are showing on the phone that gets deleted). "


Yes - when I opened the first sent item and closed it one of them disappeared but I challenge anyone to determine which, as they appear identical.

Sep 28, 2019 2:56 PM in response to LD150

Having the same issue since updating to ios 13. Before on ios 11 and 12 I had no problem. I was wondering if it could be an issue with Microsoft?


Also, on the Contacts app when you edit a contact, then update then you go back to your whole list and you close it. You go on main screen and swipe up the Contact app. If you go back to your Contacts app, it stays at the last contact you edited.


If someone have a fix for that I would appreciate.

Sep 29, 2019 1:55 PM in response to LD150

I have a long list of faults, all linked to this and now stupidly I updated my 2018 iPad to new iPad OS which has the same. my new iPhone 11 has ..


1) Double send email

2) Fails To sync emails - error at bottom

3) Empty sender details (13.1.1 seems to fix) but has shown a couple of times

4) Calendar fails to show and sync and then shows double calendar in settings - error on settings screen 

5) Settings email or calendar will at times prevent setting to no limit on sync 

6) No sender showing in inbox


i have had 3 calls with apple, been the Genius Bar who blame it on Microsoft, I’m using hotmail.co.uk account. Genius Bar checked phone and agreed I have done everything possible


1) reinstall of back up x4

2) wipe phone start again x3

3) multiple removal of email and re adding

4) hardware checks fine on apple diagnostic


im now in Twitter private chats and they keep asking questions, but no solution.





IOS13 Mail outlook.com duplicate sent items

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