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Sent email message is different on iOS Mail than Desktop Outlook

Hello, I had a very unusual email situation that happened earlier and wanted to see if anyone knows anything about this kind of thing?


My corporate email uses Office 365 for Business/Corporations.


Earlier today, I started a draft email on my iPhone (not my personal but my corporate, MDM device) on the plane with the intention of finishing and sending from my laptop while waiting for my connection. Which is exactly what I did. I opened the draft in Outlook, magically there from my iPhone, and continued my email and fine tuned it, removing my own notes and annotations for self-reminders as I went (some potentially damaging).


I must have proofread it a thousand times from being anxious due to its recipients high profiles, I added their names to the distribution list. I sent it, reread it on my computer a bunch of times in my sent mail folder, was satisfied, and called it a day.


A while later I wanted to check if I had put in the attachment. I was almost certain I had but was doubting. So I opened sent mail folder in iOS Mail app and opened my email. To my horror it still had the recipients names all there but it was my original saved draft from my iPhone that was showing sent to these people and not the proper one that I literally sent from Outlook, and no attachment. Comparing devices they were sent at the exact same second, but each device only showed its “own version” of the mail. The proper one showed in desktop and also had the attachments, which is where it was sent from.


In an effort to see if it was just a delay loading and was showing cached email, I rebooted my phone several times. Same thing, the original draft was sent it appeared and I panicked! After a painstaking search on Google, I went with a suggestion of turning the account off and then on again in settings which would force it to re-sync and download mail again.


After doing so it showed my proper, desktop sent message in the sent folder on Mail on iOS, and the draft was nowhere to be found. I think (I really hope) that my recipients only got that proper version based on it downloading the right one to my phone after, but what if they opened their iPhones mail app before me having done that account cycle, would they have seen the iPhone only version showing only my original draft, or the proper email that was actually sent from my pc?


It seems to be a uniquely iPhone phenomenon from what I have found online with others experiencing it, but VERY little confirmation as to which version the recipient received with absolute clarity.


Is this very common, and what is the reason it happens on iPhones? It’s not even exclusive to the Mail app but also third party ones like Gmail and Outlook for iOS also. I’ve owned and used iPhones exclusively since 2008 and never, ever had this happen until today… but searching online yields the same phenomenon occurring on iPhones occurring at least as far back as four years ago.


What’s the deal? And if anyone can shed some light, what’s the actual version that was sent?


Thanks!!!!

Adam’s iPhone

Posted on Jul 28, 2023 4:55 PM

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Question marked as Top-ranking reply

Posted on Jan 20, 2024 1:45 PM

Why, so we can be told to go ask you guys? Is this problem at least on the to-do list for Apple?


Several months later here and I have a very similar problem, phone shows an older draft without my resume — which I never tried to revise there anyway, unlike the OP, whereas off my HP computer using Outlook was the correct version, and I checked Gmail online and it matches, but again, the one in the Mail app is incorrect.


I don’t expect by any means that my specific problem will be resolved here but come on, at least put this on the list of problems to fix if it isn’t already

3 replies
Question marked as Top-ranking reply

Jan 20, 2024 1:45 PM in response to 1ssmith

Why, so we can be told to go ask you guys? Is this problem at least on the to-do list for Apple?


Several months later here and I have a very similar problem, phone shows an older draft without my resume — which I never tried to revise there anyway, unlike the OP, whereas off my HP computer using Outlook was the correct version, and I checked Gmail online and it matches, but again, the one in the Mail app is incorrect.


I don’t expect by any means that my specific problem will be resolved here but come on, at least put this on the list of problems to fix if it isn’t already

Apr 8, 2024 12:03 PM in response to AHal10

I have the same problem. Drafted an email using Outlook on the web.

After several drafts and reviews, it was ready and I hit send. The next day I checked my iPhone mail app to verify the email was sent by looking at the sent items folder. It was but the version was different. It was an earlier draft version but it was in the sent items folder. I was pretty sure I didn't send that version but thought it was possible so I checked the outlook website and the correct version was in the sent items folder. Same time and date. Different versions in the sent items folder.


I don't know what the problem is but since I never used the iPhone to draft the email, it seems possible IOS mail is only showing what Microsoft is providing from their mail server. To me it seems unlikely to be IOS mail problem because none of my drafts were created on the iPhone and I sent it using outlook on the web.


I hope the recipient got my intended email but, in my case, there was no embarrassing content in the earlier draft just less detail.

Sent email message is different on iOS Mail than Desktop Outlook

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