Sent Mails Suddenly Disappeared from Hotmail

Question

Sent Mails Suddenly Disappeared from Hotmail

DSW 0

My Sent emails (from 1990 to 8/8/26) have disappeared from Hotmail. New Sent emails (from 8/8 to today) are there. I've worked all the steps MicroSoft recommends and believe the only solution is to have MS restore the old Sent emails from their server.

Perhaps there is something else going on. For example, I can get to the website for Contact Support but do not see "Still Need Help?", or any options (e.g., Chat). I get looped rigjht back into Hotmail. The issue is on my IPhone and my Mac laptop. BTW, when I went into look at my sign in Activity ... I can only see activity on my account since 8/8. No precious history shows up ...

I have business emails but the most important to me right now are temails to & from my 83 year-old cousin in England. I was going to put our email exchanges in a Shutterfly book for her ... a gift for the holidays.

Any ideas? I really appreciate any ideas on how to get in touch with MS Support to get these restored. Even better, I would like them to contact me since it seems my entry to reach them is broken. Thank you!

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Answer 1

Ian-T 10,615 Microsoft External Staff Moderator

Hi DSW
I’m very sorry, especially because some of the missing emails have significant personal value.

Since the same Sent messages are missing on both the iPhone and Mac, first sign in directly at Outlook.com on a desktop browser. Search All folders for a known recipient or subject, then check Deleted Items, Archive, and Deleted Items > Recover items deleted from this folder. Microsoft normally keeps items in the recoverable area for up to 30 days after removal from Deleted Items.

Also review Settings > Mail > Rules for anything that may have moved or deleted messages. The account activity page only shows the previous 30 days, so activity appearing from August 8 does not by itself confirm what happened to the older messages.

Since you can't find the "Still need help" - you can still reach out to Microsoft Support by visiting Microsoft Support - Contact us

Finally, check whether an older Mac backup or local mail archive contains copies before changing or removing the account from any device.

Hope this helps, have a great day

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Ian-T 10,615 Reputation points Microsoft External Staff Moderator

2026-08-16T23:16:35.4766667+00:00

Hi DSW

I’m following up to check on the status of this issue.

Have you had an opportunity to review the answer shared earlier?

Any update you can provide would be greatly appreciated.
DSW 0 Reputation points

2026-08-18T16:11:12.9266667+00:00

Thank you. Did all those ... when I get to Still Need Help, I click Support and the only choice I get reads: "Was this informtaipn helpful? Yes or No" I see no options for Chat, e-mail Support, nothing... Then, I get looped back to Help. Going down each tree, I get looped back to the same "Information helpful." Can Geek Squad help>
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DSW 0 Reputation points

2026-08-18T16:26:01.91+00:00

When I get to Support Option, a link says ... Outlook.com app support. I click that and I am asked to sign in again...over and over. Do you think Geel Squad could help?
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Ian-T 10,615 Reputation points Microsoft External Staff Moderator

2026-08-19T00:06:14.79+00:00

Hi

Geek Squad may help check the Outlook configuration, local mail data, or backups on your Mac and iPhone. However, Geek Squad cannot access Microsoft’s Outlook.com servers or restore messages that are no longer recoverable from the mailbox.

Please try again in incognito mode to see if you still in a loop or you can visit this link: https://support.microsoft.com/contactus that I have sent you above to reach out to support as well.

Thank you for your time
DSW 0 Reputation points

2026-08-19T00:45:39.7866667+00:00

Something is wacky with MS servers. I downoaded another Outlook. The current situation: My sent e-mails were in Archive and they are not showing up by date ... I had to filter in the Search field to bring anything up. If I filter, search, add the name of the person, select to or from, I can see most of that person's emails. Some dates are missing. Clearly, this is a workaround that is cumbersome and not the way Outlook was designed.

Another area says I have 14000 emails in my inbox ... huh? It also says I have 2 Sent emails in Sent. It seems that the 8/11-8/16 Sent emails (which appeared in the Sent folder after all the historical Sent emails disappeared) have now moved on their own ... They are no longer in Sent. One minute they were there, the next vaporized. (I have not searched for them, yet.)

My Outlook reminds me of the pieces of a jigsaw puzzle scattered on a table ... I think it is MircoSoft's job to group, sort, and put the pieces in the right place. I still need tech help to get this "picture perfect."