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Email not sending on iPhone

Hi, I am having a very big problem with the mail app in iOS 16. I have two emails set up and when I reply to a email, it can’t send, it just goes straight to my outbox and a error message says server not found. I tried everything, I looked to see if my server for the emails is turned on and it is and I also re-added my two emails again and it still did not fix the problem. I did not change anything about my two emails since I had iOS 15. In iOS 15, did not have these problems but now I do. This is definitely a iOS 16 problem.


[Re-Titled by Moderator]

iPhone 13 Pro

Posted on Oct 7, 2022 9:19 AM

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Question marked as Top-ranking reply

Posted on Oct 27, 2022 4:47 AM

I’m having similar problem on both iPad and iPhone after updating to iOS 16. When I send an email reply, I hear the swoosh but the email never gets sent. It just disappears. Sometimes it shows in my sent inbox, but the original email I’m replying to doesn’t show the arrow on it indicating that I have replied to this email.

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Nov 28, 2022 5:02 PM in response to Lcarrow

The problem I have is when using the Apple Mail app with iOS 16.1.1. My email account is a Gmail one. Since discovering this issue I’ve used the Gmail app on my iPhone rather than the Apple Mail app. I’ve had no problem while using the Gmail app. It’s possible the problem only occurs with “replies”. I’ve not created any “new” emails recently. They’ve all been replies.

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Nov 29, 2022 10:15 AM in response to Metro287

My wife has had some "sent" e-mails not sending since 16.1.1 was automatically installed. She has now gone into settings and there was a red notice to say that she needed to accept the terms and conditions. On accepting this the e-mails seem to be working and hopefully will continue to work.

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Nov 29, 2022 11:12 AM in response to Help!MRT

I did accept the terms and conditions right away - before trying to send email and realizing some was disappearing. I have disabled the “undo send” feature and that appears to fix the issue. But I’m still double checking that each email I send is actually sent….

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Dec 5, 2022 10:30 AM in response to anthonyg916

I've installed the latest iOS 16.1.2 update that was released on November 30th, 2022 last Thursday 12/1/22 on the affected users iPhone that I had mentioned in a previous post. There weren't any specifics to the native iOS mail app at the time and I have yet to look for more release notes. I am hoping this fixes the experience my user was having:

"Cannot Send Mail - An error occurred while delivering this message"

Not seeing a Sent item within Sent mail, although the message was indeed sent; I was able to notice this when I saw duplicate sent items within the users Sent folder on their computer (vs iPhone).


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Dec 8, 2022 4:01 PM in response to rkrim

Same problem here. After the update to 16, I hear a woosh when sending an email. Later I check because I have not heard a reply, and the email is not in the outbox, drafts, or in sent mail. I am thinking that I might be closing too quickly and undoing the send. It is so frustrating that it just disappears.

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Dec 13, 2022 9:27 AM in response to rkrim

Same. Both of my emails that disappeared had attachments. One was a loan application - caused me to miss the deadline. Another was a legal document and thankfully I called my lawyer two hours later and she let me know the email never came through. A month I had an email that she didn’t receive as well, but I’ve only been checking my sent box recently, confirming the email wasn’t sent. I receive no error messages and I hear the swoosh as well.

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Dec 13, 2022 11:43 AM in response to Rydia5

I’m copying in the advice that helped me below….it was because of the Undo Send we got in the 16.1.1 update. I haven’t had any problems since I turned it off…


Hope this helps:


Turn off Undo Send Delay in the mail app settings, or don’t close the mail app immediately after sending an email. It appears that if the app is closed during the undo send window, the email will disappear. This fixed the issue for me.

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Dec 15, 2022 5:27 AM in response to Metro287

I have a slightly different problem after installing IOS 16.1.2. Earlier this week two emails simply did not go out after clicking the send. I could not find those emails in the draft or any other folder. This morning same thing happened. I retyped multiple time the same reply and same issue. The mail did not go to the outbox or sent folder. I also did not hear the swoosh. After rebooting the mail program works as intended (until the next time). There is something wrong with IOS 16.1.2

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Dec 19, 2022 11:11 AM in response to Metro287

A lot of my emails just straight don’t send. Like I press send and then some of them get sent to their destination and some don’t. coin toss. And if they don’t get sent, they’re just lost forever. Not in outgoing, not in sent, not in drafts. Just gone. VERY frustrating. Sure, unsend is cool but maybe just be careful before you hit send so it doesn’t duck up email sending all told!!

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Dec 22, 2022 7:10 PM in response to Metro287

I figured out the problem. It’s the time setting for “unsend email”. 10 and 20 seconds work. 30 seconds does not.


Change to 10 or 10 seconds and fixed. 30 seconds conflict with my Gmail main setting of 30 seconds for unsend so emails disappear to la la land.

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Dec 24, 2022 6:50 AM in response to Metro287

I’m having the same issue. I suspect it’s because “undo send” is too close to the swipe up feature. I’m starting to realize that when I immediately close the email app after sending an email I might be also accidentally hit “undo send”. It’s a design flaw. Can’t believe that Apple didn’t catch this during the UAT phase of development.

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Jan 9, 2023 3:01 PM in response to Metro287

Sporadically when forwarding/replying to an email we get "Cannot Send Mail An error occurred while delivering this message" We have turned off "Undo Send" and the problem still occurs. The problem started at IOS 15.7 and continues to 16.2


I opened a ticket with our HCL Email Vendor. They reviewed the logs of the devices with this error on the server.

This is HCL's response:

"IOS Mail app randomly providing a policy key 0


To be technically accurate, we are talking about the following policy key that flows in the http request header


X-MS-PolicyKey: 0


The 0 is unexpected and will force Traveler to return a 449 so that the client and server will negotiate a new policy key. Typically its going to have a value like the following:


X-MS-PolicyKey: 369126834


That value comes from Traveler in response to an Exchange ActiveSync "Provision" command.

Example response payload:

<Provision xmlns="Provision:">

<Status>1</Status>

<Policies>

<Policy>

<PolicyType>MS-EAS-Provisioning-WBXML</PolicyType>

<Status>1</Status>

<PolicyKey>369126834</PolicyKey>

</Policy>

</Policies>

</Provision>


So something is happening with the iOS Mail app such that it is losing the current policy key. Its not possible to see what is triggering this from the traveler server. Its possible that the client is seeing some error (network?) for which it then gives up and starts with a policy key 0. That is pure speculation and something Apple support will need to comment on. When communicating with apple, use the header term X-MS-PolicyKey. Hopefully they recognize what we are talking about."


I've worked with Apple Tier 2 support and they aren't aware of the issue. I don't know how to get the right help on this. I've tried to open a Developer Ticket.

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Email not sending on iPhone

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