Microsoft Exchange autodiscover broken in IOS 11

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Level 1

6 points

Microsoft Exchange autodiscover broken in IOS 11

It seems after we upgrade to IOS 11.0 we have issues with iPhones populating the server names. I've noticed that it prompts saying it will be sent to Microsoft (even though this isn't an Exchange server on Office 365) but it still fails.

I've tested my wife's IOS 10.3.3 phone with the same Exchange account and it works without any issues and configures with just the username, password, and description.

My IOS 11.0.3 (and others) won't populate the server name at all and requires additional information.

Wireless network, Exchange account, and autodiscover record is the same. Only thing different is the IOS verison.

iPhone 5, iOS 6.1, Calendar

Posted on Oct 9, 2017 9:17 PM

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Answer 1

jdd86 Author

Level 1

6 points

Oct 10, 2017 6:01 PM in response to jdd86

Tonight I took my wife's phone and tested once again on 10.3.3 and it worked. I upgraded her to 11.0.2 and now it doesn't work.

Apple you broke something! My guess is you are not event checking for the autodiscover redirect method because I don't even see the packets hit the server when watching Wireshark.

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Answer 2

ChrisJ4203

Level 10

230,371 points

Oct 25, 2017 3:01 PM in response to jdd86

You are not addressing Apple here. This is a user to user support forum, and Apple does not participate here. So you questions about Apple are not getting to them.

If you wish to speak to Apple Support, use the Contact Support link at the top right of the pages here.

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Answer 3

jdd86 Author

Level 1

6 points

Oct 25, 2017 3:22 PM in response to ChrisJ4203

Thank you, I was not aware of that. Either way I figure other people using iPhones in business would most likely be running into the same issues. I figure contacting Apple Support will be a waste of time since I have zero support with them business wise.

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Answer 4

ChrisJ4203

Level 10

230,371 points

Oct 25, 2017 3:35 PM in response to jdd86

I have not experienced any problems with my Exchange account, but then it has been on the device for a while. I use it on my iPhone 7 and my iPad Mini 4, and it is working fine. I've not had to remove it and add it back, so I cannot really comment. I know there was an issue with something in iOS 10, I believe, where Exchange was not working correctly, but I remember an update fixed it. Which version of Exchange Server?

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Answer 5

jdd86 Author

Level 1

6 points

Oct 25, 2017 3:42 PM in response to ChrisJ4203

This is happening on Exchange 2013 CU15/16 and 2016 CU6. It is only a problem with autodiscover when setting up a new account and from what I've heard from other techs is that it doesn't affect Office 365. With IOS 11 there are some new prompts with Exchange such as it saying "Your information will be sent to Microsoft" but in reality that is not true because it should do an autodiscover lookup and send it to the Exchange server hosting the mailbox (Office 365 isn't the only Exchange environments lol).

This only started with IOS 11 and there are other things like the validation for email addresses I listed above. They changed some stuff here for sure. I see in the security notes it said something about Autodiscover v2 but there is nothing on the web what Autodiscover v1 and v2. I don't know what that is.

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Answer 6

ChrisJ4203

Level 10

230,371 points

Oct 25, 2017 3:46 PM in response to jdd86

Okay, our IT department has provided all of the information that we need to set up ours, and I've not heard of any issues with new devices. I've not read of other issues here, and to be honest, you may find more help over at Microsoft. If it is an issue, they would have heard of it by now, and whether or not they are working with Apple to fix it. I'd have to wipe my device to test it completely, and I don't really have the time to do that right now.

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Answer 7

ChrisJ4203

Level 10

230,371 points

Oct 25, 2017 3:56 PM in response to jdd86

We are not using Office 365 for mail yet, however they are talking about changing over. I do know that our version of Exchange does not work with Outlook 2016 yet, just Outlook 2013. Not sure the exact issue, but since we are teaching Office 2016 with Windows 10, we load it, but don't load Outlook on the machines. Reasons above my level of knowledge, all I know.

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Answer 8

Nov 29, 2017 3:00 PM in response to jdd86

After further investigation:

Before iOS 11, Autodiscover would first come across port 80 which would allow the Hosted Exchange provider to redirect the request to a secure VIP on the F5.

All requests from the mail app are now on port 443 and now dropping all other connections, which is causing this problem.

The Hosted Exchange provider can not include 443 as all their hundreds of thousands of users would get continual certificate prompts due to the CNAME redirect that is done. We can also not target these with an irule as port 443 is encrypted and we can not unencrypt the traffic.

It looks to be the only solution for these Hosted Mail Providers is for Apple to allow the Autodiscover Request over http and port 80 again.

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Answer 9

jdd86 Author

Level 1

6 points

Oct 12, 2017 5:26 AM in response to jdd86

The new 11.0.3 doesn't resolve this issue.

Come on Apple!

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Answer 10

jdd86 Author

Level 1

6 points

Oct 21, 2017 9:03 AM in response to jdd86

Also the email validation is broken! Something like: 15553330111@txt.domain.io doesn't work either! What is going on at Apple?

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Answer 11

jdd86 Author

Level 1

6 points

Oct 25, 2017 3:53 PM in response to ChrisJ4203

If your company uses Office365 for Exchange then it may work. This is only on-premises customers. Also I posted this on technet as well but people don't respond much over there.

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