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Apple, Microsoft Working to Fix iOS 11 Mail App Issues With Outlook.com, Office 365 & Exchange Accounts

GadgetBen said:
Dear Microsoft,

The only reason I use your @hotmail.com domain is because I signed up back in 1998. There is nothing else about your crappy software or hardware that I enjoy using anymore.
Click to expand...

So I have a @mac.com email address so I have been using Apple's cloud services for a while now. I love my Apple hardware but Apple's cloud services, .mac, .me and .icloud are NOT examples of great cloud services. They are the best they have ever been now but they still are not as good as Microsoft or Google when it comes to email, cloud storage, etc.

Let's not even talk about Microsoft Office 2016 vs iWork on the Mac in 2017.
 
This started happening to both my iPad and iPhone when iOS11 GM was installed. It worked fine before that. I reported it to Apple last week but they acted like it was news to them . On my native Outlook Mail app (which I despise) it worked just fine. So last week, in my hell with Hurricane Irma, I spent my few moments with wifi sending the same email 1, 2, or even 5 times before it really sent. Fun times. This email glitch seems to be improving as of yesterday though.
 
Stopped using iOS native mail app since it's unreliable garbage. Now only use Aqua Mail, Gmail and/or Nine.
 
mattynat said:
There were no changes within iOS 11 GM and the official release yesterday. The issue is still happening on tenants within O365 that have HTTP/2 turned on. I had the pleasure of working with Apple and MS over the last 2 weeks sending them logs and other information. You also have to understand, Apple does not use O365 internally or externally so they wouldn't have caught this issue. They have a lot of bug reports that people send in. Most of those users don't even try to troubleshoot by turning it off and back on again. Beta software is supposed to be run on non-production devices. So part of the troubleshooting expecting by Apple is for a restore to be done, eventually. Most people that run the public beta, its on their full time device so many of the bug reports weren't complete and others just didn't work with Apple on the issue. Plus, with everyone saying they sent a bug report, they can't get to everyone who reports a bug.
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"You also have to understand, Apple does not use O365 internally or externally so they wouldn't have caught this issue."

I get that they don't use it.

That said I have been managing Exchange servers since the Exchange version 4....24 years ago. When the iPhone first came out it did not have Active Sync support, they wanted Exchange admins to turn on IMAP. It might have happened in a few places but for the most part the iPhone did not work in the corporate world.

Then Apple licensed Active Sync and that was one of the BIG reasons Enterprise adopted the iPhone after that. To not test this thoroughly test Active Sync against Microsoft's email offerings it a mistake on Apple's part. Microsoft still owns the Enterprise Email market and will for a long time. Apple has dumped on the Enterprise market enough over the last 5-10 years. Doing stuff like this only gives those MS fanboys in most Enterpise IT shops more fuel to the "Apple does not do Enterprise" fire. They are probably trying to push some Android option.

This is NOT the first iOS update to break Active Sync support.
 
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mattynat said:
Its not every O365 tenant. just the ones that Microsoft turned on HTTP/2. They are rolling the affected servers back now. plus, it was only with emails with attachments or replies with a signature with an icon.
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Mystery solved! Couldn’t figure out why it happened (once) after updating my iPad but not since. Damn administrative overlords and their fancy mail signatures!
 
Our company uses Office 365, and we've had no problems sending or receiving email on our iOS devices since updating to iOS 11 yesterday. After reading this story, we tested specifically just to make sure, and yep, the built in Mail app is working fine with our O365 system.
 
What problems ? My office 365 account works as it used to be after upgrades both on iphone and ipad. Send and receive, with attachments etc. I guess it is not a generic issue but specific to something ?
 
tmanini said:
Nice post: sane, measured, professional, polite, practical, experienced.
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hey, thanks! I try...
[doublepost=1505923220][/doublepost]
TheMacDaddy1 said:
"You also have to understand, Apple does not use O365 internally or externally so they wouldn't have caught this issue."

I get that they don't use it.

That said I have been managing Exchange servers since the Exchange version 4....24 years ago. When the iPhone first came out it did not have Active Sync support, they wanted Exchange admins to turn on IMAP. It might have happened in a few places but for the most part the iPhone did not work in the corporate world.

Then Apple licensed Active Sync and that was one of the BIG reasons Enterprise adopted the iPhone after that. To not test this thoroughly test Active Sync against Microsoft's email offerings it a mistake on Apple's part. Microsoft still owns the Enterprise Email market and will for a long time. Apple has dumped on the Enterprise market enough over the last 5-10 years. Doing stuff like this only gives those MS fanboys in most Enterpise IT shops more fuel to the "Apple does not do Enterprise" fire. They are probably trying to push some Android option.

This is NOT the first iOS update to break Active Sync support.
Click to expand...


As far as I know, this isn't an active sync issue. It is an HTTP/2 issue. HTTP/2 isn't implemented on every O365 business/personal tenant so you are still limiting the pool there too. I don't believe this was an Apple issue since it works on iOS 11 devices that don't use HTTP/2 but honestly, it doesn't really matter at this point. in about 24 hours from now, every CAFE server that has HTTP/2 will have it disabled. Apple will release 11.X.X and then MS will turn it back on for every tenant/forrest and we will all be happy campers (fingers crossed...)
 
No problems here with normal Outlook.com emails.

Although I always configure them as Microsoft Exchange instead of Outlook.com on iOS settings
 
mattynat said:
every CAFE server that has HTTP/2 will have it disabled. Apple will release 11.X.X and then MS will turn it back on for every tenant/forrest
Click to expand...

I am reassured even though I have no idea what this language means. (I view servers and networks as I probably would have regarded leeches and bloodletting: with faith and fear.)
 
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Wow so much FUD and ignorance on this thread, lol.

The root of the issue here is Apple improperly handling the handoff from http/2 back down to http/1.1 in ios11. This is why not a single non-ios11 activesync device is affected by this (millions of android and windoze phones, and all ios10 and earlier devices).

The reason the issue doesn't affect everyone with ios11 and that the bug probably didn't get as much traction as it should have during the beta process is that only Exchange 2016 running on Windows Server 2016 offers http/2 at all. This includes o365 servers that are running on Server 2016 vs Server 2012r2. Macduke's server at work may be Exchange 2016, but is likely running on Server 2012r2 - hence not seeing the problem. Since Exchange 2016 preceded the release of Server 2016, lots of organizations won't see this at all as their servers are running the older OS. MS itself has a mix of operating systems in the o365 infrastructure and mailboxes are activated on different servers constantly so it can be a mixed bag as far as what OS is serving a mailbox at any given time.

The http/2 support of Server 2016 can be disabled with a registry change, which is a workaround from the MS side that prevents Apple's bug from being encountered. Ultimately Apple will fix the root issue with an update.
 
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MacRumors said:
To work around this issue, download the free Outlook for iOS client from the App Store. The Outlook for iOS client fully supports various email services, including Outlook.com, Office 365, and Exchange Server 2016.

If you use the Mail app to sync data from Exchange Server 2016 that is running on Windows Server 2016, you can ask the system administrator to disable HTTP/2 in Windows Server 2016 as a workaround. The instructions on disabling HTTP/2 can be found in the Workaround section of KB 4032720: How to deploy custom cipher suite ordering in Windows Server 2016.
Click to expand...

This is not a viable solution because the Outlook on iOS It doesn't support certificate-based authentication...
 
fairuz said:
Haha. I actually have been annoying for a long time that Exchange doesn't use standard email protocols. Of all things, this should be the easiest to get right.
Click to expand...

Actually activesync is a fantastic mobile protocol. That's why google themselves licensed and used it for years until they decided they didn't want to pay for it any longer. It's far easier to configure (and, more importantly for businesses, support) than having to deal with imap/smtp/port numbers/auth settings/etc.
 
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dumastudetto said:
Nobody needs Microsoft for email or calendaring anymore.
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...says someone clearly not informed or interested in enterprise level collaboration systems.
[doublepost=1505930077][/doublepost]
fairuz said:
Haha. I actually have been annoying for a long time that Exchange doesn't use standard email protocols. Of all things, this should be the easiest to get right.
Click to expand...
What exactly do you consider "standard e-mail protocols?" Do you have something better than ActiveSync to suggest?
[doublepost=1505930254][/doublepost]
mattynat said:
hey, thanks! I try...
[doublepost=1505923220][/doublepost]


As far as I know, this isn't an active sync issue. It is an HTTP/2 issue. HTTP/2 isn't implemented on every O365 business/personal tenant so you are still limiting the pool there too. I don't believe this was an Apple issue since it works on iOS 11 devices that don't use HTTP/2 but honestly, it doesn't really matter at this point. in about 24 hours from now, every CAFE server that has HTTP/2 will have it disabled. Apple will release 11.X.X and then MS will turn it back on for every tenant/forrest and we will all be happy campers (fingers crossed...)
Click to expand...
Thanks for the nice explanation. I'd say the only reason it matters is to answer all those that would like to blame MS over Apple. In my experience (based on their lousy track record with ActiveSync), this is going to end up being an Apple issue unless iOS 10 didn't support HTTP/2 at all.
[doublepost=1505930326][/doublepost]
Gjwilly said:
So Apple borked their implementation of HTTP/2 in iOS11 but it wasn't a problem until MS activated HTTP/2 on some of their servers without telling anyone.
Is that it in a nutshell?
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This seems like the most likely explanation.
[doublepost=1505930603][/doublepost]
pesos said:
Wow so much FUD and ignorance on this thread, lol.

The root of the issue here is Apple improperly handling the handoff from http/2 back down to http/1.1 in ios11. This is why not a single non-ios11 activesync device is affected by this (millions of android and windoze phones, and all ios10 and earlier devices).

The reason the issue doesn't affect everyone with ios11 and that the bug probably didn't get as much traction as it should have during the beta process is that only Exchange 2016 running on Windows Server 2016 offers http/2 at all. This includes o365 servers that are running on Server 2016 vs Server 2012r2. Macduke's server at work may be Exchange 2016, but is likely running on Server 2012r2 - hence not seeing the problem. Since Exchange 2016 preceded the release of Server 2016, lots of organizations won't see this at all as their servers are running the older OS. MS itself has a mix of operating systems in the o365 infrastructure and mailboxes are activated on different servers constantly so it can be a mixed bag as far as what OS is serving a mailbox at any given time.

The http/2 support of Server 2016 can be disabled with a registry change, which is a workaround from the MS side that prevents Apple's bug from being encountered. Ultimately Apple will fix the root issue with an update.
Click to expand...

This is the best explanation and is exactly what I suspected. There's no way Microsoft borked HTTP/2 if non-iOS 11 devices weren't affected.
 
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