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iOS 4 and Exchange ActiveSync

Recently Apple released iOS 4 (the new name for the operating system that runs on iPhones, iPod touches, and iPads). Since its release there have been numerous reports (link, link, link) of a number of issues with new iPhone 4s (and older iPhone models running the updated software version) when using Exchange ActiveSync (EAS). I wanted to put up a quick posting about what issues users may be seeing and what we’re doing about it.

Issues:

  1. Exchange administrators are seeing heavier than normal loads on their servers from users with iOS devices: We are in contact with Apple’s engineering team and are trying to help them fix this issue. In the meantime Apple has released a support article (link) which directs administrators who are experiencing this issue to push an iOS profile (link) that changes the timeout their Exchange ActiveSync connection uses to their users to four minutes which should be long enough for the vast majority of users. Those that need longer can edit the XML file in any text editor by searching for ‘240.0’ (no quotes) and changing it to the desired number of seconds, or you can use Apple’s configuration utility editor (link) to make this change.
    Update 7/15: Apple has released iOS 4.0.1, which includes the iOS profile change discussed earlier in this post.

    Update 7/1 1:10 PM: We had suggested using Apple's configuration utility to make this change. Apple has informed us that you should not use the configuration utility to edit or install the update. Use a text editor such as Notepad to change the timeout value in the update, if required. The configuration utility doesn't know about the timeout key used in the update.

  2. Email, calendar, or contacts are not syncing: We believe this is the same issue as #1. The support article and solution listed above are the current recommendation from Apple while a fix is being worked on.
  3. iPhone is not working with Google Apps over Exchange ActiveSync: Google licenses the server portion of Exchange ActiveSync from Microsoft (link) but Google wrote their own software to implement the protocol. Google is responsible for making sure their implementation of Exchange ActiveSync runs correctly and in this case Google claims that they had a server issue (link).

We have been in contact with Apple about each of these issues (as well as some others that seem to not be directly related to EAS but are more email related in general). Apple has assured us that a fix is being worked on though they have not commented on a release timeline for the fix. We will be continuing to work with Apple to help resolve the current issues relating to iOS 4 using Exchange ActiveSync.

Adam Glick
Sr. Technical Product Manager

Published Thursday, July 01, 2010 9:48 AM by Exchange

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Comments

 

Jeff Guillet [MVP] said:

Aweome that you guys are working with Apple on this.  Microsoft is head and shoulders above Apple "support" and demonstrates how customers should be treated.
July 1, 2010 1:12 PM
 

Mark E. Smith [MCM] said:

Thanks for the communication Adam. It's extremely valuable for customers to just know the status of the problems – keep the communication channels open and the customers informed (a hint to Apple)....
July 1, 2010 1:19 PM
 

Andrew E said:

Adam, thanks for the timely update, will you be updating this blog post as new information is publicly available?  And thanks for posting an informative status update before the issue is resolved, this provides an authoritative source of information (better than newsgroups and non-authoritative blogs).
July 1, 2010 1:24 PM
 

Jeff Guillet [MVP] said:

Agreed. We alsways know we can count on Microsoft for timely, useful, and authoritative information.  Thanks, Adam!
July 1, 2010 1:34 PM
 

Kjell Andorsen said:

From what I can determine there is a separate issue that is similar, but not identical to issue 2 described here. We see with some of our customers who are running Exchange 2010 that they can connect, receive mail and sync calendars, but are unable to send mail after upgrading to IOS4. The profile fix posted by apple does not appear to fix this issue. The users get "Cannot Send Mail
An error occurred while delivering this message."
Everything else works.

From what I see on various online forums this particular issue seems unique to environments running E2010
July 1, 2010 1:37 PM
 

They Call Me PEte said:

Can MS or Apple elaborate on : "In addition, some Exchange Server administrators may notice their servers running slowly." . Are all versions of Exchange 2007/2010 affected? Is it specific to any server roles (CAS, Mailbox)? What kind of performance hits should we be looking at (Disk I\O, CPU, etc)? Thanks.
July 1, 2010 1:39 PM
 

Dean S said:

Can you comment about which Exchange Servers have been affected?  The one article indicates 2007 and 2010 CAS servers.  Have you heard of admins of Exchange 2003 also complain of issues as well?  Thanks for the updates on this issue.  Agree with others that this info is really helpful to read and be aware of.
July 1, 2010 1:41 PM
 

Arun said:

Question, If we have x no of users using iOS 4 devices then we might notice this specific issue or is it also with only few devices?. Do you have any answer on what could be the value x?. Just to see if anyone is noticing the same issue if they would have fewer users connecting through iOS 4 devices.
Thank you.
July 1, 2010 2:05 PM
 

Mike said:

Any "fix" that does not update the user agent of the device is useless as its is impossible to tell who applied an update otherwise. If Apple does this as an updated firmware fix, the user agent will be updated and you can give users a week to fix or block the old user agent from connecting...
July 1, 2010 2:21 PM
 

Sysadminlab said:

I did some testing which ActiveSync Policies (EAS) that works on iPhone OS 4.0. The result: http://www.sysadminlab.net/activesync/iphone-os-4-and-exchange-activesync-policies-what-really-works

Let me know if you have tested and experienced something else.
July 1, 2010 3:17 PM
 

Scott said:

Is there a way to tell which devices (i.e. iPhone OS 3.1 vs iPhone 4.0) are connecting the CAS?
July 1, 2010 3:19 PM
 

Jason said:

I have been tracking this issue since it was announced a few days ago. We have an Exchange 2007 server with ISA 2006 handling OWA FBA, Autodiscover rules and now activesync.

We have a 3GS and updated it to 4.0. I cannot replicate the issue, i'm not sure if ISA is throttling the requests from the device.
July 1, 2010 3:34 PM
 

Mike Logan said:

We have 2000 users with iphone in our company. 100 users have updates their 3GS iphones to IOS 4. Only 1 user so far with the IOS4 has brought one of our exchange 2007 SCC clusters to a state slower that driving miss daisy. The issue is that the iphone does not wait for a timeout and therefore keeps making read requests to the CAS server (2007) which keeps openning multiple sessions to the mailbox server (2007 SCC cluster) increasing the average latency to an extermly high level. The profile fix has worked for us so far. The bottom line is that not all updated iphones show this bahavior which is odd.
July 1, 2010 3:40 PM
 

JasonL said:

the problem we ran into was that the cpu usage on the mailbox server was very high, in the 70% range, that slowed down everything else to a crawl. used perfmon, look at rpc average latency under msexchangeis client, the activesync counter was over 100. Also, used exmon to find out who is using all that cpu. turn off activesync for the guy and then restart corresponding active sync app pool in iis of the cas server.

ios4 has the useragent string 801.293, use ps to get a list.
July 1, 2010 3:52 PM
 

John Nicholson said:

I'm having some massive issues getting exchange 2003 SP2 to play nice with the new iOS.
July 1, 2010 4:20 PM
 

Charlie O said:

Are you also aware that Exchange/2010/2007 NOTES also do not sync? I am told this is some kind of authentication issue. Any word on this??
July 1, 2010 4:49 PM
 

Panagis said:

ALL HAIL NOTEPAD!!!
July 1, 2010 5:01 PM
 

Reed W said:

Our organization has had an issue where any iPhone user that has upgraded to iOS4 only gets "Immediately, After 1 Minute, After 5 Minutes, After 15 Minutes, and After 1 hour" for the Require Passcode lockout time period.  We used to have an option for "After 4 hours" which is the setting most users set their devices to.  Users that have not upgraded to iOS4 still have the 4 hour setting available.  We have an ActiveSync Policy that requires a password to be set, but we do not have the "Time without user input before password must be re-entered" option configured.  We're running Exchange 2007 SP2.  Has anyone else run into this?
July 1, 2010 5:48 PM
 

Jeff Sullivan said:

Thanks for the updates! Microsoft seems to be doing a much better job of communicating with customers than Apple. We're glad you're helping Apple resolve the issue - it demonstrates what a company that cares about its customers does at times like these, and that is to forget rivalry in one segment (mobile phones, where Microsoft catching up to do with Windows Phone 7) and collaborate to help resolve customer issues. We love the Exchange team and Microsoft for it.
July 1, 2010 5:52 PM
 

EthanM said:

This issue affects all versions of Exchange that have EAS (2003, 2007, 2010).  The symptoms are random, but typically occur on mailboxes with high item counts (inbox/calendar are the usual culprits) and/or are already comprimised perf wise.  In other words: if your server is already near the tipping point, this will bring it over the edge.  Just because you don't see any perf issues because of the firmware update doesn't mean your user base's iPhone population shouldn't apply the config file.  Apply to all your iPhone users with the iOS 4 update.

Exchange Server 2010 gives you the ability to quarantine devices based on the user agent until the owner contacts the admin and confirms they've applied the update.  Yes it's time consuming, but it's a lot better than having your server down. :)
July 1, 2010 6:39 PM
 

bvig said:

You can identify iOS4 devices with the "DeviceUserAgent" value of 801.293

Get-ActiveSyncDeviceStatistics -Mailbox

Apple-iPhone1C2/801.293           = iPhone 3G on iOS 4.0
Apple-iPhone2C1/801.293           = iPhone 3GS on iOS 4.0
Apple-iPhone3C1/801.293           = iPhone 4 on iOS 4.0
Apple-iPod2C1/801.293               = iPod Touch 2G on iOS 4.0
Apple-iPod3C1/801.293               = iPod Touch 3G on iOS 4.0
July 1, 2010 6:47 PM
 

Jason said:

Does anyone know why apple would not recommend using the configuration utility to install this change on the IOS4 devices? I am already creating a custom profile with our attached verisign cert to the profile / Exchange configuration and thought it would be easier just to add this in during the install.

July 1, 2010 7:47 PM
 

Scott said:

Bvig thanks for the info.
July 1, 2010 8:17 PM
 

EthanM said:

@Jason: because they have communicated to us that their configuration utility can't address these changes.  Apple support would be the best point of contact to ask why that is.
July 1, 2010 8:59 PM
 

thesurg3on said:

I wonder if apple is also using their own implementation of activesync. Does ms provide the binaries for each os?
July 1, 2010 9:34 PM
 

Peter Sam said:

Anyone know if it is true that a iPad connected via activesynch increases the IOPS by several times compared to a "normal" mailbox user?

July 1, 2010 9:40 PM
 

EthanM said:

@thesurg3on: Microsoft doesn't provide any binaries.  It's a licensed protocol they write the code for themselves.  You can find the useage of them on MSDN.  Bing it and you'll find links like this:
http://msdn.microsoft.com/en-us/library/cc307725(v=EXCHG.80).aspx

@Charlie O: We don't sync  notes (as in Outlook/OWA notes) with any version Exchange ActiveSync as far as I know.
July 1, 2010 10:11 PM
 

Frank T said:

Shouldn't the server throttle a client - any client - that is causing a perfomance problem?
July 2, 2010 12:29 AM
 

Charlie O said:

Wrong! Notes have always sync'd. There are also 3rd party iPhone apps that sync Notes and tasks. IOS4 also introduced Note sync for GMAIL... which is also now having problems as reported all over the web as they luicense active sync.
July 2, 2010 3:02 AM
 

Aaron S said:

While the updated config for iOS4 devices is helping, we're still seeing high CPU utilization on our 2k7 CAS servers.  We're watching for them in ExMon and trying to capture client side logs to see what they are doing that causes such high utilization.

Anyone else seeing something similar?
July 2, 2010 9:43 AM
 

Andreas Greiner said:

Hi,

wen hafe the same problem   Kjell Andorsen discriped.
User with an updated iphone 3gs to iOS4 can not send emails to an Exchange 2010.

Is there a fix or workaround availible?
July 2, 2010 10:34 AM
 

Adam said:

Does anyone know if this is related to another EAS/iOS4 bug that occurs when connecting to the Exchange server via WiFi?

It's detailed in this Apple discussion:
http://discussions.apple.com/thread.jspa?threadID=2475890&tstart=0

But basically, when connected via WiFi, there are sporadic errors that state a connection occurred or the account information can't be verified.

Anyone seen this?
July 2, 2010 11:32 AM
 

Mark E. Smith [MCM] said:

@Kjell Andorsen -- Re: In ability to sending email. This was confirmed yesterday as another bug buy Apple. See: http://marksmith.netrends.com/Lists/Posts/Post.aspx?ID=104 for the tracking of this issue.
July 2, 2010 11:53 AM
 

Mark Texas said:

When is Apple going to allign with Enterprise needs and actually work and share information PRIOR to releasing their half baked crap?

Thank god we have ActiveSync disabled and made Blackberry the standard.
July 2, 2010 1:05 PM
 

Jason said:

I'm having a little trouble using PS to query for ActiveSync devices at our Exchange 2010 server.  I can do it for individual mailboxes, of course, but I'm trying to get them all to display or dump to a file.  I tried using one of the included examples in the get-help info, but most of the output is errors, followed by a few devices' info.  Can anyone show me what command I should be using to return the sync'd device info for all mailboxes?
July 2, 2010 3:36 PM
 

Bharat Suneja [MSFT] said:

@Jason: You can list ActiveSync user and device info using the examples in the following post:
Listing Exchange ActiveSync users and device information
http://exchangepedia.com/2008/06/exchange-server-2007-listing-exchange-activesync-users-and-device-information.html
July 2, 2010 3:49 PM
 

Jason said:

@Bharat:  The first command you have on your page returns results, but not what accounts the devices are linked to, nor the agent version.  The second command (with the Filter parameter) doesn't execute successfully: "Cannot bind parameter 'Filter' to the target."  This is, again, on Exchange 2010.
July 2, 2010 4:10 PM
 

Jason said:

Just an update - this command did/does work on Exchange 2010:

$mbx = get-casmailbox -Filter {HasActivesyncDevicePartnership -eq $true -and -not DisplayName -like "CAS_{*"}; $mbx | foreach {$name = $_.name;$identity = $_.identity;$device = get-activesyncdevicestatistics -mailbox $_.identity; $device | foreach {write-host $mbx.name, $_.devicemodel, $_.devicephonenumber, $_.Identity, $_.deviceid, $_.FirstSyncTime, $_.LastSuccessSync} }
July 2, 2010 4:24 PM
 

Joshua said:

Running iOS4 on iPhone 3GS. ActiveSync not working properly through third party apps to sync tasks with exchange server. Some apps include "TaskTask" and "iMTasks" and "iMExchange"
July 3, 2010 11:16 PM
 

ilantz said:

I wish nokia will be as responsive as apple, it's been quite a while that Mail for Exchange is "working" really bad against Exchange 2007 and Exchange 2010, tons of bugs and nothing a customer can do...

except of course going 3rd party sync software which makes no sense..
July 4, 2010 6:08 AM
 

Weinedk said:

I had some of the same issues describe above. I have an iPhone 3GS running iOS4, it worked fine on Exchange 2003, but after migrating to Exchange 2010, it suddenly stopped working.

I am truly sorry to say, that my issue was not caused by Apple, but a new security settings set by default on Exchange 2010. See this forum thread: http://social.technet.microsoft.com/Forums/en-ZA/exchange2010/thread/37a1cb86-d4e3-4851-b41b-f8e42997dd6c

I had the same symptoms. The event (1053) was present on our CAS, that Exchange ActiveSync doesn’t have sufficient permissions to create the user object. I am member of Domain Admins, and thereby member of a protected group.

I did as described in the forum thread, Included inheritable permissions from the object’s parent, on my own user object. And after deleting the exchange account on my iPhone and setting it up again it all worked fine again.
July 5, 2010 10:05 AM
 

John M said:

To Mark Texas - iOS 4 has been available for public beta test for months - you just needed to be part of their developer program. Small cost - hight benefit to access early release and test on your infrastructure before you get your user to deploy. Also they publish a knowledge base on their support site where you can find authoritative information and the latest info.

http://www.apple.com/support/iphone/


For users with additional problems look at default domain name (.local is not supported).

See http://support.apple.com/kb/TS3389




July 6, 2010 7:53 AM
 

Rick said:

John M, am I hallucinating, or is that article actually suggesting that those with Windows domains ending in .local *change their domains* for the sake of the debacle know as iOS 4?!  First, isn't it extremely common for domains to end in .local?  Second, wouldn't changing the domain have all sorts of repercussions due to the domain being specified in all sorts of nooks and crannies both on Server itself and elsewhere?  Third, I'm surprised they're not recommending switching over to OS X Server (or whatever it's called).
July 6, 2010 12:42 PM
 

gregg said:

is there a method to determine which users may be causing the high RPC latency values we are seeing after some users have updated their iPhone to IOS 4

in particular can we turn up logging and identify which users may be causing problems,  I am running exchange 2007 sp1 with cas, hub and ccr mailbox servers

fyi, so far we have identified users with very large numbers of calendar items are never able to synch their calendars, if  we apply the update file from Apple, their calendars do sync, but we are still experiencing heavy loads on mailbox servers

Thanks
July 6, 2010 3:02 PM
 

Andy said:

Gregg - you can identify users by running exmon on the mailbox server. We had 4 iPhone users each consistently consuming over 20% on one of our mailbox servers.
July 7, 2010 7:55 AM
 

EthanM said:

@Rick & @John M - The .local issue only occurs if you're accessing your corporate resources internally.  For example mail.domain.local accessed internally only.  The best solution (though maybe not in all circumstances) would be to use a split brain DNS solution, so that you have the ability to address both mail.domain.com internally as well as externally, but have different IPs for both (internal/external).
July 7, 2010 11:12 AM
 

Jason said:

Is anyone familar with how to restrict users from deleting the 'defaultEASTaskTimeout.mobileconfig' from their device? I can control this through the iphone Configuration utility for the Exchange profile that I am loading on each device.

If this is the temporary fix, I am concerned the end-user could easily just go into general/profiles and delete this profile.

Any thoughts are appreciated!
July 7, 2010 5:44 PM
 

Jason said:

I think I answered my own question -

this will prevent the profile from being removed from the device by the end user. Add this into the config file:

<key>PayloadRemovalDisallowed</key>
<true/>

you will have to remove it via the Iphone configuration utility.
July 7, 2010 8:40 PM
 

testt said:

I think it is ridiculous that you can not create a patch for Exchange to resolve this. So lame. So lame. Basically you are doing NOTHING.
July 8, 2010 10:41 AM
 

pikey said:

'  testt said:
I think it is ridiculous that you can not create a patch for Exchange to resolve this. So lame. So lame. Basically you are doing NOTHING.'

Eh? It's Microsofts fault that Apple have a problem with this and all the other devices out there using EAS don't? does not sound like a MS problem to memore like the way apple have implemented the standard.
July 8, 2010 10:59 AM
 

Douglas said:

There also appears to be an issue with email getting stuck in people's outboxes.  See:
<http://discussions.apple.com/thread.jspa?threadID=2469497&tstart=0>
July 11, 2010 11:34 AM
 

forumirule said:

Have you heard of admins of Exchange 2003 also complain of issues as well?  Thanks for the updates on this issue.  Agree with others that this info is really helpful to read and be aware of.
July 12, 2010 2:39 PM
 

sean said:

are there any updates for this yet? thanks
July 13, 2010 9:49 AM
 

Max said:

We're using Exchange 2003 and various iPhone devices (3.X and 4). Everything works so far, except for the fact that the first sync takes about 10 Minutes...When I check my mails on my test device the little circle keeps moving for about 1-2 minutes until it's fully synced. Does anyone know the origin of this slow sync?
July 14, 2010 3:53 AM
 

Evan said:

I saw bvig's comments about the Device User Agent string but the strings I am seeing in my environment are different. For instance, my own iPhone is a 3GS with the iOS4 and the patch correctly applied but my Device User Agent string is Apple-iPhone/705.18. Any ideas why this is different?
July 14, 2010 2:10 PM
 

bvig said:

@Evan; In our testing an iPhone 3GS running 3.1.3 showed as device string (Apple-iPhone/705.18).  Once upgraded to iOS 4.0, this same device showed as device string (Apple-iPhone2C1/801.293)

This was also true of an iPod Touch G2 running 3.1.3 showed as device string (Apple-iPod/705.18).  Once upgraded to iOS 4.0, this same device showed as device string (Apple-iPod2C1/801.293).
July 14, 2010 7:40 PM
 

Evan said:

bvig - that is the strange part. I would expect that to occur but it is not. It seems that the DeviceUserAgent stayed the same even after the upgrade to iOS4. My phone (which is a 3GS with iOS4 and the Apple patch) shows a DeviceUserAgent of Apple-iPhone/705.18. The one thing to note is that we are fronting the EAS configuration with a TMG Array - the TMG logs shows my device string as Apple-iPhone2C1/801.293.

Another question - is there a way to determine if the patch is applied to an iPhone?
July 15, 2010 9:12 AM
 

Jason said:

We are on Exchange 2003 SP2 with a separate front end server and ISA 2004 in front of it doing the publishing.

A couple of us have gone to 4.0 on the 3GS iPhone.  I did 4.0.1 last night and am still having issues.  Basically, the sync works fine for a little while, but every so often it just won't sync anymore.  Sometimes you have to go into the mail app and it does a pull of all the mail on the server (push just isn't working).  Most of the time, it sits there saying connecting and never connects.  The fix from apple didn't help.  The only thing I have found that works is to power off the phone and power it on again, then it starts syncing again.
July 16, 2010 11:12 AM
 

EthanM said:

@Jason - You have to apply the new firmware update/patch to every iOS4 device in the environment.  Applying the firmware/patch to just one of the iOS4 devices and expecting it to fix your specific device issues isn't the right approach.  Approach it holistically.  That said, if after applying the update to all iOS4 devices you still have the issue, try restarting the W3SVC on both the FE & BE servers during off hours.  If after that you still have an issue, and it's only with the Apple devices, we recommend contacting Apple.  Of course you can open a case with Microsoft as well.
July 16, 2010 11:50 AM
 

Martin said:

Well BPOS Exchange email has totally stopped working on my iPhone running OS 4.0.1.

It is 9:14pm Saturday 17 July 2010 Sydney time and whilst it was working yesterday all day after installing OS 4.0.1 it has totally stopped working today.

I tried deleting the account, turning off the phone and I've tried to re-establish the account but now I can't even do that. Every attempt to setup the account again gives me the same message 'Exchange Account Unable to verify account information'.

I have access to my email via my desktop client Outlook 2010 connected to BPOS and I have no problems via OWA.

Anyone else having the same problem? I have tried everything and now have BPOS email working on my iPhone.
July 17, 2010 7:17 AM
 

daniel cowdrey said:

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July 20, 2010 4:48 AM
 

Alex said:

Hello,

we have still problems on 300 users with iOS4 and sending emails with large attachements (bigger as 100kb).
They will not send and stuck in outbox.
We´re using Hosted Exchange 2003. All was working fine.

Is there a know issue?
July 20, 2010 10:38 AM
 

RJ said:

We are having the same issue. iOS 4.0.1 with Exchange 2003 SP2. ANy updates on resolution?
July 21, 2010 1:51 PM
 

Swift said:

Any Update on this issue? This problem was first published here 21 days ago. Is Apple ever going to do something about it or are they happy to dismiss the issue and have thousands of their customers accept their fate! would they really go so far and not bother about it until their next release? That certainly puts apple in a very bad light.
July 22, 2010 8:51 AM
 

EthanM said:

@Swift & @RJ - Apple released a new iOS firmware update (4.01) to address this.  If you still have the issue after applying this update to all your iOS4 devices then we recommend opening a case with Apple and/or Microsoft support to investigage.

@Alex - Have you contacted your hosted Exchange provider?  They can open a case with Microsoft support to investigate.
July 22, 2010 11:38 PM
 

RickP said:

Also having issue with messages stuck in the outbox on 4.0.1. Might be a restricted account issue because I am the exchange admin. Other users arent having an issue sending. I checked that inherited permissions is checked on my account. No idea what to try now.
July 23, 2010 7:14 PM
 

RickP said:

I also have logs if someone wants to check them out...here is a snippet
Fri Jul 23 19:54:22 iPhone MobileMail[65] <Warning>: EAS|server returned null sync key for sync of folderID 6.  Will erase local messages, perform full sync.
Fri Jul 23 19:54:22 iPhone MobileMail[65] <Warning>: EAS|mail db had no sync anchor for folderID 6.  Will erase local messages, perform full sync.
Fri Jul 23 19:54:24 iPhone MobileMail[65] <Warning>: EAS|EAS Protocol Manager set to ASProtocol14_0
Fri Jul 23 19:54:26 iPhone MobileMail[65] <Warning>: EAS|Erasing locally cached messages for folderID 6
Fri Jul 23 19:55:55 iPhone MobileMail[65] <Warning>: EAS|connection died with error Error Domain=NSURLErrorDomain Code=-1005 "The network connection was lost." UserInfo=0x60bd7b0 {NSErrorFailingURLStringKey=https://sync10.oakwoodvpr.org/Microsoft-Server-ActiveSync?User=user&DeviceId=Applsomething&DeviceType=iPhone&Cmd=SendMail, NSErrorFailingURLKey=https://URL/Microsoft-Server-ActiveSync?User=user&DeviceId=Applsomething&DeviceType=iPhone&Cmd=SendMail, NSLocalizedDescription=The network connection was lost., NSUnderlyingError=0x18da40 "The network connection was lost."} 0x60b8990
Fri Jul 23 19:55:55 iPhone MobileMail[65] <Warning>: EAS|ASSendMailTask failed: Error Domain=NSURLErrorDomain Code=-1005 "The network connection was lost." UserInfo=0x60bd7b0 {NSErrorFailingURLStringKey=https://URL/Microsoft-Server-ActiveSync?User=user&DeviceId=Applsomething&DeviceType=iPhone&Cmd=SendMail, NSErrorFailingURLKey=https://URL/Microsoft-Server-ActiveSync?User=user&DeviceId=Applsomething&DeviceType=iPhone&Cmd=SendMail, NSLocalizedDescription=The network connection was lost., NSUnderlyingError=0x18da40 "The network connection was lost."}
Fri Jul 23 19:55:56 iPhone MobileMail[65] <Warning>: ERROR: MFMessageErrorDomain/Socket Read - An error occurred while delivering this message.
Fri Jul 23 19:54:03 unknown kernel[0] <Debug>: launchd[65] Builtin profile: MobileMail (sandbox)
Fri Jul 23 19:54:07 unknown MobileMail[65] <Warning>: MKBGetDeviceLockState() returned 3
Fri Jul 23 19:54:11 unknown MobileMail[65] <Warning>: EAS|EAS Protocol Manager set to ASProtocolUnknown
Fri Jul 23 19:54:18 unknown MobileMail[65] <Warning>: EAS|mail db had no sync anchor for folderID 6.  Will erase local messages, perform full sync.
Fri Jul 23 19:54:21 unknown MobileMail[65] <Warning>: EAS|EAS Protocol Manager set to ASProtocolUnknown
Fri Jul 23 19:54:22 unknown MobileMail[65] <Warning>: error syncing folder: Error Domain=MFMessageErrorDomain Code=1028 "The operation couldnt be completed. (MFMessageErrorDomain error 1028.)"
July 23, 2010 8:10 PM
 

RickP said:

Fri Jul 23 19:45:27 iPhone ReportCrash[70] <Error>: Saved crashreport to /var/mobile/Library/Logs/CrashReporter/MobileMail_2010-07-23-194520_iPhone.plist using uid: 0 gid: 0, synthetic_euid: 501 egid: 0
July 23, 2010 8:11 PM
 

Storm said:

Can someone post instructions on how to block by device ID?

Here are all the apple devices that have ios 4

4 iPod Apple-iPod2C1/801.293
4 iPod Apple-iPod3C1/801.293
4 iPhone 3G Apple-iPhone1C2/801.293
4 iPhone  3GS Apple-iPhone2C1/801.293
July 29, 2010 2:54 PM
 

Dave said:

@RickP - we're also having the same issue even with the 4.01 patch and the increased timeout (we've tried as high as 360 seconds).  None of the OS3 devices have any problems and every OS4.01 device does.  Suffice to say we're not rolling out OS4.
July 29, 2010 6:36 PM
 

Ron said:

So what is Apple doing about this? We are now using VPN connections on the phone so the users can send email. Is there anything that can be done on our end without Apple's help to change a setting in Exchange or ISA to fix this? This is ridiculous!
August 3, 2010 3:37 PM
 

Ron said:

We have several users on OS 4.0.1 that are stil experiencing issues when sending email. The process just hangs trying to send. It can sometimes be cleared by turning the radio off/on but generally requires a restart of the phone. How can Apple expect to have their phones used in the Enterprise and not address this big issue in a timely manner?
August 5, 2010 9:39 AM
 

Russell Vandercook said:

Exchange 2010 does not seem to function through the Mail application in IOS 4 at all for me (though the "lite" version does seem to work in Safari). Are all these tests being done using previous versions of exchange servers?
August 5, 2010 3:08 PM
 

Dave said:

http://www.experts-exchange.com/Software/Server_Software/Email_Servers/Exchange/Q_26374879.html

Synchronization with your iPhone failed for 1 items.
The following items couldn't be sent to your mobile phone. They haven't been deleted. You should be able to access them using either Outlook or Outlook Web App.

       Item Folder:       Inbox
       Item Type:       IPM.Schedule.Meeting.Resp.Pos
       Item Created:       3/08/2010 3:09:25 a.m.
       Item Subject:       Accepted: Test 4

This not only effects iPhones also had this for Nokia devices. The problem occurs with the Accepted: or Declined: email that come back from booking a meeting with a resource or person. It is related to the unread/read mark.

In my client if I leave these Accepted/Declined messages unread I do not get the "Synchronization with your mobile failed for 1 items" once I have read the message I get the error. Basically what's happening (or not happening) is that the message remains unread on my mobile device. So the unread/read mark is not transferred to the mobile device.

When I then look at the message on the device it says "This message cannot be displayed because of the way it is formatted. Ask the sender to send it again using a different format or email program. text/plain"

If I open an Accepted/Declined message on the device before it has been read on the client it reads fine "Your request was accepted"

It's like reading the message in the client is changing the format of the message some how.
August 5, 2010 3:12 PM
 

Dave said:

I should have said our configuration is Exchange 2010 R4 on Windows 2008R2.

I believe this is only happening for EWS clients (Entourage and the up coming Outlook for MAC 2011)
August 5, 2010 4:28 PM
 

Kevin said:

We are seeing messages stuck in Outbox on 4.0.1 phones (both iPhone 4 and 3Gs). Cannot recall having any reports of this prior to 4.0.1. Server is Exchange 2010 RTM RU2. No other mail accounts are configured on the iPhone.

We're stuck here .. want to require folks running 4.0.0 to upgrade to 4.0.1, but from the end user experience, 4.0.1 is worse then 4.0.0.
August 6, 2010 5:16 PM
 

Doug said:

Our single Exchange 2003 server gradually over the course of about 4 days came to a grinding halt after many of our users upgraded to the iPhone 4.  

Last Friday I noticed that the full backup of our 275GB mailbox database took almost twice as long to complete (16 hours instead of the normal 8 hours).  The next couple nights were equally bad, and then the business day started on Monday and almost immediately the normal daily email was queuing up and messages were being delivered up to 90 min late.  The server just couldn't keep up, but this didn't really make any sense because everything was working properly, but it was just not fast enough.  What possibly would cause such a sudden and large performance hit?  Eventually we tracked down that it was the iPhones, so we stopped it at the firewall, witnessed Exchange start to improve almost immediately, and then we let the mail queues catch up.  At that point we decided to open the necessary ports once again, and things remained fine for a couple hours until...  all of a sudden the mail queues jumped way up again.  The mailbox store actually began to refuse everything.  Outlook clients wouldn't send mail at all at that point and got immediate bouncebacks, so of course our users weren't too happy about this, and neither were we.  The application log was littered with events from Exchange, and I was extremely concerned about possible database corruption.  The store.exe process was constantly churning away, but no mail was coming or going, and fortunately a simple restart fixed everything.  But that was only after a lot of sweating since the previous few night's backup had not completed yet either.  

We have since gone back to using just IMAP for now, so that our Exchange server can keep up until we upgrade to a 4-server Exchange 2010 solution next month, but of course our users want the calendar and contact sync functionality from ActiveSync, as well as the push email.  I would love to see Apple and Microsoft address this immediately.

August 8, 2010 11:10 PM
 

Kevin Partridge said:

Ron - I work for a University and our users are also experiencing the issues with sending e-mail in iOS 4.0 and 4.0.1.  It sits at "sending" 50% of the time.  If you let it sit there, the phone heats up and eventually kills the battery.  Do you know of any solution?  Is Apple aware of this issue(admitting it/ working to fix it)?  Users running iOS 3.x.x don't have this issue.  We are running Exchange 2010 RTM.
August 11, 2010 12:08 AM
 

Jim Goings said:

Just posted an article on my blog with a fix for Exchange 2010 users.  We got a NEW profile from Apple that reverts EAS support to 12.1.  So far, 100% fix rate.

http://www.jimgoings.com/2010/08/fix-for-iphone-ios-4-and-exchange-2010-active-sync-issues/
August 25, 2010 2:27 PM
 

Exchange said:

PLEASE NOTE: Regarding Jim Goings's comment above:

We DO NOT suggest that you follow the procedure on the blog. Instead, you should contact Apple support and work with them to receive a fix.
August 25, 2010 7:11 PM

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