iOS 7 and sending emails larger than 40KB from Exchange accounts

Remove and re-add the account on the device.

If possible, turn off the size restriction in Exchange then re-enable to see if that rectifies the issue.

Anyone else have this same problem. Only happens with IOS 7 devices. Attachments smaller than 40KB go through, others get stuck in outbox. However it works fine over wireless. Fails over Cellular.

We are using certificate based authentication Active Sync. Not sure if that matters.

We are seeing intermittent issues with IOS 7 devices on Exchange with smaller messages. Cannot find a log of the message on the iPhone, but it indicated it was rejected by the server. At first it seemed to be an issue of a period at the end of the email. We were able to recreate this once, but then subsequent attempts to recreate faile and all emails were processed correctly.

I justed tested with an iPhone 5 and an iPhone 5s, both running iOS7.0.1, both AT&T, both with Wi-Fi disabled. I sent a 1MB photo attachment to an iCloud account. Both worked just fine.

Does not seem to be a general issue with iOS7. Running Exch 2010 SP2 RU 6, though.

I just received the same message when trying to send a reply to a message on my corporate Exchange Mail account. This has only occurred since I upgraded to ios7. I can compose a new email fine but received the message that the emails was too large when trying to send a reply.

Here is the error we experienced. Only found this on IOS7, a 4s and a new 5s

Update to my scenario. I figured it out. We are on Exchange 2007 on Server 2003 and we are using Active Sync with Client Certificates. We did not notice much of a problem when sending using IOS 6 but with IOS 7 it was much more prevalent, any message over 100K would get rejected as too large. turns out it was a problems with IIS 6 and the uploadreadaheadsize value in the IIS metabase. Here is a link regarding it for 2010

http://social.technet.microsoft.com/Forums/exchange/en-US/52f58b47-b95e-4f44-bb4 e-6bd8b1b4eb94/iphone-sending-attachment-problems

here is one for 2007

http://technet.microsoft.com/en-us/library/cc737382%28WS.10%29.aspx

I bumped mine up to 10Mb and now attachments are going through fine. THis probably should have been done a long time ago, but the symptoms really just reared its ugly head after the ios 7 upgrade.

I hope this helps others, as i was pulling my hair out all weekend trying to figure this out.

We are having the same issue since we upgraded to ios7 but we have Exchange 2010 on Windows 2008 R2 so we have IIS7. Is that solution applicable to our case as well? Don't want to be the Guinea pig and be the first one trying in a Prod env. :-)

Thank you

I would go for it. THis is the link to do it on 2008. Just look up how to back up the metabase first. Also find out how to query the current values in metabase to ensure your changes went through and or to revert back. At lease look for more information using the link below as a starting point.

http://social.technet.microsoft.com/Forums/exchange/en-US/52f58b47-b95e-4f44-bb4 e-6bd8b1b4eb94/iphone-sending-attachment-problems

See thread here for similar issues

https://discussions.apple.com/thread/5322387?answerId=23226266022#23226266022&tstart=0#23226266

I had a similar problem when sending large attachments and used the solution below. I tried everything on here without luck.. Just a small change in he web.config and it solved my issue:

http://www.mountainvistatech.com/2013/12/04/iphone-and-exchange-2010-error-canno t-send-mail-an-error-occurred-while-delivering-this-message/

hope it helps...

I dont get it, why do people spend their time try to fix this when there is dropbox or sites like http://emailattachment.net/ , you can send much larger files, safer and quicker :/

just sayinnggggg

My email administrator rejects this saying if other ios works why ur iphone 4 with ios7 not? Only I have is to change the iphone pls help. My phone works with yahoo too