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Can't Send Attachments Using Exchange Account

For some reason I can't send attachments using my Exchange account on my iPhone. Pictures, Word docs, Excel Docs, doesn't matter. They just get stuck in my out box and I get the following message, "Cannot Send Mail - An error occurred while delivering this message." I can receive attachments just fine, but cannot send or forward them. If I use any of the other email accounts on my phone, it works fine. The Exchange account is the only issue. Is this some limitation with Exchange on an iPhone or something? Anyone ever have the same problem as was able to fix it? Thanks!

Windows Vista

Posted on Dec 31, 2009 10:51 AM

Reply
46 replies

Mar 13, 2011 6:58 AM in response to ChrKrikl

Before you go making changes to exchange or IIS, check the basics. I was having this problem for the last couple of days. I logged in to our Front End Exchange server to make the changes listed above. I figured before I do anything I should just check the health of the box. Low and behold, the C drive was completely fullUser uploaded file I deleted about 3GB of IIS logs and presto! PNG and JPG attachments are flowing once again. Just proves that you should always start with the lowest common denominator.

Jul 28, 2011 2:28 PM in response to Ben Murphy

This is what worked for us:


Environment:
ActiveSync configured on Exchange 2003 SP2 running on Windows Server 2003 SP2with IIS 6

Issue:

  • Email message with attachment (regardless of attachmentsize) sent from a mobile device(smartphone, iPhone, iPad, etc.) remains “stuck” in mobile device’s Outbox, but NOT in Exchange account Outbox
  • No error message(s) displayed on mobile deviceor on Exchange server
  • NOTE:NO problems receiving/opening/reading Incoming emails that have attachments on a mobile device

Fix:

Go to the %SystemRoot%\Temp( WINNT\Temp or WINDOWS\Temp)directory on the Exchange server:

  • Click on the Security tab and add Authenticated Users
  • Grant AuthenticatedUsers the following permissions:
  • Modify
  • Read & Execute
  • List Folder Contents
  • Read
  • Write

Aug 24, 2011 7:40 PM in response to Jeffred

@Jeffred OH MY GOD THANKYOU!!!


That problem has existed for so long on a customers server and I've never been able to figure why!!

Every 6 months I'd have another look at it and try so many different things, I can't believe it was something so simple!!


This is the first time I've every actually signed up and logged in to say thanks, so means a LOT thank you!!


Phil

Mar 16, 2016 8:56 AM in response to Ben Murphy

SOLUTION for setup = Any iPhone using Exchange email account (all versions)

this works in a business environment, tested on Exchange 2007, 2010, 2013, change is instant and does not require a server reboot.


#Exchange Client Access Server Administrators {set all your send & receive connectors to the the same value, then double that value and use it in the steps below}


There are client-specific message size limits you can configure for Outlook Web App and email clients that use ActiveSync or Exchange Web Services (EWS)

ACTIVESYNC FILES

%ExchangeInstallPath%FrontEnd\HttpProxy\Sync\web.config

%ExchangeInstallPath%ClientAccess\Sync\web.config

%ExchangeInstallPath%ClientAccess\Sync\web.config

you will need to update the entries for maxRequestLength & maxReceivedMessageSize to a value depending on your Send/Receive Connector size limits.

example to allow 50MB attachments to be sent from iPhones via ActiveSync

maxRequestLength="100000"

maxReceivedMessageSize="100000"

The reason why i have set the value to 100MB is to allow for a 33% increase in size due to Base64 encoding, multiply your desired new maximum size value in megabytes by 4/3. To convert the value into kilobytes, multiply by 1024. To convert the value into bytes, multiply by 1048756 (1024*1024). Note that the size increase caused by Base64 encoding could be greater than 33%, and depends on several factors, for example, the attachment file size, type, compression, and the email client used to compose and send the message.

Sometimes you will see a 9MB attchment appear as 11MB or 12MB on the iPhone (this is why)

I hope this fix is helpful to all Server Administrators out there 🙂

Can't Send Attachments Using Exchange Account

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