Ben Murphy

Q: 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

Close

Q: Can't Send Attachments Using Exchange Account

  • All replies
  • Helpful answers

first Previous Page 3 of 3
  • by ChrKrikl,

    ChrKrikl ChrKrikl Nov 18, 2010 4:53 AM in response to Ben Murphy
    Level 1 (0 points)
    Nov 18, 2010 4:53 AM in response to Ben Murphy
    Hi Guys,

    it seems that i have found a solution that work for me.

    When you use certificate authentication you have to set the uploadReadAheadSize in the IIS metabase to your max email size, the default is 48KB so nearly any attachment cannot be sent/forwarded.

    With the following command you can change the value (in this case 10MB):
    C:\Windows\System32\inetsrv\appcmd.exe set config -section:system.webServer/serverRuntime /uploadReadAheadSize:"10485760" /commit:apphost

    C:\Windows\System32\inetsrv\appcmd.exe set config "Default Web Site" -section:system.webServer/serverRuntime /uploadReadAheadSize:"10485760" /commit:apphost

    After this restart the IISAdmin service to affect the change.

    The folling articel helped me:
    http://www.expta.com/2010/02/how-to-securely-deploy-iphones-with_25.htm


    The only things i want to know now.
    - Why does this only occur on Iphone and not on WinMo
    - Why doesn't this occur without certificate authentication.
  • by atsekhanskiy,

    atsekhanskiy atsekhanskiy Mar 1, 2011 12:07 PM in response to MPower
    Level 1 (0 points)
    Mar 1, 2011 12:07 PM in response to MPower
    MPower,

    What was your fix for this?
  • by Brandon Riffel,

    Brandon Riffel Brandon Riffel Mar 13, 2011 6:58 AM in response to ChrKrikl
    Level 1 (0 points)
    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 full 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.
  • by teufelm,

    teufelm teufelm Jun 28, 2011 11:04 AM in response to MPower
    Level 1 (4 points)
    Jun 28, 2011 11:04 AM in response to MPower

    Hi MPower!

     

    Can you please provide me the fix for the size problem?

     

    I have got one exchange 2003 server with 2 mailboxes. one mailbox/account can send mails with attachments >50 kb - the other not.

     

    Thanks!

  • by Sage2791,

    Sage2791 Sage2791 Jul 19, 2011 10:11 AM in response to ChrKrikl
    Level 1 (0 points)
    Jul 19, 2011 10:11 AM in response to ChrKrikl

    ChrKrikl, that was the correct solution.  Thank you very much.       

  • by Jeffred,

    Jeffred Jeffred Jul 28, 2011 2:28 PM in response to Ben Murphy
    Level 1 (0 points)
    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
  • by teufelm,

    teufelm teufelm Jul 28, 2011 10:41 PM in response to Jeffred
    Level 1 (4 points)
    Jul 28, 2011 10:41 PM in response to Jeffred

    Hi!

     

    I  had the same Problem with the TEMP directory. After hours i found it our. Only Admins and System were allowed to write to the folder. Changing it to Authenticated Users solved my issu.

     

    Martin

  • by CyberWired,

    CyberWired CyberWired Aug 24, 2011 7:40 PM in response to Jeffred
    Level 1 (0 points)
    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

  • by JohnGeero,

    JohnGeero JohnGeero Jul 5, 2012 2:04 PM in response to Jeffred
    Level 1 (0 points)
    Jul 5, 2012 2:04 PM in response to Jeffred

    Does this work for Exchange 2010?

  • by Sage2791,

    Sage2791 Sage2791 Jul 5, 2012 3:59 PM in response to JohnGeero
    Level 1 (0 points)
    Jul 5, 2012 3:59 PM in response to JohnGeero

    ChrKrikl solution worked for me on Exchange 2010. 

  • by Zedsee,

    Zedsee Zedsee Feb 24, 2016 3:18 AM in response to Jeffred
    Level 1 (0 points)
    Feb 24, 2016 3:18 AM in response to Jeffred

    Just had to fix this issue. Thanks Jeffred for providing the solution. Works for 2003

  • by alexander.niazi,

    alexander.niazi alexander.niazi Mar 16, 2016 8:56 AM in response to Ben Murphy
    Level 1 (0 points)
    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

  • by toondh,

    toondh toondh Apr 20, 2016 9:40 PM in response to Ben Murphy
    Level 1 (4 points)
    Apr 20, 2016 9:40 PM in response to Ben Murphy

    In my case a large video blocked the outgoing mail folder (Mail, Exchange, Out). Go in flight mode and then delete the mail.

  • by atulat,

    atulat atulat Jul 13, 2016 4:49 AM in response to MPower
    Level 1 (4 points)
    Jul 13, 2016 4:49 AM in response to MPower

    Can you please let me know the fix? Cheers.

  • by atulat,

    atulat atulat Jul 13, 2016 4:51 AM in response to MPower
    Level 1 (4 points)
    Jul 13, 2016 4:51 AM in response to MPower

    Can you please let me know the fix? Cheers

first Previous Page 3 of 3