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

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Q: Can't Send Attachments Using Exchange Account

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  • by GeoffreyS,

    GeoffreyS GeoffreyS Jan 4, 2010 2:56 PM in response to Ben Murphy
    Level 1 (20 points)
    Jan 4, 2010 2:56 PM in response to Ben Murphy
    I have seen the issue before but I just checked mine and it worked. I forwarded a message with one each Word, Excel, PDF and PNG attachments. All came through. I have an iPhone 3GS running 3.1.2 and Exchange 2003 SP2 32 bit. Assuming you're using ActiveSync?
  • by Graham Outterside,

    Graham Outterside Graham Outterside Jan 11, 2010 2:40 PM in response to Ben Murphy
    Level 4 (2,915 points)
    Jan 11, 2010 2:40 PM in response to Ben Murphy
    How are you adding the attachment to the email ?

    Presumably a third part app or are you talking about forwarding emails with attachments ?

    I didn't think that the native email application allowed the attachment of files, other than through the Photo Library etc ?
  • by GeoffreyS,

    GeoffreyS GeoffreyS Jan 11, 2010 3:26 PM in response to Ben Murphy
    Level 1 (20 points)
    Jan 11, 2010 3:26 PM in response to Ben Murphy
    In my case I was forwarding messages that already had attachments.
  • by Graham Outterside,

    Graham Outterside Graham Outterside Jan 12, 2010 1:56 AM in response to GeoffreyS
    Level 4 (2,915 points)
    Jan 12, 2010 1:56 AM in response to GeoffreyS
    And are you getting the prompt that says about downloading the rest of the message before sending ? This should download the attachment and then forward it on, but if you say "No" then the forwarded email will be incomplete.

    It sounds like your email is behaving as if it is downloading headers only, but if you are able to read the actual attachment, its not - very curious !
  • by iMeerkat,

    iMeerkat iMeerkat Jan 14, 2010 7:41 AM in response to Ben Murphy
    Level 1 (5 points)
    Jan 14, 2010 7:41 AM in response to Ben Murphy
    Exact Same issue on my bosses Iphone with a hosted Exchange solution. Can recieve emails with and without attachements, but can only send emails without attachements. So forwarding of attachments seems to be disallowed.

    Since the exchange server is hosted and the hosting company reckon its not there problem i'm at a loss what to do next.
  • by radar349,

    radar349 radar349 Jan 15, 2010 8:43 PM in response to iMeerkat
    Level 1 (0 points)
    Jan 15, 2010 8:43 PM in response to iMeerkat
    Got the same problem using GMail. Any suggestions appreciated. The forwarding of email(s) with existing attachments could be the culprit.
  • by Techarcana,

    Techarcana Techarcana Feb 3, 2010 5:34 AM in response to Ben Murphy
    Level 1 (0 points)
    Feb 3, 2010 5:34 AM in response to Ben Murphy
    I've got 38 iPhones deployed running the 3.1.2 OS against an Exchange 2007 server. Several of my users complain about the same issue, and I've seen it myself. I have found a workaround of sorts - I've found that if I've sent a message with an attachment and I get a failure to send, if I manually browse down to the Sent Items folder, that forces a replication of the Sent Items. The next time I do a manual sync, the e-mail with the attachment will go.

    I presume this has something to do with Exchange trying to put a copy of the e-mail in to your Sent Items at the same time the iPhone is trying to send the message.

    Potentially, this might be solved by turning off the option to always store your sent e-mails in the Sent Items. I have not yet tested that as a workaround as from a corporate standpoint and an ease-of-use standpoint, we want that e-mail in the Sent Items for reference.

    If anyone has any success with this fix, please let me know.
  • by jclopez0101,

    jclopez0101 jclopez0101 Feb 3, 2010 9:29 AM in response to Techarcana
    Level 1 (0 points)
    Feb 3, 2010 9:29 AM in response to Techarcana
    I'm in the same boat as Ben. I've got 15+ in production running 3.1.2 as well. Has anyone upgraded to 3.1.3? Maybe this was fixed yesterday.

    -JC
  • by johnzapf,

    johnzapf johnzapf Feb 3, 2010 10:39 PM in response to jclopez0101
    Level 1 (0 points)
    Feb 3, 2010 10:39 PM in response to jclopez0101
    I am having the same problem. take a picture and cant sent it. works fine on my network with wifi, so it must be AT&T's network or a port or something in our firewall. the thing is it worked great 2 weeks ago. and also kills the battery in 3 hours as it continually tries to send that picture.

    3.1.3 didn't fix it....

    I have been trying to fix this for 8 days now...
    My wife is going to have a baby any day now and I was hoping to take and send a picture from the hospital. I will bring these phones back and tell them what to do with them if it doesn't work on that day!!!

    John
  • by Techarcana,

    Techarcana Techarcana Feb 12, 2010 6:19 AM in response to Techarcana
    Level 1 (0 points)
    Feb 12, 2010 6:19 AM in response to Techarcana
    Finally got a chance to test the proposed fix... doesn't do it. I have got more data, though - my users are able to send their attachments once they reach a WiFi network the phones are associated with - implying the problem is somewhere in the AT&T 3G network.

    Has anyone talked to AT&T about this issue?
  • by Turtle353,

    Turtle353 Turtle353 Feb 17, 2010 7:39 PM in response to Techarcana
    Level 1 (0 points)
    Feb 17, 2010 7:39 PM in response to Techarcana
    Anybody have any luck fixing this? I am able to send regular emails without attachments and even receive attachments. I can send attachments via google, yahoo, and mobile me. It is only exchange that will not send attachments.
  • by TechnaPeter,

    TechnaPeter TechnaPeter Mar 3, 2010 9:47 AM in response to Turtle353
    Level 1 (0 points)
    Mar 3, 2010 9:47 AM in response to Turtle353
    We have the same problem with Exchange 2007, latest fixes, patches etc.
    We have had this problem while using two different ISPs and firewalls.
    The problem is similiar by design. Cannot send emails with forwarded or new attachments while using 3G. If the user connects to a WIFI, the email sends fine.
    However, what is interesting is that the emails always send after a longer period in the outbox, like days!
  • by Techarcana,

    Techarcana Techarcana Apr 1, 2010 7:43 AM in response to TechnaPeter
    Level 1 (0 points)
    Apr 1, 2010 7:43 AM in response to TechnaPeter
    Just to keep my fellow sufferers up-to-date... I've engaged AT&T, Microsoft and Apple on this issue. We've been working with multiple paths to determine the root cause.

    I have found that a properly configured HTC Fuze WILL send attachments, albiet a bit slowly, to my Exchange 2007 server without any changes to the server.

    I've also, at Apple's request, provided diagnostic information retrieved from an iPhone exhibiting the non-delivery behavior yesterday.

    I'll post more as we continue researching the problem.
  • by Qberry22,

    Qberry22 Qberry22 Apr 5, 2010 12:22 PM in response to Ben Murphy
    Level 1 (0 points)
    Apr 5, 2010 12:22 PM in response to Ben Murphy
    Using Exchange 2007 fully patched
    iPhone 3GS 3.1.3

    I just found out I can forward word and excel files. Recieve the same error as everyone else when trying to forward PDF attachments and JPG attachments. Take a picture on the iphone or video and cannot send those as well. Going to try to apply diffrent (wide open) active sync policy to see if that makes a diffrence.
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