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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

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46 replies

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 !

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.

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.

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

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!

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.

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.

Can't Send Attachments Using Exchange Account

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