Can't Send Attachments Using Exchange Account

Hi Dave,

sure - SSL is still used with you settings for the communication channel. When you ignore client certificates you force Exchange and iPhone to use password authentification over SSL. Also when the communication is "protected by SSL" you are using a very lower security level now. I do not want to do this in my environment, but you are free to do so in yours. Also your users need to change their passwords on iphone every time their domain passwords changes.
Have a look at the Apple whitepaper "iPhone in Business" here at page 2 about certificate settings: http://images.apple.com/iphone/business/docs/iPhoneMSExchange.pdf
Apple does not commend to set "ignore client certificates".

However - this does not explain why non-pdf and non-jpg attachments are working fine with client cerificates all the time.

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

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?

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 ?

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 !

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.

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.

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?

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.

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!

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.

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.

I just wanted to chime in and say we also have this issue. We just recently deployed two iPhone 3GS models with 3.1.3 on a wide open Activesync policy within a fully patched Exchange 2007 environment. Can't send images or PDFs but office attachments seem to work just fine. Looking forward to hopefully getting some resolution to this.

-Just tested creating a new wide open policy. Did not work

-Performed remote wipe on iPhone. Did nothing else to iPhone except resetup exchange account. Did not work

-disabled reenabled activesync on my account. Did not work

mee too with several iphones 3.1.3.
Sometimes emails with attachments immediatley goes through, a few minutes later I run into that error with the same email.
I also can confirm that this happens only with pdf and jpg files.