Can't Send Attachments Using Exchange Account

-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

I have the same issue in my firm. Word and Excel files work fine. PDF's and JPG's can't be forwarded. The user claims that it was working until a few weeks ago.

What's going on?

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.

I experienced same issue...exchange attachments wouldn't send but regular emails without will send. Although it was intermittent for some users.

I ended up resolving this by modifying two areas in my exchange active-sync settings...here you go and hope this helps.

Server Configuration----> client Access ----> Exchange ActiveSync tab.

Double click Microsoft-Server-ActiveSync Properties. Go to Authentication tab...Make sure check on Basic authentication (mine was already set to this) and check "Ignore client certificates" (mine was set to Accept).

I also changed the external url on the general tab. I replaced the fqdn with IP address. I'm not sure which or both fixed my issue, but it is resolved and I can send attachments every time.

Let me know how it goes....

-Dave

@derismano
disableing cerficate authentifiacion will not be possible in most cases because it is the best and most secure authentification method. But maybe this is the focus of the bug.
Changing external (or internal or both) url to IP adress (and leave "request client certificates" enabled) unfortunatly does not change anything on my systems.

Hello, I didn't disable certifacte authentication. I left SSL checked, I only selected to ignore the client certificates. I know for sure I'm still using SSL authentication as when I setup the iphone's they all use ssl.

-Dave

Here's more info on SSL and authentication. All I'm doing is ignoring client certificate's. I still confirm that IIS has SSL checked. Here's more info from MS. This applies to both exchange 2003 and 2010.

MS quote: By default, when you install Microsoft Exchange Server 20xx, Exchange ActiveSync is configured to use Basic authentication with Secure Sockets Layer (SSL) encryption. Other standard authentication methods include Digest authentication and Integrated Windows authentication. If you must return Exchange ActiveSync to Basic authentication, you can use the procedures in this topic.

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.

SOLUTION:

I can confirm that if you set your IIS that runs Outlook web access and Activesync to "Ignore Client Certificates", the attachments will send. You do not need to turn off "Require Secure Channel (SSL)" or "Require 128 bit encryption". You just need to switch from "Accept client certificates" to "Ignore Client Certificates".

To do this:
1. On your Exchange server that runs your active sync or outlook webaccess, open IIS
2. Right click on the website that contains exchange components and choose properties (for me it is "Default Website).
3. Select the "Directory Security" tab
4. Under "Secure Communications", click the "Edit" button
5. Under "Client Certificates", select "Ignore Client Certificates"
6. *IMPORTANT STEP*: When you click ok and ok again, it may ask you whether you want to change other subfolders within the main container with the modifications you have just made, dont select any of these subfolders, just click OK. It is only the main properties you need to change. Those that need to inherit, should already inherit properly. If you select other subfolders to change with the modifications you have just made, it will likely ruin your active directory setup as some subfolders need different security settings to others.
7. IISRESET and you are done.

Note:
Just in case my other settings play a part (i doubt it though):
- I have anonymous and integrated security turned on, everything else is off (basic authentication is also off).
- My FQDN is not an IP address, someone else suggested this but it is not required.

Hi Mentossss,

are you prompted for a password on iPhone with your settings?

EXCERPT:

Techarcana wrote:
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.

Assuming I'm understanding your post correctly, I will recommend another route to try:

When I have found myself in a situation whereby my Exchange is stuck on a task & won't budge, even by killing the Mail.app process & re-launching it, I try the following & it usually works:

Go to Settings --> Airplane Mode

Activate it.

Wait 30 seconds, maybe even go back into Mail so that it registers the fact that your iPhone socket is closed due to the activation of the airplane provision, (hit okay to any error popups), then go back & turn OFF Airplane Mode.

In my experience, Exchange then re-tries whatever it was hanging up on without being bogged down by any other simultaneous Exchange (or other) network activities in the background that you don't see happening.

--
+Remember one thing that is almost always applicable with software: Never fully rely on status messages displayed on the screen. Those are merely displayed at the mercy of them being programmed to be triggered properly. If you know what I'm talking about, always use a means of debugging to see what's REALLY going on, such as XCODE, etc.+

+That shows you tons of lines of activity processes every few seconds. That's what I consider useful, not the lame errors that apps typically display, which many of times are wrong all together.+

To those having the problem, please confirm the issue is not related to attachment size. If it's related to size, I have a fix.

I also have the same issue with Ben. But with, iPad I didn't encounter the said issues. I can sent/forward any attachments - Word, Excel, pdf, and jpg files.

Has anyone found the solution for this issue?

Hi MPower, can you please share how you fix the issues with attachment size? Thanks.

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.