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Cannot Send Mail (iPhone + Exchange 2003)

Posted on 2013-01-09
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Last Modified: 2013-02-21
We host an Exchange 2003 server.
I have multiple users with iPhones that access their exchange mail accounts.

A couple of users are unable to forward emails that contain attachments.

Error message they receive is...
Cannot Send Mail -  An error occurred while delivering this message

Open in new window


I have tried...
1. Closing re-opening Mail app.
2. Switch iPhone off and on again.
3. Resetting iPhone using Power and Home button function.
4. Backing up the iPhone, erasing it and restoring the backup.

All of the above have not resolved the issue.
I have added one of the users accounts to a "known working" iPhone, the issue persists.
Indicating to me this is a problem with the users mailbox, rather than the iPhone.

Can anyone assist me on this problem? I have tried searching Google, and not found any solutions yet.
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Comment
Question by:antonioking
11 Comments
 
LVL 12

Expert Comment

by:Imtiaz Hasham
ID: 38758642
There is a problem with Exchange 2003 and iPhones as they have a compatibility issue.
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LVL 16

Expert Comment

by:PaciB
ID: 38758647
Hi,

Does it have something to do with the attachment size ? Did you try several attachments of different type and size ?

If you try to do a forward directly in the OWA page for these mailboxes, does it work ?

For my part I really doubt this is a mailbox malfunction, but if it is you should have the same exact problem with OWA. So just try and tell us.

This may be caused by some specific ActiveSync policy for these mailboxes about how to manage attachments.
Also, is there a difference when you "forward" the mail with attachment and when you create a new mail with attachment. Can you try to see if this occirs only when forwarding or also when sending new mail ?

Have a good day.
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LVL 1

Expert Comment

by:Slagwag
ID: 38758653
One issue I had in the past with Exchange 2003 seems similar. The e-mails would forward if there was no attachment, however forwarding e-mail with an attachment would fail every time. This would be regardless of the file size of the attachment.

The solution ended up being that our mailbox limit for an attachment was set too large and it caused mobile devices to not be able to forward attachments. Bizarre issue but it was something that was discovered a few months after opening a case up with Microsoft. What I would check first is what you have your attachment limit set to. Perhaps it is something over 100mb?

I ended up dropping it down to 30mb at the time and everything was resolved.
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LVL 76

Expert Comment

by:Alan Hardisty
ID: 38758657
How big is the attachment that you are trying to send?  If large, there is an issue around about 8Mb where it won't send.
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LVL 52

Expert Comment

by:Manpreet SIngh Khatra
ID: 38758695
Is the issue with certain format of File ?
I assume they can do normal forwarding :)

- Rancy
0
 

Author Comment

by:antonioking
ID: 38759044
@PaciB
Does it have something to do with the attachment size ? Did you try several attachments of different type and size ?
Tried multiple files types of different sizes. Both users mailboxes are way under their sending restriction limits too.

If you try to do a forward directly in the OWA page for these mailboxes, does it work ?

For my part I really doubt this is a mailbox malfunction, but if it is you should have the same exact problem with OWA. So just try and tell us.
Forwarding via OWA works fine.

Also, is there a difference when you "forward" the mail with attachment and when you create a new mail with attachment. Can you try to see if this occirs only when forwarding or also when sending new mail ?
Sending new messages with attachments works fine.

@slagwag
What I would check first is what you have your attachment limit set to. Perhaps it is something over 100mb?
Attachment send limit is 40MB, which incidently was recently increased from 20MB. However, out of 15+ iPhone users, only 2 are experiebsncing this issue.

@alanhardisty
How big is the attachment that you are trying to send?
I have tried a variety of attachments ranging from a few KB upto a <10MB.

@Rancy
Is the issue with certain format of File ?
I assume they can do normal forwarding :)
I've tried pdf, xls doc and image files, all varying in size.
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Accepted Solution

by:
antonioking earned 0 total points
ID: 38896859
I bit the bullet and re-created the users user account.
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LVL 52

Expert Comment

by:Manpreet SIngh Khatra
ID: 38896866
Did that fix the issure for you

- Rancy
0
 

Author Comment

by:antonioking
ID: 38896904
Yes it did.
0
 

Author Closing Comment

by:antonioking
ID: 38913140
Issue wasn't resolved, but "worked" around be re-creating  the user account
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