Outlook 2010 using Exchange 2010 - cannot send this item after updating draft email

I have a client who has the following setup.
SBS 2011 server (Exchange 2010) and a Windows 2008 R2 Terminal Server (with Office 2010 SP1 installed).
This particular user has a Windows XP PC with Office 2010 SP1 installed (joined to SBS 2011 domain).
This user creates a email at their office on their PC and saves it in draft to continue working on it when they get home.
At home they RDP into the terminal server and load outlook and start updating their saved (Draft) email. They then try to send it and the following error pops up. "Cannot send this item".
If they try to save the changes they have made it pops up with "The operation failed".
I have tried various settings all with the same results.
Office 2010, Office 2010 SP1, Online mode and Cache mode (on the Windows XP PC).
Any ideas?

Hi Rajkumar,
OK. After further testing I have narrowed it down to the email signature?
If I save a draft email in Outlook on the Fat client (Windows XP + Office 2010), then go straight into Drafts folder and open the email and add one line of text and try to send or save again it fails.
If I don't have a signature, it works fine.
I currently trying to determine what part of the signature it doesn't like (it is quite a large signature, multiple images and a disclaimer etc). I'm having mixed results - I can remove the signature totally from the draft email and then it will save
or send fine.
Strange that it can save the email to Draft in the 1st place but doesn't like updating it a 2nd time???
I have also created a new outlook profile (online mode) with the same results.

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OUTLOOK 2010 error "cannot sent this item"

Hai,
When i try to forwarding / replying via
Outlook 2010, i am getting an error "Cannot send this item" . The error occurred only when forwarding / replying a
particular MAILS.

We have the issue in our office from time to time, and after alot of test lately, here is what i came up with soo far
French:
Erreur HTML: Impossible d'envoyer cet élément.
Erreur Richtext: Impossible d'envoyer cet élément. La propriété n'existe pas. Le champ que vous voulez modifier n'est pas valide pour ce type d'élément
English:
HTML Error: Cannot send this item.
Richtext Error: The property does not exist. The field you want to modify is not valid for this type of item.
To reproduce the issue
Create a signature doing the following:
Open Word 2010, Type a word and hyperlink it to google
Insert a picture bellow, you can pick the default pictures in the pictures folder
Save the signature as .htm in your C:\Users\%user%\AppData\Roaming\Microsoft\Signatures folder
Create a new email and send it to yourself including your new signature and a file that isn't a .msg, lets pick a .docx file for now
From the email you've just received, transfer the email.
Insert your new signature again and resize one of your picture
While the new email is opened, the email must be saved at some point either by Outlook automaticly or manualy ctrl-s or clicking on the appropriate icon before sending the email
Send the new email, you'll get the error message after the dictionary lookup if the resize was made before saving the email, otherwise the send button won't click
Take note than if your windows resolution has bin changed to anything else than 100%, the picture will be automatically resize by inserting the signature
You must transfert the email, a reply won't create the issue
If we resize a picture and then we delete that picture before the error message, we don't have the issue
Possible solution to resolve the issue with this email:
- Close the email and get the last save in the draft
- Copy and past the body text, file etc in a new email
- Delete all the pictures in the email and send it, note that you cannot add any picture after that, otherwise you'll still have the issue

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Hi Nigel,
How is the impact, just one user or all users, Outlook or OWA?
If just one user, it seems like an issue on the Outlook Client side.
Please trying to re-create new profile to fresh the caches.
Please runing Outlook under safe mode to avoid some AVs, add-ins and firewall.
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http://social.technet.microsoft.com/Forums/exchange/en-US/d9b33281-d7bb-4608-8025-16fb26643d0d/calendar-sharing-not-available-error-message?forum=exchangesvrclientslegacy
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