Found the Fix for this. Simply enough just unregister the dll and reregister it and the send to mail recipient will reappear, and autosize pics in emails.... Method 1: Unregister and then reregister the Sendmail.dll file For Microsoft Outlook Express 5.0 and Microsoft Outlook Express 6.0, follow these steps. When the .MAPIMail file does not exist in the Disk:/Documents and Settings/username/SendTo folder, the Mail Recipient command is not shown when you point to Send To on the File menu. 1. Click Start, click Run, type regsvr32 /u %windir%\system32\sendmail.dll, and then click OK. 2. Type the following command to reregister, and then click OK: regsvr32 %windir%\system32\sendmail.dll