Using Win7\Windows Live Mail

I select pictures to send as Attachments;  Open New message, select Attachment symbol, go to folder where pictures are saved, select Pictures I want to send....the pictures appear in the New Message Full size, no way to send smaller.....so that won't work because pictures are sized in MB size.

I then go to the My Pictures Folder, select Pictures I want to send, click E-Mail in Tool Bar, get the window to resize the pictures, select Smaller....pictures populate in Windows Live Mail New Email Window, I select SEND....and the email hangs in the Out Box.

I get the Windows Live Mail Window.....

Some errors occurred while processing the requested tasks.  Please review the list of errors below for more details.

         Delete the photo email. create a new one and try to send again

                   Server:  smtp. XXX email address  XXXXXX

                   Windows Live Mail Error ID:  0x8CCC0003

                   Protocol: SMTP

                   Port: 465

                   Secure(SSL): Yes 

I have another PC running Microsoft Outlook 2007...and I send these Pictures at the smaller size using the same Mail Provider with no issues.  In Outlook 2007 I am able to open New Message, Select ATTACHMENT Icon, select Pictures, as the Populate in message....the window opens asking me to send as original size or resize, I normally always select the smallest size and the email\Pictures send fine.

So why can't I send these pictures using Live Mail?