Cllick send; mail never makes to mail server

For some, but not all emails, I click send and it appears it is being sent but later I discover that it never went out, there is no record of it in the sent folder and the email never hits my company's IMAP server so there is no record there either. And the draft has disappeared from the drafts folder. I have used spotlight to see if the emails have been saved to some weird place on my harddrive but am not finding them. I feel like I am going mad ('I could swear I sent that email but where is it???)

Am deploying  Ms Exchange Server 2010, but I need you to assist me  to solve a problem.
This is the scenario below:
My client is made up three subsidiaries using same web mail service hosted by a provider.
One of the subsidiaries has decided to deploy their email in-house using Exchange Server 2010. So, while we are expected to migrate these  users to the Exchange server, remaining users from the two subsidiary will still be retained on  hosted web
mail.
The users are to retain their email addresses in the new environment.
So far,
I have deployed Exchange Server, exchanging mail within the local network and outside domain like  yahoo.com, gmail.com etc.  This is working fine... OWA is also working fine.
Technical details:
Port 25 enabled on the firewall, 
External registered domain: tsllimited.com
Host name : mail.tsllimited.com
local domain:tsl.local
ISP has created MX record to tsllimited.
Since users are expected to retain their email addresses we configured 
REPLY AS  to use   tsllimited.com (eg [email protected]) so users are currently using same address format  as they have on the web mail.
But there is a problem, that is :
We can send mail to the hosted web mail  from the exchange server ,
but receivers can not deliver mail to the Exchange server from the web mail.
What do we need to solve this problem. PLS  HELP!!!!

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