Unable to send mail to some addresses after move to Leopard

I am not sure, whether I am in the right forum with my question. If not, please tell me where I should go.
I am traveling a lot for work and have clients in many countries. Since 2004, I have been using Mac laptops and have not encountered any problems sending mail through clients' LANs, from my own place to clients, or from any number of hotels to clients. I migrated from Tiger to Leopard on the day the latter OS became available.
Since the move, I am experiencing a problem sending mail to one specific client. I can no longer send mail to my various contacts within that client's premises (all of whom share the same domain name) from outside. I also cannot send mail to any of those contacts when I am hooked up to the client's network (but not the domain) whilst within the client's premises.
I use Mail and a mac.com address. I do not use web-mail. It is further noteworthy that messages from my side without attachments will sometimes (perhaps 20% of the time) go through. However, messages with attachments never go through. I have discussed the matter at length with the two IT-experts at the client (a government office) and we have not been able to come up with suggestions.
Since I am now forced to use a USB-stick to exchange info with my client, I would much welcome your suggestions as to the cause of the problem and possible solutions. Many thanks in advance.

Thank you for taking up the issue, Type17. The mails do not disappear, they remain in my outbox (on my Mac). The intended recipient does not get a message. I, for my part, see a box with the message 'Cannot send the message using the server 'smtp.mac.com: myloginname'. The server name is highlighted in blue in a box below and I get the choices: 'Edit message', 'Try later' and 'Try with selected server'. None of these resolves the problem. The last option, i.e. 'Try with selected server', is a bit strange, because pressing the button 'Edit server list', shows only the server already mentioned. I have tried 'Connection doctor' several times over the past months, but this consistently gives me a green light against the smtp and the message: 'Connection and login to server successful'.

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Unable to send mail to some addresses after move to Leopard

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