If problem is SSL sertifiaction you have to Click Yes every time ist ask. Otherwise is there any restriction fro your server side (ie helo,relay)You have to ask your Mail Admin to permit your request from out side.
There is another way to use your mail from out of the office, if your mail server has configured a Webmail Client. you can send/receive email from the out side through the web browser.
At work with mails I usually use next tool-how to open dbx,because it is free and has lot of features.Besides that tool helped me many times,and it can restore mails,attached files,fix other mail files.