Need Email Service that Connects with Outlook 2010

[Spud]

Hi, I am getting quite frustrated getting 'web mail' available in cpanel (web site hosting software) to connect with outlook 2010 (on my office computer). Support is mediocre at best and am considering finding an email service that has a solid track record of working with outlook 2010. Any suggestions on what email service I should consider that is secure, has a solid 'up time' history, support, is a reasonable cost would be appreciated.
Also if I can get an understandable explanation of how to implement email that meets 'Medicare's email requirement where beneficiary phi is exchanged' would be appreciated.