Re: SBS 2008 to office 295 exchange single sign on question.

Hi Eddie,

Based on your description, I understand that you would like to use the same password for both DirSync and Office 365.

Currently, it is not available for DirSync to sync passwords. As a workaround, please try to deploy an AD FS (Active Directory Federation  Service) infrastructure.

For more information about deploying AD FS, please refer to Plan for and deploy AD FS 2.0 for use with single sign-on

Thanks,
Allen Zhang