I ran into this problem the other day. Use Windows/IE to import your self-signed SSL cert. After importing, the cert can be viewed with IE (Tool->Internet Options->Content->Certificates->Trusted Root Certification Authorities) . From this menu, export your cert to a file. (Repeat the import/export procedure if you have more than one SSL cert.) Anyone connecting to your mail server w/ Outlook will have to import/install your exported cert(s). -Cha Nate Carlson wrote: >I know it's OT, but we use Linux mail servers, so that makes it on topic, >kinda. :) > >>From Outlook 5.5sp2 on, it appears Microsoft actually checks to make sure >that the SSL cert of the remote POP/IMAP server came from one of the >recognized CA's, and puts up an annoying popup if it isn't. Anyone know >how to either install another CA, or just tell OE to accept the cert? Of >course, they can't make it easy like in Mozilla/IE (just click accept it >permanently.. heh).. >