S/MIME support for Exchange Outlook Web Access (OWA) was introduced in Exchange 2003. In Exchange 2007 SP1, we are adding S/MIME support back and making it more reliable and powerful. Below, is a sho...
Updated Jul 01, 2019
Version 2.0
Blog Post
Hi Chongwen Xie,
what troubles me for a time about Microsoft and handling S/MIME mail is the following. When the option 'send clear text signed messages when sending signed messages' is checked (this is the default) outlook sends messages that a really old mail client (e.g. mail under UNIX) can read. The signature is sort of an added extra for clients that do understand it. However a lot of Microsoft webmail (including OWA 2003 and OWA 2007, possibly older OWA's and hotmail) suppress the plain text content and display an empty message having only an attachment people don't get.
Don't know if this is really a client or a server issue but there used to be time when this did work. To me, getting responses from my customers that they only receive empty mail was the reason to forego on S/MIME totally which is rather a shame in a world where thrustworthy email is a grood gift.
Can you give your view on this?
what troubles me for a time about Microsoft and handling S/MIME mail is the following. When the option 'send clear text signed messages when sending signed messages' is checked (this is the default) outlook sends messages that a really old mail client (e.g. mail under UNIX) can read. The signature is sort of an added extra for clients that do understand it. However a lot of Microsoft webmail (including OWA 2003 and OWA 2007, possibly older OWA's and hotmail) suppress the plain text content and display an empty message having only an attachment people don't get.
Don't know if this is really a client or a server issue but there used to be time when this did work. To me, getting responses from my customers that they only receive empty mail was the reason to forego on S/MIME totally which is rather a shame in a world where thrustworthy email is a grood gift.
Can you give your view on this?