Outlook S/MIME Issues

Not sure if this is the correct channel to report issues discovered while testing Outlook's native S/MIME handling.
Some issues seem to affect certain Outlook versions only - possibly fixed or broken along the way as Outlook got updated.

Outlook S/MIME Issue #1:
Loss of Rich Text formatting and embedded images go missing

1. Compose an email
2. Turn on “Encrypt with S/MIME”
3. Put your own email address in the “To:” field
4. Switch to “Rich Text’ format
5. Embed an image into the email body
6. Send the email
7. Check the email in your “Sent Items” folder
8. Is the embedded image missing and replaced by “<<…>>” text?
9. Repeat the above with embedded inline attachments positioned within the email body
10. Are the inline attachments converted to normal attachments? i.e. no longer embedded in the body?

Outlook S/MIME Issue #2:
Corrupted email sent when manually saving and turning off encryption after “Send Unencrypted” prompt

1. Compose an S/MIME encrypted email to someone whose cert is unavailable on your machine
2. Click on “Send” button, Outlook will prompt whether to “Send Unencrypted” or to “Cancel” the send
3. Click on “Cancel” button, to return to the compose window
4. Manually “Save” the draft by pressing Ctrl-S or using the compose window’s “FileàSave” action
5. Make sure not to close the compose window in the step above
6. Deselect the “Encrypt” option, i.e. no encryption
7. Click on “Send” button, Outlook will send out the email successfully
8. Try opening the email that was just sent out in the “Sent Items” folder
9. Is Outlook able to open the email for viewing?
10. Check with the recipient if his/her Outlook is able to open the email for viewing as well

Outlook S/MIME Issue #3:
ItemSend event handlers are fired BEFORE the dialog in Issue #2 above

1. Create and install a simple Outlook addin which listens to the ItemSend event
2. Compose an S/MIME encrypted email to someone whose cert is unavailable on your machine
3. Click on “Send” button
4. The ItemSend event handler of the addin installed in step #1 is triggered
5. Thereafter, Outlook will prompt whether to “Send Unencrypted” or to “Cancel” the send
6. Expected behaviour is that Outlook should take the lead in showing the above dialog first and cancel the ItemSend event upfront if necessary

Outlook S/MIME Issue #4:
Unencrypted draft reply to previously encrypted HTML email becomes Plain Text when saved as MSG file

1. Send yourself an S/MIME encrypted email in HTML format
2. Reply to the received encrypted email (still in HTML format)
3. Turn off the "Encrypt" option while composing the reply
4. Make some edits to the email body
5. Save the edits (e.g. press Ctrl-S)
6. Save the Draft email as a Unicode MSG file - do not send it
7. Open the MSG file - it seems to have lost the HTML format and is now downgraded to Plain Text format?