Outlook 2013, multiple email accounts and encrypted email: Only last S/MIME settings used

Question

I have multiple email accounts properly setup in Outlook 2013 (can send/receive fine otherwise). Lets say they are:

[email protected]
[email protected]
[email protected]

All belong to me and I have 3 separate SMIME certificates for these, installed into the Windows Certificate Store.

I even have 3 separate profiles in Outlook 2013 in the "Settings" section (via File => Options => Trust Center => Trust Center Settings => E-mail Security).

Issue: Outlook 2013 selects the last profile as the "Default setting" (say [email protected]) and then applies this to all emails I send out, even from [email protected] and [email protected] !!! This is ridiculous!

Required: Obviously, When I send an email from my

• [email protected] account, I want certificates from [email protected] to apply.
• [email protected] account, I want certificates from [email protected] to apply
• [email protected] account, I want certificates from [email protected] to apply

Question: How can I tell Outlook 2013 to properly map these accounts => SMIME settings/certificate relationships?

There is also a posting on two of MSFT's message boards, but the moderators are being lazy by asking the poster to message on the "other" message board. The actual issues was addressed on neither (!).

• MSFT message board #1
• MSFT message board #2

Solution

I just found the answer for this:

File > Options > Trust Center > Trust Center Settings > E-mail Security > Settings

Create a new "Security Settings Name" for each of your certificates. When you send a signed or encrypted mail, just make sure the certificate selection is set on "automatic" in:

Properties > Security Settings