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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

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 (!).

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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

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I think the problem is that, when you create the separate profile settings for each S/MIME certificate, there's a checkbox within the profile that is enabled by default - this says that each profile is the default profile for signing/encrypting all e-mails. If you create two profiles, each of which state they are the default certicates (effectively 2 default certificates), by default, Outlook is creating a conflict.

I just went into the Security Center and unchecked the default setting checkbox in both profiles, then went to test. SUCCESS!!!!

I now have two separate Exchange/Office 365 accounts configured in Outlook 2013, each of which are using their respective S/MIME certificates.

Thanks for the hint!!! That was what allowed me to finally figure out an issue I've encountered for years! :-D

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