Hi everyone,
Following situation:
- Outlook Profile: Outlook
- Accounts: 1 Personal Account (Hotmail), 1 Work Account and 4 mapped shared mailboxes
- All Exchange Online!
- One Security Setting with a DigiCert Cert. for my work mailbox and the shared
- S/MIME works perfectly with all work-related accounts
Then I decided to add a second security settings with a WiseID Cert. for my hotmail, cause I have one and I want to use it. As soon as I try to send an email from this account, this error message pops up...

Okay, so I've made a second profile with just the hotmail Account set up and the security setting with the cert. for this email. Works perfectly...
My question:
Why does it work in a separate profile and not in my main profile with the other accounts?
Thanks for every reply <3