What Happens When an Email Is Encrypted
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If email encryption is enabled in Microsoft 365, the email is secured using Microsoft’s encryption keys.
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Crossware Email Signature cannot decrypt the email (it does not have access to the encryption keys).
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As a result:
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Crossware will not append signatures inside the encrypted portion.
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However, a signature may be added to any plain-text or HTML wrapper around the encrypted component.
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What You Can Do
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Use Client-side Signatures, a signature configuration is appended at composition time (when the message is being written).
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Because the signature gets applied before the message is sent (rather than afterwards via Crossware’s servers), encryption does not block the signature.