This issue was addressed with improved state management of S/MIME encrypted emails. This issue is fixed in macOS Monterey 12.6.8. A S/MIME encrypted email may be inadvertently sent unencrypted.
[
{
"vendor": "Apple",
"product": "macOS",
"versions": [
{
"version": "unspecified",
"status": "affected",
"lessThan": "12.6",
"versionType": "custom"
}
]
}
]