i believe msdb.dbo.sysmail_allitems will only have a single row per mail_id, along with it's current status (sent/unsent/failed)
when a mail does fail, an entry is created in sysmail_event_log
select
mailitem_id,
count(*)
from msdb.dbo.sysmail_event_log
group by mailitem_id
having count(*) > 1;
SELECT * FROM from msdb.dbo.sysmail_event_log
Lowell
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