I am trying to help a family member with an email problem I haven’t run into before.
Emails they send from their mac . com / icloud . com [edited: spaces added for clarity of domains] email account are not getting through to the recipient. They are using the stock Mail apps on iOS and Mac. This is true across several different recipient account types (to another mac.com address, to a fast mail address, to gmail addresses), so the problem is on the sender side. The emails they write end up in their “Sent” folder across all their devices. (So the emails aren’t just in “Sent” on the device they sent from.)
It’s pretty disturbing that the email is ending up in “Sent” across all devices, but the recipient never sees it. From the family member’s perspective they’re wondering why no one is answering their emails!
From what I can tell this has been going on for a week or two. But a few of their emails have gotten through in that time, which is bizarre. (Maybe 1 in 5 or 1 in 10?)
Possibly related, or possibly red herring unrelated: Around the time this problem started their contact card for themself in Contacts disappeared. We don’t know exactly when this happened, so maybe it’s unrelated.
I want to have them try sending email from logging in to the iCloud.com web interface and see if that works or not and will report back what we find there, as that may be a useful clue.
Has anybody seen anything like this with emails acting like they’re sent but not sending? (From iCloud or other providers)
Has anybody seen someone’s “Self” contact card disappear? Any suggestions on whether to do a restore of Contacts vs. creating a new “Self” contact card? (They had quite a bit of information stored in the Note of their self card, such as numerous old addresses and such, that would be a pain to recreate. Thankfully we don’t think they’ve made edits to other contacts in the meantime so a restore shouldn’t be too painful in terms of other data loss.)