iCloud email not sending, but emails show up in Sent

Tech Support
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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.

Questions:

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.)

Thanks,
-Henry

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Email is a complicated beast. I’m not sure you can assume that the problem is on the sending side.

Mail seems to mark things sent as soon as it sends them, which, I suppose, is all that Mail can do. It has no idea if the recipient ever receives it. The recipient’s email server may send a reply that the mail wasn’t deliverable — but not always. And that reply doesn’t mark the “sent” mail as “unsent”.

I periodically have this problem with my personal email account which is sent from Hover and uses a custom domain. Emails are marked as sent, but the recipient never sees them. This kind of blocking is done to reduce spam, and custom domains can result in being flagged as spam. (To be clear, the email messages do not end up in spam folders; they are never delivered. But it’s all part of spam filtering done by mail servers.)

This blocking often happens with Gmail, which is very aggressive about blocking email it deems as “bad”. Gmail sometimes tells me that it wasn’t delivered, but not always. It also happens with AOL, yahoo, and hotmail addresses. Emails get blocked before the recipient ever sees them, so there’s nothing the recipient can change to allow this legit message through.

Is the email address a @icloud.com address? I haven’t heard of a big problem with that domain, but it’s always possible it has been given a high spam score. The fact that email sometimes goes through is exactly what I’ve experienced.

Usually, when this flagging occurs, it’s not permanent and suddenly my emails are being delivered again. But often by that time, I’ve moved on to other email addresses!

Using the iCloud.com interface is a good check. But an even better check is to use it to resend the same email immediately after finding out that it wasn’t delivered. If the quickly re-sent email fails to go through, I would suspect blocking on the recipient’s end.

For now, though, I recommend that your relative use a second method to follow up when they don’t receive a reply. Annoying, but it’s about all you can do.

The loss of the “My Card” contact card could be related, I suppose. It’s definitely tied with the Apple ID, and that might be tied whether or not you’re authenticated on that Mac, which I suppose could result in messed up email sending.

I’m not sure if restoring contacts from a backup will restore the My Card and its connections. Unless there were problems with other cards, I would just create a new card and move on.

Another reason why stuff related to Apple IDs and contacts goes wrong is if you’re using the same Apple ID on both old and new operating systems. Usually what happens is that my clients have an old Mac whose OS is many years out of date, but they also have an iPhone with the most recent iOS on it. That seems to cause weirdness — and the only permanent fix is to get the Mac as up to date as possible. I don’t think it always happens if you’re running old & new, just that it sometimes causes issues around Apple ID and authentication.

All that said, you can check the Mac’s connection to the mail server. Use Connection Doctor under the Window menu and it will run a test. But, of course, it’s only valid for that moment. If the email connection is going up and down (not uncommon), you are not likely to catch any problem.

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That’s always possible. A “Sent” status only means the message was passed to a mail server. It can never be intrpreterd as delivered.

Plus all the relevant IETF RFCs for email do not guarantee delivery. It is possible for a message to be sent to a mail server en route to the destination but the onward network connection is down causing the message to be held until one of the connection is restore, an alternative route is found, or the message is bounced back to the originator (sometimes after 30 days of being held). Occasionally some mail servers will quietly delete such stuck messages.

There have been some very high profile instances recently where email services have effectively been knocked offline by careless modification of network routing tables.

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I have a process on a Linode server that’s supposed to send a weekly report to one of my gmail accounts and to a friend’s gmail account. Google frequently (but not always) refuses delivery because they think it’s suspicious. You could be seeing something similar.

Also, Is this a situation that’s unique to a single recipient, or is it happening to all email that your family member is trying to send?

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Do they receive regular emails? What happens if they send an email to a non-existing address? (i.e. something like abcffff010101@gmail.com)?

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I just experienced this. I sent an email yesterday to my senior leadership team. The email shows sent but they never received it.

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If any of this is for a custom domain, make sure your domain has SPF/DKIM records set up properly. That can hose up lots of things.

Agree with all the stuff above about email being a strange beast. Delivery Status Notifications exist (i.e. “your email couldn’t be delivered because…”, but some servers don’t send them because that effectively generates backscatter spam. Those servers just drop the most egregious stuff right on the floor.

And being on a shared sending IP means that if the server your friend/family member is connecting to at iCloud was recently used by somebody else for spamming, the legit emails from your friend/family member could get dropped on the floor due to spam mitigation efforts.

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Any idea if this is stopped by the spam filter on the sending server or the receiving server?

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Usually sending servers don’t aggressively filter spam, as the user is authenticated - typically via a username/password. But receiving servers are far less trusting, and routinely throw away email that looks like spam.

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To numerous recipients.

We have narrowed down that we think all of the identified cases of missing email were sent from iPhone (vs. Mac, which they only rarely use for email). Coincidentally we’re in the process of upgrading them to a new iPhone, so going to sit tight and hope that resolves whatever the issue is.

-Henry

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So you think the “sender” is the problem, and not the intermediary transport across the internet, nor the “receiver”? That seems unlikely to me, but there you go.

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I’m having the same issue. Emails go in the sent folder but never arrive. I fixed it by formatting my computer but then it started back up again. All other non Apple provided emails that are housed in the Mac Mail app work just fine. No idea how to stop this from happening.

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Email is a store and forward prototcol. If the recipient’s system is not online then the message is sent to the first in a chain of servers that should eventually deliver the message to the recipient. It is possible for a message to get “stuck” somewhere along the chain. Network outages are a common cause of breaks in the chain. All of which means the message has been “sent”.

Email is not a guarenteed service. It was never defined to be. That it works 99.99% of the time is sheer dumb luck.

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