iCloud Mail STILL Silently Rejecting Mail

[kwright817]

Normally I appreciate Apple's approach to privacy and protecting the customer, but in 2018 to still be straight up blocking email that they believe is spam without the any customer notification isn't that.



Now for the context: I like many forward my mail from Gmail to my iCloud mail account to take advantage of IOS Mail push notifications and to serve as a backup should Gmail flake out and delete my mail. It usually works well, until it doesn't.

Yesterday I noticed this message in my Gmail box. The time stamp is exactly the same as an important email notice from my bank that was just below in my Gmail inbox. Checked iCloud, just to be sure, and the bank's email is nowhere to be found. A quick search of my Gmail account revealed that I had 4-5 of these notices. All of those matched timestamps of messages in Gmail's spam folder, so ok, no loss.

Again, I appreciate Apple trying to protect me, but why not just place it in my Spam folder so I can decide?

 

[Just_Me_D]

Thus far, it hasn't been a problem for me and in regard to SPAM filters in general, I've yet to find one that gets it right EVERY time.

 

[kwright817]

Thus far, it hasn't been a problem for me and in regard to SPAM filters in general, I've yet to find one that gets it right EVERY time.

Thanks for the feedback. I guess that is part of my point. If they would simply place suspected spam in the spam folder then the user can catch the false positives since, as you note, none are 100% accurate, then I'd not have an issue. But simply dropping the message with no user notification is my concern, particularly for those who use iCloud as their primary email provider; they don't know what they don't know and can't correct the issue.

Speaking of correcting the issue, I can't even do that by telling iCloud that it was wrong and that the message was legit other then by sending a message to the iCloud Postmaster, which I did, only to get the expected "we have received your message and will not contact you unless we have further questions" message. So, unless the Postmaster decides to whitelist my bank as a result of my sending the headers, since I can't even do it for my account, i'll never get these account alerts directly.

For now, my temporary solution is either forward those rejection notifications to my iCloud account or try another provider. I am doing both.

 

[Just_Me_D]

Thanks for the feedback. I guess that is part of my point. If they would simply place suspected spam in the spam folder then the user can catch the false positives since, as you note, none are 100% accurate, then I'd not have an issue. But simply dropping the message with no user notification is my concern, particularly for those who use iCloud as their primary email provider; they don't know what they don't know and can't correct the issue.

Speaking of correcting the issue, I can't even do that by telling iCloud that it was wrong and that the message was legit other then by sending a message to the iCloud Postmaster, which I did, only to get the expected "we have received your message and will not contact you unless we have further questions" message. So, unless the Postmaster decides to whitelist my bank as a result of my sending the headers, since I can't even do it for my account, i'll never get these account alerts directly.

For now, my temporary solution is either forward those rejection notifications to my iCloud account or try another provider. I am doing both.

I get SPAM via my iCloud account on occasion, but they've always appeared in my iCloud Junk folder.

 

[kwright817]

I get SPAM via my iCloud account on occasion, but they've always appeared in my iCloud Junk folder.

As do I, in most cases. In fact, I had 5 other rejection notifications from Google when they attempted to forward messages in my Gmail inbox. In each of those cases, they were also caught by Gmail's spam filter and properly placed in the spam folder. Rather than doing that, iCloud Mail simply rejected the messages outright.

Now, I am also aware that the action of forwarding a message may be affecting whether a message is rejected, but the fact is they are still rejecting messages without user notification. Here is Apple's policy as referenced in the rejection message: https://support.apple.com/en-us/HT204137

Again, I appreciate Apple's stance on privacy. I simply intended for this to be both a PSA that the issue from years ago may be persisting and to open a discussion. Nothing more on iMore (see what I did there) Lol?

 

[kwright817]

Ahh, the irony, the iMore Newsletter was dropped last night .

 

[iN8ter]

"Now for the context: I like many forward my mail from Gmail to my iCloud mail account to take advantage of IOS Mail push notifications and to serve as a backup should Gmail flake out and delete my mail."

Is this a joke, or for real? I cannot tell. I dare not guess.

Gmail is I first Italy more reliable than iCloud, so I'm not sure why anyone would do that.

Just I stall the Gmail app? I'm pretty sure it gets push notifications.

As for Apple blocking spam, many providers block things at the server. It sucks, but sometimes it's a symptom of a different problem. I think so nothing about the way gmail is forwarding is tripping it off.

Does iCloud have a setting to automatically check your mail from their end, like many other email services? That can fix the issue immediately, at the cost of Sync speed (potenyially).

 

[kwright817]

"Now for the context: I like many forward my mail from Gmail to my iCloud mail account to take advantage of IOS Mail push notifications and to serve as a backup should Gmail flake out and delete my mail."

Is this a joke, or for real? I cannot tell. I dare not guess.

No joke.

Gmail is I first Italy more reliable than iCloud, so I'm not sure why anyone would do that.

I'm not sure that is accurate, but I'll take your word for it. Other than this specific issue, I've not personally experienced an appreciable performance variance from that of Gmail.

Just I stall the Gmail app? I'm pretty sure it gets push notifications.

Yup, the Gmail app does essentially "push" but I simply prefer native Apple mail.

As for Apple blocking spam, many providers block things at the server. It sucks, but sometimes it's a symptom of a different problem. I think so nothing about the way gmail is forwarding is tripping it off.

True, but in my testing of others, including FastMail, the messages are assigned a Spam score moved to a spam folder for user review unless the user sets different behavior. Again this has been my experience as an end user.

Does iCloud have a setting to automatically check your mail from their end, like many other email services? That can fix the issue immediately, at the cost of Sync speed (potenyially).

No, iCloud, unlike Gmail and FastMail, the two with which I have the most personal experience, does not offer Fetch account options. The closest is an alias address.

 

[iN8ter]

It's accurate, even of you do a fairly trivial comparison of the downtime and issues each have suffered over the years. Gmail is far more reliable - practically enterprise-class. iCloud has had multiple outages, downtime, or other issues. Outlook.com is also very reliable.

Worrying about Gmail flaking out and deleting your mail, as if they don't use a backup plan... seems like a bit of exaggeration. They took over that market for a reason. Flakiness isn't it. Apple's cloud services have never been known for reliability or robustness, so your statements are far out of the mainstream.

Apples privacy focus is literally the only reason to ever consider their services over Google's, and that comes either a number of compromises. A downgrade in reliability and robustness is one. Apple has also had more "faux pas" than Google when it comes to Account Security.

About the fetch option: best thing to do would be putting in a feature request, and connect the Gmail account to your iOS/macOS mail apps.

 

[Lee_Bo]

I see those in my Gmail box on occasion as I also have my Gmail forwarding to my iCloud account. Not a big deal for me as they are spam emails anyway.

 

[kwright817]

It's accurate, even of you do a fairly trivial comparison of the downtime and issues each have suffered over the years. Gmail is far more reliable - practically enterprise-class. iCloud has had multiple outages, downtime, or other issues. Outlook.com is also very reliable.

Fair enough. The purpose of the discussion was Apple's mail rejection policy, so I've not intention to focus discussion on reliability.

Worrying about Gmail flaking out and deleting your mail, as if they don't use a backup plan... seems like a bit of exaggeration...

No exaggeration, just redundancy is your friend .

privacy focus is literally the only reason to ever consider their services over Google's, and that comes either a number of compromises. A downgrade in reliability and robustness is one. Apple has also had more "faux pas" than Google when it comes to Account Security.

No argument there. Again, the purpose of posting was to discuss Apple's mail rejection policies.

A

About the fetch option: best thing to do would be putting in a feature request, and connect the Gmail account to your iOS/macOS mail apps.

I doubt that there is enough interest nor does Apple seem very interested in focusing resources on services, particularly iCloud and mail; just looking at the web interface gives one a hint.

 

[kwright817]

I see those in my Gmail box on occasion as I also have my Gmail forwarding to my iCloud account. Not a big deal for me as they are spam emails anyway.

Most of mine are/were too, but not all. Some were from my bank, and iMore. I've not seen similar results with FastMail.

Upon casual review of mail headers, I've noticed that Google adds "+caf_=" to the Return-path line for all messages forwarded to iCloud; it doesn't for mail forwarded to FastMail. It looks like this: Return-path:
<username+caf_=username=icloud.com@gmail.com>. So, perhaps that along with a combination of the sender address and slightly elevated spam scores is what may be triggering the rejection?