iCloud Mail Hinkiness

Posted on
Sun Nov 19, 2017 6:07 am
DaveL17 offline
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iCloud Mail Hinkiness

Lately, I've noticed that messages I send to an iCloud email address often aren't delivered, whereas messages sent to a Gmail address arrive instantly. I suppose that it could be something between my ISP and Apple; I was just wondering if anyone else is seeing this inconsistent behavior. I have a separate email account for Indigo with my ISP--this doesn't have anything to do with the Indigo application--and I can reproduce the behavior using Mail.app.

Posted on
Mon Nov 20, 2017 10:11 am
PeteVis offline
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Re: iCloud Mail Hinkiness

Dave, a few years ago I had noticed something similar, but my problem was both ways. Some mails sent to my icloud account never arrived, and some mails I sent from my icloud account never got delivered.

The problem came to my attention as I was not receiving e-mail invoices from our electricity provider anymore which resulted in late payments and finally escalated into a bigger problem.
From time to time, but not often, I also heard from people that they did not receive a certain message from me or the other way around, people would e-mail me something and I'd never receive it. At the time, I always assumed it got stuck in their spam folder, but after the problems with my provider started I investigated.

I set up several mail accounts and started testing with both the messages that were never delivered to and from my friends, and also with my electricity provider. Mails simply vanished from iCloud as if they never existed. I tested and re-tested, and every time, certain messages would disappear and never get delivered when I used my iCloud account. When sending the exact same message over different accounts, they would arrive as intended.

I then stumbled onto a few blog posts describing the same behaviour, so I knew I was not alone. Allthough I don't think this is a widespread problem, I am positive that Apple has a very strict spam filter in place. A spam filter that we can not access, nor train or release messages. When I switched my mail account from iCloud to a self hosted account I iniatially received a huge amount of spam... which proves that iCloud is discarding lots of mails on the server level, before they get sent to the actual inbox.

I sent a bug report to Apple, but never got a reply.

I'm afraid, this again, is such an amazing and magical service from Apple that just works... except when it doesn't.

Posted on
Mon Nov 20, 2017 12:07 pm
Shutter offline
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Location: London, UK

Re: iCloud Mail Hinkiness

Just to ask the obvious, but have you updated the OS anywhere else this account is used, which would require app specific passwords for iCloud mail?

[Edit: Never mind. I see that it happens in Mail as well.]

Posted on
Mon Nov 20, 2017 4:44 pm
DaveL17 offline
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Re: iCloud Mail Hinkiness

@PeteVis: thanks for responding. Your post is unsettling at best. :shock:

I haven't really come across the situation where I was waiting for something to come through that didn't--until now. I'll definitely keep an eye on it; I'd hate to have to go back to Gmail because I keep that as my 'toss' account for all the cruft.

Posted on
Mon Nov 20, 2017 4:45 pm
DaveL17 offline
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Re: iCloud Mail Hinkiness

Shutter wrote:
Just to ask the obvious, but have you updated the OS anywhere else this account is used, which would require app specific passwords for iCloud mail?

[Edit: Never mind. I see that it happens in Mail as well.]

Indeed. This is definitely on Apple's mail servers as everything I send gets through to other accounts and I have zero app-specific passwords for iCloud mail (I checked). It's troubling.

Posted on
Tue Nov 21, 2017 2:30 am
PeteVis offline
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Re: iCloud Mail Hinkiness

Yes, it really was unsettling...

Here's an article describing the issue :
https://www.macworld.com/article/2029570/silent-email-filtering-makes-icloud-an-unreliable-option.html

This dates back to 2013, which is when I went through all the misery as well.
iCloud filtering may have improved since then, but I'll never trust my mail to Apple again.

One test I did to make sure this was iCloud misbehaving, was to change the wording in the mail a little. I recall that certain combination of words would trigger iCloud to discard the mail.

Posted on
Tue Nov 21, 2017 12:26 pm
DaveL17 offline
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Re: iCloud Mail Hinkiness

Thanks for that. I've switched the offending thing over to Gmail and it's working as expected. I'm really not looking forward to switching email providers again, but may have to.

What a pain that is.

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