iCloud email rules error

Aha. So it's not just me.

I have now set up a completely new iCloud account with a few (obviously new) rules and directed email to that. As I suspected, messages are again being misdirected. This new account has only about 20 rules, way fewer than the first problematic account that was accused of having so many rules it was probably 'confusing the servers'. Ha, that was a laughably naive comment by Apple support and now proven to be nonsense.

So this can only be due to a newly introduced BUG in the iCloud servers' email filtering algorithms.

I've still not been able to determine any common factor in the messages that get misdirected, nor in those that are handled correctly. However, it looks to me like it is to do with the 'List-ID contains…' type of rule. As I've said, some messages pass through ok (for some as yet unknown reason), but those that do not, seem to get matched by the first 'List-ID contains…' rule. It doesn't matter what text the rule is looking for, the first of those rules, i.e. the one nearest the top of the list of rules grabs the messages and does whatever the rule specifies.

I had thought it was simply the first rule that grabbed the message in error, but it is not. It just so happened that my 'List-ID contains…' rules were at the top of the list. When I moved them further down the list so they were then below many other rules looking for 'Addressed to…' or 'From…' etc. (i.e. anything NOT looking for 'List-ID contains…'), none of those other rules ever wrongly grabbed a message. It was always the first 'List-ID contains…' rule that molested the message, even when that rule was buried right down in the list of rules.

Part of the problem appears to be that some messages are not matched when they should be. It is these messages that then have the problem and are grabbed by the first 'List-ID contains…' rule. However, if there is no such rule, the message just passes through unmatched at all and hence ends up in the INBOX instead of being moved to where it should have been. So the problem is twofold. Some messages are not matched by a rule they should match and then, if there is a 'List-ID contains…' rule, they get grabbed by that (or the first of those if more then one). Although, for some messages it all works correctly. So a bit of a mess really.

Not sure it's worth spending any more time trying to isolate the cause as this is purely an Apple problem and they need to do the troubleshooting. I will follow up on my previous contact with them and update them to the fact it is still happening with a completely new account with new rules and that it's not just me. They're the richest company on the planet so they can surely afford to spend some time fixing a problem of their own making. We'll see.

It appears there are 2 problems:-

• 1) Emojis or other multi-byte characters in the Subject will cause any attempt at matching on text in the Subject to fail.

Thinking back on it, I believe this to be a very long-standing issue that I had not identified as the reason why rules were not working on messages from eBay that I now realise is caused by their (perfectly acceptable) use of an emoji in the Subject of some messages.

I only identified this when examining the reasons for…

• 2) Some messages are matched by the first 'List-ID contains…' rule that exists in the list of rules for that account. It can be anywhere in that list, but the first (i.e. topmost) rule of that type grabs some messages. Might be a message that should match nothing and might be a message that should match a different rule, but for whatever reason I've been unable to determine, it gets incorrectly grabbed by the first 'List-ID contains…' rule. This errant behaviour began a few days before my first post but had NOT existed prior to that with the same account, same rules, untouched for years.

My conversations with Apple Support showed that 1) was repeatable - we were able to consistently reproduce this in both my and his accounts. For this reason he elected to push this forward to 'engineering' to be dealt with as a bug. I have yet to hear further from them about this, but I suspect no fix yet (to be tested).

2) is the recently introduced bug that has been consistently mis-matching messages for a couple of weeks, but no bad matches this morning. This is either because they have now fixed the recently introduced flaws in their code, or it's because none of the messages I received this morning happened to trigger the error.

Time will tell.

In conjunction with Apple support, I have now been able to establish that if a subject contains any emoji, it will NOT be matched by any rules looking for text contained in the Subject. Doesn't seem to matter where the emoji is in the Subject text and the rule doesn't have to be looking for the emoji. The rule can be looking for any other regular text contained in the Subject, but if the Subject contains an emoji, it will NOT match even when it should.

This is a reproducible problem that has now been sent on to the engineers (i.e. programmers) and hopefully they'll be able to find the error in their code.

Still unclear however, is what causes some messages to be matched by the first 'List-ID contains…' rule. This seems to be unconnected to any emoji issue and may require separate investigation. At least Apple are now aware of a problem with their iCloud mail rules system.

Well for almost a week now I have had NO misplaced incoming messages due to the 'List-ID contains…' rule matching error. So I hope that has been fixed.

I also just spoke to Apple Support and we conducted a test for emojis in the Subject and that also proved positive. I think they really only just fixed that in the last day or so.

My incoming emails are now being correctly sorted, so unless it all goes haywire again, hats off to Apple for responding to such a problem and then actually fixing it. I'm impressed.

To follow up on this:-

I just spoke to Apple Support which was a worrying experience, but I guess they have to deal with all sorts. It was hard enough trying to convince them this was an Apple iCloud server problem and not a local issue, but then I had to fight through the "the rule must be faulty". I explained that I had tried 3 different rules at the top of the list and no matter which, it was the first rule erroneously grabbing some messages, although I still have no idea why it incorrectly grabs some and correctly ignores others.

Of great concern was their comment that I have a lot of rules and that might be confusing their servers. This despite the fact that a. computers are very good at (and designed to be exactly that) dealing with more data than our little brains can comprehend and b. up until 4 days ago they didn't find this confusing at all. The naivety of the comment was astounding.

In the end I complied with their suggestion that I should delete those top 3 rules and report to them what occurred.

They were convinced all would now be good and I would just have to recreate those deleted rules (despite the fact my new test rule was only created after this started happening). I tried to tell them that in fact, all that would now happen is the rule that is now the first rule will start grabbing and moving messages, but to no avail.

So I deleted those top 3 rules that had each misbehaved and guess what? Now messages are being grabbed by what was the 4th rule but is now at the top. Surprise, surprise.

What really worries me about this is that I was told they do not support rules. I accept that they cannot support all their customers in the basics of how to create and use rules, but this is a fundamental error in their software, not some ignorant user not understanding how rules work. But it concerns me that they may wash their hands of this on the basis they "don't support rules" which would be a dereliction of their actual responsibility.

We'll see what happens when I report the result of their 'fix'.

Although it mystifies me how after so many years since iCloud was introduced, its email rules are so utterly primitive. Apple should be embarrassed by how dreadful they are. But, they have always worked correctly for me. As long as they have been structured correctly (i.e. correct identifiers and correct placement in the list) they do what they are supposed to do - until now.

I am still finding some messages processed correctly, while most of them get caught in error by the first rule.