The pitfalls of iCloud Mail - systematic failures and user hostility
Table of Contents
For years, iCloud Mail has been sold as a seamless extension of the Apple ecosystem. It’s private, it’s secure and it just works. In reality, though, it’s broken.
It’s a service riddled with opaque filtering logic, half-baked features, a total lack of essential functionality, and completely unresponsive support.
The journey to this point #
I’ve been using iCloud Mail since it was called MobileMe. I’d been a paying, loyal subscriber using iDisk and other services. When iCloud was announced, I was migrated to the “new and improved” service.
Things worked fine at first and when custom domains made a comeback with actual mail support, I was one of the first to jump on board. I’ve been using it for years and it had mostly been fine.
Forgiving a total lack of decent filtering functionality and a poor webmail interface, I was happy. I had my own domain and it was working.
But lately, I’ve been having issues… and seemingly a lot of other people have been having issues too.
I’ve had such severe issues that I’ve missed critical, time-sensitive contracts.
I decided to investigate and see if I could fix the problem.
TL;DR: I couldn’t and seemingly nor could Apple.
Part 1: Is it the sender? #
Proofpoint: or, Apple’s silent email rejector #
Apple appears to be using Proofpoint. If you haven’t heard of them, they’re an enterprise-grade email filtering system built for corporate compliance, not consumer email.
To be clear, my only evidence that Apple is using Proofpoint is the presence of a couple of X-Proofpoint-* headers in each of the emails I received.
Unlike business deployments, where users can review quarantined messages, iCloud Mail offers zero visibility. Emails either arrive, vanish without a trace, or get dumped into spam for reasons even Apple support can’t explain.
It’s not entirely clear if Proofpoint is the issue in this mix, but scrolling back through my inbox I can see that the issues started around the time these headers started appearing.
They even appeared in a recent email from GAIL’s, my favourite UK bakery
X-Proofpoint-GUID: CCb5feGUTMhaeVe-FEV1mB1yc1MUesA5
X-Proofpoint-ORIG-GUID: CCb5feGUTMhaeVe-FEV1mB1yc1MUesA5
What I’ve observed:
- Transactional emails from known senders have ceased.
- Messages from my family, other iCloud users, are marked as spam.
- I no longer get messages from mailing lists.
- DocuSign just doesn’t get through - more on this later.
Is it Authentication? Trying a relay #
I set up a relay in front of iCloud’s MX records to see if I could get a better idea of what was going on. I used Migadu with a simple relay rule to forward all mail to my iCloud address.
The good thing about this is that the ARC headers are preserved, so I can see what the original sender’s server is saying about the message.
This experiment showed me which emails were getting through and which weren’t. For those that made it through, the Authentication-Results header always showed a pass
The ones that didn’t make it through? They also passed.
In September 2024, I reached out to Apple to investigate. I was connected to a “Senior Advisor” who was polite and promised to investigate.
They never got back to me.
Giving up for now #
I’ve decided this isn’t a big issue for now and thankfully I can ask people to send emails to my work address (not ideal) to get around the issue.
Part 2: The frontend lies about the back-end reality #
Rules that do nothing #
iCloud Mail has a rules feature. It’s basic, but it’s there.
I decided to use this to filter emails with the subject line containing “Receipt” or “Uber Receipt” or “Uber Eats Receipt” (don’t judge me) into a folder.
I set up the rule and it worked. But I realised that lots of emails I don’t want in the “Receipts” folder were making their way in there. So, I deleted the rule.
The emails kept going into the folder.
To this day, I have NO rules set up in iCloud Mail, but emails with “Receipt” in the subject line are still being filtered into the “Receipts” folder.
My guess is that there’s a disconnect between the customer-facing rules interface and the back-end filtering system. Apple used to ship Cyrus and Postfix within Mac OS X Server, so I’m guessing they’re using a similar setup for iCloud Mail. It’s not working.
I again reached out to Apple support. They said they’d look into it.
Crickets.
Domain management #
As to not spoil part 3, I’ll just say that when you delete a domain… it doesn’t delete.
Part 3: The final straw #
DocuSign: The missing contracts #
We’ve all received contracts from DocuSign. I’ve been sent a few recently and my partner was sent one too for their new job.
They never received it.
Off to the work email again and it arrived instantly. We looked at the headers and (as expected) it passed all authentication checks.
I urgently contacted Apple Support about this. I got put through to another “Senior Advisor” who was also very polite and continued to say they’d look into it.
Crickets.
I followed up a week later. Tumbleweed and crickets.
Fastmail: the saviour (almost) #
Since this issue kept recurring and I own my domain, switching providers was easy — I moved to Fastmail.
It was disgustingly easy - almost as if many others had done the same. I set up my domain, changed the MX records and off I went.
I get all my emails now. I don’t know if Fastmail does any shadow filtering, but I found a great setting to disable automatic deletions from spam filtering. It seems to work.
I’ve also moved my calendars to Fastmail, so everything is in the one spot.
Calendar Invites: The iCloud black hole #
I receive calendar invites from my partner, family and friends who use iCloud Calendar.
They are still going to iCloud Calendar.
Apple provides advice on how to change the setting so that they’re delivered to your email address instead.
Shockingly, this doesn’t work—nor does the user interface for changing it.
I’ve reached out to Apple support about this. They said they’d look into it.
Crickets.
Part 4: My two cents on the matter #
Just don’t use it #
iCloud Mail’s failures aren’t just technical; they’re systemic. The combination of invisible filtering, broken authentication and a walled-garden approach to interoperability makes it one of the worst mainstream email services for anyone who relies on consistent, reliable communication. If you’re serious about email, look elsewhere.
Apple’s ecosystem #
I’m not sure I can trust Apple’s ecosystem anymore. I’ve been a loyal customer for years, but lately I see more red flags and errors than I do a seamless experience.
It’s also increasingly worrying to me that new operating system releases contain novelty features or ride the coattails of the latest trends, rather than fixing the core issues that have plagued the ecosystem for years.
Apple Intelligence is such a victim of this. It’s a great concept, but it’s not reliable in a way that any genuine user would trust it. I’m even failing to see which customers would even want it. The majority of users just want their device to work. If they want something to re-write an email or generate a picture of a cat, they’ll find something that’s dedicated to doing that.
The fact they’ve had to make the “Genmoji” button more prominent in iOS 18.4 is such a testament to this.
Apple Support #
Apple Support is beyond a joke. They don’t care about your issues and they don’t care about fixing them — they’re just there to make you feel heard.
But they don’t even do that. They force me onto a phone call, which I hate, and then they don’t even follow up.
I have not had a single good support response from Apple since 2015. What is going on?
Use your own domain #
Make sure you’ve got your own domain. If there’s one argument I can make for this, it’s that you can move providers easily. I’ve moved from iCloud to Fastmail in a matter of hours.
If you use an @icloud.com, @me.com or @mac.com address, you’re stuck with Apple. You can’t move away from them without changing your email address.
You’ve got many providers to choose from, here are some of my favourites:
Each has pros and cons, but they’re all better than iCloud Mail.
Keep backups #
The biggest risk I’m feeling right now is that I’ve placed so much trust in this monolithic company. I rely so heavily on iCloud just to preserve my personal data.
I have recently setup a 3-2-1 backup strategy for my two decades of iCloud Photos I’m terrified of losing access to.
Apple has got me stuck relying on them. But if they can so badly mess up email, what’s to say they won’t mess up Photos or iCloud Drive?
Thanks for reading this far. I apologise if this sounded like a bit of a rant, but I’ve been so frustrated with this saga and I wanted to share it.