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iCloud+ custom email domains should be better

domlaut.com

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Re: iCloud+ custom email domains should be better

#31
post #28

I'm surprised Apple supports custom email domains to any extent. Apple is a consumer electronics company. Hosted email on custom domains is very distinctly not a typical consumer behavior.

Apple has been moving towards services as a major part of their business for the better part of a decade now

They have been moving to services, but all of their other services are distinctly mass consumer oriented; e.g. TV+, Music streaming, Fitness+ videos, Arcade, News+, iCloud photo backup, Card

https://www.apple.com/apple-one/

https://www.apple.com/services/

Re: iCloud+ custom email domains should be better

#33
I jumped onto iCloud emails as soon as it became available this past fall and immediately ran into #6. I set up test email accounts in my iCloud account including my wife's just to see if it would work - Evidently that was a mistake because when I removed then attempted to reregister her email under her iCloud account (same "Family") it blocked her with the same opaque error message mentioned. I reached out to Apple support and after going back and forth for 1-2 months, they finally said it was "by design." Because my iCloud account first set up her email address (then subsequently removed it) it was permanently tied to my iCloud account even though we were in the same family. The support rep said there was nothing more that could be done other than moving to another email provider.

tl;dr; Emails can only ever be registered with one iCloud account ever, even in the same Apple family

Re: iCloud+ custom email domains should be better

#34
post #6

I would say another main issue is that while they ask you to setup DKIM records, they do not actually DKIM-sign your emails. Hence your mails may be more easily flagged as spam. Several people have reported this to Apple, but AFAIK it still hasn’t been fixed.

This sounds bad, does it have practical implications? Have people switched to apple hosted custom domains for email and suffered deliverability problems?

Re: iCloud+ custom email domains should be better

#36

I'm surprised Apple supports custom email domains to any extent. Apple is a consumer electronics company. Hosted email on custom domains is very distinctly not a typical consumer behavior.

For as long as iCloud existed, people have been clamoring for custom domains. I think it might have been possible back in the iTools or MobileMe days? Maybe I'm mis-remembering.

Me, I've experimented with migrating some of my domains from self-hosted to iCloud+, simply for the ease of management and reducing the headache from SPF, DKIM, DMARC, etc. It turns out I have a spurious DNS record that was causing all my headaches, which I had forgotten to remove from older experiments, and I didn't need to migrate to solve this.

In either case, it's a nice convenience feature. Despite the trend, and the HN-think, Apple DOES do things for power-users sometimes.

Re: iCloud+ custom email domains should be better

#37
Catch-all addresses are a must have for me now. I allocate unique addresses to every website as these are more robust then using the + operator because they can't be stripped off.

I've already busted one company (I presume selling) my email address to a cloud provider for them to send me marketing material.

I emailed their privacy officer and didn't even get a reply, but that's OK, if it continues, one sieve rule and I can delete any mail that arrives on that address.

I just hope the spammers don't get so advanced they start forging other web sites addresses, maybe I'll have to move to a hashed and salted version that they can't forge.

Re: iCloud+ custom email domains should be better

#38
post #21
post #14

Earlier quoted context omitted.

We just went down the rabbit hole of trying to migrate to Microsoft 365 Family with custom domain. You (officially) need to move your domain to GoDaddy, which was unfortunately a blocker for us as they don’t support our domains TLD. From what I read DKIM also isn’t offered on Family which is disappointing. Business plans get expensive quickly when you want Office apps as well.

I know they really try to sell you on GoDaddy, but it's possible to set it up with using another registrar.

I found some info on setting up DNS for other providers, but it isn’t officially supported and for something as important as email I don’t want them randomly breaking it one day, which they could since they expect all customers to be configured through their API integration with GoGaddy. No need to advise in advance of MX host changes etc when it’s supposed to be entirely managed by them.

I understand their target demographic here might not be super technical, so the deep integration with godaddy makes sense, but would be nice for a supported advanced user pathway too.

Re: iCloud+ custom email domains should be better

#39
post #11
post #6

I would say another main issue is that while they ask you to setup DKIM records, they do not actually DKIM-sign your emails. Hence your mails may be more easily flagged as spam. Several people have reported this to Apple, but AFAIK it still hasn’t been fixed.

You're right -- this is something I missed mentioning. As of right now, it's still only the web-based iCloud Mail that makes use of DKIM. Using any other client/app will deliver your emails unsigned. Would you mind if I updated the article crediting you for the DKIM addendum?

Does the desktop mail app count as iCloud mail?

Re: iCloud+ custom email domains should be better

#40

After the end of legacy G Suite was announced, I tried using iCloud+ to forward my personal domain to Gmail. However, because iCloud does not seem to support ARC for forwarding, Gmail was sending too much to Spam. I tried many other mainstream forwarding options and settled on Pobox as the best overall option, and moved my personal domain over. It's working pretty well, flowing to my regular Gmail account and having…

When I got burned by the legacy G Suite announce, I had similar bad experience with Microsoft 365 for Families. They - for some reason - only support custom domains that were registered/moved to GoDaddy (there is unsupported 3rd party guides on how to bypass checks but anyone with the requirement of stable email reachability will obviously not rely on that). Too bad you find that out after you setup your account, bil…

Also, from the faq:

"Outlook.com currently does not support DomainKeys Identified Mail (DKIM) or Domain-based Message Authentication, Reporting and Conformance (DMARC)."

This is an odd oversight considering this recommendation from their commercial product:

https://docs.microsoft.com/en-us/microsoft-365/security/offi...

The whole m365 for families product is weirdly crippled, I assume to keep people from running their small business using the cheaper subscription?

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