From my perspective of running a campaign/little store, Apple’s Hide My Email/Sign In With AppleID is a source of so many problems.

People forget they used it, create multiple accounts, but most importantly *I cannot reach people who paid me money to send them stuff*. Not even automated emails ā€“ just 1:1 handwritten ones, too. More often than not, not even a bounce.

It’s really bad. Over a hundred of people for me, I spent so many hours dealing with this, and I won’t be able to resolve it all.

I have sent so many things like these, and this is *after* I figured out what was going on, which was not easy, either.

(This is via Kickstarter’s messaging system, but if that one was plugged into Hide My Email email, then it’s likely also not getting through, silently.)

I liked the idea as a concept, but I would pretty much advise people avoid using it, seeing on the other hand how unreliable and error-prone it is.
(For people unaware, Sign In With Apple ID creates an obfuscated email like this [email protected] and I think adds a lot more rigid spam filters or something like this. Both seem to be a source of problems – the layer of obfuscation only works transparently when you use Safari password filling, I think, and emails are marked as ā€œdeliveredā€ even if they bounce off of the over-eager spam filters.)
From my experiences (with Kickstarter and BackerKit), I would actually advise services to either block creating accounts with @privaterelay.appleid.com, or throw all sorts of warnings on entry. It really feels very bad.
If you use this feature, I am curious if this matches your experiences and if you’ve ever been ā€œgaslitā€ by these features losing your emails.

@mwichary I used Sign In With Apple with TikTok which they didn’t have support for in the Vision Pro app, and I was trying to set my password using my anonymous email, and suspecting TikTok was pretending they sent it in hopes of getting my phone number instead.

I wish there was a service where you had infinite emails but you got the whole domain for yourself so it’s easier for you to locate something.

Better tooling would help a ton here.

@harpaa01 Look up ā€œplus addressingā€ if you’re unfamiliar. Works great with Fastmail.

@mwichary Not that I'm aware of, but I mostly use them for things that require an email address, but I'm not actually all that concerned if things don't get through.

For things like Kickstarter/BackKit where I do care, depending on the level of trust I'll either use a ā€œrealā€ email address or manually create a new, ā€œnormalā€ forwarding address/alias.

@mwichary I use hide my email a lot but it always produces addresses like [email protected] which seem pretty stable. I’ve never seen the private relay kind?
@CTD Apparently it’s for signing with Apple ID! A different kind of email hiding.
@mwichary ah. I understand. I wonder if that’s what you get when a customer buys something online with Apple Pay too? You never enter an email then either and I don’t think yours is revealed. Super convenient as customer but possibly problematic for seller.
@CTD Perhaps! I don’t think I have direct experience with that flow, though.
@mwichary not really. I use this all the time. I don’t think the spam filter is any different for those than for my normal accounts, so messages are just forwarded directly into my inbox. Since there is a field to write a note when you create the address (that defaults to the site you were on), I don’t have much of a problem remembering what address was used where either. Addresses can be deactivated by the user, but they can also be reactivated any time after that

@mwichary Im not aware of any emails going missing. For me it seems to work as intended.

But I have found Kickstarter outgoing emails to my normal email address to be unreliable. They don’t seem to use DKIM and the emails sometimes have the characteristics of spam (wanting more money for a stretch goal and click this link to pay).

@mwichary I used them for a foreign hotel booking and of course I didn’t get the confirmation email and caused all sorts of last minute panicking about wether or not I’d actually made a booking in the first place.

@mwichary I tend to use Hide My Email only where I think there is a good chance of the vendor spamming me, or if I don't care whether I hear from them again.

For things where I'm purchasing something I'd tend to use my iCloud or own domain email addresses. I’ll be even more careful on this having heard of the issues that you are experiencing!

@mwichary I have seen instances where Apple Mail would automatically sort some of these messages as Spam too aggressively (definitely with Hide My Email, possibly with Sign In with Apple too). I haven’t suffered serious consequences like you describe with Kickstarter, but I agree that Apple could improve the situation. I’ve considered building custom rules to sort messages addressed to ā€˜private-relay’ or ā€˜[email protected]’ to a separate folder for monitoring, but haven’t tried yet.
@mwichary I use this feature and I really like it. It's not great for the website if it's a small business but I appreciate not having my info sucked into some large corporation's CDP. It's good for e.g. signing up to a streaming service, bad for signing up to a ticket service. Requires some forethought before using.
@mwichary if you do that apple will reject your app from the App Store.

@mwichary A friendly clarification: The privaterelay.appleid.com email addresses are not created by the ā€œHide My Emailā€ feature. They’re created when someone creates an account using "Sign in with AppleID.ā€

The ā€œHide My Emailā€ feature creates email addresses that look like (for example) [email protected]

@bradlau Thank you! That explains things! I edited some of my posts to clarify.
@mwichary IF it worked better it would be great. But Apple doesn't mind shipping half baked features that help it keep control over the ability to message the customers they own under the guise of "privacy"
@mwichary inb4 apple requires the use of this feature when using Safari in order to protect your grandma
@mwichary @danhon
I wonder if Apple lets their customers hide their email from them.
@ian Miraculously, it's only all the other companies (and browsers, app stores, payment systems etc.), that can't be trusted. What are the chances.
@mwichary @danhon
@mwichary they've got some assumptions about how people use their products that are problematic. I had a work iPhone and it got wiped with some update. I didn't use iTunes so it had no backup. I forgot the password and they assumed it had cell service. Um, no, company wouldn't pay cell for a test phone, it only had WiFi. Tons of time, frustration, and work to fix. Sorry you are going through this.

@mwichary I just set up a Thinkific course and I’ve turned ā€˜Sign in with Apple’ off. And I’m all Apple, all day.

The user experience is 100% pants. You end up with an account called ā€œA Userā€ or somesuch, and you still have to give the platform an email address, so now what, you have two? It made no sense.

We tested LinkedIn (!) and Google: seamless. I don’t have a Facebook account to use to test but I also assume it works fine.