macOS Monterey, iOS 15: My Apple betas experience

An illustration showing Apple's commitment to privacy-respecting features

macOS Montrey and iOS 15 are the latest versions of macOS and iOS. They were announced at WWDC 2021. The public beta was released a couple of days ago, and I downloaded it as soon as they were available. I wanted to download them when the developer beta was announced, but I don’t have an Apple developer account. And, admittedly, I was worried about how developer beta may fare. Glad I decided to wait for the public Apple betas.

I am quite happy with the experience so far. I installed both betas on my personal devices and on my work Mac as well. They seem rock solid, and I don’t see a hit on battery life either, which I hear is often the case on Apple beta rollouts.

I blogged about my favorite iCloud+ features previously, which I will be focussing on in this article.

Mail Privacy Protection

I have enabled it on my Mail app for now, but haven’t found if there are stats/analytics of how many trackers are blocked. As I am a pi-hole user, that must cover DNS-level blocks throughout my home but I am curious on seeing how this new feature complements pi-hole.

A screenshot from iOS 15 that shows the new Mail Privacy Protection feature. It blocks trackers on your mailboxes.

Private Relay on both Apple betas

Private Relay is Apple’s double-hop VPN-like service that prevents networks from monitoring your traffic, and prevents trackers and websites from identifying your IP addresses. It’s available on both Apple betas as of today.

My original understanding was that this is basically Apple-backed VPN service, but that doesn’t seem to be the case.

Is it basically a VPN service?

From a technical reading (I don’t have the link to it at the moment) of this service, it appears this is a double-hop tunneling system. Think of Tor, where there are 3 hops involved — entry node, middle node and exit node.

In Apple’s Private Relay case though, the first hop gets you an anonymous, shared IP address, while the second hop decrypts the website address. In this fashion, none of the parties in these tunnels are able to fully map the original address of the requester and the website address.

DNS leaks with Private Relay on these Apple betas?

Private Relay has assigned me a Cloudflare and Fastly address so far. I hear there are other providers that Apple has partnered with, but my experience so far has been limited to the two of them.

I have also noticed that my pi-hole on the Tailscale network doesn’t work when Private Relay is active. That’s alright in my opinion, because the very purpose of tunneled connections is to prevent leaks to other networks. Think of using a VPN, which assigns its own DNS resolvers, vs using the one assigned by your DHCP on the router. That’s precisely what’s happening here.

A screenshot from iOS 15 that shows the Private Relay functionality's settings.

Private Relay is limited to Safari. That works great for me. When I need to browse websites from my regular, ISP-based IP address, I can use a different browser like Firefox.

My pi-hole setup continues to work normally on other browsers, and other apps throughout the device.

A couple of other things that I noticed:

  • Private Relay on iOS 15 allows me to choose servers from the same geolocation, or from other areas of my country. That’s just a feature of iOS 15 though. I don’t see it on macOS Monterey.
  • Private Relay was enabled by default on my WiFi network. That wasn’t the case for a friend though.
  • As expected on a beta software, Private Relay disconnected a few times as I was browsing.

All in all, I am happy about this functionality, which is one of the many first steps that Apple is taking in privacy.

Hide My Email

Hide My Email is basically an email alias service that generates new addresses on demand. These aliases forward incoming email to your primary address, thus avoiding exposure of your actual email address from spam. I am a huge fan of this concept. I use SimpleLogin already for which I am a paying customer.

It is limited to 100 aliases per account (read so on a beta thread on reddit.) That can be limiting for power users. On SimpleLogin, I have over 1000 aliases, spread across website and apps signups, newsletters, shopping and everything in betwee.

A screenshot showing the new Hide My Email functionality on Apple's iOS 15.

If you start using Hide My Email, consider saving them on a password manager like 1Password or Bitwarden. Otherwise, it’s very easy to lose track of your alias usage across sites.

iCloud Mail with a custom domain

This is probably my most favorite feature announced at WWDC 2021. It’s not available on the beta just yet. Fingers crossed for its availability in the next release!

Safari re-design on both Apple betas

I hate it. Multiple things about this design are distracting:

  • The box-like layout of the tabs resize as I change tabs.
  • The background of the tabs change colors depending on the website’s background color. While it seemed interesting initially, I have noticed that it comes with illegible reading, especially on my non-retina MacBook Air.
  • The position of the search/address bar changes every time I navigate between tabs.

I am not a fan.

Other things I noticed

  • I was late to learning that Shortcuts is available as well! As someone that automates a lot of things with Keyboard Maestro, I am curious to see how Shortcuts can work with it, or how it can complement the former’s features.
  • Universal Control is not available on this beta either. It allows one to use the same input devices (mouse and keyboard) across multiple macOS or iOS devices. I can imagine myself using my MacBook Air’s (2015 model) keyboard for MacBook Pro (2019 model). The latter doesn’t have a butterfly keyboard, which is a good thing, but I still prefer my MacBook Air’s keyboard. There is a mechanical typing sensation which makes the typing experience rich.
  • Tailscale works okay on both betas!

If you want to enroll your devices for Apple betas, the signup program is available here.

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