Current Status:

Is iCloud Mail Just Good Enough

I’ve been spending an inordinate amount of time looking at email services recently. I really have no need for anything smart or clever when it comes to email, yet that’s not stopping me trawling through YouTube videos and written reviews of all that are available, yet again.

I’ve been a Gmail user since day 1, and I have an iCloud account which, again, I’ve had for years. I have one of the coveted addresses even. Both of these accounts contain a lot of history, and I’m unlikely to ever leave any of them, so the fact I’m insistent on still looking around is causing me no end of frustration.

The obvious choice as a main service for me is iCloud mail. It’s relatively privacy conscious, I’m already paying for all the storage I’ll ever need and I have a decent address for it.

There are two main things that prevent me from fully using it for everything, however. The first is search. The search functionality of iCloud mail really is quite atrocious. I have a bit of email OCD, so I like to file my emails away in folders1 and then rely on either looking in the folders for an email or searching for it. I had a recent example of looking for some emails from my accountant I had during a stint as a Contractor. iCloud search came up with absolutely nothing of value, and I had to end up digging around the folder structure I created to eventually find it. Having a lot of storage and a long history, in this case, ended up being a hindrance more than a positive point. This is where I definitely missed the HEY feature of being able to view all messages from a particular contact. The flowing of emails in HEY, and the eventual dilution of decent search results because of it, was another nail in the coffin of HEY for me. Their search is already criticised so I can’t imagine how it’ll fair In a few years time.

The second issue for me is that my iCloud email address is tied to my Apple ID. Not only is it the address connected to it, but the full email is my Apple ID and I’m unable to change it apparently. Because of this, I’m not very happy with throwing my real address out there as often for things like newsletters or signing up to whatever it is I need to sign up to. This then leads me to often fall back to my Gmail account and having to maintain two systems again.

I recently found an interesting feature / service from Mozilla / Firefox called Firefox Relay which may help with this, somewhat. This lets you create a selection of email aliases that will forward to your email address so you can freely share or sign up to things with this burner address whilst maintaining the privacy of your address itself. This should prevent much damage from your address being sold and ending up for sale somewhere. iCloud itself allows you to create a few aliases as well, and I often use for newsletter sign ups, though some people may find it a bit rude that I’ve used an address including the word junk in it!

My journey into all things email recently has shown me that there are a few options available to make Mail on macOS a bit more feature rich and powerful, there are a lot of limitations on what you can do with iOS and the Mail client. Even with the enhancements, I can’t see anything being able to address the search shortcomings.

Gmail, obviously, solves the search question instantly, and I can easily move an archive of my email from iCloud to Gmail. This service is also feature rich and, again, on desktop I can enhance it even further. Despite this, I’ve been slowly moving everything away from Google and don’t really want to focus on moving things back. It’s not a moral point, really, I just don’t like too much stuff tied to them, for various reasons.

So, really, this again leaves me in a bit of a (totally unimportant in the grand scheme of things) quandary. I’m 90% happy with sticking fully with iCloud mail and just utilising aliases for the occasion I want to sign up to something, saving my main @mac or @me addresses for really important things and moving on. The sticking point remains that darn search, however. If I can’t find any of the emails I’m keeping what’s the point of even keeping them?

With just a few tweaks Apple Mail / iCloud mail would be all I need I think, though I am a bit of a magpie and will always be tempted by shiny new services. I’d love to see Apple add the following, as server side enhancements:

  • Labels - I think this would definitely help a lot with finding correspondence from certain people, or related to a particular topic.
  • Search improvements - Of course, labels would be less necessary if search was actually decent …
  • View all from contact - The free flowing nature of HEY didn’t work for me, but they did have some interesting ideas. I’d love Apple to borrow the idea of viewing a contact and then seeing all related messages from that individual along with attachments etc. You can do it in iMessage, so Apple obviously thinks it’s a good idea in general.

To give you an idea of how much email soul searching I’ve done recently, here are a few of the addresses I have:

  • (plus my @mac and @me addresses)
  • (I actually really like this service)

For a service I use for receipts for online purchases, newsletters and spam I’m investing far too much brain space to be perfectly frank. I really do have an issue with this. Overthinking small things so I can procrastinate and avoid working on or dealing with larger, far more important and impactful things. Here we are, however, and I’m still not really fully committed to anything. I’m going to forward everything I have into iCloud for a while and just see how that goes. There have been rumours of some Mail improvements in iOS 15, though the same rumours were circulated ahead of iOS 14 and 13 also, so I won’t hold my breath, but I’ll keep my fingers crossed.

  1. Which may be a big reason why I struggled to stick / click with HEY email. [return]