Replacing my mail service with iCloud mail

I have for years kept the same email address. However, the server behind it has changed over the years. At first, I setup my own mail server until the reality of security became more than I wanted to handle. I switched over to Optimum which provided me a mailbox, then over to Godaddy, to gmail with that sweet promise of 5gb of storage. Finally, with me nervous about Google, switching over to Zoho.

In each case, I used their setup to mask their account with my email address. It looked like I sent and received email at my email address, but if you looked carefully at the headers, you’d see it was a sham.

Zoho has been a big fat pain. I can’t email to AOL and Yahoo addresses, and various email servers claim Zoho is spam. Customer service is awful. I am willing to switch from a free account to a paid account, but can’t find anyone there willing to take my money.

Is have an unused iCloud email address and was thinking maybe I can use that. I am paying for 2 terabytes of storage which trumps my current 15Gb limit.

However, I’d like to use that as a “front” to my preferred email address. People should see my email and not my iCloud email address.

First, is this possible (I have Zoho setup this way, and I had Gmail setup that way when I was using that). Second, what Taking Control book would be good for me to use in order to do this. There’s an Apple Mail one and an iCloud one. Which one covers this type of setup?

You can’t use iCloud that way. It only lets you use @iCloud or @Mac not your own domain.

I recommend Fastmail. It’s for-pay, but it’s well worth every penny, the support is great, and email is their primary business, unlike Apple and Google and so many others.

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Ditto for; I’ve been using it for years. They can handle mail for your domains, they allow several hundred aliases using their domains, and they can fetch mail from other services via pop. They also provide some disk space for static web sites, simple photo galleries and file sharing, plus caldav and carddav.

You can do a trial period without giving your credit card up front.

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Another vote for FastMail. I wrote last year about my own decision-making process in this regard:

I bit and I’m thrilled. Zoho was giving me trouble. I tried moving over before to other services, but six other people in my family use my email domain to forward their emails. Fastmail allowed me to use my own domain and allow the rest of my family to keep their email forwards.

Setup took minutes. My questions were quickly answered. Even configuring my email was simple. Fastmail sent me a profile to use with iOS and macOS. All I had to do was click on the profile and install it.

I ended up paying although they gave me a free month to try it.


FastMail works in your case because your family relies on forwarding. If you want actual mailboxes, however, FastMail quickly becomes ridiculously expensive.

I wouldn’t call Fastmail ridiculously expensive, or even expensive, considering the services and resources that each user gets and the quality of the service. It’s not cheap to run a service well, and mail is the hardest of all.

They mostly aren’t using off the shelf software, either, but are doing significant development on things such as working to replace imap with their own jmap, and they made it open source. jmap has been adopted by the IETF and is now an RFC standard. It will probably become the new mail transfer standard at some point.

I still remember the dark days when Opera bought Fastmail, and that worked kind of ok but service was a little iffy. Then a few years later Facebook wanted to buy the Fastmail part (along with all of that tasty email) from Opera and Opera was willing to sell. We (the users) were horrified, then thrilled when the original devs managed to buy it back in the nick of time and make it independent again. I’d happily pay double or more if that’s what it took for them to stay in business.

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What’s wrong with Gmail? I have one of those grandfathered in accounts that allow up to 50 addresses in my personal domain for free. Each account can have up to 15 GB of storage. After like 20 years I have upped that to 100 GB for just my account because I was running out of space. But the service is good. Why don’t people like it?

I am still looking for the perfect solution of the same e-mail client on Mac and iOS. I am flirting with Canary Mail, but it’s currently not working consistently with my iCloud address. My gmail account on it is fine.

Late last year they released version 3.0 and added some features (great) but took some away I used all the time (not so great).

I don’t think there is such a thing as the perfect e-mail client across platforms. It is so frustrating.

Gmail service is good. It’s also free in the sense I don’t pay cash for if. However, Google’s motto went from Don’t be evil to Fools! I will rule them all!, and I’m not too comfortable with that.

I had Gmail. I still have that Gmail address. In fact, I have two, but Google knows too much about me already.

I use Safari with 1Blocker and Firefox for websites that don’t work with Safari for some reason. These block Google’s trackers that track about 80% of the websites you visit. Have a Google account, and Google can even identify that you visited that particular website – even if you’re logged out of that Google account.

I’ve decided to stop using Google as much as I can. I won’t use an Android phone and I won’t use Google’s smart speakers or WiFi routers. Google still reads my email and tracks me whenever someone with a Gmail account emails me. Occasionally, I must watch a YouTube video and Google tracks me doing that too.

I’ve switched to DuckDuckGo for web searches and I was looking for an email service that doesn’t read through my emails and sells that information to advertisers. I tried Zoho because it copied Google’s implementation, but I still wasn’t that comfortable with it. And Zoho has a lot of issues. Mail gets delayed for hours. Certain email accounts can’t receive my email. And their customer service sucked.

By the way, Gmail’s IMAP is a flawed implementation of that protocol, and that’s done on purpose. If you use Apple’s mail client, Google doesn’t send push notifications. You either have to constantly fetch which kills battery life or use Google’s iPhone client which allows Google to track you on your iPhone.

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My thinking is that via my constant searching and occcasional use of Google Maps, Youtube and Waze, Google already knows more about me than I prefer. Though they do claim they do not search and retain info from the content of Gmail messages to sell advertising in Gmail, they do save the content of the subject field. And they do scan subject and message content to use in their other other services, including ad sales for YouTube, DoubleClick, AdEx, etc.

And they do use the content of emails and texts for use in their multitude of products, including its AI research, and smart home and business stuff. I think that this is a big reason why Google Assistant and Alexa are better than Siri, is because Siri is a privacy focused Apple product. So I stick with Mail. Apple has no interest in what brand of underware I buy from what retailer.

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I have been moving my many emails away from gmail as I use iOS a lot and gmail does not work well with it. Just this week I checked my gmail account to see a message briefly before it disappeared to who knows where. Not in Trash or Junk. Just gone. Who knows how many I have never even noticed that are swallowed up in the process. And the privacy thing too.

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This is my main objection. While I don’t like the tracking, I’ve been burned too many times by “free” services that just stop working or change and since I’m not paying anything, I have no voice in the direction of the product. (I’ve also heard horror stories of people whose gmail account was closed with no recourse simply because they were accused to sending spam or doing something else google didn’t approve of. I can’t imagine relying on that for my business.)


I’ve had this issue on iOS 13 as well, but I think it’s an issue with the Apple Mail client rather than gmail. If I check gmail using the gmail iOS app, another client, or, of course, the web site on a computer browser, I’ll find mail in my gmail inbox that is not showing in the inbox of Apple’s mail client (or even in All Mail when I check that folder in the Mail app.) Obviously I’m not using the stock mail app as my primary mail client for my gmail accounts.

I’ve been using Gmail since 2011, and I’ve been very happy with it. It’s a safe bet that I receive more mail than most people, and Gmail has no problems dealing with what must be many hundreds of thousands of stored messages. Currently, all my mail goes through easyDNS’s easyMail system first—that’s how gets forwarded to my Gmail account.

I don’t use Mail on the Mac or on iOS, but instead stick with Mailplane (a front end to the native Gmail Web interface) and the Gmail app, and the native experience is far better. Every time I do something in Mail, I’m amazed that people would put up with the delays in retrieving and displaying messages that I see. Using Mail feels like reading email through a hazmat suit in comparison.

In my user support experience gmail isn’t all that good compared to standard imap systems.

They don’t use standard protocols, they use their own proprietary system. They mimic parts of imap, but it’s a fragile kluge. That can cause problems because gmail’s labels aren’t the same as mailboxes/folders in a regular imap mail client. The sync state between an imap client and gmail is sometimes weird. Things show in a gmail label via the browser client, but not in the corresponding local mailboxes/folders, or versy vicey. Sometimes a message seems to be duplicated, but isn’t really–delete one of those ‘duplicates’, and all copies might disappear. Or not. It isn’t consistent. If you only use the gmail web interface, this isn’t an issue, but most of my users need a local client so that mail is directly on their laptop, especially if they need to travel. Most users also have multiple mail accounts, and want them in the same client, so it can’t be a gmail specific client.

gmail filters are a joke, not only feature-poor but unreliable. We have staff (including one using only the gmail web client) who have to frequently check their spam labels throughout the day because mail from one or two of the faculty they work for cannot be kept out of spam no matter how we try to tell the filters that the sender is good. But those same faculty can send mail with no trouble to other gmail users. I’ve also tried using gmail filters to sort out mailing lists to their own labels, but it has never been at all reliable. Some list messages stay in the inbox, some go to spam, some to the label they should have, some to the wrong list label, some can only be found in All Mail. Feh.

Note that we’re using the fancy educational google services, which are supposed to be supported. I suppose it is supported if you can get through the bottlenecks along the way. Google won’t talk to individual users–they only talk to a few designated IT staff and they drag their feet about it, especially if it’s ‘only’ a user problem. The vast majority of user problems never get resolved, or even acknowledged. It’s caused the department to require new staff to use Exchange (which has it’s own problems, but different ones).

They aren’t unique in this, but gmail doesn’t deliver much mail from smaller independent mail servers, no matter how correctly the server is set up and how much the recipients want the mail. The mail isn’t rejected and doesn’t go to the recipient’s spam folder, it just gets dropped on the floor. No recourse for either the sender or the recipient. gmail users aren’t customers, and aren’t entitled to support beyond the help pages.


It would not surprise me if Google’s buggy implementation of IMAP is done to encourage people to use Google’s default client and move all of their email over to Gmail. After all, if you use the Gmail browser or the Gmail app in iOS, you can’t see non-Gmail accounts.

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David Weintraub wrote: “It would not surprise me if Google’s buggy implementation of IMAP is done to encourage people to use Google’s default client”

Maybe, but gmail came out in 2004 before google was so huge and creepy, and all of the basic structures were there from the start. It’s quite possible that they really thought they had a better system, and obviously it’s adequate for many people. But google really doesn’t have much clue about which features would be useful to go beyond simple email, and there haven’t been any real improvements, or even fixes for the cruft such as filtering, since it first came out.

MS did their email much better with Exchange (which also has a fake imap mode for now), by knowing what their target audience, large organizations, needed. Exchange has a lot of useful stuff for collaboration and management controls such as not allowing mail to be truly deleted by a user if you have records retention requirements. Unfortunately, MS isn’t as good as google at the reliable mail server thing, though they seem to be improving lately.

This has not been my experience at all. Filters may be the second biggest reason (after the spam filtering) I stay with gmail. Powerful and 100% reliable for me. I have dozens of them and never have any problems.

Agreed. Most folks I know wish that other mail services did filters as well as Gmail and it’s one of the things that keeps people using it.