iCloud Need new main/permanent email address; is iCloud good?

[theorist9]

I had a main email account for many years that's going away, and need to replace it with a new main email address. I mostly read my emails through Outlook, where the emails are all downloaded locally onto my Mac and saved within Outlook. This is the case for all my email accounts.

I have some gmail accounts, but don't like Google's bad privacy policies;plus Gmail isn't always reliable (I've had people send me plain-text messages from their own Gmail accounts that never got through); and I don't like their clunky web interface on the occasions I need to use it.

I believe my internet provider (Spectrum) offers a free account, but that would go away if and when I switch providers. Since changing emails is a pain (I have to reset all the accounts that use the email for authentication), while nothing is forever, I'd like something that would be as permanent as possible.

So my desired characteristics are:

1) Permanency
2) Reliability
3) Integrates seamlessly with Outlook
4) Nice web interface
5) Excellent privacy
6) High speed (emails appear in my Outlook account immediately after they are sent).

I have an iCloud account, and will likely use Macs for the rest of my life, so an iCloud email seems like the obvious choice. But how well does it work in practice? And are there any others I should consider?

 

[Sweet_Caroline]

We just moved to Fastmail A week or 2 ago. We also got a domain, so it’s easy to switch email providers if needed. I am starting to use the masked emails for stuff also. It’s just going to take a while.

We dropped iCloud because my husband was never a fan of it. He’s the nerd in the family, so I just listen to him 😂

 

[Rnd-chars]

I’ve use Outlook.com, Gmail, Yahoo and iCloud. Of the four, iCloud’s privacy policies are the best and they’ve started building privacy in with features like Hide My Email (which I use *a lot*)

I use the default Mail clients so I can’t speak to Outlook integration. Calendaring functions generally work well (eg you can share calendars, invite folks and use FaceTime for the meeting) but I have had instances where someone proposed a new time using their email client and I wasn’t notified (however, I don’t know if that’s an iCloud or Mail bug/limitation, or if it was an error on the Gmail side used by the attendee).

Server-side rules filtering is best on Outlook.com accounts, but iCloud still offers some capabilities there.

I started my migration by moving over a few low criticality accounts (eg newsletters, lists, etc and used Hide My Email for each). Once I felt confident in its functionality and behavior, I started moving over trusted contacts and more important accounts. I then turned on mail forwarding for my old account for anything I missed and migrated them over as needed. All in all, I’m glad I did and don’t have any regrets.

As for web mail clients, I find iCloud’s a bit spartan but clean. Outlook’s is the noisiest with ads and upsells, but provides the most functionality. Gmail sits in the middle, but insists you don’t need/want folders (“just give us labeled data so we can train our models”)

Since you’re planning on being in the Apple ecosystem for a while and you’re concerned about privacy, I think iCloud seems like a good choice. I hope you enjoy it!

 

[brinkeguthrie]

In almost three years of usage- I have never received one spam email. Not one.

 

[BrianBaughn]

If you want to pay for your own domain name and pay for email hosting of that domain I'd say the best fit for Outlook would be Office 365 Hosted Exchange.

An Outlook.com email address would be the best free fit for Outlook.

 

[circatee]

I own a M365 domain and thus a personal email address. I do need to start using it, for friends and such.

My Outlook Dot Com email address gets so much spam/junk. Then again, I’ve had that email address for around 12 years or so…

 

[sgtaylor5]

If you want to pay for your own domain name and pay for email hosting of that domain I'd say the best fit for Outlook would be Office 365 Hosted Exchange.

An Outlook.com email address would be the best free fit for Outlook.

Office Outlook was created as “Exchange Client” in the ‘90’s. It’s never strayed far from its roots.

 

[BigMcGuire]

We just moved to Fastmail A week or 2 ago. We also got a domain, so it’s easy to switch email providers if needed. I am starting to use the masked emails for stuff also. It’s just going to take a while.

We dropped iCloud because it’s because my husband was never a fan of it. He’s the nerd in the family, so I just listen to him 😂

I moved my custom domain to Apple for awhile but ... Apple Mail was so disappointing I went back to Fastmail and I am very happy that I did. I had been using Fastmail for years and years before Apple allowed custom domain emails and using it since it came out, I finally gave up because I do not like Apple Mail at all. Fastmail it is.

Complaints about Apple Mail? No spam filtration at all. Attachments limited to 20MB, really? (Fastmail 70mb). There were times where I just didn't get mail, for no reason. No idea why, it just didn't show up. Thankfully it was rare but it did happen.

Biggest complaint of Apple Mail? It took me 5? mins to transfer 3.8 GB of mail to Fastmail. It takes Apple Mail 2 days to import this amount of mail.

Positives about Apple Mail? Free with Apple One Premier. Data is encrypted to Apple standards. Bout it.

Fastmail is so much better - accessible via web and not tied to my Apple ID and works really well with custom domains. Spam filtering works.

 

[BrianBaughn]

Fastmail may end up being the greatest IMAP/CardDAV/CalDAV mail service of all time but is currently a terrible suggestion for the Outlook application on macOS.

How to set up Outlook

The instructions and screenshots in this setup guide are for Outlook 2016. However, previous versions of Outlook are very similar, and you should be able to follow the same steps to set up. Outlook...

www.fastmail.help

At the bottom of that page see:

Outlook for macOS doesn't use third-party plugins so Fastmail doesn't even pass the sniff test.

The only way to utilize Outlook for macOS with a single provider for email, calendars and contacts is to connect it to an Exchange service.

 

[Sweet_Caroline]

I moved my custom domain to Apple for awhile but ... Apple Mail was so disappointing I went back to Fastmail and I am very happy that I did. I had been using Fastmail for years and years before Apple allowed custom domain emails and using it since it came out, I finally gave up because I do not like Apple Mail at all. Fastmail it is.

I’m pleasantly surprised how much I am liking Fastmail. I feel like my account are more organized.

Complaints about Apple Mail? No spam filtration at all. Attachments limited to 20MB, really? (Fastmail 70mb). There were times where I just didn't get mail, for no reason. No idea why, it just didn't show up. Thankfully it was rare but it did happen.

I didn’t realize how bad Apples spam filter was until we moved to Fastmail.

Biggest complaint of Apple Mail? It took me 5? mins to transfer 3.8 GB of mail to Fastmail. It takes Apple Mail 2 days to import this amount of mail.

Positives about Apple Mail? Free with Apple One Premier. Data is encrypted to Apple standards. Bout it.

Fastmail is so much better - accessible via web and not tied to my Apple ID and works really well with custom domains. Spam filtering works.

I’m happy with it, and I hope so, we paid for 3 years 😂. I wish they had a family plan.

 

[circatee]

Fastmail may end up being the greatest IMAP/CardDAV/CalDAV mail service of all time but is currently a terrible suggestion for the Outlook application on macOS.

How to set up Outlook

The instructions and screenshots in this setup guide are for Outlook 2016. However, previous versions of Outlook are very similar, and you should be able to follow the same steps to set up. Outlook...

www.fastmail.help

At the bottom of that page see:

View attachment 2238443​

Outlook for macOS doesn't use third-party plugins so Fastmail doesn't even pass the sniff test.

The only way to utilize Outlook for macOS with a single provider for email, calendars and contacts is to connect it to an Exchange service.

...thanks for sharing. I was just about to create an account on Fast Mail and test it.

 

[splifingate]

I had a main email account for many years that's going away, and need to replace it with a new main email address. I mostly read my emails through Outlook, where the emails are all downloaded locally onto my Mac and saved within Outlook. This is the case for all my email accounts.

I have some gmail accounts, but don't like Google's bad privacy policies;plus Gmail isn't always reliable (I've had people send me plain-text messages from their own Gmail accounts that never got through); and I don't like their clunky web interface on the occasions I need to use it.

I believe my internet provider (Spectrum) offers a free account, but that would go away if and when I switch providers. Since changing emails is a pain (I have to reset all the accounts that use the email for authentication), while nothing is forever, I'd like something that would be as permanent as possible.

So my desired characteristics are:

1) Permanency
2) Reliability
3) Integrates seamlessly with Outlook
4) Nice web interface
5) Excellent privacy
6) High speed (emails appear in my Outlook account immediately after they are sent).

I have an iCloud account, and will likely use Macs for the rest of my life, so an iCloud email seems like the obvious choice. But how well does it work in practice? And are there any others I should consider?

I've held a domain/host for decades, and it has served me well for my own, personalised email(s).

For the past handful of years, I've been using Postbox on my systems for email retrieval, to great effect.

My live.com addy works just as well as all my others.

What client are you using?

Your criteria makes it sound like you are asking advice about an effective email client *shrugs*

 

[theorist9]

I've held a domain/host for decades, and it has served me well for my own, personalised email(s).

For the past handful of years, I've been using Postbox on my systems for email retrieval, to great effect.

My live.com addy works just as well as all my others.

What client are you using?

Your criteria makes it sound like you are asking advice about an effective email client *shrugs*

I'm not looking for an email client; I'm using Outlook for Mac, and plan to stick with it. Every few OS's I check Apple Mail to see if it's good enough, but it never is (at least for me). I just needed to replace my main email account.

I had a main email account for many years that's going away, and need to replace it with a new main email address. I mostly read my emails through Outlook, where the emails are all downloaded locally onto my Mac and saved within Outlook. This is the case for all my email accounts.

 

[circatee]

@theorist9 my personal opinion is that a M365 domain and email address would suit you. Additionally, you can control it as you wish. Albeit, there is a monthly subscription (around $8-15), depending on the license type you choose...

 

[Mr. Heckles]

I’m pleasantly surprised how much I am liking Fastmail. I feel like my account are more organized.

I didn’t realize how bad Apples spam filter was until we moved to Fastmail.

I’m happy with it, and I hope so, we paid for 3 years 😂. I wish they had a family plan.

I’ve been using it for over a year and I’m very happy with it.

...thanks for sharing. I was just about to create an account on Fast Mail and test it.

I think if someone sends your a referral, you can get 10% off.

@theorist9 my personal opinion is that a M365 domain and email address would suit you. Additionally, you can control it as you wish. Albeit, there is a monthly subscription (around $8-15), depending on the license type you choose...

$8-15 a month? I’m paying less a month for my wife and myself for Fastmail.

 

[splifingate]

I'm not looking for an email client; I'm using Outlook for Mac, and plan to stick with it. Every few OS's I check Apple Mail to see if it's good enough, but it never is (at least for me). I just needed to replace my main email account.

Ah, yes. I see.

Retaining your own domain/host would probably provide you the greatest degree of control and privacy.

Most provide cost-effective email-only options.

Have fun choosing

 

[circatee]

I’ve been using it for over a year and I’m very happy with it.

I think if someone sends your a referral, you can get 10% off.

$8-15 a month? I’m paying less a month for my wife and myself for Fastmail.

No, no, I hear you. Additionally, the price offers up to 5 email addresses, and access to the Microsoft suite (that I prefer on a few computers).

My only reservation with FastMail, is that apparently for syncing of Contacts & Calendar, this is only offered via a third party tool/plugin. A shame really...

 

[sgtaylor5]

No, no, I hear you. Additionally, the price offers up to 5 email addresses, and access to the Microsoft suite (that I prefer on a few computers).

My only reservation with FastMail, is that apparently for syncing of Contacts & Calendar, this is only offered via a third party tool/plugin. A shame really...

And that plug-in, if you’re talking about “CalDAV Connector” is only available on Windows.

 

[exi]

I had a main email account for many years that's going away, and need to replace it with a new main email address. I mostly read my emails through Outlook, where the emails are all downloaded locally onto my Mac and saved within Outlook. This is the case for all my email accounts.

I have some gmail accounts, but don't like Google's bad privacy policies;plus Gmail isn't always reliable (I've had people send me plain-text messages from their own Gmail accounts that never got through); and I don't like their clunky web interface on the occasions I need to use it.

I believe my internet provider (Spectrum) offers a free account, but that would go away if and when I switch providers. Since changing emails is a pain (I have to reset all the accounts that use the email for authentication), while nothing is forever, I'd like something that would be as permanent as possible.

So my desired characteristics are:

1) Permanency
2) Reliability
3) Integrates seamlessly with Outlook
4) Nice web interface
5) Excellent privacy
6) High speed (emails appear in my Outlook account immediately after they are sent).

I have an iCloud account, and will likely use Macs for the rest of my life, so an iCloud email seems like the obvious choice. But how well does it work in practice? And are there any others I should consider?

As someone who has agonized over choosing accounts and services, I wanted to like iCloud for mail, but the countless posts about deliverability/reliability and "silent filtering" (search, you'll find them) ultimately drove me away despite using it with a custom domain.

Fastmail with a custom domain has been a good blend for me, and I feel it would be a good blend of your priorities.

 

[theorist9]

As someone who has agonized over choosing accounts and services, I wanted to like iCloud for mail, but the countless posts about deliverability/reliability and "silent filtering" (search, you'll find them) ultimately drove me away despite using it with a custom domain.

Fastmail with a custom domain has been a good blend for me, and I feel it would be a good blend of your priorities.

Interesting. I have encountered those issues with Gmail--even a gmail from a friend who had his own gmail account never got to me. Surprised that's the case with iCloud as well. Did you experience that yourself, or just found there were a lot of complaints about it?

Alas, from what others have posted, Fastmail does not integrate well with the Mac Outlook desktop client.

 

[theorist9]

Retaining your own domain/host would probably provide you the greatest degree of control and privacy.

Could you explain what "Retaining your own domain/host" means/involves? It sounds like you mean registering my own web domain, paying someone to host it, and then adding email functionality to it, which sounds quite a bit more involved than I'd like.

 

[theorist9]

Fastmail may end up being the greatest IMAP/CardDAV/CalDAV mail service of all time but is currently a terrible suggestion for the Outlook application on macOS.

How to set up Outlook

The instructions and screenshots in this setup guide are for Outlook 2016. However, previous versions of Outlook are very similar, and you should be able to follow the same steps to set up. Outlook...

www.fastmail.help

At the bottom of that page see:

View attachment 2238443​

Outlook for macOS doesn't use third-party plugins so Fastmail doesn't even pass the sniff test.

The only way to utilize Outlook for macOS with a single provider for email, calendars and contacts is to connect it to an Exchange service.

Thanks--good to know.

 

[Phil A.]

I use Outlook with my iCloud account (along with other accounts) and it works fine (including calendar and contact sync) but there are a couple of caveats:

Firstly, you have to enable “New Outlook” which is the next gen outlook client (from what I remember, it’s quite a bit different from the old design), which is an option under the Outlook menu

Secondly, you need to create an app password for your iCloud account and use that when logging in

Thirdly (and most controversially) you have to enable syncing with Microsoft cloud: this will sync the entire contents of your mailbox with Microsoft’s data centre and then enable the full functionality of outlook. If you don’t do this and just connect it as an IMAP account, you don’t get contact or calendar sync. This has been controversial as people don’t like the fact their email is getting stored on a third party server, but I trust Microsoft to keep my corporate data secure (I’m an M365 subscriber) so I trust them with this too

 

[exi]

Interesting. I have encountered those issues with Gmail--even a gmail from a friend who had his own gmail account never got to me. Surprised that's the case with iCloud as well. Did you experience that yourself, or just found there were a lot of complaints about it?

Alas, from what others have posted, Fastmail does not integrate well with the Mac Outlook desktop client.

I experienced some of it myself, at times unpredictably, along with some significant delivery delays which all had the net effect of poisoning iCloud Mail as an option in my mind. Though a minority of messages, it also left me wondering what was going on or what might happen to emails of importance.

 

[theorist9]

Firstly, you have to enable “New Outlook” which is the next gen outlook client (from what I remember, it’s quite a bit different from the old design), which is an option under the Outlook menu

I contacted Outlook Support, and I'm getting some confusing answers. It looks like iCloud works with both Legacy Outlook and New Outlook, and that this syncing workaround functions for both:
Sync your iCloud calendar with Outlook for Mac
In addition, they are working on doing a direct sync, but this is for New Outlook only, and it's having issues:

The new Outlook for Mac - Microsoft Support

An introduction to the new Outlook for Mac.

support.microsoft.com

Secondly, you need to create an app password for your iCloud account and use that when logging in

Could you explain what you mean by "create an app password"? All my email accounts have passwords that are stored in the Outlook desktop client, so I don't need to do separate logins. Is a separate login needed for iCloud every time I reboot?

Thirdly (and most controversially) you have to enable syncing with Microsoft cloud: this will sync the entire contents of your mailbox with Microsoft’s data centre and then enable the full functionality of outlook. If you don’t do this and just connect it as an IMAP account, you don’t get contact or calendar sync. This has been controversial as people don’t like the fact their email is getting stored on a third party server, but I trust Microsoft to keep my corporate data secure (I’m an M365 subscriber) so I trust them with this too

I'm getting confusing answers from Outlook Support on this as well. First they're telling me one thing, then another. I assume this is what you're referring to:

Sync your account in Outlook to the Microsoft Cloud - Microsoft Support

Explains how to sync your Google, Yahoo, iCloud, and IMAP mail, contacts, and calendar to the Microsoft Cloud.

support.microsoft.com