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

[Phil A.]

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

View attachment 2244044


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?


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

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

support.microsoft.com

If you enable "New Outlook", you don't have to bother with that workaround - you just add your iCloud account and it automatically syncs up your contacts and calendars into Outlook.

An App Password is a password that will allow an application to log in on your behalf (you don't have to login every time, just the once) - This Apple Support Page explains what they are and how to create one. Once you have it, you add your iCloud account by providing your main iCloud email address and the App Password (not your normal password): Your account will be added and you shouldn't have to ever enter the password again.

That Microsoft Support page you linked is the right one that explains what syncing to the Microsoft Cloud entails

 

[theorist9]

If you enable "New Outlook", you don't have to bother with that workaround - you just add your iCloud account and it automatically syncs up your contacts and calendars into Outlook.

An App Password is a password that will allow an application to log in on your behalf (you don't have to login every time, just the once) - This Apple Support Page explains what they are and how to create one. Once you have it, you add your iCloud account by providing your main iCloud email address and the App Password (not your normal password): Your account will be added and you shouldn't have to ever enter the password again.

That Microsoft Support page you linked is the right one that explains what syncing to the Microsoft Cloud entails

OK, here's what I got from Outlook Support:

There are in fact *three* potential ways to sync your iCloud calendar to the Outlook for Mac desktop client:

1) “Subscribe your iCloud calendar to Outlook on the web”. This is available for both Legacy and New Outlook. In this case Microsoft gets your *calendar info. only*.
https://support.microsoft.com/en-us...-for-mac-c9c67e41-274f-4527-ae5e-ea1003d89fc5

2) “…. sync your non-Microsoft accounts (including their emails, contacts, and events) to the Microsoft Cloud. Syncing your account to the Microsoft Cloud means that a copy of your email, calendar, and contacts will be synchronized between your email provider and Microsoft data centers.” This is available for New Outlook only and, as stated, MS gets all your email data.
https://support.microsoft.com/en-us...1d-0c6f32f8e981#OfficeVersion=Outlook_for_Mac

3) Direct sync using the the CalDAV or CardDAV Internet standards. According to the link in no. 1, “Currently, Outlook for Mac doesn't support the CalDAV or CardDAV Internet standards.” However, according to this article ( https://support.microsoft.com/en-us...-for-mac-6283be54-e74d-434e-babb-b70cefc77439 ) , the Outlook Product Team is trying to get this working for New Outlook only, but they’ve not been sucessful thus far (“Unable to create or sync local Contacts or Calendars for IMAP Direct sync and IMAP Cloud cache accounts.”). Also, the type of IMAP accounts they are referring to may not include iCloud.

We can eliminate no. 3, so that leaves nos. 1 and 2. According to Outlook Support:

"The functional difference between approaches no.1 and no.2 is, say for example you have an iCloud account as 123@me.com and an Office365 account as 123@harvard.edu.

When you use approach no.1, the calendar events are synced and shown in Outlook for Mac, under the Office365 account. And this works in both Legacy and New Outlook.

Whereas, when you use approach no.2, the iCloud calendar events are synced and shown under the iCloud account (as per example 123@me.com). And this works only in the New Outlook."

So my question: Is it less convenient, or otherwise problematic, to have your calendar synced under your Office 365 acct (approach no. 1) rather than under your iCloud acct (approach no. 2)? Or is it just less convenient to set up? The reason I ask is that, since I prefer Legacy Outlook, no. 1 is the only option available to me.

To put it another way, other than less convenient setup, if you used New Outlook (and thus could do either 1 or 2), is there any reason you wouldn't want to use no. 1? An obvious benefit to no. 1 is that Apple's privacy policies are stronger than MS's.

 

[BrianBaughn]

OK, here's what I got from Outlook Support:

There are in fact *three* potential ways to sync your iCloud calendar to the Outlook for Mac desktop client:

1) “Subscribe your iCloud calendar to Outlook on the web”. This is available for both Legacy and New Outlook. In this case Microsoft gets your *calendar info. only*.
https://support.microsoft.com/en-us...-for-mac-c9c67e41-274f-4527-ae5e-ea1003d89fc5

2) “…. sync your non-Microsoft accounts (including their emails, contacts, and events) to the Microsoft Cloud. Syncing your account to the Microsoft Cloud means that a copy of your email, calendar, and contacts will be synchronized between your email provider and Microsoft data centers.” This is available for New Outlook only and, as stated, MS gets all your email data.
https://support.microsoft.com/en-us...1d-0c6f32f8e981#OfficeVersion=Outlook_for_Mac

3) Direct sync using the the CalDAV or CardDAV Internet standards. According to the link in no. 1, “Currently, Outlook for Mac doesn't support the CalDAV or CardDAV Internet standards.” However, according to this article ( https://support.microsoft.com/en-us...-for-mac-6283be54-e74d-434e-babb-b70cefc77439 ) , the Outlook Product Team is trying to get this working for New Outlook only, but they’ve not been sucessful thus far (“Unable to create or sync local Contacts or Calendars for IMAP Direct sync and IMAP Cloud cache accounts.”). Also, the type of IMAP accounts they are referring to may not include iCloud.

We can eliminate no. 3, so that leaves nos. 1 and 2. According to Outlook Support:

"The functional difference between approaches no.1 and no.2 is, say for example you have an iCloud account as 123@me.com and an Office365 account as 123@harvard.edu.

When you use approach no.1, the calendar events are synced and shown in Outlook for Mac, under the Office365 account. And this works in both Legacy and New Outlook.

Whereas, when you use approach no.2, the iCloud calendar events are synced and shown under the iCloud account (as per example 123@me.com). And this works only in the New Outlook."

So my question: Is it less convenient, or otherwise problematic, to have your calendar synced under your Office 365 acct (approach no. 1) rather than under your iCloud acct (approach no. 2)? Or is it just less convenient to set up? The reason I ask is that, since I prefer Legacy Outlook, no. 1 is the only option available to me.

To put it another way, other than less convenient setup, if you used New Outlook (and thus could do either 1 or 2), is there any reason you wouldn't want to use no. 1? An obvious benefit to no. 1 is that Apple's privacy policies are stronger than MS's.

In either scenario (1 or 2) is that syncing a "read only" situation?

 

[theorist9]

In either scenario (1 or 2) is that syncing a "read only" situation?

Update: Based on @Phil A. 's response, #1 is limited to read-only, but #2 is not.

 

[Phil A.]

To put it another way, other than less convenient setup, if you used New Outlook (and thus could do either 1 or 2), is there any reason you wouldn't want to use no. 1? An obvious benefit to no. 1 is that Apple's privacy policies are stronger than MS's.

One big problem with 1) is you get a read-only copy of your iCloud calendar in Outlook (I.e you can see events but can’t add new ones or edit them) as it says on the screenshot

You are also publishing your calendar to the internet protected only by an obscure URL and if anyone ever got that url they could see your calendar

 

[theorist9]

One big problem with 1) is you get a read-only copy of your iCloud calendar in Outlook (I.e you can see events but can’t add new ones or edit them) as it says on the screenshot

View attachment 2244379

You are also publishing your calendar to the internet protected only by an obscure URL and if anyone ever got that url they could see your calendar

Thanks! That's exactly the kind of real-world info. it's normally hard to uncover on your own.

 

[theorist9]

FYI, a higher-tier tech guy at Outlook Support added this info. I can't quite follow it, since it's "technical but not technical enough" (technical enough that I need more technical details in order to understand it), but perhaps someone here can:

"As you have mentioned earlier, iCloud is added as IMAP, but these accounts are not specifically called IMAP accounts with respect to configuration, as iCloud along with Gmail and Yahoo have been given additional features due to them being more used by the general public. The same is observed when adding the accounts as 3rd party providers are added using the IMAP CC or DS feature while all iCloud, Google and Yahoo accounts have separate sections where we can add.

With respect to sync, as of now we don't have reports for iCloud other than some delay in calendar sync. You would have to add the account as Cloud cache though. With respect to Direct sync, it depends on the providers ability to use the CalDAV protocol. Hence, we have seen limited results of calendar sync when adding via that protocol. Cloud cache however works differently, and you may look into the following article on how Microsoft captures data from iCloud and syncs across the app.

https://support.microsoft.com/en-us...1d-0c6f32f8e981#OfficeVersion=Outlook_for_Mac "

[Note: That article has already been mentioned in this thread.]

 

[splifingate]

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.

That's, basically, what it's about

Yes, there is a certain degree of administration that's entirely on you. I say 'certain', because most of the whole self-hosted experience is automated.

It's up to you to pay whatever yearly fees for domian/host, but that's about all the management one needs to do over the duration. After the initial setup, and step-by-step integration with whatever email reader you prefer to use to handle your daily consumption, it's really no more arduous than monitoring any other basic utility bill.

After playing both sides of the fence (I still have my skin in the game on both sides), I've found that self-domain'ing is no more difficult than subbing to Johns Fab Email Service, LTD.

For about the cost of one botique cup of coffee per month, one can retain a bespoke domain. You, personally, could retain&maintain an email addy of theorist9@theorist9-dot-com in perpetuity for--effectively--very little $£€/year

 

[theorist9]

That's, basically, what it's about

Yes, there is a certain degree of administration that's entirely on you. I say 'certain', because most of the whole self-hosted experience is automated.

It's up to you to pay whatever yearly fees for domian/host, but that's about all the management one needs to do over the duration. After the initial setup, and step-by-step integration with whatever email reader you prefer to use to handle your daily consumption, it's really no more arduous than monitoring any other basic utility bill.

After playing both sides of the fence (I still have my skin in the game on both sides), I've found that self-domain'ing is no more difficult than subbing to Johns Fab Email Service, LTD.

For about the cost of one botique cup of coffee per month, one can retain a bespoke domain. You, personally, could retain&maintain an email addy of theorist9@theorist9-dot-com in perpetuity for--effectively--very little $£€/year

My concern is I don't think there are many simple domain names left available, so it would be [something simple, like my first name]@[something long and complicated.com] That's an issue when having to say it over the phone when verifying your email, etc. At least if you have, for example, @icloud.com or @fastmail.com, you don't need to spell out the domain name.

 

[splifingate]

My concern is I don't think there are many simple domain names left available, so it would be [something simple, like my first name]@[something long and complicated.com] That's an issue when having to say it over the phone when verifying your email, etc. At least if you have, for example, @icloud.com or @fastmail.com, you don't need to spell out the domain name.

Name.com | Domain Names, Registration, Websites & Hosting

Name.com is your complete source for domain names, hosting and other online presence solutions.

www.name.com

I'm just sayin'

 

[splifingate]

Name.com | Domain Names, Registration, Websites & Hosting

Name.com is your complete source for domain names, hosting and other online presence solutions.

www.name.com

I'm just sayin'

[addendum]

I picked [other-me].info back in the day when I was geek'ed to the proper use of TLD's, and I sometimes find that it's a job to vocally submit my email to businesses.

Sometimes it's a tennis-match of a dialogue; other-times, I can just type it in.

[edit]

btw . . . most domain providers offer the functionality of domain-forwarding, such that (for-example) you can find [me].net, which is directly linked to [other-me].info (seamless DNS-resolution).

In the end, all of it is really not that difficult

 

[BrianBaughn]

A simple solution for me with a custom email domain (admittedly seldom-used): I have a very cheap ($12/year) domain host for the domain which includes IMAP email (multiple accounts if you want) in a small storage space situation. I additionally sync a Gmail account and use Google for calendars and contacts and to store (move from IMAP folders) my custom email in the Gmail folders.

 

[theorist9]

Name.com | Domain Names, Registration, Websites & Hosting

Name.com is your complete source for domain names, hosting and other online presence solutions.

www.name.com

I'm just sayin'

OK, fair enough . And it seems if I'm willing to go with one of the less common suffixes, I could shorten it further, though that could lead to more frequent errors where people on autopilot just add .com...

What about performance and syncing? We've been discussing Fastmail vs. iCloud, where some have said iCloud is less reliable and has poorer spam filtering. Plus neither can do direct sync using CalDAV or CardDAV. With your approach are you using the host's (say, GoDaddy's) email system, and how would that compared to Fastmail or iCloud with respect to these issues?

 

[splifingate]

OK, fair enough . And it seems if I'm willing to go with one of the less common suffixes, I could shorten it further, though that could lead to more frequent errors where people on autopilot just add .com...

What about performance and syncing? We've been discussing Fastmail vs. iCloud, where some have said iCloud is less reliable and has poorer spam filtering. Plus neither can do direct sync using CalDAV or CardDAV. With your approach are you using the host's (say, GoDaddy's) email system, and how would that compared to Fastmail or iCloud with respect to these issues?

I access all my email accounts via Postbox (which is, basically, Thunderbird), and I have not trouble synch'ing any accounts.

My iCloud account has been changed to use a specific account on my own email host account.

On occasion, accessing my live.com account (which is, basically, using the Exchange infrastructure) produces an error, but I attribute this to the inherent whimsy of cloud availability.

The up-time availability of my email/domain/host is as near 100% as to effectively quantify it as such.

I avoid GoDad for a number of reasons. There are *many* much-more satisfying registrars out there. I was with name.com for years, but have since switched to Porkbun.

We all find what fits, with use; and experience

 

[exi]

OP, unsure if I misinterpreted what you were saying, but Fastmail readily supports CalDAV and CardDAV.

As to performance and synchronization: I moved from iCloud with custom domain to Fastmail with custom domain because of my reliability/deliverability concerns, but I did also notice along the way that Fastmail was far more reliably quick to deliver new mail.

I would love to be able to count on iCloud with custom domains and stick with it, but at least for now, I can't.

Additionally, Fastmail is known for excellent push support and background read status synchronization on Apple's native client (e.g., Mail on iOS) which iCloud does not do. That is, push email works fine, but updating a message's status in the background on a push basis doesn't work as you'd expect. I know you mentioned your adherence to Outlook; if you mean this for Outlook on iOS as well, I suppose that part doesn't matter to you.

Speaking for myself, Fastmail with custom/personal domains via Cloudflare has given me precisely zero functional concerns. Your earlier comment about changing email addresses, etc, is something that I did over hours and days, again, but for the last time, with this move to custom domains -- because once it's your domain, it's far easier to change email platforms while retaining your domain/email address than it is to change the address across who knows how many websites.

 

[theorist9]

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

Just found this:

Outlook CalDav Synchronizer

Download Outlook CalDav Synchronizer for free. Sync Outlook with Google, SOGo or any other CalDAV / CardDAV server . Free Outlook Plugin, which synchronizes events, tasks and contacts between Outlook and Google, SOGo, NextCloud, Horde or any other CalDAV or CardDAV server. Supported Outlook...

sourceforge.net

Anyone here heard whether it works with either iCloud or FastMail?

I searched its Forums (https://sourceforge.net/p/outlookcaldavsynchronizer/discussion/general/).

The most recent ticket for iCloud (from 2019) seems to indicate it works: https://sourceforge.net/p/outlookcaldavsynchronizer/discussion/ticket-like/thread/3364d55f3b/

The most recent post for Fastmail is old (2015), and seems to indicate there are issue:

Outlook CalDav Synchronizer / Discussion / General Discussion: Sync contacts

sourceforge.net

 

[theorist9]

OP, unsure if I misinterpreted what you were saying, but Fastmail readily supports CalDAV and CardDAV.

What's being discussed is instead that Outlook doesn't support these (yet)....though see my last post.

Speaking for myself, Fastmail with custom/personal domains via Cloudflare

Is it essentially the case that doing this allows you to create personalized aliases of your Fastmail email address using your domain?

And does this add an extra potential point of failure/slow-down because instead of going from sender -> Fastmail -> you, it needs to go through both the Fastmail server and the server hosting your domain?

 

[exi]

So if you get your own website using Cloudflare, and use Fastmail for email, then your address names can be XYZ@[your domain] instead of XYZ@[fastmail.com]?

You got it. It has worked well for me thus far.

 

[exi]

The iCloud website was recently updated (as covered by MacRumors). Of course, there is no reason to assume anything changed on the back end, but does anyone have any observations or anecdotes about whether there have been any recent changes in reliability / "silent filtering" / the read status background update issue?

 

[sgtaylor5]

What's being discussed is instead that Outlook doesn't support these (yet)....though see my last post.

Is it essentially the case that doing this allows you to create personalized aliases of your Fastmail email address using your domain?

And does this add an extra potential point of failure/slow-down because instead of going from sender -> Fastmail -> you, it needs to go through both the Fastmail server and the server hosting your domain?

Domain registrar just gives you a domain, the email is totally hosted through Fastmail’s DNS.

 

[theorist9]

.

 

[theorist9]

.

 

[theorist9]

I got a paid Fastmail standard account. But their surprising lack of instructions on how to set up Fastmail on Outlook for Mac made it tricky*. Fortunately I was able to figure it out.

The key is that, when requesting an app password from the Integrations tab, you can't use the default settings (Email/Contacts/Calendars). I found a password generated with those setting will not be accepted by Outlook (likely b/c Outlook doesn’t integrate with Fastmail contacts & calendars). Instead, you need to change the settings to Email only.

*Here's what they offer instructions for. Seriously, they have instructions on how to set up MailMate for Mac, but not Outlook for Mac? This makes their support team look like they're not on top of things.

 

[OldCorpse]

Well, this is water under the bridge, as you already made your decision. I keep revisiting the email issue from time to time, but I keep coming back to a position which I'm sure is not only controversial, but unacceptable to many/most.

Basically, when I consider the totality of the context, the one that wins out for me is... gmail... yeah, I know. Do I think gmail is the greatest thing in email since sliced bread? Hardly. For one, the interface is just medieval. I mean, seriously, it's 2023 - almost 2024, what are those google UI guys doing over there? And I know the OP said that he's had some emails not reach him through gmail. I totally get it, we all go on our personal experiences, so I don't doubt anyone's report. All I can say is that for me, gmail has been rock solid. Don't seem to miss emails. Don't get spam. I'm sure google spies like crazy, but... for whatever reason I'm not super annoyed (I'm much more annoyed by Amazon's ads following me constantly whenever I make any purchase).

It's possible that I'm just used to gmail (I've been an early adopter, back in early 2004), so soon it'll be 20 years. The integration with calendar, google docs, drive etc., just works - for me, I'm not saying it works for everyone or generally, just reporting on my experience. Plus, I'm not stuck with a provider associated with a particular product like Apple - in my experience Apple has never been good at the whole cloud/internet thing, it's had rotten DNA in that respect from day one, SJ even raged about it, but ultimately, never could make it a leader in that space, there's been one screw up after another. Will I always live in the Apple hardware ecosystem? Probably. Still don't want to be tied to their inferior cloud solutions.

Say what you will about google - it's their bread and butter, this is their whole reason for existing, as long as they're around, I think gmail will always be there. I'm much less sure about iCloud or even MSFT products not to mention stuff like Fastmail (I've been around long enough to have seen various highly touted paid email providers disappear overnight, so just because it has a great rep today does not guarantee tomorrow).

I know it's not a popular opinion, and I'm definitely not trying to steer anyone toward gmail (nor do I have any motive or reason to do so!), I'm just saying, that for someone like me, once you account for ALL the pros/cons, gmail, sadly seems like the best choice. Of course, if you can do the domain and hosting yourself, great, but many don't want to bother - for those, gmail has a number of advantages, which when balanced against disadvatages, and all that compared to the other options out there, kinda gets me back to gmail. And believe me, I keep revisiting the issue every once in awhile, to see if the landscape has changed, but nope, it's still gmail FTW. Obviously, it's a highly personal decision, and many will avoid anything to do with google on principle, regardless of any pros/cons of a particular service, and I totally get it. All I'm saying is that if you don't have an ideological position on this, just looking at the merits or demerits of each provider, you might just find that gmail is the least bad option. All IMHO, and YMMV.

 

[theorist9]

Well, this is water under the bridge, as you already made your decision. I keep revisiting the email issue from time to time, but I keep coming back to a position which I'm sure is not only controversial, but unacceptable to many/most.

Basically, when I consider the totality of the context, the one that wins out for me is... gmail... yeah, I know. Do I think gmail is the greatest thing in email since sliced bread? Hardly. For one, the interface is just medieval. I mean, seriously, it's 2023 - almost 2024, what are those google UI guys doing over there? And I know the OP said that he's had some emails not reach him through gmail. I totally get it, we all go on our personal experiences, so I don't doubt anyone's report. All I can say is that for me, gmail has been rock solid. Don't seem to miss emails. Don't get spam. I'm sure google spies like crazy, but... for whatever reason I'm not super annoyed (I'm much more annoyed by Amazon's ads following me constantly whenever I make any purchase).

It's possible that I'm just used to gmail (I've been an early adopter, back in early 2004), so soon it'll be 20 years. The integration with calendar, google docs, drive etc., just works - for me, I'm not saying it works for everyone or generally, just reporting on my experience. Plus, I'm not stuck with a provider associated with a particular product like Apple - in my experience Apple has never been good at the whole cloud/internet thing, it's had rotten DNA in that respect from day one, SJ even raged about it, but ultimately, never could make it a leader in that space, there's been one screw up after another. Will I always live in the Apple hardware ecosystem? Probably. Still don't want to be tied to their inferior cloud solutions.

Say what you will about google - it's their bread and butter, this is their whole reason for existing, as long as they're around, I think gmail will always be there. I'm much less sure about iCloud or even MSFT products not to mention stuff like Fastmail (I've been around long enough to have seen various highly touted paid email providers disappear overnight, so just because it has a great rep today does not guarantee tomorrow).

I know it's not a popular opinion, and I'm definitely not trying to steer anyone toward gmail (nor do I have any motive or reason to do so!), I'm just saying, that for someone like me, once you account for ALL the pros/cons, gmail, sadly seems like the best choice. Of course, if you can do the domain and hosting yourself, great, but many don't want to bother - for those, gmail has a number of advantages, which when balanced against disadvatages, and all that compared to the other options out there, kinda gets me back to gmail. And believe me, I keep revisiting the issue every once in awhile, to see if the landscape has changed, but nope, it's still gmail FTW. Obviously, it's a highly personal decision, and many will avoid anything to do with google on principle, regardless of any pros/cons of a particular service, and I totally get it. All I'm saying is that if you don't have an ideological position on this, just looking at the merits or demerits of each provider, you might just find that gmail is the least bad option. All IMHO, and YMMV.

Another reason I want to move away from gmail is privacy. The amount of stuff google collects about you is scary. And to use gmail you need to be logged into your google account, which I've found allows google to track stuff that has nothing to do with your emails.

Also, I'm currently doing performance testing on fastmail vs. icloud vs. gmail, and my preliminary resuts, at least, are that fastmail is significantly faster than both (at least for receiving emails; I haven't tested sending yet).

Also, gmail is not google's bread-and-butter; that's their search engine. Indeed, I would argue iCloud is more central to Apple than gmail is to google.

You are right about spam, though. Gmail is remarkably effective at filtering it. And if anyone is going to have the sophistication to filter spam, it's google. But perhaps it's that aggressiveness which caused them to accidentally filter out that email that wasn't spam. I wondeer how fastmail will compare.