iCloud iCloud, Fastmail, Exchange Online: revisiting PIM options

[exi]

Periodically, I look at whether there's anything to gain by changing how I handle email/contacts/calendars and notes/reminders.

Currently:
- Fastmail with custom domain for email and contacts/calendars via CardDAV/CalDAV, accessed via all Apple hardware and native clients, through trialing Outlook for Mac;
- iCloud for notes, reminders, etc.

Previously tried:
- iCloud+ / custom domain, stopped due to concerns regarding the reliability/silent filtering issues discussed here and elsewhere by myself and others, as well as lack of push updates of message status in background (not just pushing of new messages).

I'm aware that Microsoft 365 custom domain options no longer exist for new setups as of end-November 2023, but I understand that a custom domain can be associated with Exchange Online accounts (as in here).

All that said, are there any benefits of which I might be unaware in using Exchange even for personal email as opposed to Fastmail? Which would you pick and why? Cost difference is negligible.

 

[Chris60549]

Can you elaborate on the lack of push updates of message status in the background? Does that include read/unread status? I thought this was faulty behavior of my iCloud account. Is that actually expected behavior?

 

[exi]

Can you elaborate on the lack of push updates of message status in the background? Does that include read/unread status? I thought this was faulty behavior of my iCloud account. Is that actually expected behavior?

It is described in some other threads here, and in some other posts by me, but yes, that includes read/unread status. iOS does not update in the background. It's not faulty behavior of your account. It's expected behavior. There used to be a support article that detailed of this (since taken down, but linked in another post by me elsewhere in one of those threads).

 

[palebluedot]

It is described in some other threads here, and in some other posts by me, but yes, that includes read/unread status. iOS does not update in the background. It's not faulty behavior of your account. It's expected behavior. There used to be a support article that detailed of this (since taken down, but linked in another post by me elsewhere in one of those threads).

That is not the case for other IMAP clients like Fastmail, right? I have not observed that behavior with FM but maybe I am not understanding what you are saying.

I too am considering b/w iCloud+ Custom Domain vs Fastmail. Fastmail is superb but the price of iCloud+ is enticing if you are already paying for Apple One.

 

[palebluedot]

Periodically, I look at whether there's anything to gain by changing how I handle email/contacts/calendars and notes/reminders.

Currently:
- Fastmail with custom domain for email and contacts/calendars via CardDAV/CalDAV, accessed via all Apple hardware and native clients, through trialing Outlook for Mac;
- iCloud for notes, reminders, etc.

Previously tried:
- iCloud+ / custom domain, stopped due to concerns regarding the reliability/silent filtering issues discussed here and elsewhere by myself and others, as well as lack of push updates of message status in background (not just pushing of new messages).

I'm aware that Microsoft 365 custom domain options no longer exist for new setups as of end-November 2023, but I understand that a custom domain can be associated with Exchange Online accounts (as in here).

All that said, are there any benefits of which I might be unaware in using Exchange even for personal email as opposed to Fastmail? Which would you pick and why? Cost difference is negligible.

Do you observe any weird behaviors with CardDAV or CalDAV and FM? I currently use FM email + iCloud for cal + contacts but would love for everything to be in one system. I vaguely recall back in the day that if you did not use iCloud it did not work as well for Siri (e.g. "Call my spouse.").

 

[exi]

That is not the case for other IMAP clients like Fastmail, right? I have not observed that behavior with FM but maybe I am not understanding what you are saying.

I too am considering b/w iCloud+ Custom Domain vs Fastmail. Fastmail is superb but the price of iCloud+ is enticing if you are already paying for Apple One.

Fastmail worked out push updating with Apple such that read, flag, unread, etc, statuses update on a push basis without requiring manual or scheduled sync. This is unique among IMAP services. They have a blog post from many years ago about it.

Do you observe any weird behaviors with CardDAV or CalDAV and FM? I currently use FM email + iCloud for cal + contacts but would love for everything to be in one system. I vaguely recall back in the day that if you did not use iCloud it did not work as well for Siri (e.g. "Call my spouse.").

I am currently doing the same. I also would like to condense into one service but don't use email with iCloud because of the above and because of deliverability / reliability concerns. I did use all three services with FM for quite some time, though, and never had an issue other than some minimal contact field mapping / event attachment type issues.

 

[palebluedot]

Fastmail worked out push updating with Apple such that read, flag, unread, etc, statuses update on a push basis without requiring manual or scheduled sync. This is unique among IMAP services. They have a blog post from many years ago about it.



I am currently doing the same. I also would like to condense into one service but don't use email with iCloud because of the above and because of deliverability / reliability concerns. I did use all three services with FM for quite some time, though, and never had an issue other than some minimal contact field mapping / event attachment type issues.

Do you remember what fields did not work?

 

[exi]

Do you remember what fields did not work?

I don't remember the details. I do remember what was displayed, or could be displayed, was a bit different. Fastmail did not always display everything, but it was still stored nondestructively.

 

[rforno]

FastMail has been nearly bulletproof for me for over 10 years using Apple Mail/Contacts and BusyCal. I trust them for email/contacts/calendar faaaaar more than iCloud, since Apple still can't run a stable/reliable cloud service to save its life....

Plus, I don't like my critical data being all locked up in the same ecosystem as my hardware authentication/sign-ons.

 

[exi]

I've posted here before for input as to optimizing mail/contacts/calendars services. Exchange has become more of an option, so I am thinking out loud and welcome input. The last thread got a little tangential.

Would be happy to use iCloud for all, but its mail service isn't an option currently (filtering issues and lack of push status update support for messages on iOS).

Am on Fastmail for mail only. Contacts/calendars remain on iCloud.

Debating moving contacts/calendars back to Fastmail, +/-reminders.

Aware all services are push-enabled via APNS.

The more recent idea was to utilize Microsoft 365 for its Exchange functionality. Would be a custom domain on a business plan.

Is there some objective or technical benefit I can't see as to using IMAP/CalDAV/CardDAV with Fastmail's Apple push implementation for native iOS/macOS apps versus Exchange?

The contact field support limitation and price difference is a non-issue.

 

[BrianBaughn]

One thing about an Exchange email account in iOS…if you also have an IMAP account you cannot move mail from the IMAP account to a folder in the Exchange account.

 

[sgtaylor5]

I’m starting to see the advantages of a heterogenous system. For Reminders iCloud can have multiple categories, but Fastmail can only have one category per email address. So I have two categories in iCloud “church” and “groceries”, which is not listed by section and has “show completed” turned on so that I have my entire grocery list visible.

I have one reminders list for work and one for personal. The nice thing about using Reminders is it has two features I haven’t been able to find anywhere else. The first is location-based reminders and I really like Apple Reminders implementation of recurring tasks better than other services I’ve tried.

I have three contacts lists: iCloud, which is default and fastmail has two lists: work and personal. Any new contact goes into iCloud, which later gets moved into either work or personal.

iCloud email is simply for purchases from Apple. Custom domain for work, which also houses my three page static website advertising my business.