iCloud mail alternatives: Fastmail vs Outlook.com

[exi]

I've posted before about this, but to prevent from bumping old threads, the short version is that I'm after these things in this order:

- Reliability (no silent filtering; things get delivered, or someone gets a nondelivery report)
- Push and background updating on iOS devices (deleting a message in webmail removes it from my iOS unread badge, etc)
- Solid IMAP or EAS
- Secure
- Private

With Microsoft transitioning Outlook.com free accounts to Office 365's infrastructure (mine is already there), I'm unsure what to expect for #1 and #2. As a superficial thing, I'm not crazy about the domain name "fastmail.com" or any of their alternatives, but that's about all I've got against them.

Would love to keep everything on one service, but iCloud mail leaves much to be desired.

Would appreciate anyone's thoughts. Seems to me Fastmail is the better choice over Outlook and even Gmail.

 

[campyguy]

I was following the posts in a couple of threads that led to Fastmail being brought up, checked it out but ended up not trialling their product. I didn't compare Outlook's offerings - I use one account to manage my Windows VMs as it's a no-financial-cost option, and I need about 15-20GB of resident storage for my personal account.

I signed up for the Office 365 Business Essentials package and prefer it's offerings over FM's. One could offer that it's more expensive than all but FM's Premier account - I'd offer that I get additional tools that I do use including Yammer (a lot of my friends and former co-workers use Yammer), Skype for Business, and 1TB of OneDrive storage (used with oDrive for synching). I also use O365 for my small business, and now pretty much stick with MS's IMAPI for email/contacts/calendaring - I've been annoyed by the oh-so-many types of iCal/vCard calendar/contact formats, but I HAVE to exchange data with others and most of them are tuned into "Exchange" while not even knowing what that means!

For my own personal needs, I'm pretty much needing their Premier plan @$120 per year as the Enhanced plan gets me trolling through my inbox to archive stuff. For a little more money I'd step up to the O365 Business Essentials package - but I snagged a couple of stackable O365 Home subs for a deep discount and am pairing that with my O365 BE plan, so there's several licenses of MS Office built into my money layout.

OTOH, there's nothing to dislike about FM, given that you can use your own domain name like the Office 365 Business plans. I've been using Outlook.com sparingly, but it's new backend is pretty impressive now and its accounts can be tweaked considerably in Win Outlook 2016 and I've read somewhere personal domains may become an option again, albeit a paid one. FWIW, I'm using iCloud only because I can use aliases in iOS/OS X Mail and because my apps are tied to and anchored down by a .Mac/Me/iCloud account - I've pretty much stopped using iCloud's other features. Cheers!

 

[BrianBaughn]

For me, Office 365 fits all of the above with the exception of the quick background updating and that could be because I'm still on iOS 8.4 (jailbreak).

 

[exi]

Thanks for your thoughts, guys.

For me, and I know I'd asked about this before, I just worry about the reliability side of things -- Outlook.com seems to have some reports of silently dropping messages, and I don't know how much of an issue this is.

That, and their iOS sync would completely distort contact field mapping if I moved contacts over.

Were either of these issues for you?

 

[Rigby]

I haven't noticed any silent dropping on Outlook.com. The only mild annoyance is that the junk filter is a bit too aggressive in moving mails from unknown senders to the junk folder. But after training it for a while (by marking mails as "not junk" in the web interface) and creating some filter rules it happens rarely now.

In terms of the migration of Outlook.com to an Exchange-based infrastructure, I'd think it can only improve performance and reliability.

I have never used Fastmail myself, but I hear good things about it. Maybe run a trial for a few weeks before you decide?

 

[BrianBaughn]

With any Exchange service, I'm pretty sure that contact fields are not as flexible (such as custom field names) as other services. I haven't seen any issues between devices and OWA contacts (I've tested them but I don't use Office 365 contacts on any devices). There's probably a lot of info out there on that subject, but like I said we don't see any weirdness.

 

[lascott]

I've been using Fastmail for a few years, and the best part is the fact my message indicator in mail updates across devices (ok thats a small thing, but something even exchange doesn't do or icloud email).

I switched after being impacted by some of the silent filters on icloud email multiple times.

 

[fastbagger]

Same here have been using Fastmail utilizing my own domain for about 7 months has been flawless love it.

 

[exi]

With any Exchange service, I'm pretty sure that contact fields are not as flexible (such as custom field names) as other services. I haven't seen any issues between devices and OWA contacts (I've tested them but I don't use Office 365 contacts on any devices). There's probably a lot of info out there on that subject, but like I said we don't see any weirdness.

Happily, I'm not too crazy about my custom fields. I only mean that email addresses marked as "home," "work," etc, sync'd to iOS as "email" and "email" last I saw years ago.

I've been using Fastmail for a few years, and the best part is the fact my message indicator in mail updates across devices (ok thats a small thing, but something even exchange doesn't do or icloud email).

I switched after being impacted by some of the silent filters on icloud email multiple times.

Definitely one of its perks for me too. Part of the polish. (Is ActiveSync really still not handling background status sync? It was intermittently doing its job last I played months back...)

 

[exi]

Definitely one of its perks for me too. Part of the polish. (Is ActiveSync really still not handling background status sync? It was intermittently doing its job last I played months back...)

Quoting myself just to mention what I've found. I added my Outlook.com account as Exchange on my MBP (Mail.app, most recent version as of this post) as well as my iPhone 6 (iOS 9.3.1) and played. What I've found:

- Email addresses lose labels when synchronized to iOS and OS X ("personal", "work", "other" all become "email" on iOS), something known for years. Contact sync is flaky and timed out a couple times during testing.
- Mail.app on OS X still has marginal Exchange support at best -- must either configure polling intervals or manually sync -- to pull messages. Changes made in Mail.app (read/unread status, flag) sync back to the webmail interface in seconds. Changes made in the webmail interface are variable and sometimes are delayed by minutes as far as showing up on Mail.app.
- Message status updating in the background on iOS happened in seconds a few times, oddly only when going from read to unread, but otherwise is delayed by ~10 minutes as others have seen. Maybe I was just on the dot on sync intervals established by Microsoft(?).

In one of my other threads, @dfgddikf mentioned that he felt Fastmail is the ideal service on iOS if using the stock apps. Seems that may be the case.

 

[Rigby]

Quoting myself just to mention what I've found. I added my Outlook.com account as Exchange on my MBP (Mail.app, most recent version as of this post) as well as my iPhone 6 (iOS 9.3.1) and played. What I've found:

- Email addresses lose labels when synchronized to iOS and OS X ("personal", "work", "other" all become "email" on iOS), something known for years. Contact sync is flaky and timed out a couple times during testing.

I can confirm the label issue (doesn't bother me much though because I use the Outlook client which doesn't have that problem). I don't have the timeout issues when syncing contacts though (on iOS).

Does the Fastmail address book sync the email labels properly on the native iOS/OSX clients?

In one of my other threads, @dfgddikf mentioned that he felt Fastmail is the ideal service on iOS if using the stock apps. Seems that may be the case.

Probably true. Not so great if you also use Windows though, since contact syncing via CardDav is not well supported.

It is also possible to mix and match (e.g. use iCloud for contacts/calendar and some other service for email).