Mail from a reliability / deliverability standpoint: iCloud vs Outlook.com vs others

[exi]

Over the years, I and a few others have created, or posted in, threads about iCloud silent filtering and general reliability issues.

I have multiple Apple devices. iCloud is currently home to everything for me -- mail, contacts, calendars, notes, reminders, pictures, so on. I like simple. But Mail leaves something to be desired as has been detailed here.

My question is simple. From the standpoint of reliability insofar as being able to count on receiving and sending without issue -- without silently dropped messages and the like -- what's my best option? I hate the feeling of "I wonder if iCloud is going to screw this up...".

iCloud has the worst reputation for this, but then a quick search shows up threads that talk about silent message dropping for Outlook and Gmail, too, albeit not as frequently. Hoping someone more versed in such things could clarify.

 

[dark_knight177]

Gmail is the most reliable and overall best email service in the world. I tried migrating to iCloud at first but I got tired of all the bugs in their system. I also tried outlook.com and their slow IMAP was horrible.

I have stayed with Gmail and will never ever try to switch to any email provider again

 

[exi]

I was formerly on Gmail, but its lack of push support is an issue for me. Outlook.com thoughts now that they're Exchange (for me; still rolling out, I hear)?

 

[mi7chy]

I use Gmail, Yahoo and Microsoft Live. I'd rate Gmail as the most reliable with fast delivery and the best spam filtering. Yahoo has been reliable but spam filtering is hit and miss with it letting spam into my inbox and valid email into spam box and there is a bit of delay with delivery even if I email myself. Live seems ok so far except for more frequent authentication errors when syncing email.

If I had to consolidate down to one email I'd go with Google since the whole ecosystem is the most reliable and responsive. For example, I backup/sync the data/files on my phones to both OneDrive and Google Drive but Google has about 4x faster throughput. Also use Google Voice/Hangouts as default dialer and SMS for years without issue.

Highly recommend these apps if on Android for reliable syncing.

https://play.google.com/store/apps/details?id=com.ttxapps.onesyncv2

https://play.google.com/store/apps/details?id=com.ttxapps.drivesync

 

[exi]

Appreciate your help.

Related, and a small and potentially silly issue, but I was considering flastname@outlook.com, where "f" is my first initial. The address lastname@outlook.com is taken. I could do firstname.lastname@outlook.com.

I prefer flastname@outlook.com but have this feeling of people inadvertently missing my first initial and messages being sent to someone else.

Any strong feelings?

 

[Maki Roc]

I prefer firstname.lastname@outlook.com, but you could use both since Outlook.com supports aliases.

 

[throwthedice]

I generally prefer firstname.lastname@ combination. All my work accounts have/had this so it's always been a slight extension for me in the sense that all my email ids are the same with just a difference in the domain names.
Gmail is the only one where my firstname.lastname is taken, so I don't use Gmail for any formal communications - those go out to my Y! Mail.

 

[gotluck]

just wanted to highly reccomend gmail with the outlook iOS app - beautiful combination - Push gmail support + cloud attachment support from dropbox, onedrive, google drive, etc...

 

[throwthedice]

just wanted to highly reccomend gmail with the outlook iOS app - beautiful combination - Push gmail support + cloud attachment support from dropbox, onedrive, google drive, etc...

Absolutely! The app is wonderful and the best part is I can "Delete" mails from the notification screen instead of "archiving it"!

 

[exi]

Read about this the other night. Apparently it's something made possible by routing through Microsoft's servers.

Figure my options are:

1. Trust iCloud more and make no changes;
2. Make Outlook.com my primary service for mail, and keep everything else in iCloud;
3. Move everything to Google;
4. Move everything to Outlook;
5. Return to Gmail, give up using Apple's default mail app and other default apps, migrate to Outlook for iOS, and allow the above for Gmail through the app.

 

[exi]

One question. Defining "reliable" to mean that emails sent get to their recipients' inboxes quickly and that incoming emails make it to my inbox or my junk folder (and are not silently dropped), which seems to be an issue for iCloud, does anyone feel Outlook is less reliable than Gmail?

(Also, interesting Reddit bit from awhile back which touches on all this: https://m.reddit.com/r/apple/comments/2tmf7g/i_was_a_victime_of_icloud_mails_censorship/)

 

[Maki Roc]

One question. Defining "reliable" to mean that emails sent get to their recipients' inboxes quickly and that incoming emails make it to my inbox or my junk folder (and are not silently dropped), which seems to be an issue for iCloud, does anyone feel Outlook is less reliable than Gmail?

(Also, interesting Reddit bit from awhile back which touches on all this: https://m.reddit.com/r/apple/comments/2tmf7g/i_was_a_victime_of_icloud_mails_censorship/)

All the big email providers do silent filtering even gmail. Feel free to google it if you don't believe me. Due to the war on spam email has become so unreliable, I just wish it was replaced by something better.
Gmail is probably the most reliable since it has the best spam filter and has good infrastructure. Outlook.com (the old version) has a very, very aggressive spam filter, but you can whitelist certain addresses or domains. Silent filtering is bypassed with whitelisting. I don't know how good the new preview version of Outlook.com works since I didn't get the upgrade. It uses the spam filter from Office 365 so it may be much better (less aggressive) since it's for business use

 

[exi]

All the big email providers do silent filtering even gmail. Feel free to google it if you don't believe me. Due to the war on spam email has become so unreliable, I just wish it was replaced by something better.
Gmail is probably the most reliable since it has the best spam filter and has good infrastructure. Outlook.com (the old version) has a very, very aggressive spam filter, but you can whitelist certain addresses or domains. Silent filtering is bypassed with whitelisting. I don't know how good the new preview version of Outlook.com works since I didn't get the upgrade. It uses the spam filter from Office 365 so it may be much better (less aggressive) since it's for business use

Right, like in that Reddit, I'm sure all the major providers do this. Luckily, I seem to be on the new Outlook. My only wonder is that if an aggressive spam filter also means that messages may be silently dropped. I don't mind an aggressive filter that sticks messages into my junk folder a little too frequently. I just don't know how likely Outlook.com is to silently filter compared to Gmail.

I would simply return to Gmail, but no push support is a bit of an issue for me. And, for what it's worth, 99% of my use of any email service is through Apple clients, not the website. I wouldn't even be using contacts within Outlook.com/Gmail.

 

[Maki Roc]

From my personal experience in the old Outlook.com the spam filter would have a lot of false positives that would end up in the junk folder. To fix this you whitelist the sender or add him to your contacts (contacts are automatically whitelisted). Never to my knowledge have I had silent filtering, but have heard many complaints from other people. The good thing is that unlike iCloud you can bypass the silent filtering with whitelisting.
With Gmail I had problems with forwarding. If their spam filter didn't like the incoming mail it wouldn't forward it. I used to blame iCloud for silent filtering until I figured out that it was Gmail causing problems.

My conclusion for this is that email sucks and whatever you pick isn't perfect.

 

[mi7chy]

I would simply return to Gmail, but no push support is a bit of an issue for me.

That only applies to 3rd party email clients with free Gmail. If you use Google app it does do push or pay as low as $50/year for Google Apps for Work that does ActiveSync push with 3rd party client plus additional perks like custom spam filter/white list, your own @yourdomain.com, no ads, more storage, etc.

https://support.google.com/a/answer/2368132?hl=en

https://apps.google.com/pricing.html

 

[exi]

From my personal experience in the old Outlook.com the spam filter would have a lot of false positives that would end up in the junk folder. To fix this you whitelist the sender or add him to your contacts (contacts are automatically whitelisted). Never to my knowledge have I had silent filtering, but have heard many complaints from other people. The good thing is that unlike iCloud you can bypass the silent filtering with whitelisting.
With Gmail I had problems with forwarding. If their spam filter didn't like the incoming mail it wouldn't forward it. I used to blame iCloud for silent filtering until I figured out that it was Gmail causing problems.

My conclusion for this is that email sucks and whatever you pick isn't perfect.

Appreciate the experience. It's just the silent filtering -- common as it is across services -- I don't like, or at least not when it's heavy-handed. Did those with Outlook issues also have any Gmail issues? Really, the only thing keeping me from taking the hour or two it would take to mass-migrate registered email addresses, emails, and redirect forwarding to my Outlook address over my iCloud address is my own uncertainty as to how much more reliable it would be.

And as compared to Gmail.

That only applies to 3rd party email clients with free Gmail. If you use Google app it does do push or pay as low as $50/year for Google Apps for Work that does ActiveSync push with 3rd party client plus additional perks like custom spam filter/white list, your own @yourdomain.com, no ads, more storage, etc.

https://support.google.com/a/answer/2368132?hl=en

https://apps.google.com/pricing.html

Did think about that. Not a huge fan of the Google app, though considered Google Apps. Probably the way I would go if I returned to Gmail.

 

[BrianBaughn]

Microsoft is transitioning all of the Outlook.com email addresses to an Exchange-compliant setup.

I just set up a new, test account at Outlook.com and set it up via Exchange on my Mac running 10.11.2.

I checked Mail, Contacts, Calendars, Reminders, and Notes to sync.

Quick observations:

• Mail and Calendars seem to work with no problems.
• Contacts/People sync when you start the application but there's some sort of error that prevents further syncing with the server. Creating a new contact on the Mac forces a sync as does restarting Contacts.
• Reminders/Tasks works similarly to Contacts/People but only seems to re-sync by restarting Reminders.
• Notes doesn't sync with anything at Outlook.com as far as I can tell...but it does sync with iOS if you set up the Outlook.com account as Exchange on your iOS device. However, you get an online OneNote account tied to your email address so that can be used on the Mac and iOS. Notes do not appear as an option when setting up an account as an Outlook.com account in iOS.

I don't know if the new Outlook.com Exchange situation is a work-in-progress or if this is what you get.

 

[colburnr]

Microsoft is transitioning all of the Outlook.com email addresses to an Exchange-compliant setup.

I just set up a new, test account at Outlook.com and set it up via Exchange on my Mac running 10.11.2.

I checked Mail, Contacts, Calendars, Reminders, and Notes to sync.

Quick observations:

• Mail and Calendars seem to work with no problems.
• Contacts/People sync when you start the application but there's some sort of error that prevents further syncing with the server. Creating a new contact on the Mac forces a sync as does restarting Contacts.
• Reminders/Tasks works similarly to Contacts/People but only seems to re-sync by restarting Reminders.
• Notes doesn't sync with anything at Outlook.com as far as I can tell...but it does sync with iOS if you set up the Outlook.com account as Exchange on your iOS device. However, you get an online OneNote account tied to your email address so that can be used on the Mac and iOS. Notes do not appear as an option when setting up an account as an Outlook.com account in iOS.

I don't know if the new Outlook.com Exchange situation is a work-in-progress or if this is what you get.

I hope it is a work in progress. I like outlook.com and the web functions, but also having "push" on my idevices. I like to be able to subscribe to a calendar from my work machine which is a windows machine. I think it is absurd that I can't see any of my subscribed calendars on icloud.com or I can't subscribe to a calendar from icloud.com. I guess this is Apple's way of trying to force people to buy Mac's?

 

[exi]

Microsoft is transitioning all of the Outlook.com email addresses to an Exchange-compliant setup.

I just set up a new, test account at Outlook.com and set it up via Exchange on my Mac running 10.11.2.

I checked Mail, Contacts, Calendars, Reminders, and Notes to sync.

Quick observations:

• Mail and Calendars seem to work with no problems.
• Contacts/People sync when you start the application but there's some sort of error that prevents further syncing with the server. Creating a new contact on the Mac forces a sync as does restarting Contacts.
• Reminders/Tasks works similarly to Contacts/People but only seems to re-sync by restarting Reminders.
• Notes doesn't sync with anything at Outlook.com as far as I can tell...but it does sync with iOS if you set up the Outlook.com account as Exchange on your iOS device. However, you get an online OneNote account tied to your email address so that can be used on the Mac and iOS. Notes do not appear as an option when setting up an account as an Outlook.com account in iOS.

I don't know if the new Outlook.com Exchange situation is a work-in-progress or if this is what you get.

Curious myself. I know you've posted about your experience with iCloud before, including in previous threads -- any thoughts as to this reliability concern of mine? Planning on switching to Outlook to avoid somewhat egregious silent filtering as in iCloud and still maintain push support with the native Mail app, which leaves Gmail out.

Basically, tired of feeling that when I send an email from iCloud, I feel like I can never quite count on it being delivered -- or me receiving a reply.

I hope it is a work in progress. I like outlook.com and the web functions, but also having "push" on my idevices. I like to be able to subscribe to a calendar from my work machine which is a windows machine. I think it is absurd that I can't see any of my subscribed calendars on icloud.com or I can't subscribe to a calendar from icloud.com. I guess this is Apple's way of trying to force people to buy Mac's?

Hope so myself. Little more interoperability would be nice.

 

[whsbuss]

Microsoft is transitioning all of the Outlook.com email addresses to an Exchange-compliant setup.

I just set up a new, test account at Outlook.com and set it up via Exchange on my Mac running 10.11.2.

I checked Mail, Contacts, Calendars, Reminders, and Notes to sync.

Quick observations:

• Mail and Calendars seem to work with no problems.
• Contacts/People sync when you start the application but there's some sort of error that prevents further syncing with the server. Creating a new contact on the Mac forces a sync as does restarting Contacts.
• Reminders/Tasks works similarly to Contacts/People but only seems to re-sync by restarting Reminders.
• Notes doesn't sync with anything at Outlook.com as far as I can tell...but it does sync with iOS if you set up the Outlook.com account as Exchange on your iOS device. However, you get an online OneNote account tied to your email address so that can be used on the Mac and iOS. Notes do not appear as an option when setting up an account as an Outlook.com account in iOS.

I don't know if the new Outlook.com Exchange situation is a work-in-progress or if this is what you get.

I just re-added my outlook.com account for iPhone and Mac mail since its been migrated to the Office365 exchange. Setup went fine, but isn't the mail accounts supposed to sync read/unread/delete flags? I get an email on the account; I read it on the mac or I read it on the iPhone; the read badge does not sync without opening the app. I even tried doing it from outlook.live.com webmail and still no dice. Now if I have the webmail screen opened and I read or delete from the iPhone it sync to the webmail...... I thought exchange was supposed to auto sync?

 

[exi]

I tried the same. Oddly, it did actually sync read status without action on my part the first time (Outlook.com as Exchange, most recent El Cap build, most recent iOS 9 to an iPhone 6).

Tried again just now, no luck.

Odd...

 

[whsbuss]

I tried the same. Oddly, it did actually sync read status without action on my part the first time (Outlook.com as Exchange, most recent El Cap build, most recent iOS 9 to an iPhone 6).

Tried again just now, no luck.

Odd...

Yeah it is strange. I never had the read status update automatically. Nothing works like it used to. Gmail with ActiveSync was really reliable (free). UPDATE: Sent email to outlook.com account; got notification on Mac and iPhone; opened outlook webmail and read the email. After about a minute the read badge on the Mac was removed automatically. iPhone still waiting..... 10 minutes and no change. Something is not right.

 

[Maki Roc]

Yeah it is strange. I never had the read status update automatically. Nothing works like it used to. Gmail with ActiveSync was really reliable (free). UPDATE: Sent email to outlook.com account; got notification on Mac and iPhone; opened outlook webmail and read the email. After about a minute the read badge on the Mac was removed automatically. iPhone still waiting..... 10 minutes and no change. Something is not right.

I think it is not a problem with Outlook.com but with iOS. Ever since iOS 8 i have been having trouble with activesync and it's z-push derative. It seems that iOS keeps droping the idled connection to the server because it goes into sleep mode. Only Apple push notifications seem to work properly.
Try to repeat your test with the phone plugged in.

 

[whsbuss]

I think it is not a problem with Outlook.com but with iOS. Ever since iOS 8 i have been having trouble with activesync and it's z-push derative. It seems that iOS keeps droping the idled connection to the server because it goes into sleep mode. Only Apple push notifications seem to work properly.
Try to repeat your test with the phone plugged in.

I'm not sure what you mean with plugged in? To my Mac or on charger?

Update: I plugged the iPhone into AC charger and it still did not update the read status unless I open the mail app (native).

 

[colburnr]

I'm not sure what you mean with plugged in? To my Mac or on charger?

Update: I plugged the iPhone into AC charger and it still did not update the read status unless I open the mail app (native).

So am I correct in assuming that with the move of the free Outlook accounts to exchange, that things like contact photos, calendar colors, etc.. will now sync properly with iOS devices and my Macbook Air?