Outlook 2016 and iCloud E-Mail Problem...

[JoelBC]

I upgraded from Office for Mac 2011 to Office for Mac 2016 and am encountering the following problem:

1. I have two different e-mail accounts where the first is an Exchange Server account and the second is an iCloud account. The below described problem does not occur with the Exchange server account but does occur with the iCloud account.

2. In Mail and my iCloud account: If i) I delete an e-mail from my inbox folder the e-mail appears in my deleted messages folder (i.e. as it should) and ii) I drop and drag an e-mail from my inbox folder to my deleted messages folder the e-mail appears in my deleted messages folder (i.e. as it should). So there is no problem with the Mail / iCloud account combination.


3. In Outlook 2016 and my iCloud account: If i) I delete an e-mail from my inbox folder the e-mail disappears (i.e. it does not appear in my deleted messages folder [or anywhere for that matter] as it should) and ii) I drop and drag an e-mail from my inbox folder to my deleted messages folder the e-mail appears in my deleted messages folder (i.e. as it should). So there is a problem with the Mail / iCloud account combination.

4. In Outlook 2016 and my iCloud account: The folders are configured as illustrated in the attachment.

Please help me solve this issue.

Thanks,


Joel

 

[BrianBaughn]

Not sure if it's possible but you're not sending, in the iCloud account, trash to the Exchange trash, are you?

Also, your "Sent" items are set to store in "Deleted Messages". Not sure you want it that way.

 

[JoelBC]

Not sure if it's possible but you're not sending, in the iCloud account, trash to the Exchange trash, are you?

No the deleted iCloud the deleted messages are not appearing anywhere in the Exchange Server account. Please note that the folder settings in the original post are specific to the iCloud account.

Also, your "Sent" items are set to store in "Deleted Messages". Not sure you want it that way.

I think this configuration is correct as it works perfectly in i) Outlook for Mac 2011 and ii) Outlook for Windows 2010. I am -- that said -- open to suggestions.

Thx!

 

[campyguy]

I had this issue with both iCloud and Outlook.com with both versions of Outlook 2016, drove me nuts. I used Little Snitch to see what was going on (my Win install runs in a VM on my Mac), for some reason IMAP IDLE wasn't "working". I solved it by unchecking the IDLE option in "Advanced IMAP account settings", synched all, then checked the option again. Funny, that I noticed IMAP IDLE working when I'd unchecked the settings option. No issues now in weeks with multiple iCloud/Outlook.com accounts.

 

[JoelBC]

I had this issue with both iCloud and Outlook.com with both versions of Outlook 2016, drove me nuts.

Like you, it is driving me nuts!

I used Little Snitch to see what was going on (my Win install runs in a VM on my Mac), for some reason IMAP IDLE wasn't "working". I solved it by unchecking the IDLE option in "Advanced IMAP account settings", synched all, then checked the option again. Funny, that I noticed IMAP IDLE working when I'd unchecked the settings option. No issues now in weeks with multiple iCloud/Outlook.com accounts.

I tried this but unfortunately it did not help...the problem still exists.

Thx.

 

[campyguy]

I tried this but unfortunately it did not help...the problem still exists.

Thx.

I've got to make the rounds to my offices this coming week, I'll sniff around and report back here when I get back. My only other recommendation is to drink more, but it's my company and I can do that...

 

[JoelBC]

Thx

I've got to make the rounds to my offices this coming week, I'll sniff around and report back here when I get back. My only other recommendation is to drink more, but it's my company and I can do that...

Thx, I very much look forward to hearing back from you next week.


Joel

PS. The really scary thing is that in the event I forget about this problem and mistakenly delete an e-mail from the inbox the e-mail will be lost, NOT GOOD...I need to decide whether to work with Mail for now even though I prefer Outlook's integration of calendar/contact/e-mail!

 

[JoelBC]

As there has been no response for a few days perhaps I should try a different approach...can one or people with i) an iCloud e-mail account and ii) Outlook for Mac 2016 please confirm / test that the problem I am encountering is a "general bug" as oppose to a "setup specific bug" (i.e. specific to my setup).

TIA.

 

[JoelBC]

As there has been no response for a few days perhaps I should try a different approach...can one or people with i) an iCloud e-mail account and ii) Outlook for Mac 2016 please confirm / test that the problem I am encountering is a "general bug" as oppose to a "setup specific bug" (i.e. specific to my setup).

TIA.

Two things....

1. I am hoping will test the above to confirm my experience / findings; and

2. Last night's upgrade to Outlook V15.17 unfortunately did not fix / solve this problem.

Thanks,

Joel

 

[JoelBC]

I have done a lot of research and work on this including taking a close look at Outlook for Windows 2016...I have concluded that Outlook for Mac 2016 is buggy and Outlook for Windows 2016 is unfortunately less configurable that Outlook for Windows 2010...I have summarized my findings in a Word document located at
https://www.dropbox.com/s/3e89suxob...configuration limitations and setup.docx?dl=0

I would be interested in feedback from others.

Thanks.

 

[campyguy]

Chiming in a bit later than I'd expected, if you're in BC you'd understand - we have had a bit of rain to cope with and I've been slammed - 87 MPH wind gusts earlier this week didn't help. My building's owner took ill and it's time to move by New Year's. Oh, and my main Mac took a dump and just got it back - which is partly why I'm posting here...

I chose to clean install and set up my Mac while everybody's out. Two bits.

Regarding IMAP accounts Outlook both synchs and polls - often on different schedules; it will poll for messages on the schedule set in an account's preferences (and keep in mind that some "free" services don't want to be polled more often than once every 15 minutes or more, and that service can reject too-frequent polling - like free Gmail and iCloud mail) - it's the synchronization that Outlook performs that reflects actions a user takes in real time, with the only way to "force" it is to Control/Right-Click on an account and choose the "Synchronize Now" command.

Little Snitch confirmed to me in real time what Outlook 2016 was doing in the background.

Regarding Outlook.com accounts, I'd read that MS is porting that platform to the Office 365 "engine". I entered those credentials in the OS X Internet Accounts Pref Pane using an "Exchange" option and it worked - my email/contacts/calendaring show up in my native OS X apps. Then, I used the Exchange option in Outlook 2016 for Mac for the same Outlook.com account and it worked as well. Mail and calendaring were pretty much instantaneous and contact sync took about 15-20 minutes, which is what I'd expect.

My take away is that MS is working on it. My only advice is to either deal with it the way it is or plan to use the "Synchronize Now" command option. I use Outlook mainly for Exchange Server and Office 365 accounts, but I'll start using it for my Outlook.com account soon. I'm sticking with Airmail 2 for my IMAP accounts for now. Cheers, and have some beers! I am.

 

[JoelBC]

Chiming in a bit later than I'd expected, if you're in BC you'd understand - we have had a bit of rain to cope with and I've been slammed - 87 MPH wind gusts earlier this week didn't help. My building's owner took ill and it's time to move by New Year's. Oh, and my main Mac took a dump and just got it back - which is partly why I'm posting here...

I chose to clean install and set up my Mac while everybody's out. Two bits.

Regarding IMAP accounts Outlook both synchs and polls - often on different schedules; it will poll for messages on the schedule set in an account's preferences (and keep in mind that some "free" services don't want to be polled more often than once every 15 minutes or more, and that service can reject too-frequent polling - like free Gmail and iCloud mail) - it's the synchronization that Outlook performs that reflects actions a user takes in real time, with the only way to "force" it is to Control/Right-Click on an account and choose the "Synchronize Now" command.

Little Snitch confirmed to me in real time what Outlook 2016 was doing in the background.

Regarding Outlook.com accounts, I'd read that MS is porting that platform to the Office 365 "engine". I entered those credentials in the OS X Internet Accounts Pref Pane using an "Exchange" option and it worked - my email/contacts/calendaring show up in my native OS X apps. Then, I used the Exchange option in Outlook 2016 for Mac for the same Outlook.com account and it worked as well. Mail and calendaring were pretty much instantaneous and contact sync took about 15-20 minutes, which is what I'd expect.

My take away is that MS is working on it. My only advice is to either deal with it the way it is or plan to use the "Synchronize Now" command option. I use Outlook mainly for Exchange Server and Office 365 accounts, but I'll start using it for my Outlook.com account soon. I'm sticking with Airmail 2 for my IMAP accounts for now. Cheers, and have some beers! I am.

Appreciate the response...

I am Canadian as well and live in Toronto but know enough that rain in Vancouver is more the norm than the exception...happy our day is getting beer, beer helps!

I too took advantage of some alone time and dug into this issue in more details (as summarized in my link) BUT I think we are talking about two different issues in that:

1. You are talking about the duration / time between synchronizations; BUT
2. I am talking about the alignment or mapping between Apple Mail's folders (in their default configuration) compared to Microsoft Outlook's folders (in their default configuration).

To make things work properly (or, at least as good as possible) a user who i) uses Apple Mail for their iCloud e-mail account on one or more of iOS, OS X or the web and ii) uses Outlook for the same account (because Outlook is *MUCH* more full featured) has to change Apple Mail's default mapping for deleted items and sent items to get things to work.

 

[campyguy]

Appreciate the response...

I am Canadian as well and live in Toronto but know enough that rain in Vancouver is more the norm than the exception...happy our day is getting beer, beer helps!

I too took advantage of some alone time and dug into this issue in more details (as summarized in my link) BUT I think we are talking about two different issues in that:

1. You are talking about the duration / time between synchronizations; BUT
2. I am talking about the alignment or mapping between Apple Mail's folders (in their default configuration) compared to Microsoft Outlook's folders (in their default configuration).

To make things work properly (or, at least as good as possible) a user who i) uses Apple Mail for their iCloud e-mail account on one or more of iOS, OS X or the web and ii) uses Outlook for the same account (because Outlook is *MUCH* more full featured) has to change Apple Mail's default mapping for deleted items and sent items to get things to work.

My point for bringing up polling and synchronization is not solely time-based. Read a bit in Outlook's own settings, such as the one that addresses local mail - the option to show, in "strikeout", until the deleted email is actually moved to the trash.

Automatically, Outlook was polling for new email in IMAP accounts' Inbox only about every two minutes, from my observing Little Snitch's Activity Menu. Automatically, Outlook was synchronizing changes (moved/deleted messages) every 15-30 minutes, regardless of whether I executed the "send/receive all" command - changes were kept locally until they were synchronized to the IMAP server.

After reading your post, I opened Outlook and Apple Mail. I moved and deleted some messages, and what I described in my post here was pretty much what I observed.

Then, I moved and/or deleted messages using Outlook, and then used the mouse-only Synchronize Now Command on the relevant folders (source destination/final destination), then switched to Mail (immediately) and used the Synchronize command (from the Menu) on the relevant folders - and the messages I had moved/deleted were in their expected place 100% of the time, every time.

MS removed the ability to edit the synchronization schedule that was present in Outlook 2011. Apple Mail isn't "instantaneous" either - this app simply shows it differently; Mail will show the message(s) in the "right" place until synched while Outlook merely hides it/them or shows it/them in strikeout mode. I've got an IMAP server on my Mini Server right next to me and can watch all of this if I want; I've got to move this week, so I'm going through everything anyway (really boring). So, yes, I'm describing the synchronization of content in terms of how you're describing it as "mapping". If you do not physically synchronize the source and destination folders, the apps will get around to it when they get around to it - to me, it's like saving a documents: do something important, save/synch your changes, verify that the changes are effected. Word/Excel use a Save command, Outlook uses a Synchronize Now command - to me, they perform the same function. I don't auto-save with Word/Excel, and I don't rely on the automatic synching built into any application. Cheers! Time for me to take off, eh?

 

[JoelBC]

@campyguy, I agree with everything you wrote and appreciate the added detail / information...the thing that troubles me the most is when companies release new versions of software that i) have less functionality that earlier versions and ii) have obvious omissions that could and should be fixed...when this happens, as in this case, I find it helpful and useful for end-users to post their experience / learnings so that others don't have to discover the grief on their own.

Enjoy the rest of the weekend, eh!

 

[campyguy]

I will, and you as well!!!

One more bit, just a note of hope? I use Outlook.com for my Win 10 VM install, as I'd alluded to earlier. MS has really upgraded that portal - not too long ago MS updated the People (Contacts) app and over the weekend I found that the People and Accounts native apps both have iCloud as an option for bringing in Contacts now along with Mail - AND there's actually some backend changes that can be made to synching of items in an iCloud account. It's not just about IMAP mail in Win 10 now. There's a bit more...

I have two iCloud accounts, one I use for my personal stuff and my old legacy one that my purchases are tied to. Using Outlook 2016 for Mac, I dragged several Contacts app contacts to my Desktop, and then dragged them to Outlook 2016's Contacts (in the Reading Pane). They were added to the Contact in Outlook 2016 (duh), but then I noticed that the contacts in Outlook were reflecting a new Category that was identical to the Group each contact was part of in the Contacts app. In other words, Outlook 2016 appears to be reflecting data that's buried in the contact's vCard (I've used both 2.1 and 3.0) - data that wasn't reflected in earlier versions of MS but is now. It's looking like MS is indeed "still working on it...".

I'm sticking with Win Outlook for now for my Outlook needs. I'm with you and others on the Mac version being a bit more short than it should be...

FWIW, I won't be making a habit of keeping Outlook.com connected to my iCloud account - Fields in the Contacts app relative to "Relationship" like "Husband" are converted to "Significant Other" and I can't recall what happened to the label for my Mother! Heck, they could be borked right now for all I know. If I figure out some tweaks, I'll pass them on.

Cheers, and take care.

 

[JoelBC]

One more bit, just a note of hope? I use Outlook.com for my Win 10 VM install, as I'd alluded to earlier. MS has really upgraded that portal - not too long ago MS updated the People (Contacts) app and over the weekend I found that the People and Accounts native apps both have iCloud as an option for bringing in Contacts now along with Mail - AND there's actually some backend changes that can be made to synching of items in an iCloud account. It's not just about IMAP mail in Win 10 now. There's a bit more...

I have two iCloud accounts, one I use for my personal stuff and my old legacy one that my purchases are tied to. Using Outlook 2016 for Mac, I dragged several Contacts app contacts to my Desktop, and then dragged them to Outlook 2016's Contacts (in the Reading Pane). They were added to the Contact in Outlook 2016 (duh), but then I noticed that the contacts in Outlook were reflecting a new Category that was identical to the Group each contact was part of in the Contacts app. In other words, Outlook 2016 appears to be reflecting data that's buried in the contact's vCard (I've used both 2.1 and 3.0) - data that wasn't reflected in earlier versions of MS but is now. It's looking like MS is indeed "still working on it...".

I agree that Outlook's current Mac version and web version are much improved relative to the past BUT they lack the full functionality of Outlook's Window version which I use repeatedly and possibly for each e-mail as my e-mails tend to be heavily formatted.

I'm sticking with Win Outlook for now for my Outlook needs. I'm with you and others on the Mac version being a bit more short than it should be...

The functional deficiencies of the Outlook for Mac are particularly disappointing given i) all / most Mac users would prefer a Mac based solution ii) the functional deficiencies are known (see Outlook for Windows) and iii) the functional deficiencies can be coded (again, see Outlook for Windows).

FWIW, I won't be making a habit of keeping Outlook.com connected to my iCloud account - Fields in the Contacts app relative to "Relationship" like "Husband" are converted to "Significant Other" and I can't recall what happened to the label for my Mother! Heck, they could be borked right now for all I know. If I figure out some tweaks, I'll pass them on.

Cheers, and take care.

I agree and things like this really annoy and puzzle me...I mean you moving data from one database to second database...why not give users the ability to map fields from the first database to the second database and to rename the fields in the second database, how hard can this be?

Take care!

 

[campyguy]

I agree and things like this really annoy and puzzle me...I mean you moving data from one database to second database...why not give users the ability to map fields from the first database to the second database and to rename the fields in the second database, how hard can this be?

Take care!

Last reply, for now - it's time to move! I've remarked here about synching contacts to/from Gmail accounts and Macs - the continual lament about why it doesn't just work. MS's Outlook for Mac seems to have a programming metaphor similar to what Google's doing with Gmail - they're both subject to a paradigm of feature creep and revision - related to this and in contrast at least MS announced that they'd be porting the Outlook.com platform to Office 365's platform (there's an in-depth portal citing features and timelines, and I wish they'd have a portal like this for Outlook for Mac). I learned - the hard way - when Google started futzing with Gmail's underpinnings and not announcing those changes to even their paying Google Apps customers. Either you were in the cloud or had to deal with incomplete sync connectors... I moved to Office 365 a couple of years ago, and it was a frickin' nightmare but I just couldn't deal with the client applications I use being borked at random when Google changed things up, sometimes more than once a week.

My advice is to stick to native clients when possible, and I never use free services when a decent paid service is available as free services are IMHO gimped by design. My Office 365 Admin portal has so many tweaks available it's just sick...

Leaving with a tip. MS's Word and Excel are two massively useful tools here. For each of my services, I save or drag to a desktop a few emails, contacts, and calendar events, and export a few contacts and calendaring events as CSV (Comma Separated Values) files. I open the saved/dragged files in Word, using the "Recover text from any file" Command, and the CSV files in Excel.

In Word, I'll see Header data, which often can include server-related data that will lead me to tweak my own client apps to optimize performance and server load. In Excel, I'll see the data fields and order of the imported files - I recall something like 256 fields in Gmail contacts, over 200 of which I'll never use such as the "Phonetic name" fields that don't map to Exchange or iCloud contacts, but seeing this mapping order in the CSV files helped me understand what was synching and what wasn't. I don't recommend this sort of probing around to anyone, but I've been dealing with analytical statistics for far too long. There's no one perfect sync conduit, sad to say - I've opted to use Outlook for my MS accounts, native Mac clients for iCloud stuff, and Gmail for my Netflix queue and Feedly account (and nothing else!).
Cheers, and Happy New Year!

 

[JoelBC]

Apologies for the deferred response but I have been tied up the last two days with family stuff!

Last reply, for now - it's time to move!

Good luck with the move that is a big job!

My advice is to stick to native clients when possible, and I never use free services when a decent paid service is available as free services are IMHO gimped by design. My Office 365 Admin portal has so many tweaks available it's just sick...

Agree! The situation I am facing is that all my contacts are stored natively on an Outlook Exchange Server at work. The problem is that home I use a MBA so was hoping that Apple Calendar, Contacts and Mail could be used to access the Exchange Server data and provide functional response / usage. The problem is that the answer is no -- calendar is workable, contacts is marginally workable and mail is forget it, lacks too many features.

I then installed Office for Mac for 2016 hoping it would do the trick but again it is functionally lacking. I the bit the bullet and installed Office for Windows for 2016 (I run Parallels) and the world is back to usable. I wish MS would simply code a "Windows functional" version of "Office for Windows" but I guess they want to punish Mac users!

Leaving with a tip. MS's Word and Excel are two massively useful tools here. For each of my services, I save or drag to a desktop a few emails, contacts, and calendar events, and export a few contacts and calendaring events as CSV (Comma Separated Values) files. I open the saved/dragged files in Word, using the "Recover text from any file" Command, and the CSV files in Excel.

In Word, I'll see Header data, which often can include server-related data that will lead me to tweak my own client apps to optimize performance and server load. In Excel, I'll see the data fields and order of the imported files - I recall something like 256 fields in Gmail contacts, over 200 of which I'll never use such as the "Phonetic name" fields that don't map to Exchange or iCloud contacts, but seeing this mapping order in the CSV files helped me understand what was synching and what wasn't. I don't recommend this sort of probing around to anyone, but I've been dealing with analytical statistics for far too long. There's no one perfect sync conduit, sad to say - I've opted to use Outlook for my MS accounts, native Mac clients for iCloud stuff, and Gmail for my Netflix queue and Feedly account (and nothing else!).

I too am a math / stat guy so that sounds like a plan!!

Cheers, and Happy New Year!

You too!