Will Outlook 2016 Desktop Sync-up With Outlook.com?

[Travis Lloyd]

For years now all of my clients use Outlook (2010, 2013 & now 2016) on their desktop computers, have Android smartphones (none are interested in getting a Windows phone) and need to be able to see and update their calendars, email, etc either when they make an entry on their phones or on Outlook on their computer. Up to now it's been hit & miss with them using Google Apps "in the middle" to sync to Outlook on the computer side & a Google Android app on the phone side but this has never worked well in the past (& now won't work at all with Windows 10 & Outlook 2016).
Now that Windows 10 is out with its "Phone Companion" which has an Outlook app for Android it looks like we're getting close to what they've been needing for years, IF Outlook 2016 desktop (part of Office 2016 Home & Business, NOT Office 360) will sync-up with Outlook.com. As I understand it the Win 10 Phone Companion will sync the Android phone with Outlook.com, so if I can just get Outlook 2016 to talk to Outlook.com I'm home free. That way ideally an entry made on the phone side will sync-up with Outlook 2016 on the desktop via Outlook.com and vice-versa. By the way, none of them are interested in directly using Outlook.com per se - for calendaring or email; they want to continue to use the desktop version of Outlook, just so you'll know. Please advise if this is now possible and if so, where I can find the instructions on how to accomplish this? Thanks!

 

[Diane Poremsky]

IF Outlook 2016 desktop (part of Office 2016 Home & Business, NOT Office 360) will sync-up with Outlook.com.

Outlook 2016 (and 2013) currently use Exchange ActiveSync to Sync to outlook.com accounts to outlook desktop and phones/tablets. In the coming months the accounts will be migrated to Office 365 exchange and it will use Exchange services to sync. Either way, the answer is yes, the account syncs to outlook desktop.

if you are using outlook.com accounts, you don't need anything to sync the account - in fact, almost everything on the phone companion list can be set up to sync without using phone companion.

none of them are interested in directly using Outlook.com per se - for calendaring or email;

I'm assuming you mean the web interface? That is not a problem.

Note that it syncs the outlook.com account email, calendar, contacts to and from the mailbox on the server, not calendar and contacts in other folders or mailboxes.

 

[Travis Lloyd]

Thanks so much, it sounds hopeful, but maybe I need to elaborate a bit more (or maybe I'm just a little slow today).
I have the Outlook 2016 desktop application that I use for email, calendaring and scheduling, which uses the standard "Travis.pst" file on my hard drive as it always has. How can I make what I enter into Outlook on the desktop (email, calendar, etc) also sync-up with Outlook.com, where in turn the Android phone app can access it? The goal here is to keep the Outlook 2016 desktop program (recall that it's Home & Business, not 360) and the Outlook Phone Companion in sync, regardless of whether emails, calendar entries or whatever are entered / generated at either end, be it on the computer end or the phone end. A Google app used to be able to do that but now it suddenly doesn't work with Windows 10 & Outlook 2016 anymore (plus, if these guys could get away from Google altogether they wouldn't mind a bit). I hope that paints a little clearer picture of what I need to do. Assuming this is now possible, could you point me toward some detailed instructions on how to set it all up? Thanks again!
As an aside, the Outlook app on the phone will communicate with Outlook.com just fine and can access its email, calendar and what-not; it's getting the information from Outlook 2016 on the desktop up to Outlook.com where it can be passed along to the phone app (& vice-versa) which is my objective. My clients need to have whatever is entered on whichever device, the phone or the computer, transferred (or synced) to the other one. These guys just use standalone email accounts, like AT&T and Verizon and are not on corporate email servers, by the way. I hope that helps make it a bit more clear what I'm aiming at here.

 

[Diane Poremsky]

How can I make what I enter into Outlook on the desktop (email, calendar, etc) also sync-up with Outlook.com, where in turn the Android phone app can access it?

If you want to sync the contents of a pst with outlook.com, you would need to use a 3rd party program or a macro. But Outlook 2013/2016 support adding an outlook.com email account to outlook desktop and syncing it's calendar and contacts between the desktop and server, the same way as it works with a corporate email account. It only syncs between the outlook.com account's folders on the desktop and the outlook.com server - it will not sync between the calendar in your pst and outlook.com, only between the outlook.com calendar in outlook desktop and the outlook.com server.

 

[Travis Lloyd]

Okay thanks, I think I somewhat better understand now. If it's not too much to ask, could you point me toward specific instructions on how to set-up the Outlook.com scenario and also recommend any 3rd-party solutions (except the crummy Google Apps Sync for Microsoft Outlook [GASMO] one, which doesn't work with Win 10 & Outlook 2016). You help is greatly appreciated. I've found that in the computer world if one guy has a particular problem then normally a lot of others do to; I doubt I'm the only one trying to figure out how to do this, what with smartphones being as ubiquitous as they are today.

 

[Diane Poremsky]

You definitely aren't the only one - i offer paid support services too and about 1/3 of my clients pay me to set it up to sync their calendar and contacts between outlook and smart phones.

I have instructions here - Configuring an Outlook.com account in Outlook - if you are only going to use it for calendar and contacts, see Sync calendar and contacts using Outlook.com

See Synchronizing Outlook on Two Computers for sync utilities - not all work with outlook.com but quite a few do. I prefer CompanionLink.

 

[Travis Lloyd]

You have been so kind I hate to ask for more of your advice but I'm still in the throes of a dilemma. I'm currently attempting to use the CompanionLink app that you recommended and while it seemed like the answer to my problem in theory, in actual fact it's falling a bit short of expectations. I'm sure you know how it works; it's supposed to extract the data from the Outlook 2016 *.pst file and synchronize it with the Outlook.com file which in turn is supposed to synchronize with my client's Android phone which has the new Outlook app installed on it via the Windows 10 "Phone Companion". While it seemed to work at first it is not now doing so, even though a random appointment or 2 seem to be getting through here & there. It appears to synchronize (sometimes - other times it gives a cryptic message about Outlook.com is unavailable due to too many logon attempts but I've only got it set to synch every 2 hours so that should not be a problem - it appears to be timing-out before all the new data can be uploaded or downloaded (synched), although that data is very minimal - maybe 1 or 2 new calendar entries and / or additions to either the Contacts in Outlook 2016 or on his phone). If all else fails I may have to try the 2nd-rate (in my opinion) EAS option, which I've never used before. I've always been of the mind that it's better to have all your stuff in a *.pst file so it's always available on your hard drive if (when) the Internet goes down. So here's my question: If I go to the EAS option (which I suppose would involve an *.ost file as opposed to a *.pst file) is there any way to migrate the data from the *.pst file over? He has a whole lot of data (email, calendar entries & the like) stored in that Outlook *pst file and he's not about to reenter all that stuff, I can tell you. Also, as a true expert (perhaps the primo one around) I would welcome your opinion about the pros & cons of using an Outlook *.pst solution vs. the (newer, I suppose) EAS option. Thanks in advance for your ongoing help; I've got to think that, as I mentioned before, I'm not the "Lone Ranger" here in having to deal with this scenario. (If he'd just break down & get a Windows Phone all of this wouldn't be necessary, I suspect).
I appreciate all your assistance, let me assure you...

 

[Diane Poremsky]

I'm sure you know how it works; it's supposed to extract the data from the Outlook 2016 *.pst file and synchronize it with the Outlook.com file which in turn is supposed to synchronize with my client's Android phone which has the new Outlook app installed on it via the Windows 10 "Phone Companion".

If you are syncing outlook.com, you won't need phone companion. That's only needed if you don't sync to an account that can't sync with the device. I would use companionlink to sync with outlook.com then sync the phone with outlook.com using EAS - you can use the default mail/calendar/contacts app or the 'outlook' app. The phone to outlook.com part should work good. EAS in Outlook to Outlook.com is a problem in part because EAS doesn't support all of the desktop features... and it only syncs what is in the outlook.com calendar & contacts.

Outlook.com is unavailable due to too many logon attempts

Something is hitting the account too frequently. Do you have other devices syncing with the outlook.com account? Try using a mail app instead of phone companion.

If all else fails I may have to try the 2nd-rate (in my opinion) EAS option, which I've never used before. I've always been of the mind that it's better to have all your stuff in a *.pst file so it's always available on your hard drive if (when) the Internet goes down.

While both are true, the outlook.com account will sync to an offline store in Outlook, so any data synced down is available when offline. EAS is 2nd rate for a number of reasons, but offline access isn't one of them. The dig thing is that you need to import your calendar and contacts into outlook.com and some features aren't supported using EAS - meetings don't always sync well, contact groups don't work.

 

[Diane Poremsky]

If I go to the EAS option (which I suppose would involve an *.ost file as opposed to a *.pst file) is there any way to migrate the data from the *.pst file over?

You need to export the calendar to an ics file then import it at outlook.com. Dragging contacts over to the outlook.com folders should work. See Export from Outlook Calendar to Outlook.com’s Calendar - Outlook Tips for the instructions. The Save as secreen is important - make sure you change it to whole calendar and full details.

Once the account is migrated to the new servers sometime in the next few months, you can remove the EAS account and add it back as an Exchange account. He'll have a much better experience after that - everything will work, all of the EAS limitations will be gone.

If he'd just break down & get a Windows Phone all of this wouldn't be necessary, I suspect).

It's not better with a win phone.