Outlook With G-Suite Sync & Exchang

[JoelM]

I have a customer that is insistent that she use Outlook. I have installed the g-suite sync and everything works fine. I then add another account she has which is a Microsoft 365 exchange account. Everything seems to work fine. Emails sync. Calendars all work.
However if I try to add or edit a contact's email address or add a new contact with an email account I get the attached message.
"The operation failed. The messaging interfaces have returned an unknown error. If the problem persists, restart Outlook"
I have setup the same configuration on a cleanly installed machine with a fresh install of Outlook and get the same exact symptoms. Everything works perfect except an issue with editing email addresses of contacts or adding a new contact with an email address.
I have tried this with the contacts from both the G-Suite account and the Exchange account. Same results.
Help!

 

[marley1]

Use to not be able to was even mentioned in Google articles.

 

[Diggs]

I'm assuming you have enabled LSA (less secure apps) in Google or you wouldn't have email working. But, OAuth is a mess with Outlook. Not everything requests permissions correctly and it is a moving target with Google.

 

[JoelM]

@marley1 could you point me to some articles

@Diggs I am using GSSMO so I did not have to enable LSA. I am using Google's own sync tool. I have other customers using GSSMO without any problems and it all works perfect until I add the second email account to the profile which is a Mirosoft 365 account.

 

[Sky-Knight]

Yes, because once Outlook is attached to Exchange it stops playing by the same rules.

The answer here is honestly... pick a service. Outlook is either on Exchange, or not. I fear any attempt to do otherwise is inviting more weirdness.

 

[kwest]

I have a client that ran into this issue as well. Called Microsoft and they said it was a google issue. Client has google sync with 4 google emails and one ms exchange account. It has worked for years and just stopped working 3 weeks ago. Same error that you were gettin. We have tried everything and can’t get it working. Our temp fix was to setup exchange as imap and he can check the calendar online.

let me know if you were able to resolve this issue.

 

[YeOldeStonecat]

Outlook and Google...like oil and water.

 

[kwest]

Outlook and Google...like oil and water.

Just crazy that everything works with 4 googles accounts. Add exchange account and you can’t send from any account.

 

[Sky-Knight]

Because there are two operating modes of Outlook... Exchange and everything else.

It's never been a great idea to mix the two, there's a reason why Exchange servers used to have POP collection support... because even back then getting Outlook to work with POP3 and Exchange was a pain.

You dig into this mess and you see why there's a real case to be made for Outlook simply being branded as terrible software... I use it every day, and I love it to death too... but in this space it's objectively terrible.

 

[JoelM]

I have a client that ran into this issue as well. Called Microsoft and they said it was a google issue. Client has google sync with 4 google emails and one ms exchange account. It has worked for years and just stopped working 3 weeks ago. Same error that you were gettin. We have tried everything and can’t get it working. Our temp fix was to setup exchange as imap and he can check the calendar online.

let me know if you were able to resolve this issue.

Yes & no.
Setup the google account as IMAP. All the contacts they want are in the exchange account & the primary calendar is on exchange. If they want to look at the google calendar they do it via the web.
Not what I want but the only way I could get it to work.

 

[kwest]

Yes & no.
Setup the google account as IMAP. All the contacts they want are in the exchange account & the primary calendar is on exchange. If they want to look at the google calendar they do it via the web.
Not what I want but the only way I could get it to work.

Guy owns 5 companies and needs to keep all contacts calendar and mail separate. I told him he needs to choose one platform and I am recommending exchange for all 5 companies. But it would be easier to just move exchange to google since he only has one exchange account.

 

[Sky-Knight]

Guy owns 5 companies and needs to keep all contacts calendar and mail separate. I told him he needs to choose one platform and I am recommending exchange for all 5 companies. But it would be easier to just move exchange to google since he only has one exchange account.

How? If you have an M365 tenant you can have as many domains on it as you want. He could have a single mailbox, and 4 shared mailboxes with send permissions enabled, and cost himself all of $5 / month to do all of that.

All he has to do is log into Outlook once, and the rest sets itself up... How is Google easier? I'm honestly curious.

 

[callthatgirl]

Gsuite is the master if you set it up first and Exchange will not work as well. Setup Exchange as IMAP and tell the customer they can't have both full options. Usually clients pick the one that requires calendar and contacts sync. If that's Exchange, then setup the Exchange in a new profile and add the Gsuite account as IMAP.

 

[kwest]

Gsuite is the master if you set it up first and Exchange will not work as well. Setup Exchange as IMAP and tell the customer they can't have both full options. Usually clients pick the one that requires calendar and contacts sync. If that's Exchange, then setup the Exchange in a new profile and add the Gsuite account as IMAP.

This is what I have done. Gsuite is the most important so we have exchange setup as imap and he checks that cal on the web. Gsuite offers caldav so I could have setup exchange as primary and setup all his gsuite to imap then added the gsuite cal to outlook through caldav.

 

[kwest]

How? If you have an M365 tenant you can have as many domains on it as you want. He could have a single mailbox, and 4 shared mailboxes with send permissions enabled, and cost himself all of $5 / month to do all of that.

All he has to do is log into Outlook once, and the rest sets itself up... How is Google easier? I'm honestly curious.

From what you are describing his cal tasks and contacts wouldn’t all sync over for each account. Again he needs to keep everything separate

 

[callthatgirl]

Another idea is using Exchange as master and sync the Gsuite with Gsyncit lol. Still need IMAP setup tho. Welcome to my daily battles.

 

[Sky-Knight]

From what you are describing his cal tasks and contacts wouldn’t all sync over for each account. Again he needs to keep everything separate

Each mailbox has its own calandar, tasks, and contacts. However, you're right it's not easy on the user to use Outlook like that. BUT it IS possible.

 

[britechguy]

Just curious if they really want to use Outlook, or if they're resistant to using Gmail's webmail interface?

The only reason I keep e-mail clients up and running on my machine is so I can do testing when I need to for my blind and visually impaired clients, since not all webmail is particularly screen reader friendly (or really screen reader friendly, anyway).

But for sighted users it doesn't get much easier than Google's own webmail and calendar interfaces, and you can add multiple accounts so that you can access them from a single login to webmail much like you add accounts to email clients.

Even though I'm quite familiar with Outlook, having done a bit of custom VBA scripting for it for one blind client, I still dislike it intensely these days. Much of a muchness . . .

 

[Sky-Knight]

@britechguy How does that scale out to 5 mailboxes though?

I find if I dedicate a browser to a given login, I can get 3 that way. But 5? Incognito windows work too, but they're not terribly convenient either.

 

[britechguy]

@Sky-Knight,

I honestly don't know. I constantly have 3 email addresses active, and sometimes a 4th, but even then I keep each one open in its own webmail session in a separate browser window, whether that be by using different browsers, or three or 4 private/incognito windows, one per active address.

I've always hated "unified inboxes" and even when using an email client kept all of the accounts as separate entities (though not going to separate profiles).

I like having each respective e-mail world unto itself, and that's a simple matter even using a single web browser and a couple of dedicated private/incognito windows. But I typically have an instance of Firefox, Chrome, Brave, and Edge going at any moment in time, so just having the 3/4 open, one in each of those browsers, works too, and is most often what I do.

It's all about what works for any given individual, and some would never do as I do, but the problem is that many have no idea that they could do so, if they so chose, so presenting this as an option never hurts. If it's rejected, then so be it.