Guides or tools to help with adding GMAIL to Desktop Outlook 2016 in Windows 10

[questorfla]

In the past, I thought having multiple provider accounts such as Yahoo, AOL , Gmail etc. all working in a desktop copy of Outlook or Outlook Express was not that uncommon.  But when I asked about doing it now, I usually get a lot of comments that say while it is still possible, it is not easy and requires a lot of tweaks in the Gmail config as well as in Outlook.

I had a coworker ask me if I could get it to work for them so I read through a number of "How To" sheets to see what has changed.  The more i read, the less it seemed that any of the current setups agreed on the proper method of doing it.   Even Google has spread out their "Fact-Sheets" to show multiple methods and all of them were much more difficult than just entering the correct mail-server, port numbers , encryption methods etc.

What this person wants is to be able to open their Outlook 2016 (a component of Office 365 for Business) and be able to switch between viewing and replying to their normal business account email and their Personal Gmail account while still inside their Desktop Outlook software as they would prefer to work with the tool-set provided within Outlook.

Any advice, tips, links, etc. on how to best accomplish this would be appreciated.  Even if it means getting a new "personal" account from a provider other than Gmail in order to achieve a dependable working solution inside the User's 'Outlook for Business 2016' desktop software.  They want to make 'Outlook 2016' their one-stop shopping for all their emailed communications both business and personal.

 

[Stoic Joker]

Even Google has spread out their "Fact-Sheets" to show multiple methods and all of them were much more difficult than just entering the correct mail-server, port numbers , encryption methods etc.

-questorfla (September 24, 2016, 12:16 AM)

Since everything from Outlook 2007 on has been auto configure (statement assumes IMAP connection), why would you be trying to enter any of that stuff? Are you - or they - trying to get a Gmail account to POP/SMTP?? If they are then you would need to ensure that the target account had Access for Less Secure Apps enabled. We frequently have to enable this for people that want to do Scan-To-Email using a Gmail account.

Other than that I really don't recall having a problem with it ... Outside of a (origin unknown) reflexive tendency to discourage that sort of configuration. Outlook always seems "happier" (more stable/less bitchy) when it's only servicing one target. But it certainly can handle multiple targets just fine.

[Shades]

You can make GMail automatically forward incoming mail to a different mail account (without adding the 'FWD:' in front of the subject line). Rules within Outlook can then separate their personal mail and professional mail.
Then you only need to configure the Google mail server as a second mail server entry and indicate per address in their address book that they want to use either the professional mail server or the GMail server to send mail.   

Assuming that this is possible in Outlook 2016 of course.

Caveat: I stopped using Outlook since their 2003 version came out and have been a Thunderbird user ever since. Sometimes I do need to check if my software keeps automatically encrypting/decrypting mail using the latest versions of Outlook and Exchange (MAPI/CAPI). Each time I see how the Outlook interface gets more mangled as versions go on, I become happier and happier I went for the Thunderbird client instead.

 

[IainB]

I would recommend @Shades' suggested approach as something that seems to work.
Very interesting too what he says about moving from Outlook to Thunderbird. I have tried for a long time to get MS Outlook to work nicely, with all my email accounts, but even with using an Outlook.com account it was nothing but trouble, though the more recent addition  of using individual app passwords seems to have helped a lot.

Also might be worth looking at - an interesting (brilliant?) concept that I tried out a while back - a FREE add-in for Outlook that enables access to Google Docs. It worked for Outlook 2007/2010. I just installed it now and it does not seem to work for Outlook 2016, but that may be because I have an obsolete version. Cannot find a newer version.
harmon.ie for Google Docs

[questorfla]

Stoic:  What "I" remember is exactly what you say.  It used to be simple as pi. (or pie)
but it no longer seems to work that way in 2016
I get errors no matter what i do saying to do things like check my password etc.
Even if i create a brand new gmail account and have a brand new password that i am 100% certain is correct, it still does not work.
Some of the mentions i have seen on this mentioned two-stage authentication as an issue.  As a additional note, this is similar to the same problem i ran into with trying to help my wife get her company email into outlook 2016.
With 2013, it was not simple but was possible.  with 2016 there is a section that seems to be missing and have no similar access.
The company she works for uses OKTA, ( a service whose purpose i have not yet been able able to discern.  It seems to be just one more level of complexity)

Anyway, back to Gmail. every time i get an error it includes a reference number and a suggested link.  Each if these tells me that there is something wrong with my password.  ALL of them tell me to go into my GMAIL account and set it to allow POP/SMTP and/or IMAP.  The setup allows you to set BOTH of them to allow and i have tried this as well.  I should also sate that unless you set your Google Search to look only at issues that fall into a time frame of the "Past Month", you wall not see much in the way of problems.  Most of the reports that are along the lines of what I am getting are from people reporting in during the past few weeks.
I assume something has changed but not sure what.

[Stoic Joker]

Some of the mentions i have seen on this mentioned two-stage authentication as an issue.

-questorfla (September 25, 2016, 04:18 PM)

Yepper, that one's a bugger. And they make it really hard to disable by burying the link (that I posted earlier..). While I haven't had occasion to deal with Office 2016 much, I have seen Gmail accounts take exception to Office 2013 a few times ... And the "fix" was always to enable Access for Less Secure Apps. Log into the target account, then past the link into the browser to get there. Enable it and then wait 10-20 minutes for it to actually take effect (I've seen it take up to an hour), and then it should behave after that.

We go through this frequently when setting up Multi-Function Printers to get Scan-To-Email working with Gmail accounts. Which is why I had - and keep - the link handy.