Outlook 2016 Send from Outlook Alias Account?

I tried the steps you linked myself to try and get this to work. Outlook always wants to send from the initial guid based outlook account:

Thanks

In the past few weeks - including 10 days of the most frustrating support calls ever - I finally cracked my issue on the day that level 3 called me back and confirmed what I had discovered (trial and error).

In Outlook 2016 desktop, there are two routes to adding an account

1. Auto Account Setup - this works with your online Outlook address / Microsoft Account - but NOT if you have a 3rd party email set as your Outlook Primary (which was my case - my Microsoft Primary was set to mike at madeupname dot com. If you use your an Outlool emai as primary, it will set you us automatically with a Microsoft Exchange type

2 Manual setup which offers Office 365, POP3/IMAP and Exchange Active Sync. On the old platform, the solution to using a madeupname email which had been set as primary on your OWA (Outlook Web Access) was to use the Manual > EAS option. So both my OWA accounts were set up in my Outlook desktop like this. And I could drag/drop emails from one to the other (as well as the POP3/IMAP accounts I had set as send only in Outlook desktop).

This worked fine until Microsoft migrated to the new platform for Outlook Web Access then the drag/drop stopped working.

I then tried to change my primary to the Microsoft Account (instead of the 3rd party) and that changed was sync'ed with Desktop but still moving mails from one account to another wouldn't work. Also got the sort of issues in sent from as highlighted in other posts here.

The solution/workround I found was to set the OWA primary to the Microsoft at outlook.com one. Remove the Outlook desktop EAS connection (make sure it's backed up in case it goes wrong). Then add the same account again using Auto Account Setup - this time it should add it as Microsoft Exchange and NOT Exchange Active Sync.

Then you can drag and drop in Outlook desktop from one account to another.

I have also setup my connected accounts in OWA (so the mail arrives in OWA and if needed I can send from it under any name).

I have setup the same accounts as send only (in Send Receive Groups) in Outlook Desktop so I can send from there in any name also.

This even works with (as I have) two Microsoft Accounts syncing with Outlook desktop which also has 3rd party accounts as described. I can send from any of them, drag and drop to the right one and reply from name2 even if the mail had been sent to name1.

The issue seems to have been that

1. you can't setup a Microsoft Account automatically in Outlook if the primary is a 3rd party one (not the outlook one) 2. so if you want to have a 3rd party email as primary, the only solution is to set it up as EAS and that won't work properly now.

However if you change your 3rd party email primary back to the outlook one, and add the same account afresh through Auto Setup, you'll get a Microsoft Exchange connection which will allow the drag / drop / send from as described above.

Be warned - if you change your primary more than twice, the system blocks any more change for 10 days (not the "next week" given in the error message) so plan first.

It is also typical of Microsoft to expect normal people to spot the difference between Microsoft Exchange and Exchange Active Sync - they both look like Exchange from a company called Microsoft to me!

Update :

At last, I (partially) fixed it!

With ******@something.else as the primary alias, and ******@outlook.com as the secondary one (and NO connected account configured in the outlook.com options. ******@something.else is only an alias.)

In Outlook2016, I removed any EAS or Exchange account, and added a new one using ******@outlook.com address in the "Add account" dialog box.

Surprisingly, the resulting account in Outllook2016 is named ******@something.else and sends emails from this address...

However, this works with my wife's account and not with mine. The only difference I identified is that she has only 2 aliases (one primary and one secondary) whereas I've got more (several secondary ones). In my case, the result is an account named with a "outlook_[long series of figures and letters]@outlook.com". Apparently there is a work-in-progress on this issue (https://support.office.com/en-us/article/Reconnect-Outlook-2016-or-Outlook-2013-to-Outlook-com-for-uninterrupted-email-access-cda1751d-9503-40bf-bf76-e79454ac5eb3)

I have just installed the Office 2016 Preview and am severely disappointed to find that I cannot send from the alias within the new client. 

It's a work in progress in conjunction with the move of Outlook.com to the Exchange Online platform. Once that is completed and your account has been migrated, sending from an alias address will be possible without any additional configuration in Outlook 2010 or later.

Until then, you can configure the alias as an additional POP3 account and configure it for sending only.

I can select the alias email address from the From: dropdown menu, but how to I make this the default?  I use my personal domain email address and would like this to be my default.  It is so simple on Outlook.com, why isn't even more simple in Outlook 2016, a major part of the Office suite!  Very frustrating.......

Just don't waste your time and money with MS, I moved my email account to other provider, cancelled office 16 subscription and installed o'l trysty office 2010 and happy!