Outlook.com in Outlook 2016 Trys & Fails to Send on Behalf of Itself

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Outlook version
Outlook 2016 64 bit
Email Account
Outlook.com (as MS Exchange)
I was using Outlook 2016 for several email accounts including an Outlook.com account, a Gmail account, and several Office 365 Exchange accounts. No problems.

Then in December, maybe upon the outlook.com transition to Exchange, sending mail or replying to mail via the Outlook.com account in Outlook 2016, I started getting an immediate failure to send with a “you don’t have permission to send on behalf of that account” message. If I logged into the Outlook.com account online (OWA), replying and sending were no problem.
  • The Outlook 2016 environment & settings:
    • Windows 10 Pro (64bit) running on a Lenovo P50
    • The Outlook.com account is listed as an Exchange account and has 6 aliases besides the primary alias, say "myaddress@outlook.com," all of which I can send “From.”
    • There are no “delegates,” nor any rules set up to send anything on behalf of anyone.
    • The failures persist whether the Outlook.com account is the only account in the Outlook 2016 profile, or whether other accounts are also present.
    • Setting up a new profile does not change the behavior,
    • Re-installing Windows 10 and Office 2016 does not change the behavior.
However, I discovered the following anomaly and work-around:

Say that myaddress@outlook.com is my primary alias.

Using Outlook 2016 for my myaddress@outlook.com account, here’s what happens:
  1. If I compose a new email or reply to an existing email, opposite the From drop-down box is “ myaddress@outlook.com “ as would be expected.
  2. But, if I run the cursor over that myaddress @outlook.com that is opposite the From drop-down box (which lists my other aliases), myaddress@outlook.com is expanded to read:
“From: myaddress@outlook.com { myaddress@outlook.com]
Send using account myaddress@outlook.com

  1. This being the case, the message or reply fails to send & I get the "you don't have permission..." error message.
  2. However, if before sending the message or replying to a message, I then click on the From drop-down box and manually choose myaddress@outlook.com , it does not change the appearance of the myaddress@outlook.com opposite the From drop-down box, but running the cursor over that myaddress@outlook.com , it expands to only “ myaddress@outlook.com “ (not the above “From…Send using….”).
  3. And the email or reply subsequently sends successfully.

I know that there are some anomalies with outlook.com addresses in Outlook 2016 when there are multiple aliases, but I have not seen this particular problem mentioned.

Why is this happening? Is there a fix?
Diane, thanks for the timely response, as well as for your diligence in maintaining the website which has been a real help over many years.
  1. The aliases are actual aliases and not connected accounts; furthermore, there are no connected accounts. Per my original post, it does not matter whether the outlook.com account is the only account set up in Outlook 2016 or is accompanied by other accounts (Office 365 Exchange & a Gmail account).
  2. Yes, I've tried removing the account and adding it back, but it's been over a month since doing that multiple times. Perhaps, I will try it again in hopes that some change has since been made to the underlying software.
  3. Also, as I was testing several new Samsung 960 SSDs (Evo/Pro) in my Lenovo P50, I installed Windows 10 Pro and Office 365 (Home) multiple times through the end of December and early January; no change in this weird behavior.
BTW, Microsoft Support has only suggested the standard answer, "create a new profile", which also does not change the behavior. Again, this all started back in November, maybe even October, which is when my outlook.com account was likely upgraded.

Thanks again for your thoughts on this. If there's nothing new, no need to respond. Until this is resolved, I just have to remember to reset the "From" field in every new email and every reply sent from the outlook.com account.
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