Adding Enterprise Exchange Email Account to Outlook Prevents Sending via Outlook.com Account

Devhack

New Member
Outlook version
Outlook 2016 64 bit
Email Account
Outlook.com (as MS Exchange)
The full error code received in bounced messages sent via outlook.com account in Outlook (version 1812) is: 0x80070005-0x000004dc-0x00000524
The error message: "This message could not be sent. You do not have the permission to send the message on behalf of the specified user." (Other than outlook.com aliases, there are no other aliases, nor send-as or on-behalf-of arrangements in any other accounts.)

Posted in these forums about 2 years ago (Diane made a valiant attempt to resolve) and in Microsoft forums last week; no good explanation/solution yet.
I've been using Outlook with a single profile for as long as I can remember, and up to about 2 years ago, all went well with the following email accounts in one profile:
  1. a personal outlook.com account with 4-5 aliases, (for this post, I'm using "myaddress" as the stand-in for my actual primary outlook.com alias.)
  2. a personal Gmail account,
  3. a single Office365 Business Essentials account, and
  4. three Office365 Enterprise E1 accounts (nonprofit).

About two years ago, it became impossible to send messages via my personal outlook.com account, messages bouncing with a "you don't have permission to send on behalf of...." message. Other than the aliases associated with the outlook.com account, there are no delegations, nor any send-on-behalf arrangements in the other email accounts.
However, for almost the last two years, I've used a work-around; in the message to be sent via the outlook.com account, I'd click on the drop-down next to the "From" field, choose my primary alias, and the message would send successfully.
  • Before using this "trick," running the cursor over my outlook.com address in the "From" field would show: “myaddress@outlook.com [myaddress@outlook.com] Send using account myaddress@outlook.com .“
  • After my "trick," running the cursor over my email address opposite the "From" field would show simply my primary alias "myaddress@outlook.com."
  • Starting around this past November, that "trick" no longer works; the longer syntax above remains no matter what I do, and the message bounces.
Currently, I just keep outlook.com open in a browser, sending messages that way, as it's the only way I can send from my outlook.com account.
There are no such problems in the iOS versions of Outlook on my iPhone or iPad which also have the same accounts set up.

After periodically reviewing related "solutions" over the past 2 years and deleting profiles, rebuilding profiles, reinstalling Outlook, etc., I conducted the following procedure last week:
I updated the Office365 Outlook version to the latest; 1812.
I created a new profile and added accounts in the following order, exiting and re-booting Outlook after each addition, then testing the outlook.com account for sending messages:
  1. the personal outlook.com account; messaging was fully functional.
  2. the personal Gmail account; both accounts fully functional
  3. the single Office365 Business Essentials account; all three accounts fulling functional
  4. the Office365 Enterprise E1 account; outlook.com account unable to send messages.
Sending messages with the outlook.com account was disabled no matter which of the 3 Enterprise accounts I added.
I also tried a separated profile in which I added the Office365 Enterprise account first, then the outlook.com account second; same result, unable to send from the outlook.com account.

Last week I raised this problem with Microsoft's Office365 Enterprise Help desk, opening a ticked after 2 phone calls. The telephone response indicated there was a conflict between outlook.com and the Office365 Enterprise Exchange accounts and that all of the "send as" bounced message errors indicated some sort of "send as" confusion between the two. Doesn't sound right to me.

MS suggested separate profiles; I'm opting for a single profile where I receive on all accounts, using a browser to send outlook.com emails and responses via OWA.

Any thoughts? Anyone else with similar issue? Is there a known conflict between outlook.com accounts and Enterprise Exchange accounts set up in the same profile?

Thanks!
 

Diane Poremsky

Senior Member
Outlook version
Outlook 2016 32 bit
Email Account
Office 365 Exchange
the Office365 Enterprise E1 account; outlook.com account unable to send messages.
I have 3 E5 accounts (one tenant), an office 365 small biz essentials, a gmail, and an outlook.com (uses a custom domain address). I add them in this order:
1 E5, 2nd E5, Small biz, last E5, gmail, outlook.com.

I can send ok from the outlook.com aliases*** (outlook.com account needs to be in the From field then select the alias) However - I can't send from the main outlook.com address. I have it set up as an office 365 contact in the E5 tenant and the address resolves to it when i add it /try to send - it tries to send from the small biz account. I've deleted the office 365 contact and now i can send from it, no problems.

(been meaning to do that for a long time - thanks for making me finally do it!)

This is from the sent folder - after I removed the alias, the display name was correct and mail sent.
2019-01-14_7-27-11.png


This is what it looks like when i open the sent message

2019-01-14_7-36-26.png



*** EASI aliases- aka, addresses not owned by outlook.com such as gmail, can't send from outlook desktop. Connected accounts can be used but will show as 'from [outlook.com] on behalf of [connect account]"


Last week I raised this problem with Microsoft's Office365 Enterprise Help desk, opening a ticked after 2 phone calls. The telephone response indicated there was a conflict between outlook.com and the Office365 Enterprise Exchange accounts and that all of the "send as" bounced message errors indicated some sort of "send as" confusion between the two. Doesn't sound right to me.
It sounds like there is some confusion, but on the other hand, there shouldn't be any conflict - unless, like me, the address was in the AD. For whatever reason, outlook appears to check the AD first, even if the account is not using *that* AD.


However, for almost the last two years, I've used a work-around; in the message to be sent via the outlook.com account, I'd click on the drop-down next to the "From" field, choose my primary alias, and the message would send successfully.
I wonder if there was "bleed" - from autocomplete or contacts. Unless, like me, its in the AD of one of the accounts.
 

Devhack

New Member
Outlook version
Outlook 2016 64 bit
Email Account
Outlook.com (as MS Exchange)
I have 3 E5 accounts (one tenant), an office 365 small biz essentials, a gmail, and an outlook.com (uses a custom domain address). I add them in this order:
1 E5, 2nd E5, Small biz, last E5, gmail, outlook.com.

I can send ok from the outlook.com aliases*** (outlook.com account needs to be in the From field then select the alias) However - I can't send from the main outlook.com address. I have it set up as an office 365 contact in the E5 tenant and the address resolves to it when i add it /try to send - it tries to send from the small biz account. I've deleted the office 365 contact and now i can send from it, no problems.

(been meaning to do that for a long time - thanks for making me finally do it!)

This is from the sent folder - after I removed the alias, the display name was correct and mail sent.
View attachment 2622

This is what it looks like when i open the sent message

View attachment 2623


*** EASI aliases- aka, addresses not owned by outlook.com such as gmail, can't send from outlook desktop. Connected accounts can be used but will show as 'from [outlook.com] on behalf of [connect account]"



It sounds like there is some confusion, but on the other hand, there shouldn't be any conflict - unless, like me, the address was in the AD. For whatever reason, outlook appears to check the AD first, even if the account is not using *that* AD.



I wonder if there was "bleed" - from autocomplete or contacts. Unless, like me, its in the AD of one of the accounts.
 

Devhack

New Member
Outlook version
Outlook 2016 64 bit
Email Account
Outlook.com (as MS Exchange)
Diane, I thought I responded over a week ago, but don't see my response here. Thanks for running through all of those scenarios and tests. I had my primary outlook.com address in the E1 domain, removed it, but still have the problem, i.e., can't send from the primary outlook.com alias. Am looking further in the AD to see if I've missed something. Thanks for your thorough and timely response!
 

Devhack

New Member
Outlook version
Outlook 2016 64 bit
Email Account
Outlook.com (as MS Exchange)
As a possible solution, this was posted by Microsoft in their forum: (This regards the failure to send messages from an outlook.com address from within the Outlook client when in my case there was an Enterprise Exchange account(s) present.)

Since Outlook may use the autocomplete email address automatically even though you select another email address, your issue may be related to Outlook cache, I recommend you can try to clear the autocomplete cache before sending email out. Navigate to File > Options > Mail, under Send messages option, click Empty Auto-Complete List. After clearing operation, type the sender’s email address manually via clicking From > Other E-mail Addresses.
In addition, if your Outlook version is not latest, please also try to update it to the latest one for more stable using experience. Navigate to File > Office Account, under Update Options, choose Update Now.


The above works for me for sending from my outlook.com email address, as long as I remember to choose "Other E-mail Addresses" from the From field drop-down list and manually enter my outlook.com address. However, if I forget and send a message without this procedure,
1) the message bounces,
2) I have to Empty Auto-Complete List again, then
3) continue sending from the outlook.com email address with the above procedure.

Hope this isn't the permanent fix.
 

Diane Poremsky

Senior Member
Outlook version
Outlook 2016 32 bit
Email Account
Office 365 Exchange
When you open the new message, what address is in
 

Devhack

New Member
Outlook version
Outlook 2016 64 bit
Email Account
Outlook.com (as MS Exchange)
When you open the new message, what address is in
In the From field of the successfully received message from my primary outlook.com account:
FirstName LastName <myprimaryalias@outlook.com>

Note that when a message is set up to send from the outlook.com account, after the Auto-Complete List has been emptied, and choosing Other Email Addresses from the From drop-down, I can choose the above email address from the list.

If I haven’t performed the above procedures and Outlook is in the failure mode, the drop-down contains only one option to send from the primary outlook.com address, and that option has the primary outlook.com email address followed by “(Outlook)” without the quotes.

FYI, after sending MS the header of the NDR message at their request, they responded:

From your NDR, the message is sent from Outlook.com account, the issue might be related to Outlook.com service. However, we are focusing on research and handle issues related to Office 365 for Business, which is using different service from Outlook.com. Therefore, I recommend you communicate with engineer works for Outlook.com service for dedicated support. I will help you move your thread to that category, the engineer there will help you further.

Best Wish!
Thanks,
Betty
 

Devhack

New Member
Outlook version
Outlook 2016 64 bit
Email Account
Outlook.com (as MS Exchange)
Just confirming that my situation was similar to Diane's, and that there is apparently some sort of "bleed" from my Office 365 Enterprise organization contact list (Azure Active Directory?) into my outlook.com account, or into the Outlook desktop client environment.

I have no problems sending or receiving via the accounts below via the Outlook app in the iOS environment, i.e., iPhone & iPad.

To reiterate, my Outlook desktop client has the following accounts set up:
  • an outlook.com email address,
  • a Gmail address,
  • an Office 365 Business Essentials address
  • four Office 365 Enterprise addresses in the same nonprofit tenant.
The precipitating circumstance: For purposes of testing external users in the Office 365 Enterprise tenant, I created myself as an external user and placed myself among the tenant's contacts with my outlook.com email address for that contact. By putting a distinctive marker (adding "Alt Mail after my name) to my name in that Office 365 Enterprise contact list, I confirmed the following.

Using the latest version of the Outlook desktop client running on the latest Windows 10, and attempting to send a message from my primary outlook.com account, the Outlook desktop client was using my outlook.com primary account to send on behalf of my contact in the Office 365 Enterprise tenant, resulting in the failure to send and the "you don't have permission....." error. (There were no send-on-behalf or delegations set up in any of my accounts.)

Removing myself (along with my outlook.com primary address) from the contacts in the Office 365 Enterprise tenant restored send functionality for the primary outlook.com address in the desktop Outlook client. It did take upwards of 10-24 hours for the send functionality to be restored after removal of the Office 365 Enterprise contact.

Some further observations....
  1. First, there may be many causes of the inability to send from the primary outlook.com account within the Outlook desktop client. So, the above circumstances and procedures may not apply to everyone's similar problem.
  2. I consider this a "work-around," not a "solution;" Microsoft has long-standing work to do.
    1. To wit, this problem has been around for about 3 years. See this thread among those in Microsoft's User Voice requests. (started April 2016 and including recent pleas for help)
  3. Over the last 2+ years, I used several work-arounds. At first, I could simply click on the outgoing email's From field and choose my primary outlook.com address from the list; it would replace the "send-on-behalf-of" language with my outlook.com address. Then, sometime late last year, that stopped working. Then more recently, as suggested on Microsoft forums, I could empty the Auto Complete List under the Mail settings and manually enter my outlook.com primary address in the From field. Then, about a week and a half ago (late January, early February 2019), that stopped working. I'm guessing that the "stopped working" events coincided with upgrades of the Outlook client, most recently from version 1812 to 1901.
  4. Even now with send functionality restored, examination of the successfully sent email's header still shows a send-on-behalf-of syntax.
Thanks, Diane, for your help.
 

Diane Poremsky

Senior Member
Outlook version
Outlook 2016 32 bit
Email Account
Office 365 Exchange
What are your address book settings? Specifically, is the exchange gal set as the default? I wonder if it makes a difference if the default is not in the Exchange account.

Ctrl+Shift+B to open the address book, then Tools, options to check.

(The link to the uservoice is not working - it points to the forum)
 

Diane Poremsky

Senior Member
Outlook version
Outlook 2016 32 bit
Email Account
Office 365 Exchange
If i read the uservoice correctly, its asking for this:

The entire middle section is outlook.com aliases or connected accounts. (EASI is non-microsoft account added as an alias) - the outlookmvps.com address is an outlook.com custom domain - gmail and another account are connected accounts.

When i send using the accounts, they are sent on behalf of - they are not sent through the account's own server, like they are in outlook on the web. This capability is expected at some point but no ETA (last I heard).

2019-02-11_1-01-53.png
 

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