Outlook 2016 - adding outlook.com account creates a new/strange address

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A

Alex Keatinge

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Outlook version
Outlook 2019 64-bit
Email Account
Exchange Server
When I add my outlook.com account to Outlook 2016 it generates a seemingly random address (e.g. outlook_d32c5a9f8hf7ea66@outlook.com) versus the address I have listed online at outlook.com. My primary alias is listed as a gmail address.
I have deleted and re-added the server account (using Auto Setup) 5-7 times now and no difference.
For reference, I do not have any connected accounts on outlook.com (just calendar and contacts), although I have tried both ways - that is, I tried adding accounts to see if it helped but it did not so I removed them.

Please help!
 
Diane, I have this exact same issue and even after creating an outlook.com email address and setting it as primary I still get this ridiculous email address as my sent from. The profile name within Outlook 2016 client says my outlook.com email address but not in the sent from when I send an email.
The other change I've experienced with MS's migration to exchange is that I am now getting the "sending on behalf of" on my emails from my primary business account (which is on my own domain) - do you know how to get rid of that??
 
I have this same issue. I use Outlook 2016 with my Outlook.com email address. The "strange" address created is the only send from option I have. Also, people cannot reply to that address. They get an error that it does not exist. This did not used to be this way.
 
I removed the outlook.com account from Outlook 2016 and then re-added it as an exchange activesync account instead. After going to account settings and clicking "new", choose "Manual setup or additional account types". Then choose Exchange ActiveSync and click Next. For the mail server, enter eas.outlook.com.
 
I have the 'strange' address too, and I have the problem that when I reply to any mail sent to my main IMAP account then the reply defaults to being sent from the 'strange' outlook email address. Q. If I set up an xxxxx@outlook.com email address as my primary outlook address instead of my current one, then will that be visible to anyone in the outside world? I don't want to start using my xxxxx@outlook.com email addy and am concerned that it might be seen from outside, (eg Skype users etc)??
 
I had the same problem with sending addresses when I moved from EAS to Exchange (having my own domain). However, despite numerous postings on several fora, no one seems to know how to get round it, other than go back to EAS. I have tried all sorts of things to no avail.

I would be happy to return to EAS but for the fact that for some unknown reason, around the time of receiving an email about the upgrade to outlook.com, I mysteriously lost emails from my inbox and extra addressees were added to my sent items! Removing the account then reconnecting made no difference, other than seeing the lost emails return and then disappear in front of my very eyes!

It appears that not even Diane is able to offer an explanation or solution to these problems.

So, if anyone has a solution to either the sending address problem or EAS problems, please let me/us know.

If anyone can also explain what changes when moving from EAS to Exchange, this too would be appreciated.
 
As of Thurs Nov 17th, things just got worse.

Note, I have outlook.com configured to send using my one.com email account. I went back to exchange active-sync in Outlook2016 after all the problems with from addresses when using exchange.

However, now my emails are not being sent. They disappear without trace from Outlook2016; they do not appear in sent items nor drafts. They definitely do not get sent. Looking in outlook.com, they are also not in sent items, but are in drafts. If i open the email from drafts and send it, it does not get sent either, just reappearing in drafts in outlook.com.

If I go to one.com and webmail and send an email, that works fine.

So, to all the experts out there, any ideas regarding either this or the Exchange problems lots of people have been reporting with their 'from' addresses?
 
I have had this trouble using a custom domain name. From what I can tell, Microsoft is pushing Outlook Premium to fix the problem. It is $19.99 until the end of this month is what I read before going up to $49.99.
 
That is the rebirth of the Custom Domain program (ex. you own jpp.com & can host 5 email accounts on outlook.com servers). The problem in this thread (with outlook_ugly@) affects email hosted elsewhere - gmail, yahoo, aol, comcast, etc. You can't use those addresses to sign into outlook.com accounts in Outlook because it requires you use autoaccount setup and that will find the server where all of the accounts are.
 
MS have supposedly been "actively working on a fix" for this issue for over a year but as far as I can tell it's STILL not fixed. Setting the outlook.com-provided email address as the primary alias on one's MS account is no good for those who need/want to use another email address (some other MS Account-based online services still don't work properly with anything other than the primary alias and/or cannot use an MS Organisational Account).

For the last year or so this "workaround" has also been an irreversible change if your primary alias' email domain is also associated with a MS Organisational Account so you can't undo it. What a mess.
 
There are a number of issues involved in the eventual solution - making it work with a mail server that is designed to block this type of behavior, doing it without getting the mail blocked as junk mail or making it easy for spammers to use.

If you use the web interface it works - outlook.com will use the address's actual smtp server. But because of the way the clients connect, they don't have direct access to the addresses's smtp server. They are working on the engineering to grab the mail from the outgoing queue and push to it the correct smtp for the address.
 
Diane Poremsky said:
There are a number of issues involved in the eventual solution - making it work with a mail server that is designed to block this type of behavior, doing it without getting the mail blocked as junk mail or making it easy for spammers to use.

If you use the web interface it works - outlook.com will use the address's actual smtp server. But because of the way the clients connect, they don't have direct access to the addresses's smtp server. They are working on the engineering to grab the mail from the outgoing queue and push to it the correct smtp for the address.
Click to expand...

Diane, regarding your comment about outlook.com will use the address's actual smtp server if using the web interface; if looking at the "sent" items in the web interface, your are correct - the address appears as it should. However, while testing this for the millionth time, the mail address on the receiving end looks like this:

First Last <outlook_numbers&letters@outlook.com> on behalf of First Last <name@owndomain.ca>

All of the POP3 settings for my own domain name in Outlook.com are correct, and it is showing as a connected account, up to date.

I don't like using the web interface - I use Outlook 2016 and have many reasons for doing so. But while I could send from my own domain name in Outlook 2016 up until a few weeks ago, none of my emails are sending at all anymore. Pardon me, they appear to be sending, and are in the Sent Items folder. But the recipients are not receiving them. It begs the question - where are they going??

And when I use the web interface, the recipients receive a mail message with the above crazy address. I have been fighting with this issue since Outlook.com first came out. What is frustrating is that I had it set to work perfectly and it was, and all of a sudden it's not. What has changed?
 
Alane McKinnon said:
First Last <outlook_numbers&letters@outlook.com> on behalf of First Last <name@owndomain.ca>
Click to expand...
Oh, yeah... it gets sent on behalf of the outlook_ugly address. I keep forgetting that, because i gave up using connected accounts (they were buggy, not sure if they still are).

Alane McKinnon said:
I don't like using the web interface - I use Outlook 2016 and have many reasons for doing so. But while I could send from my own domain name in Outlook 2016 up until a few weeks ago, none of my emails are sending at all anymore. Pardon me, they appear to be sending, and are in the Sent Items folder. But the recipients are not receiving them. It begs the question - where are they going??
Click to expand...

These are connected accounts? Do you have the accounts configured in Outlook as accounts too? Outlook has always sent the message from the default outlook.com address, which sounds like it is outlook_ugly, which is not routable.
 
I have this same problem; well, my wife does - that makes it my problem. My wife only sees this behavior when she is sending email from Outlook on Android. I have not only removed and replaced her account, I have even set her up on a new phone with the same behavior. The big problem is that in some cases, though not all, emails she sends cannot be replied to, as the ugly_outlook email seems to not be deliverable. We're looking at more than a month of this trouble, and I am not sure what is going on here to cause it or to help it. I do think I could solve this whole thing by using POP3 instead of Exchange, but then, of course, there goes tons of mail and calendaring functionality. She is an Office 365 Home user. I am, too, but I use Windows everything (including Phone - if you can imagine) and I don't see these problems. Let's hope resolution is forthcoming.
 
This happens because you have a 3rd party address linked to the outlook.com account. if you add an outlook.com alias to the account then set it as default, the problem should go away - and the outlook.com alias will be routable if you accidently use it. you'll need to use the outlook.com address to log into outlook desktop and maybe on the device, but can continue to use the other address to log into windows.
Add an Alias to an Outlook.com Account
 
I have this identical issue and even in the wake of making an outlook.com email address and setting it as essential regardless I get this crazy email address as my sent from. The profile name inside Outlook 2016 customer says my outlook.com email address however not in the sent from when I send an email.
 
In Outlook.com Settings - Outlook.com - Microsoft free personal email - what do you have set for the default email address?

If the account was in your profile before you added the alias and set it as primary, you may need to remove it from the profile and add it back.
 
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