Secondary smtp address is not syncing.

Amit Rawat 26

hello,
We have Exchange online and exchange 2010 in hybrid mode as migration is on. We have few non mailbox users in Active Directory those login id is different (let say 456@keyman .com) whereas their email id would be like "username@keyman .com" and "username@keyman .onmicrosoft.com". I need both for business reason. Now what is happening , when AD connect sync ( on prem to O365, we have one way sync setup), "username@keyman .com" is syncing but not the other one, instead it is making smtp address in user email address like "456@keyman .onmicrosoft.com". Now this is happening when i didnt add anything in proxy address of user in Active Directory except SMTP:username@keyman .com . I tried to add smtp:username@keyman .onmicrosoft.com but NADA.. nothing is happening. I tried to add smtp:test@keyman .com and it is syncing to O365. Can ayone let me know how to get thsi smtp:username@keyman .onmicrosoft.com in mailbox email adddress.

Regards
Amit Rawat

Andy David - MVP 147.9K Reputation points MVP

2020-10-10T12:38:10.047+00:00

Not sure I understand the problem.
Here is the process on how Azure stamps proxy addresses, but not sure what your issue is exactly. Can you explain in more detail?

https://video2.skills-academy.com/en-us/troubleshoot/azure/active-directory/proxyaddresses-attribute-populate
Amit Rawat 26 Reputation points

2020-10-10T12:51:40.147+00:00

Thank You Andy for response.
I need 2 smtp address for an AD user on O365 . Challenge is user has different login name (SAM@keyman .com) whereas his email id is sam.jason@keyman .com and for some reason i need additional smtp address sam.jason@keyman .onmicrosoft.com. I simply put these 2 smtp addresses in proxy address of users and run AD connect sync. now only sam.jason@keyman .com syced but for other addresse O365 added SAM@keyman .onmicrosoft.com whereas it should be sam.jason@keyman .onmicrosoft.com . i need to edit/change SAM@keyman .onmicrosoft.com to sam.jason@keyman .onmicrosoft.com on O365 . I have no clue how to do that if proxy setting in AD doesn't change it. Hope i have put this in details.

Note:- This problem is happening when i have different login name than email id.

Regards
Amit

Accepted answer

Andy David - MVP 147.9K Reputation points MVP

2020-10-11T16:47:37.363+00:00
So thats the question.
If they need that mailbox, then you can't remove the license and purge the user unless you move the mailbox back on-prem, then remove all the licenses and purge from Azure and resync.

I tested this and this works every time using msolservice module:
Change the values on-prem. Make the primary SMTP address and UPN match. Set the alias/mailnickname as required so it will be
mailnick@keyman .onmicrosoft.com

Then:

connect-msolervice remove-MsolUser -UserPrincipalName SAM@domain.com remove-MsolUser -UserPrincipalName SAM@domain.com -RemoveFromRecycleBin

Resync and it should be as you want it.

However -as I said, ONLY do this if you do not need the mailbox or any existing data in the current Azure account since you wont be able to recover it from Azure once you remove it from the Recycle Bin
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2 people found this answer helpful.
Amit Rawat 26 Reputation points

2020-10-11T17:07:27.263+00:00

Ok. User doesn't need mailbox right now as we are still setting it up. I am going to try it tomorrow purging/Re-Syncing etc. Will let you know how it goes. Thanks fur the suggestion.

Amit Rawat 26 Reputation points

2020-10-12T04:55:07.86+00:00

Andy- This worked ! Thank you very much . I have been struggling with this issue for long and it is a surprise to know that MS support has no solution for this . in last support ticket they had suggested to remove user from AD and create it on cloud for this problem. Thank you very much Man ! Your solution and suggestion were crystal clear to the point. Thanks again for helping me. Have a great day !
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Andy David - MVP 147.9K Reputation points MVP

2020-10-10T15:35:11.303+00:00

Ok I think I understand.
You should make the UPN/User Logon match the Primary SMTP Address. Not only is that a best practice and recommended.

If you want sam.jason@keyman .onmicrosoft.com, then make the following changes:

UPN: sam.jason@keyman .com
PrimarySMTPAddress: sam.jason@keyman .com
Alias/MailNickName: sam.jason

If you do not want to change the UPN to match the Primary, then at minimum set the following:
PrimarySMTPAddress: sam.jason@keyman .com
Alias/MailNickName: sam.jason

After it syncs, then you should see a proxy address of

sam.jason@keyman .onmicrosoft.com in Azure/365.
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1 person found this answer helpful.
Amit Rawat 26 Reputation points

2020-10-10T17:09:59.163+00:00

Will it break any thing for domain user if I change UPN to match email address? I think this is the best solution so far.

Andy David - MVP 147.9K Reputation points MVP

2020-10-10T17:13:01.843+00:00

Well, they will need to logon as the new UPN :)
So you will need to let them know if you change it

Also, be aware of One Drive issues if is changed:
https://video2.skills-academy.com/en-us/onedrive/upn-changes

Amit Rawat 26 Reputation points

2020-10-10T17:22:44.723+00:00

Hmm. I will give it a try tomorrow. Will post the result. Thanks man. Appreciate you assistance.

Amit Rawat 26 Reputation points

2020-10-11T07:16:43.773+00:00

I run a test and see that after changing UPN ,it is not changing the initial domain email address. It is still showing me SAM@keyman .onmicrosoft.com. This is painful. I tried to use mailNickname method, that didn't work either. it is not letting SAM@keyman .com to be removed. I will try to run delta sync and see if it changes to sam.jason@keyman .onmicrosoft.com . Though initial sync didnt help.

Amit Rawat 26 Reputation points

2020-10-11T07:18:08.013+00:00

I run a test and see that after changing UPN ,it is not changing the initial domain email address. It is still showing me SAM@keyman .onmicrosoft.com. This is painful. I tried to use mailNickname method, that didn't work either. it is not letting SAM@keyman .com go. I will try to run delta sync and see if it changes to sam.jason@keyman .onmicrosoft.com . Though initial sync didnt help.

Andy David - MVP 147.9K Reputation points MVP

2020-10-11T14:35:14.477+00:00

Ive seen it get stuck like that.

What sort of object is this? In your intial post you said " few non mailbox users"

is this a contact or a mailbox? If a contact or user you can remove from Azure and re-sync. If a mailbox, you can not of course without some major disruption.

One option that sometimes works for a mailbox is to remove the license and resync, but I cant say I would recommend that.

Amit Rawat 26 Reputation points

2020-10-11T14:48:19.573+00:00

It is AD user and i created mailbox for it post assigning the license. Then i tried to make these changes. I also tried to remove license and synced the then assigned the license again but no changes for initial domain. It seems it is not taking any change for initial domain once it has made the changes first time. Any idea what should we do in such case?
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