[ntsysadmin] Linux Mail Servers Not Talking To Microsoft Outlook

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Fraser Coast Digital Solutions

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Aug 20, 2022, 5:19:18 PM8/20/22
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Hi All I’m Have Problems with Webhosted Provider’s Linux Mail Servers Not Sending and Receiving Email on Outlook IOS App And Desktop Outlook Client For Two Separate Clients Of Mine

Client 1 Has problems On Outlook IOS with Her New Email Account Not Sending Email Yes Try Email Settings Multiple Times and Talking to Webhosting Provider’s IT support With No Luck but Its Works on Gmail App for IOS For Sending Email and Receiving email.

 

Client 2 Has Problems with Not Sending and Receiving Email on Outlook 2019 Desktop Client on cPanel Mail Server I’m Waiting On email settings From Client

These Ave Australia Webhosted Provider’s Linux Mail Servers

 

 

Thank You

Tim Mayfield

IT Support Technician - Photographer 

Fraser Coast Digital Solutions

Mobile: 0477106489

Email: T...@frasercoastdigitalsolutions.com.au

 

Michael B. Smith

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Aug 22, 2022, 8:18:13 AM8/22/22
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What errors do you get?

 

Thanks.

 

Regards,

Michael B. Smith

Managing Consultant

Smith Consulting, LLC

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Fraser Coast Digital Solutions

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Aug 22, 2022, 11:06:26 AM8/22/22
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Hi Michael I have screenshot of outlook of client 1 iPhone please see attached she try to send a test email to me but no luck this email account is IMAP 

Thank You

Tim Mayfield

IT Support Technician - Photographer 

Fraser Coast Digital Solutions

Mobile: 0477106489

Email: T...@frasercoastdigitalsolutions.com.au

Sent From Outlook On IPhone

From: ntsys...@googlegroups.com <ntsys...@googlegroups.com> on behalf of Michael B. Smith <mic...@smithcons.com>
Sent: Monday, August 22, 2022 10:18 pm
To: ntsys...@googlegroups.com <ntsys...@googlegroups.com>
Subject: RE: [ntsysadmin] Linux Mail Servers Not Talking To Microsoft Outlook
 
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Shawn K. Hall

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Aug 22, 2022, 12:17:46 PM8/22/22
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I queried your MX servers from your own name servers 5 times and the
lookup failed twice. I suspect your name servers are either having
problems or are too aggressively filtering requests.

-S

> -----Original Message-----
> From: ntsys...@googlegroups.com
> [mailto:ntsys...@googlegroups.com] On Behalf Of Fraser
> Coast Digital Solutions
> Sent: Monday, August 22, 2022 08:06
> To: ntsys...@googlegroups.com
> Subject: Re: [ntsysadmin] Linux Mail Servers Not Talking To
> Microsoft Outlook
>
> Hi Michael I have screenshot of outlook of client 1 iPhone
> please see attached she try to send a test email to me but no
> luck this email account is IMAP
>
>
> Thank You
>
> Tim Mayfield
>
> IT Support Technician - Photographer
>
> Fraser Coast Digital Solutions
>
> Mobile: 0477106489
>
> Email: T...@frasercoastdigitalsolutions.com.au
>
> Sent From Outlook <https://aka.ms/qtex0l> On IPhone
> Mobile: 0477106489 <tel:0477106489>
>
> Email: T...@frasercoastdigitalsolutions.com.au
> <mailto:T...@frasercoastdigitalsolutions.com.au>
>
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> 90ED1101A14FEF55946F9%40SY4PR01MB5772.ausprd01.prod.outlook.co
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> <https://groups.google.com/d/msgid/ntsysadmin/SY4PR01MB5772CAC
> A90ED1101A14FEF55946F9%40SY4PR01MB5772.ausprd01.prod.outlook.c
> om?utm_medium=email&utm_source=footer> .
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Michael B. Smith

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Aug 22, 2022, 8:02:16 PM8/22/22
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Email is never sent via IMAP. It is an email retrieval protocol.

 

You didn’t answer my question: what error(s) did you get?

Fraser Coast Digital Solutions

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Aug 22, 2022, 9:00:09 PM8/22/22
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Hi Michael  this only error I get can't be saved to draft when my client is sending to any email address 

Thank You

Tim Mayfield

IT Support Technician - Photographer 

Fraser Coast Digital Solutions

Mobile: 0477106489

Email: T...@frasercoastdigitalsolutions.com.au

Sent From Outlook On IPhone
Sent: Tuesday, August 23, 2022 10:02 am
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Chad Johnson

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Aug 23, 2022, 8:46:49 AM8/23/22
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In general, if the account works in some places but not others, it is a client configuration issue.
If it works via webmail, it is almost definitely a client configuration issue.

Do other users successfully use these clients successfully with your email configuration?  Can you use these email clients for your email account?  Use a controlled environment to make sure it is not a problem with the client itself.  From there, you can work with the users to determine what needs fixed on their specific configuration.  

You need to start eliminating variables:
1) Rule out account problems by utilizing web mail (a client configured by you / the email provider that you know will work)
2) Rule out (some) email client incompatibility by using a known good account (presumably yours) with the specific email client being utilized by the users.  
3) Rule out (some) email client incompatibility by checking successful usage of this email client by any user in the organization
4) Troubleshooting client issues can be annoying and frustrating, but a good start is to blow it all away and start with a fresh configuration.  Then put in values you know work based on your troubleshooting in step 2.

The error you're getting looks very much like a client permissions error.  

On Monday, August 22, 2022 at 9:00:09 PM UTC-4 Fraser Coast Digital Solutions wrote:
Hi Michael  this only error I get can't be saved to draft when my client is sending to any email address 

Thank You

Tim Mayfield

IT Support Technician - Photographer 

Fraser Coast Digital Solutions

Mobile: 0477106489

Email: T...@frasercoastdigitalsolutions.com.au

Sent From Outlook On IPhone

Fraser Coast Digital Solutions

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Aug 23, 2022, 9:10:32 AM8/23/22
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Hi the web hosting is done and email hosting is done by ventraip Australia all email configuration is done by ventraip Australia on their Linux email Servers 
My theory is thier Linux email Server has been missing a cert or a dns some where because it works on Gmail App for IOS but not outlook for iOS  but it doesn't work with inbuilt mail for iOS for some reason 
It's just one user my client has small business she runs by herself 

Thank You

Tim Mayfield

IT Support Technician - Photographer 

Fraser Coast Digital Solutions

Mobile: 0477106489

Email: T...@frasercoastdigitalsolutions.com.au

Sent From Outlook On IPhone

From: ntsys...@googlegroups.com <ntsys...@googlegroups.com> on behalf of Chad Johnson <cjoh...@adw1.com>
Sent: Tuesday, August 23, 2022 10:46 pm
To: ntsysadmin <ntsys...@googlegroups.com>

James Iversen

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Aug 23, 2022, 10:12:57 AM8/23/22
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Hive mind,

I look to you all for guidance and advice regarding an issue which has plagued our audit logging...
On all my DC's I get a "Login Failed (NTLM - Unknown Username) for user 'User...@Big.Corp.prv' from ISEPSN on DC1 at 'date\time'.
These occur whenever anyone attempts to access the Interwebz.

Our flesh and blood users have had their UPN suffix changed from @Big.Corp.prv to @Corp.com to allow for provisioning in AzureAD.
The @Big.Corp.prv suffix still exists, however is not the primary UPN suffix on their AD User Object.
Microsoft in their infinite wisdom has chosen to require a ".com" login for O365 and AzureAD
We have been using O365 for a long time, however AzureAD Sync was never previously enabled.
Now, we are testing the AzureAD Sync with a few users in a selected OU. I suppose changing the users who are not :synched" back to @Big.Corp.prv, but this does not solve for the larger issue...
Since this change, the logs have exploded with Unknown Username Error Code: 0xc0000064. Even for those who are being synched.

Does anyone know if there is a provision for making the authentication process from an ISE device less noisy?
Is there a configuration which can be modified to allow for
Authentication still succeeds, however is seems sloppy to me having all these failures in our logs...


Thoughts?
James Iversen
Network Systems Analyst
IT Infrastructure


 
 


1899 Central Plaza East
Edmeston, NY 13335

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Michael B. Smith

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Aug 24, 2022, 6:29:49 PM8/24/22
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>> Microsoft in their infinite wisdom has chosen to require a ".com" login for O365 and AzureAD

 

This isn’t accurate.

 

I don’t know Cisco ISE, but in general, you should sync only validated domains in Azure/O365 and that is the normal configuration of Azure AD Connect.

 

Thanks.

 

Regards,

Michael B. Smith

Managing Consultant

Smith Consulting, LLC

 

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Kurt Buff

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Aug 24, 2022, 9:53:04 PM8/24/22
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Yep.

We have a .com external presence with O365, and a completely unrelated .lan domain on-prem.

It's been a while since I checked, but I believe that our on-prem AD accounts have secondary UPNs, as I do know that when a new account is created the UPN displayed in ADUC is the external one, but I sign into machines on-prem with my on-prem UPN all the time.

Kurt

David Svirskis

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Aug 24, 2022, 10:27:10 PM8/24/22
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This is covered well here - Prepare a non-routable domain for directory synchronization - Microsoft 365 Enterprise | Microsoft Docs

 

Microsoft verifies your control of a domain through public DNS. Any publicly routable domain should work (it doesn’t have to be a .com) but it *must* be publicly routable.

 

Microsoft cannot verify your exclusive control of a non-routable domain - you and dozens of unrelated organisations might be using the exact same internal domain name. Accordingly they will not allow validation of such domains within your Azure/Office 365 tenancy, and correspondingly non-routable domains *cannot* be used as a basis for account synchronisation.

 

Cheers,

David

 


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Melvin Backus

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Aug 25, 2022, 7:51:25 AM8/25/22
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We do a similar setup. The secondary UPN only exists for users who are in the sync group and are therefore licensed and synced for M365.

 

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James Iversen

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Aug 25, 2022, 8:39:57 AM8/25/22
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Hi David!

Yes, that is the procedure which was followed to prepare our users in the non-routable domain Big.Corp.prv to Corp.com for directory synchronization using AzureAD Connect.

The issue is with an ISE PSN interpreting the existing on-prem users authenticating using the Corp.com suffix. The non-routable .prv domain is still a valid secondary UPN.

Upon new user creation, the non-routable domain .prv is applied and must be modified to .com for provisioning by synch in AzureAD.

The .com is valid and we are the verified holder of the managed domain.
James Iversen
Network Systems Analyst
IT Infrastructure


 
 


1899 Central Plaza East
Edmeston, NY 13335
Phone: (607) 965-2706

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From:        "'David Svirskis' via ntsysadmin" <ntsys...@googlegroups.com>
To:        "ntsys...@googlegroups.com" <ntsys...@googlegroups.com>
Date:        08/24/2022 10:27 PM
Subject:        RE: [ntsysadmin] Authentication issue with On-Prem AD and Cisco ISE after Suffix change





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James Iversen

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Aug 25, 2022, 8:41:54 AM8/25/22
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The dripping

My ignorance is showing ;-)

I agree a .com, .biz, .net, .org, etc... should be required with a public cloud service.



From:        "Michael B. Smith" <mic...@smithcons.com>
To:        "ntsys...@googlegroups.com" <ntsys...@googlegroups.com>
Date:        08/24/2022 06:29 PM
Subject:        RE: [ntsysadmin] Authentication issue with On-Prem AD and Cisco ISE after Suffix change
Sent by:        ntsys...@googlegroups.com





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>> Microsoft in their infinite wisdom has chosen to require a ".com" login for O365 and AzureAD


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Michael B. Smith

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Aug 25, 2022, 9:00:29 AM8/25/22
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The dripping? 😊

 

My test tenant (blogging) domain is “essential.exchange”. Azure understands all the TLDs, to the best of my knowledge.

 

What it _syncs_ is up to you (the admin).

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