Can't add exchange email to Outlook after upgrading server license from 2013 to 2019

Question

Can't add exchange email to Outlook after upgrading server license from 2013 to 2019

PSVirtualBkkpg 0

Yesterday, I updated my server email license from MS Exchange 2013 to 2019. Prior to the update, I exported the files from Outlook (MSO365) and removed the email address from Outlook (per instructions from my hosting co). Now I can't add the email back into Outlook (desktop). Through "advanced" setup [autodiscover does not work], I've tried IMAP and Exchange. I even had a tech from my hosting company spend an hour trying to troubleshoot. No success. Most times it is just prompting me to re-enter the password.

I CAN access the email address through the web so p/w is not the problem, Outlook/my computer is.

I'm thinking it's trying to use data from the old (2013) exchange setup but I'm not finding anything about fixing that/clearing it out, if that is the problem.

For reference:

Windows 10 Pro on PC

MS Office365

Bitlocker enabled

everything up to date

non-MS email address (my bz email)

The email address is no longer showing in

Settings -> Accounts -> Email & accounts

nor in

Settings -> Accounts -> Email & accounts -> Access work or school

But it does show up when I'm adding the email to Outlook and entering the email address itself b/f the p/w. It appears in the dropdown as an option.

Yuki Sun-MSFT 41,376 Reputation points Moderator

2023-01-27T02:42:33.74+00:00
Hi @PSVirtualBkkpg ,

updated my server email license from MS Exchange 2013 to 2019.

By this, you meant the Exchange environment has been migrated from Exchange 2013 to Exchange 2019 and the mailbox has been moved to Exchange 2019, right?

Through "advanced" setup [autodiscover does not work],

Did you see any error message or other clues which indicated "Autodiscover does not work"?

Please try to use the Test E-Mail Autoconfiguration service in Outlook to help check if Autodiscover is fine:

While Outlook is running, click the CTRL key and then right-click the Outlook icon in the system tray, select “Test Email Autoconfiguration”.

Confirm that your email address is in the address field, uncheck “Use Guessmart” and “secure Guessmart authentication” boxes. Then click the “Test” button.

Once it runs, check the Log tab and Results tab.
PSVirtualBkkpg 0 Reputation points

2023-01-27T14:14:35.67+00:00

I was initially getting an error on the autodiscover route (I don't recall the problem). But now it "thinks" for a while then the advanced setup screen comes up.

Clicking CTRL + right-click Outlook icon does not give the "Test Email Autoconfiguration" option.
Yuki Sun-MSFT 41,376 Reputation points Moderator

2023-01-31T01:33:48.9133333+00:00

Hi @PSVirtualBkkpg ,

Clicking CTRL + right-click Outlook icon does not give the "Test Email Autoconfiguration" option.

Actually, I meant right click Outlook icon while Holding Down CTRL. Sorry for leading to the misunderstanding. Could you give it a shot again and share the output here after removing all privacy info?
PSVirtualBkkpg 0 Reputation points

2023-02-01T14:19:59.71+00:00

That's what I was doing. Holding CTRL + right clicking the icon does not produce a different result than simply right clicking the icon.
Yuki Sun-MSFT 41,376 Reputation points Moderator

2023-02-02T01:10:08.48+00:00

Hi @PSVirtualBkkpg ,

That's what I was doing. Holding CTRL + right clicking the icon does not produce a different result than simply right clicking the icon.

Could you share a screenshot of what you see? Remember to obfuscate all personal information involved. You can also refer to the visual instructions in this link.

1 answer

Your answer

Yuki Sun-MSFT 41,376 Reputation points Moderator

2023-01-27T02:42:33.74+00:00

Hi @PSVirtualBkkpg ,

updated my server email license from MS Exchange 2013 to 2019.

By this, you meant the Exchange environment has been migrated from Exchange 2013 to Exchange 2019 and the mailbox has been moved to Exchange 2019, right?

Through "advanced" setup [autodiscover does not work],

Did you see any error message or other clues which indicated "Autodiscover does not work"?

Please try to use the Test E-Mail Autoconfiguration service in Outlook to help check if Autodiscover is fine:

While Outlook is running, click the CTRL key and then right-click the Outlook icon in the system tray, select “Test Email Autoconfiguration”.

Confirm that your email address is in the address field, uncheck “Use Guessmart” and “secure Guessmart authentication” boxes. Then click the “Test” button.

Once it runs, check the Log tab and Results tab.
PSVirtualBkkpg 0 Reputation points

2023-01-27T14:14:35.67+00:00

I was initially getting an error on the autodiscover route (I don't recall the problem). But now it "thinks" for a while then the advanced setup screen comes up.

Clicking CTRL + right-click Outlook icon does not give the "Test Email Autoconfiguration" option.
Yuki Sun-MSFT 41,376 Reputation points Moderator

2023-01-31T01:33:48.9133333+00:00

Hi @PSVirtualBkkpg ,

Clicking CTRL + right-click Outlook icon does not give the "Test Email Autoconfiguration" option.

Actually, I meant right click Outlook icon while Holding Down CTRL. Sorry for leading to the misunderstanding. Could you give it a shot again and share the output here after removing all privacy info?
PSVirtualBkkpg 0 Reputation points

2023-02-01T14:19:59.71+00:00

That's what I was doing. Holding CTRL + right clicking the icon does not produce a different result than simply right clicking the icon.
Yuki Sun-MSFT 41,376 Reputation points Moderator

2023-02-02T01:10:08.48+00:00

Hi @PSVirtualBkkpg ,

That's what I was doing. Holding CTRL + right clicking the icon does not produce a different result than simply right clicking the icon.

Could you share a screenshot of what you see? Remember to obfuscate all personal information involved. You can also refer to the visual instructions in this link.

Answer 1

This turned out to be a known scenario, where Exchange 2019 does not install all necessary certificates when it noted an existing Exchange 2013 has a compatible certificate that it can piggy-back off of. When Exchange 2013 was retired from the domain, that certificate was no longer available, and caused "quirky" behavior with Outlook clients.

The following simple commands regenerated the certificate and put it in place:

New-ExchangeCertificate -KeySize 2048 -PrivateKeyExportable $true -SubjectName "cn=Microsoft Exchange Server Auth Certificate" -FriendlyName "Microsoft Exchange Server Auth Certificate" -DomainName "OURDOMAIN"

$Thumbprint = (Get-ChildItem -Path Cert:\LocalMachine\My | Where-Object {$_.Subject -match "Microsoft Exchange Server Auth Certificate"}).Thumbprint;

Set-AuthConfig -NewCertificateThumbprint $Thumbprint -NewCertificateEffectiveDate (Get-Date)

Set-AuthConfig -PublishCertificate

Set-AuthConfig -ClearPreviousCertificate

PSVirtualBkkpg 0 Reputation points

2023-01-27T14:01:22.2+00:00

Thank you for this reply. Where/how do I go about entering/changing this info?

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Can't add exchange email to Outlook after upgrading server license from 2013 to 2019

1 answer

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