Connect-ExchangeOnline EXO V2 - Facing issues while connecting to Exchange Online PowerShell using a local certificate for unattended script scenario

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Connect-ExchangeOnline EXO V2 - Facing issues while connecting to Exchange Online PowerShell using a local certificate for unattended script scenario

Nijas B Rawther 1

Details: We are getting the following exception while connecting to Exchange Online PowerShell using a local certificate using the following command

Connect-ExchangeOnline -CertificateFilePath "xyz.pfx" -CertificatePassword (ConvertTo-SecureString -String "xyz" -AsPlainText -Force) -AppID "xyz" -Organization "xyz.onmicrosoft.com"

Connecting to remote server outlook.office365.com failed with the following error message : The SSL connection cannot be established. Verify that the service on the remote host is properly configured to listen for HTTPS requests. Consult the logs and documentation for the WS-Management service running on the destination, most commonly IIS or WinRM. If the destination is the WinRM service, run the following command on the destination to analyze and configure the WinRM service: "winrm quickconfig -transport:https". For more information, see the about_Remote_Troubleshooting Help topic.

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Answer 1

Vasil Michev 123K MVP Volunteer Moderator

When using CertificateFilePath, the -CertificatePassword parameter is mandatory. Other than that, make sure that you have granted the appropriate admin role to the service principal corresponding to your "Testing app".

To exclude any network-related issues, make sure you can connect with "regular" PowerShell session on the same machine.

Nijas B Rawther 1 Reputation point

2021-10-30T17:42:38.607+00:00

Yes, we are giving -CertificatePassword

Here's the connection script:
Connect-ExchangeOnline -CertificateFilePath "xyz.pfx" -CertificatePassword (ConvertTo-SecureString -String "xyz" -AsPlainText -Force) -AppID "xyz" -Organization "xyz.onmicrosoft.com"

The service principal has all the required permissions (ManageExchageAsApp) and roles(Exchange Administrator).

Even from the regular PowerShell in the same machine as the service running, connection is failing with the same exception as above.
Vasil Michev 123K Reputation points MVP Volunteer Moderator

2021-10-30T18:28:52.913+00:00
So your problem is likely on the network stack. Check the usual: firewall, proxies, etc. Also make sure you're using TLS 1.2:

[System.Net.ServicePointManager]::SecurityProtocol = [System.Net.SecurityProtocolType]::Tls12
Nijas B Rawther 1 Reputation point

2021-10-30T18:43:28.94+00:00

TLS is set properly to 1.2

The trickiest part is it is intermittent. Most of the time it fails with the above exception but the connection goes through sometimes.
KyleXu-MSFT 26,396 Reputation points

2021-11-01T08:43:38.99+00:00

Could you temporarily disable the firewall to check whether it is related to its configuration? You can also try to access from another computer to check about this.
Nijas B Rawther 1 Reputation point

2021-11-01T09:42:29.52+00:00

Thanks for your reply.

Firewall is currently turned OFF and still getting the same error related to SSL.

Even if it is some configuration that's causing this problem, how the connection goes through and gets successfully established some times while most of the other time it fails ?
KyleXu-MSFT 26,396 Reputation points

2021-11-04T09:13:15.82+00:00

I have a customer who encountered the same problem before. He solved this issue by check firewall configuration.

Based on your description, this issue is random in your organization and you could connect to Exchange online successfully sometimes, I think there doesn't exist issue on the server side. It may related with unstable network, so, if this issue occurs again, I would suggest you try with another computer or another network. Check whether you could connect to Exchange online from other computer or network.

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Connect-ExchangeOnline EXO V2 - Facing issues while connecting to Exchange Online PowerShell using a local certificate for unattended script scenario

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