Exchange Online Powershell not connecting in scheduled Task script

Hello everyone, I am having this issue where I can't find any useful answer. We are connecting to Exchange Online with certificate based authentication and it works fine when we run the script m...

admin

exchange online

office 365

Patrick0411
Jan 13, 2025
It took me long time, but after creating a seperate scheduled script (only for testing Exchange Online connection), I finally found the issue.
The new script worked fine, so it had to be something about my old script.
As it turned out, we had a Webserver API Call executing before the ExO connect in our script and I assume the connection never closed correctly. After I removed / moved this API call, the script is working fine.
Maybe it was blocking the same socket, which the script uses to connect to Exchange?
Probably not really useful for you, but I hope it helps anyway.

Patrick0411

Copper Contributor

Aug 07, 2024

ThomasStensitzki-MVP thank you for your help.

We are running this on Windows Server 2016 Datacenter.

TLS 1.2 client is enabled.

Here you can see all the tls settings:

Path                                                                                       Name                         Value
----                                                                                       ----                         -----
HKLM:\SOFTWARE\Microsoft\.NETFramework\v4.0.30319                                          SystemDefaultTlsVersions         1
HKLM:\SOFTWARE\Microsoft\.NETFramework\v4.0.30319                                          SchUseStrongCrypto               1
HKLM:\SOFTWARE\WOW6432Node\Microsoft\.NETFramework\v4.0.30319                              SystemDefaultTlsVersions         1
HKLM:\SOFTWARE\WOW6432Node\Microsoft\.NETFramework\v4.0.30319                              SchUseStrongCrypto               1
HKLM:\SOFTWARE\Microsoft\.NETFramework\v2.0.50727                                          SystemDefaultTlsVersions         1
HKLM:\SOFTWARE\Microsoft\.NETFramework\v2.0.50727                                          SchUseStrongCrypto               1
HKLM:\SOFTWARE\WOW6432Node\Microsoft\.NETFramework\v2.0.50727                              SystemDefaultTlsVersions         1
HKLM:\SOFTWARE\WOW6432Node\Microsoft\.NETFramework\v2.0.50727                              SchUseStrongCrypto               1
HKLM:\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.3\Server Enabled                  Not Found
HKLM:\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.3\Server DisabledByDefault        Not Found
HKLM:\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.3\Client Enabled                  Not Found
HKLM:\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.3\Client DisabledByDefault        Not Found
HKLM:\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.2\Server Enabled                          1
HKLM:\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.2\Server DisabledByDefault                0
HKLM:\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.2\Client Enabled                          1
HKLM:\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.2\Client DisabledByDefault                0
HKLM:\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.1\Server Enabled                          0
HKLM:\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.1\Server DisabledByDefault                1
HKLM:\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.1\Client Enabled                          0
HKLM:\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.1\Client DisabledByDefault                1
HKLM:\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.0\Server Enabled                          0
HKLM:\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.0\Server DisabledByDefault                1
HKLM:\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.0\Client Enabled                          0
HKLM:\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.0\Client DisabledByDefault                1

ThomasStensitzki-MVP

MVP

Aug 08, 2024

Can you login to Exchange Online PowerShell using another account?
And can you check if the use of Remote PowerShell is enabled for the account having the issues?

Get-User -Identity <UserIdentity> | Format-List RemotePowerShellEnabled
-Thomas

Patrick0411
Copper Contributor
Aug 12, 2024
I don't really see how this is relevant when using certificate based authentication.
The User running the script is not synced tho Azure at all. But he still can connect to exchange online when running the script manually. So I am pretty sure, this is not a requirement.
- Joepelus
  Copper Contributor
  Dec 20, 2024
  Did you figure this out, im running into the same issue, script works fine manually (Certificate based authentication) but fails as a scheduled task.
  - Patrick0411
    Copper Contributor
    Jan 13, 2025
    It took me long time, but after creating a seperate scheduled script (only for testing Exchange Online connection), I finally found the issue.
    The new script worked fine, so it had to be something about my old script.
    As it turned out, we had a Webserver API Call executing before the ExO connect in our script and I assume the connection never closed correctly. After I removed / moved this API call, the script is working fine.
    Maybe it was blocking the same socket, which the script uses to connect to Exchange?
    Probably not really useful for you, but I hope it helps anyway.

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Exchange Online Powershell not connecting in scheduled Task script

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