Description

The Exchange SecurityCompliance step in Connect-Maester fails intermittently (more often than not) with the following error:

I can reproduce the error by running the following (extracted from the function).

~/Code > [string]$ExchangeEnvironmentName = 'O365Default'

~/Code > $Environments = @{
>          O365China        = @{
>             ConnectionUri    = 'https://ps.compliance.protection.partner.outlook.cn/powershell-liveid'
>             AuthZEndpointUri = 'https://login.chinacloudapi.cn/common'
>          }
>          O365GermanyCloud = @{
>             ConnectionUri    = 'https://ps.compliance.protection.outlook.com/powershell-liveid/'
>             AuthZEndpointUri = 'https://login.microsoftonline.com/common'
>          }
>          O365Default      = @{
>             ConnectionUri    = 'https://ps.compliance.protection.outlook.com/powershell-liveid/'
>             AuthZEndpointUri = 'https://login.microsoftonline.com/common'
>          }
>          O365USGovGCCHigh = @{
>             ConnectionUri    = 'https://ps.compliance.protection.office365.us/powershell-liveid/'
>             AuthZEndpointUri = 'https://login.microsoftonline.us/common'
>          }
>          O365USGovDoD     = @{
>             ConnectionUri    = 'https://l5.ps.compliance.protection.office365.us/powershell-liveid/'
>             AuthZEndpointUri = 'https://login.microsoftonline.us/common'
>          }
>       }

~/Code > Write-Host "$($Environments[$ExchangeEnvironmentName].ConnectionUri)`n$($Environments[$ExchangeEnvironmentName].AuthZEndpointUri)"

https://ps.compliance.protection.outlook.com/powershell-liveid/
https://login.microsoftonline.com/common

>> Connect-IPPSSession -BypassMailboxAnchoring -ConnectionUri $Environments[$ExchangeEnvironmentName].ConnectionUri -AzureADAuthorizationEndpointUri $Environments[$ExchangeEnvironmentName].AuthZEndpointUri 

Error Acquiring Token:
Unknown Status: Unexpected
Context: Operation did not start in the allotted time.
Tag: 0x1e3d43d2 (error code 0) (Internal error code 507331538)
OperationStopped: Unknown Status: Unexpected Context: Operation did not start in the allotted time. Tag: 0x1e3d43d2
(error code 0) (internal error code 507331538)

~/Code >

The connection works consistently with the simpler Connect-IPPSSession -UserPrincipalName $MyUPN -BypassMailboxAnchoring. (However, this may not be an option in all scenarios.)

Environment

PowerShell 7.5.0, 7.5.1
Windows Terminal 1.22.11141.0
Visual Studio Code 1.99.3

May 01 '25 18:05 SamErde

I am also running into this issue when running Connect-Maester -Service Graph,ExchangeOnline,Teams,SecurityCompliance

Connect-Maester -Service Graph,ExchangeOnline,Teams,SecurityCompliance                                             
Error Acquiring Token:
Unknown Status: Unexpected                                                                                              
Context: Operation did not start in the allotted time.                                                                  
Tag: 0x1e3d43d2 (error code 0) (internal error code 507331538)                                                          
OperationStopped: Unknown Status: Unexpected Context: Operation did not start in the allotted time. Tag: 0x1e3d43d2 (error code 0)                                                                                                              (internal error code 507331538)

If I skip the SecurityCompliance tests, I do not get these errors. If I use Connect-IPPSSession -UserPrincipalName '<UPN>' -BypassMailboxAnchoring I can connect to SecurityCompliance without error.

Environment

PowerShell 7.5.1
Windows Terminal 1.22.11141.0
OS: Windows 11 24H2 (26100.3775)
PSModule versions (AllUsers scope)
- Maester 1.1.0
- ExchangeOnlineManagement 3.7.2
- Microsoft.Graph.Authentication 2.28.0
- MicrosoftTeams 7.0.0

May 13 '25 15:05 MarcoJanse

I am also getting the same error while the following runs fine: Connect-ExchangeOnline -UserPrincipalName 'username@<tenant>.onmicrosoft.com' -ShowBanner:$false

PowerShell 7.5.1
Windows Terminal 1.22.11141.0
OS: Windows 11 23H2 (22631.5189)
PSModule versions current & all users scope
- Maester 1.1.0 AND Maester 1.1.1
- ExchangeOnlineManagement 3.7.2
- Microsoft.Graph.Authentication 2.28.0
- Pester 5.7.1

PS C:\Temp> $error[0] | Select *

PSMessageDetails      :
Exception             : MSAL.NetCore.4.66.1.0.MsalServiceException:
                                ErrorCode: unknown_broker_error
                        Microsoft.Identity.Client.MsalServiceException: Unknown Status: Unexpected
                        Context: Operation did not start in the allotted time.
                        Tag: 0x1e3d43d2 (error code 0) (internal error code 507331538)
                           at Microsoft.Identity.Client.Platforms.Features.RuntimeBroker.WamAdapters.HandleResponse(Aut
                        hResult authResult, AuthenticationRequestParameters authenticationRequestParameters,
                        ILoggerAdapter logger, String errorMessage)
                           at Microsoft.Identity.Client.Platforms.Features.RuntimeBroker.RuntimeBroker.SignInInteractiv
                        elyAsync(AuthenticationRequestParameters authenticationRequestParameters)
                           at Microsoft.Identity.Client.Platforms.Features.RuntimeBroker.RuntimeBroker.AcquireTokenInte
                        ractiveAsync(AuthenticationRequestParameters authenticationRequestParameters,
                        AcquireTokenInteractiveParameters acquireTokenInteractiveParameters)
                           at Microsoft.Identity.Client.Internal.Broker.BrokerInteractiveRequestComponent.FetchTokensAs
                        ync(CancellationToken cancellationToken)
                           at Microsoft.Identity.Client.Internal.Requests.InteractiveRequest.FetchTokensFromBrokerAsync
                        (String brokerInstallUrl, CancellationToken cancellationToken)
                           at Microsoft.Identity.Client.Internal.Requests.InteractiveRequest.GetTokenResponseAsync(Canc
                        ellationToken cancellationToken)
                           at
                        Microsoft.Identity.Client.Internal.Requests.InteractiveRequest.ExecuteAsync(CancellationToken
                        cancellationToken)
                           at Microsoft.Identity.Client.Internal.Requests.RequestBase.<>c__DisplayClass11_1.<<RunAsync>
                        b__1>d.MoveNext()
                        --- End of stack trace from previous location ---
                           at Microsoft.Identity.Client.Utils.StopwatchService.MeasureCodeBlockAsync(Func`1 codeBlock)
                           at Microsoft.Identity.Client.Internal.Requests.RequestBase.RunAsync(CancellationToken
                        cancellationToken)
                           at Microsoft.Identity.Client.ApiConfig.Executors.PublicClientExecutor.ExecuteAsync(AcquireTo
                        kenCommonParameters commonParameters, AcquireTokenInteractiveParameters interactiveParameters,
                        CancellationToken cancellationToken)
                           at Microsoft.Exchange.Management.AdminApiProvider.Authentication.MSALTokenProvider.GetAccess
                        TokenAsync(String claims, String cmdletId)
                                StatusCode: 0
                                ResponseBody:
                                Headers:
TargetObject          :
CategoryInfo          : OperationStopped: (:) [], MsalServiceException
FullyQualifiedErrorId : Unknown Status: Unexpected
                        Context: Operation did not start in the allotted time.
                        Tag: 0x1e3d43d2 (error code 0) (internal error code 507331538)
ErrorDetails          :
InvocationInfo        : System.Management.Automation.InvocationInfo
ScriptStackTrace      : at Connect-ExchangeOnline<Process>, C:\Users\\Documents\PowerShell\Modules\ExchangeO
                        nlineManagement\3.7.2\netCore\ExchangeOnlineManagement.psm1: line 754
                        at Connect-IPPSSession<Process>, C:\Users\\Documents\PowerShell\Modules\ExchangeOnli
                        neManagement\3.7.2\netCore\ExchangeOnlineManagement.psm1: line 903
                        at Connect-Maester,
                        C:\Users\\Documents\PowerShell\Modules\maester\1.1.0\public\Connect-Maester.ps1:
                        line 197
                        at <ScriptBlock>, <No file>: line 1
PipelineIterationInfo : {}

May 16 '25 14:05 kevinblumenfeld

Unfortunately I think we need to re-open this issue and track it as unrelated to the DLL version conflict. I'm still getting this error unless I use either a UPN or an application identity to connect.

Error Acquiring Token:
Unknown Status: Unexpected
Context: Operation did not start in the allotted time.
Tag: 0x1e3d43d2 (error code 0) (internal error code 507331538)
OperationStopped: Unknown Status: Unexpected Context: Operation did not start in the allotted time. Tag: 0x1e3d43d2 (error code 0) (internal error
code 507331538)

Jun 18 '25 15:06 SamErde

Connect-IPPSSession -UserPrincipalName '<UPN>' -BypassMailboxAnchoring

With this one I was also able to run this part of Maester.

Jun 19 '25 12:06 royklo

I'm also having this issue when using All for the modules. Using Exchange or Office365 on their own have worked without issue.

Jul 31 '25 00:07 RFarnellEq

Connecting to SecurityCompliance (IPPSSession) fails in Connect-Maester

Description

Environment

Environment