MicrosoftI applied update and ran the EEP, got everything looking good on that end and...Outlook 2021 no longer connected to my Exchange 2019 server running on Windows Server 2019. I've checked authentication and it is set to 5 through GPO. Autodiscover does report an error during diagnostics, along with DNS Forwarders and Health Monitor. Here are the results of the various scripts:
Warnings (yellow text) from HealthChecker.ps1
Certificate:
FriendlyName: Microsoft Exchange Server Auth Certificate
Thumbprint: <removed>
Lifetime in days: 1503
Certificate has expired: False
Certificate status: Valid
Key size: 2048
Signature Algorithm: sha1RSA
Signature Hash Algorithm: sha1
It's recommended to use a hash algorithm from the SHA-2 family
More information: https://aka.ms/HC-SSLBP
Bound to services: SMTP
Current Auth Certificate: True
SAN Certificate: False
Namespaces:
Microsoft Exchange Server Auth Certificate
Certificate:
FriendlyName: Microsoft Exchange
Thumbprint: <removed>
Lifetime in days: 1529
Certificate has expired: False
Certificate status: Valid
Key size: 2048
Signature Algorithm: sha1RSA
Signature Hash Algorithm: sha1
It's recommended to use a hash algorithm from the SHA-2 family
More information: https://aka.ms/HC-SSLBP
Bound to services: IMAP, POP, IIS, SMTP
Current Auth Certificate: False
SAN Certificate: True
Namespaces:
ServerName
ServerName.DomainName.com
Warnings from Get-CASHealthCheck.ps1
----- Internal URL Health Checks:
Testing https://autodiscover.domainname.com/Autodiscover/healthcheck.htm Error
----- Per-Server Health Checks:
Server: ServerName.domainname.com
Testing https://ServerName.domainname.com/Autodiscover/healthcheck.htm Error
Unhealthy flags on Get-ServerHealth.ps1
Server State Name TargetResource HealthSetName AlertValue ServerComponent
------ ----- ---- -------------- ------------- ---------- ----------
ServerName NotApplicable DnsServerForwarde... ServerName Network Unhealthy None
ServerName Online AutodiscoverProxy... MSExchangeAutodis... Autodiscover... Unhealthy AutoDis...
ServerName NotApplicable HealthManagerWork... Monitoring Unhealthy None
RunspaceId : fbf160ba-19f8-4374-ba6d-833e79189a6e
Server : ServerName
CurrentHealthSetState : NotApplicable
Name : DnsServerForwardersMonitor
TargetResource : ServerName
HealthSetName : Network
HealthGroupName : KeyDependencies
AlertValue : Unhealthy
FirstAlertObservedTime : 11/22/2022 3:20:25 PM
Description :
IsHaImpacting : False
RecurranceInterval : 600
DefinitionCreatedTime : 11/22/2022 3:12:12 PM
HealthSetDescription :
ServerComponentName : None
LastTransitionTime : 11/22/2022 3:20:25 PM
LastExecutionTime : 11/22/2022 3:30:25 PM
LastExecutionResult : Succeeded
ResultId : 5830
WorkItemId : 2145191010
IsStale : False
Error :
Exception :
IsNotified : False
LastFailedProbeId : 222666936
LastFailedProbeResultId : 24302852
ServicePriority : 2
Identity : Network\DnsServerForwardersMonitor\ServerName
IsValid : True
ObjectState : New
RunspaceId : fbf160ba-19f8-4374-ba6d-833e79189a6e
Server : ServerName
CurrentHealthSetState : Online
Name : AutodiscoverProxyTestMonitor
TargetResource : MSExchangeAutodiscoverAppPool
HealthSetName : Autodiscover.Proxy
HealthGroupName : ServiceComponents
AlertValue : Unhealthy
FirstAlertObservedTime : 11/22/2022 3:14:29 PM
Description :
IsHaImpacting : False
RecurranceInterval : 0
DefinitionCreatedTime : 11/22/2022 3:12:11 PM
HealthSetDescription :
ServerComponentName : AutoDiscoverProxy
LastTransitionTime : 11/22/2022 3:21:29 PM
LastExecutionTime : 11/22/2022 3:33:30 PM
LastExecutionResult : Succeeded
ResultId : 6754
WorkItemId : 1795977589
IsStale : False
Error :
Exception :
IsNotified : False
LastFailedProbeId : 1194805124
LastFailedProbeResultId : 24303150
ServicePriority : 1
Identity : Autodiscover.Proxy\AutodiscoverProxyTestMonitor\MSExchangeAutodiscoverAppPool
IsValid : True
ObjectState : New
RunspaceId : fbf160ba-19f8-4374-ba6d-833e79189a6e
Server : ServerName
CurrentHealthSetState : NotApplicable
Name : HealthManagerWorkItemQuarantineMonitor
TargetResource :
HealthSetName : Monitoring
HealthGroupName : ServiceComponents
AlertValue : Unhealthy
FirstAlertObservedTime : 11/22/2022 3:12:11 PM
Description :
IsHaImpacting : False
RecurranceInterval : 0
DefinitionCreatedTime : 11/22/2022 3:12:11 PM
HealthSetDescription :
ServerComponentName : None
LastTransitionTime : 11/22/2022 3:12:11 PM
LastExecutionTime : 11/22/2022 3:12:11 PM
LastExecutionResult : Succeeded
ResultId : 39
WorkItemId : 1628252781
IsStale : False
Error :
Exception :
IsNotified : False
LastFailedProbeId : -1
LastFailedProbeResultId : -1
ServicePriority : 0
Identity : Monitoring\HealthManagerWorkItemQuarantineMonitor\
IsValid : True
ObjectState : New
So far everything I've researched and tried since the end of September hasn't fixed the issue. Any advice, guidance is appreciated.
