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Hi @Glenn Maxwell

Thank you for posting your question in Microsoft Q&A. 

I have reviewed all relevant articles and references but found no specific information regarding changes to health probes in Exchange Server 2019. From my perspective, the healthcheck.htm probe might not work as expected due to architectural updates or the integration of Managed Availability.

If possible, you could consider these workaround: 

1. Using  the Exchange Management Shell (EMS) to check the health of various components: 

This command may assist you in viewing a health set, which is a collection of monitors, probes, and responders associated with a specific component. Together, they determine whether the component is functioning in a healthy state.

Run:

Get-HealthReport -Server <ServerName> 

References: Manage health sets and server health | Microsoft Learn 

2.Using Health Checker: 

This could collect useful information of your server to help speed up the process of common information gathering of your server. 

You can refer via: HealthChecker - Microsoft - CSS-Exchange 

Note: Microsoft is providing this information as a convenience to you. The sites are not controlled by Microsoft. Microsoft cannot make any representations regarding the quality, safety, or suitability of any software or information found there. Please make sure that you completely understand the risk before retrieving any suggestions from the above link 

You could give these workarounds a try and evaluate their output first. Please understand that our initial reply may not always immediately resolve the issue. However, with your help and more detailed information, we can work together to find a solution. 

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