Is there a way to pull a report of your systems most common error messages and validation rule messages? Basically a way to quickly see where users most commonly have trouble that triggers some sort of err or validation message.

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Not that I know of but a very interesting ask

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Hello! This is a great question. Depending on the specific, there are a few things to consider.
If your client has the Salesforce Shield product (which comes including with Gov Cloud in case you are on a state or federal project. Add on license fee for all other customers) then you can leverage the event logs that Salesforce generates. Here is a link to the supported event types:
https://developer.salesforce.com/docs/atlas.en-us.api.meta/api/sforce_api_objects_eventlogfile_supportedeventtypes.htm
Once you enable these event types, you will be able to injest them into a SIEM tool such as Splunk.
If you do have Shield but do not have a logging platform, a quick and easy way to view the logs is to use use the ELF browser (just keep in mind that this is a Heroku app and is not FedRAMP compliant so be careful when deciding which environments to connect this to: https://salesforce-elf.herokuapp.com

The aforementioned approach will help you see system generated error logs. But what if you want to see system errors AND custom handled errors from triggers, classes, flows, etc that you create? This is where a custom logging framework comes in. IMO, every single Salesforce implementation large or small should implement a logging framework. Check out the beginning of this video for an explanation, but long story short, it’s a custom way to collect error logs that you can then easily report on:
https://www.salesforce.com/video/1779405/

Lastly, your question specifically mentioned validation messages. TBH I am not sure off the top
of my head if validation messages will show up in any of the event log types. If you truly need validation messages it could be difficult and you might need to augment those with the custom logging approach (e.g., send a platform event to the logging tool when it happens) but that will be more complex architecturally whereas the Splunk type logging and custom on-platform logging are more straightforward and common.

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Wow thank you for such a thorough response

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