Auto-Labeling based on data in Document Properties doesn't work

Hello CameronStephens2,

I haven't tried this personally, but based on the research, a few things to consider,

1. If you plan to use document properties as a condition (Document property is), this option uses SharePoint managed properties in the same way as they are used for DLP policies. Use exact string matches; regex patterns aren't supported. Refer to: https://learn.microsoft.com/en-us/purview/apply-sensitivity-label-automatically#prerequisites-for-auto-labeling-policies
2. Consider using only letters and digits in managed property names. Although it is possible to create custom managed properties with special characters (such as hyphens, dots, and underscores), many of those characters act as operator characters in the query syntax. For example, a hyphen means negation. Such property names have to be enclosed in double quotation marks when used in queries. Many tools and applications that create queries don’t handle this correctly, and therefore it is better to use only letters and digits in managed property names. Refer to: https://learn.microsoft.com/en-us/sharepoint/manage-search-schema#create-a-new-managed-property 
3. Also explore trainable classifiers/document fingerprinting if that fits your scenario.
   Refer to: Get started with trainable classifiers | Microsoft Learn
   About document fingerprinting | Microsoft Learn

Hope this helps!

Regards,

PI

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