@Brendan Short - I'm glad that you were able to resolve your issue and thank you for posting your solution so that others experiencing the same thing can easily reference this! Since the Microsoft Q&A community has a policy that "The question author cannot accept their own answer. They can only accept answers by others ", I'll repost your solution in case you'd like to accept the answer.
Ask: Outlook attachments are not being scanned for SIT data
Solution: The issue occurred because attachments sent externally were not being scanned for Sensitive Information Types (SIT).
This happened because the "Auto-labeling for files and emails" functionality within the sensitivity label policy was used to automatically apply a sensitivity label to the email after detecting particular SITs, which then triggered encryption for outgoing emails. However, this method of applying encryption only scans the body of the email for SITs and does not scan the attachments.
To resolve the issue, Data Loss Prevention (DLP) functionality within Purview was used to create the necessary policies for DLP. With this approach, M365 attachments in emails were scanned correctly for SITs as per Purview documentation.
OCR is only required when scanning image files.
If I missed anything please let me know and I'd be happy to add it to my answer, or feel free to comment below with any additional information.
If you have any other questions, please let me know. Thank you again for your time and patience throughout this issue.
Please don’t forget to Accept Answer
and Yes
for "was this answer helpful" wherever the information provided helps you, this can be beneficial to other community members